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Title: Synthesis and In Vitro Evaluation of Some Novel Nucleoside analogs and DNA lntercalators as Potential Anticancer or Antiviral Agents.
Creator: Zhao, Yuxiang, Florida Atlantic University, Parkanyi, Cyril, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Thiadiazoles can be considered as analogs of pyrimidines because of the well known analogy between a -CH=CH- group in benzenoid hydrocarbons and bivalent sulfur, -S-, in aromatic heterocycles. Therefore, 5-amino-2H-1 ,2,4-thiadiazole-3-one and 5-amino-3H-1 ,3,4-thiadiazole-2-one are the analogs of cytosine. In our first project, the preparation of six thiadiazole nucleoside analogs is reported: 5-diacetylamino-1 ,2,4- thiadiazol-3-one (1), 5-amino-2-(tetrahydrofuran-2-yl)-1 ,2,4-thiadiazol-3...
Show moreThiadiazoles can be considered as analogs of pyrimidines because of the well known analogy between a -CH=CH- group in benzenoid hydrocarbons and bivalent sulfur, -S-, in aromatic heterocycles. Therefore, 5-amino-2H-1 ,2,4-thiadiazole-3-one and 5-amino-3H-1 ,3,4-thiadiazole-2-one are the analogs of cytosine. In our first project, the preparation of six thiadiazole nucleoside analogs is reported: 5-diacetylamino-1 ,2,4- thiadiazol-3-one (1), 5-amino-2-(tetrahydrofuran-2-yl)-1 ,2,4-thiadiazol-3-one (2), 5- amino-3-((2' -hydroxyethoxy)methyl)-1 ,3,4-thiadiazol-2-one (3), 5-amino-3-( 4' -hydroxy- 2' -hydroxyrnethyl-butyl)-1 ,3,4-thiadiazole-2-thione ( 4), (R)-5-am ino-3-(2' ,3' - dihydroxypropyl)-1 ,3,4-thiadiazole-2-thione (5), and (S)-5-amino-3-(2' ,3 ' - dihydroxypropyl )-1 ,3,4-thiadiazole-2-thione (6). (R)-5-amino-3-(2' ,3' -dihydroxypropyl)-1,3,4-thiadiazole-2-thione (5) and (S)-5-amino-3-(2' ,3' -dihydroxypropyl)-1 ,3,4- thiadiazole-2-thione (6) are stereoisomers. Their racemic mixture 7 was also prepared and tested. The synthesis, characterization, and properties of these new synthesized thiadiazole derivatives are discussed. A dimerization of 5-amino-3H-1 ,3 ,4-thiadiazole-2- thione (18) to produce di-(5-amino-1 ,3,4-thiadiazol-2-yl) disulfide (23) by sodium nitrite with either acetic acid or stannic chloride is also reported. Preliminary results indicate that 3 and 23 possess antimicrobial activity. In the second project, the synthesis of three series of bis-aminochloropyrimidine derivatives with different types of linkers as potential DNA intercalators is described. The first series are aminochloropyrimidines bridged by polyrnethylene chain linkers with various lengths. The second series are bridged by polyether linkers to lower the lipophilicity. The third series are bridged by linkers containing benzene rings to limit the flexibility. The spectral data and other physical properties of the new compounds are discussed. The preliminary screening results indicate that many new synthesized bisintercalators are biologically active. The relationship between bioactivity and structure is discussed as well.
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Date Issued: 2007
PURL: http://purl.flvc.org/fau/fd/FA00000886
Subject Headings: Biopharmaceutics, Antineoplastic agents--Pharmacodynamics, Nucleosides--Metabolism, Pharmaceutical chemistry, Antiviral agents--Synthesis
Format: Document (PDF)

Title: Isolation and Structural Elucidation of Novel Bioactive Natural Products from Marine Organisms of the Western Atlantic Ocean.
Creator: Zhang, Long, West, Lyndon, Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The aim of this dissertation was to elaborate the exploration of biologically active secondary metabolites from the marine sponge Cacospongia cf. linteiformis collected from the Bahamas and the soft coral Briareum asbestinum collected from two different sites in Florida State, Boca Raton and Dry Tortugas. In chapter one, a review on previous chemical and biological studies of the marine sponge C. cf. linteiformis and soft coral B. asbestinum is provided. Particular attention is given to...
Show moreThe aim of this dissertation was to elaborate the exploration of biologically active secondary metabolites from the marine sponge Cacospongia cf. linteiformis collected from the Bahamas and the soft coral Briareum asbestinum collected from two different sites in Florida State, Boca Raton and Dry Tortugas. In chapter one, a review on previous chemical and biological studies of the marine sponge C. cf. linteiformis and soft coral B. asbestinum is provided. Particular attention is given to spongianolides and briarellins, two important classes of compounds isolated from C. cf. linteiformis and B. asbestinum, respectively, and their structural features and diverse bioactivities. In chapter two, the isolation and relative configuration determination of four epimeric sesterterpenoids, spongianolides E & F (18c, 18d, 19c, 19d) from C. cf. linteiformis collected from the Bahamas are discussed. Thanks to chemical modification (acetylation), diastereomeric 18c&18d and 19c&19d, respectively, were able to be isolated using chromatographic techniques for the first time, and then the relative configurations of 18c, 18d, 19c, 19d were determined based on NOESY NMR experiments. The bioactivity of mixture of compounds 18c, 18d, 19c, 19d were tested and it exhibited inhibition against Schnurri-3 (a regulator of postnatal bone mass). In chapter three, the isolation and structural elucidation of four new compounds, florellins A-D (49-52), from B. asbestinum collected off the coast of Boca Raton, FL are discussed. The molecular structures of these compounds were established by spectroscopic analysis. Compounds 49-52 are the first briarellins containing an acyl group at C-13, while 49 and 50 are the first briarellins possessing acylation at C-15. Florellins A–C (49-51) were screened and found cytotoxic against three human cell lines, BT474, WM266−4 and HEK293. In chapter four, the isolation and structural elucidation of four new compounds, florellins E-H (57-60), from B. asbestinum collected in Dry Tortugas, FL are discussed. The molecular structures of these compounds were established by spectroscopic analysis. Florellins F (58) and H (60) were screened against three human cell lines, BT474, WM266−4 and HEK293, but no cytotoxicity was exhibited. In chapter five, all the experimental procedures are described, including analytical instruments, animal materials, extraction and isolation processes, spectroscopic data and protocols of bioassays.
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Date Issued: 2017
PURL: http://purl.flvc.org/fau/fd/FA00004850, http://purl.flvc.org/fau/fd/FA00004850
Subject Headings: Pharmacognosy., Natural products--Analysis., Marine pharmacology., Marine biotechnology., Marine algae--Biotechnology., Bioactive compounds.
Format: Document (PDF)

Title: Photodegradation of 2-mercaptobenzothiazole disulfide and related benzothiazoles.
Creator: Zajickova, Zuzana, Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Benzothiazoles are heterocyclic compounds used predominantly as rubber vulcanization accelerators. The overall goal of our research was to investigate the photodegradation behavior of 2-mercaptobenzothiazole disulfide, its degradation product 2-mercaptobenzothiazole, and further degradation product benzothiazole. Modern analytical techniques were utilized to follow photodegradation process at arbitrary intervals. A chromatographic method using reverse phase liquid chromatography was developed...
Show moreBenzothiazoles are heterocyclic compounds used predominantly as rubber vulcanization accelerators. The overall goal of our research was to investigate the photodegradation behavior of 2-mercaptobenzothiazole disulfide, its degradation product 2-mercaptobenzothiazole, and further degradation product benzothiazole. Modern analytical techniques were utilized to follow photodegradation process at arbitrary intervals. A chromatographic method using reverse phase liquid chromatography was developed for the separation of benzothiazoles in the irradiated mixture. Direct photolysis of benzothiazole and 2-mercaptobenzothiazole in methanol at 253.7 and 313 nm in the presence or absence of oxygen was investigated at first. Benzothiazole was found to undergo photodimerization into 2,2'-bibenzothiazole, and in the presence of oxygen to give two additional photoproducts - 2-hydroxybenzothiazole and 2-methylbenzothiazole. The major degradation products of 2-mercaptobenzothiazole are benzothiazole and 2-benzothiazolesulfonic acid, with 2,2'-thiobisbenzothiazole, 2,x'-thiobisbenzothiazole (x = 4, 5, 6, 7), and 2-mercaptobenzothiazole disulfide as the minor degradation products. Direct photolysis of 2-mercaptobenzothiazole disulfide was investigated in four different solvents, at two different wavelengths (253.7 and 313 nm) and concentrations in the presence or absence of oxygen. In all cases 2-mercaptobenzothiazole and 2,x'-thiobisbenzothiazole were detected as the degradation products and in acetonitrile 2-thiocyanatobenzothiazole was also detected. A mechanism is proposed to rationalize the formation of photodegradation products. The effects of solvent, irradiation wavelength, and duration of irradiation time, concentration of the starting material and presence or absence of oxygen are summarized as well. It was observed that photodecomposition at 253.7 nm occurred at a much faster rate than at 313 nm and that less concentrated solutions decomposed faster. At higher concentration of 2-mercaptobenzothiazole its disulfide was detected as one of the degradation products. Methylated products were detected in methanol and acetonitrile and photoreaction took longer in polar protic solvents. Oxygenated products were formed in presence of oxygen and the photoreaction was slower as well in comparison to degassed solutions.
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Date Issued: 2006
PURL: http://purl.flvc.org/fcla/dt/12219
Subject Headings: Chemistry, Analytical, Chemistry, Physical
Format: Document (PDF)

Title: Study of cell penetrating peptides with Raman spectroscopy and microscopy.
Creator: Ye, Jing., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Cell penetrating peptides (CPPs) have drawn the attention of researchers due to their ability to internalize large cargos into cells including cancer cells. The mechanism(s) with which the peptides enter the cell, however, is/are not clear and full of controversy. The peptide conformations and their microenvironment in live cells had been unknown until the development of a technique developed in our lab. As a first demonstration of principle, penetratin, a 16-residue CPP derived from the...
Show moreCell penetrating peptides (CPPs) have drawn the attention of researchers due to their ability to internalize large cargos into cells including cancer cells. The mechanism(s) with which the peptides enter the cell, however, is/are not clear and full of controversy. The peptide conformations and their microenvironment in live cells had been unknown until the development of a technique developed in our lab. As a first demonstration of principle, penetratin, a 16-residue CPP derived from the Antennapedia homeodomain protein of Drosophila, was measured in single, living melanoma cells. Carbon-13 labeling of the Phe residue of penetratin was used to shift the intense aromatic ring-breathing vibrational mode from 1003 to 967 cm-1, thereby enabling the peptide to be traced in cells. Difference spectroscopy and principal components analysis (PCA) were used independently to resolve the Raman spectrum of the peptide from the background cellular Raman signals., On the basis of the position of the amide I vibrational band in the Raman spectra, the secondary structure of the peptide was found to be mainly random coil and b-strand in the cytoplasm, and possibly assembling as b-sheets in the nucleus. Next, label-free transportan was studied with the same methodology. The peptide, besides predominantly a-helix, adopted a significant portion of b-sheet conformation in the cytoplasm and nucleolus, which is different from the peptide in aqueous solution. The peptide microenvironment was also probed through H-bonding reported by the tyrosine Fermi doublet. Transportan displayed a tendency to accumulate in the cytoplasm over time which was unlike penetratin, which concentrated in the nucleus. The relative concentration of CPPs in various locations of live melanoma cells was directly estimated from the Raman spectra using average Phe concentration in the cell as an internal standard., The rapid entry and almost uniform cellular distribution of both peptides, as well as the lack of correlation between peptide and lipid Raman signatures, indicated that the mechanism of CPP internalization under the conditions of study was probably non-endocytotic. Last, transportan and penetratin were studied using polarized Raman spectroscopy for more detailed vibrational spectroscopic information of the two peptides in water and TFE solutions. The majority of the bands in the Raman spectra of the peptides were highly polarized, consistent with the high symmetry of aromatic ring side chain vibrational bands dispersed throughout the spectra. This work has provided new insights into the structure of CPPs in live cells and in solutions.
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Date Issued: 2011
PURL: http://purl.flvc.org/FAU/3342344
Subject Headings: Peptides, Analysis, Infrared spectroscopy, Raman spectroscopy, Cellular signal transduction
Format: Document (PDF)

Title: DIASTEREOSELECTIVE ADDITION OF H-PHOSPHINATES TO ALKENYL KETONES UNDER PHASE-TRANSFER CONDITIONS AND SYNTHESIS OF BRIDGED BICYCLIC COMPOUNDS FOR BIOLOGICAL EVALUATION.
Creator: Yadavalli, Krishna Prasad, Lepore, Salvatore D., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: In the present dissertation, we discuss the development of a stereoselective method for the production of phosphorus compounds that utilizes a phospha-Michael addition reaction. Separately, the design and synthesis of compounds that contain an all-carbon bridged bicyclic scaffold is reported; these compounds were used in initial SAR studies in different in vivo models. In Chapter one is presented a mechanistic framework to develop a highly diastereoselective method catalyzed by phase transfer...
Show moreIn the present dissertation, we discuss the development of a stereoselective method for the production of phosphorus compounds that utilizes a phospha-Michael addition reaction. Separately, the design and synthesis of compounds that contain an all-carbon bridged bicyclic scaffold is reported; these compounds were used in initial SAR studies in different in vivo models. In Chapter one is presented a mechanistic framework to develop a highly diastereoselective method catalyzed by phase transfer chemistry leading to phosphinate compounds. In this method, phosphinate nucleophiles were added to various alkenyl ketones as Michael acceptors using crown ethers as phase transfer agents to obtain highly diastereoselective products with the generation of a carbon-based quaternary centers. A closed transition state mechanism is proposed to describe the diastereoselectivity observed in the reactions that is consistent with product outcome as established by X-ray crystallography. Analysis using the 31P NMR technique is also reported to ascertain the diastereomeric ratios in product formation. Using products obtained with the newly developed method, we disclose for the first time a novel phospha-heterocycle with high control of stereochemistry. Relative stereochemistry of the phosphorus containing heterocycle was reported using 2D NMR analysis. In Chapter two focus is placed on the use of acrylates as Michael acceptors in both the diastereoselective and enantioselective studies of phospha-Michael addition. In the asymmetric method development, screening of various chiral catalysts and development of HPLC method to quantify the enantiopurity of products obtained under reaction conditions are reported. The role of crown ether catalysts towards diastereoselectivity is reported.
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Date Issued: 2022
PURL: http://purl.flvc.org/fau/fd/FA00014015
Subject Headings: Bridged bicyclic compounds, Chemistry, Organic, Organic compounds--Synthesis
Format: Document (PDF)

Title: Immunoassay test strip for Microcystin-LR detection.
Creator: Xu, Jiesi., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Microcystin-LR (MCLR) is hepatotoxic to animals and humans with disruption of liver structure causing cytoskeletal damage, necrosis and pooling of blood in the liver, leading to large increase in liver weight. It is also a strong liver tumor promoter and protein phosphatase inhibitor. Microcysin-LR binds protein phosphatases 1 and 2A, and influences regulation of cellular protein phosphorylation. In the present study, a colloidal gold based immunoassay test strip was developed for Microcystin...
Show moreMicrocystin-LR (MCLR) is hepatotoxic to animals and humans with disruption of liver structure causing cytoskeletal damage, necrosis and pooling of blood in the liver, leading to large increase in liver weight. It is also a strong liver tumor promoter and protein phosphatase inhibitor. Microcysin-LR binds protein phosphatases 1 and 2A, and influences regulation of cellular protein phosphorylation. In the present study, a colloidal gold based immunoassay test strip was developed for Microcystin-LR detection. The detection limit was found to be 1 ng/mL. 5 nm colloidal gold test strips exhibits more efficient for detection, compared with 20 nm colloidal gold test strips. The interaction between Microcystin-LR antibody (immunoglobulin G) and colloidal gold nanoparticles was investigated by various analytical methods, including Ultraviolet/Visible (UV/VIS), Fourier Transform Infrared (FTIR) and Fluorescence spectroscopy as well as transmission electron microscopy (TEM).
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Date Issued: 2010
PURL: http://purl.flvc.org/FAU/2683532
Subject Headings: Immunoassay, Biosensors, Environmental chemistry, Cyanobacterial toxins, Drinking water, Microbiology
Format: Document (PDF)

Title: GULF STREAM INTRUSIONS AS CONDUITS FOR LARVAL FISHES ALONG FLORIDA’S EAST COAST.
Creator: Woodward, Caroline, Chérubin, Laurent, Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: The mechanisms of larval fish transport have been rigorously studied in the past several decades, building foundational knowledge of key biological and environmental factors with which to inform decisions about species management. This study has been built upon information gained from previous studies to further elucidate the processes involved at the recruitment stage of larval fishes. Vertical swimming behaviors of larval fishes enable deliberate orientation within the water column to allow...
Show moreThe mechanisms of larval fish transport have been rigorously studied in the past several decades, building foundational knowledge of key biological and environmental factors with which to inform decisions about species management. This study has been built upon information gained from previous studies to further elucidate the processes involved at the recruitment stage of larval fishes. Vertical swimming behaviors of larval fishes enable deliberate orientation within the water column to allow organisms of limited mobility greater control over their horizontal movements. Vertical accumulation patterns of larvae are found to be tightly dependent on the strength of stratification within the water column at nursery entrances, such as estuaries. Onshore currents, such as upwelling and surface intrusions, are found to be conduits for entry into these systems. This study observed and analyzed the influence of intrusions by the Gulf Stream into the Fort Pierce Inlet and the vertical accumulation patterns of late-stage larvae associated with those events. This study incorporated a well-established zooplanktonic abundance sampling technique to achieve two primary goals: (1) to analyze the vertical abundances of larval fishes in stratified flow during Gulf Stream intrusions and (2) to assess the correlation between larval influx and intrusion events. The results of this study show a significant and positive correlation between propagule pressure of larval fishes and incidence of Gulf Stream intrusion events. Whereas previous studies have primarily described the spatiotemporal aspects of larval transport in a broader sense, our findings revealed a greater layer of complexity in the mechanisms of transport by incorporating localized hydrographic features. The information gleaned from these results can inform the ecological considerations of future fisheries management and study efforts via additional understanding about the role of physical oceanographic events in a critical life stage.
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Date Issued: 2023
PURL: http://purl.flvc.org/fau/fd/FA00014263
Subject Headings: Gulf Stream (Fla.), Larvae--Dispersal, Fishes--Larvae
Format: Document (PDF)

Title: Therapeutic potential, mechanism of action, and ecology of novel marine natural products.
Creator: Winder, Priscilla L., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The projects described in this dissertation are focused on compounds derived from the marine environment. Chapter 1 gives an introduction to the study of marine natural products to treat human ailments and a thorough review on compounds from lithistid sponges that have been isolated or synthesized since 2000. Chapter 2 describes the isolation and structure elucidation of two sesquiterpene substituted benzoquinone derivatives, petrosiquinones A and B, from a deep-water marine sponge from the...
Show moreThe projects described in this dissertation are focused on compounds derived from the marine environment. Chapter 1 gives an introduction to the study of marine natural products to treat human ailments and a thorough review on compounds from lithistid sponges that have been isolated or synthesized since 2000. Chapter 2 describes the isolation and structure elucidation of two sesquiterpene substituted benzoquinone derivatives, petrosiquinones A and B, from a deep-water marine sponge from the Family Petrosiidae. Although initially purified following activity in a (Sb(B-catenin/Tcf4 assay they were later followed using tumor cell line cytotoxicity assays. Petrosiquinone A was the more active of the two compounds with moderate cytotoxicity in the DLD-1, PANC-1, and AsPC-1 cell lines. In Chapter 3, the isolation and structure elucidation of two new marine-derived macrolides, madeirolide A and B, isolated from a deep-water lithistid sponge of the genus Leiodermatium is described., They were isolated using numerous chromatographic techniques and the structures were elucidated on the basis of 1D and 2D NMR spectra coupled with high resolution-mass spectrometry (HR-MS) data. Madeirolide A and B inhibited the growth of the fungal pathogen Candida albicans with minimum inhibitory concentrations (MIC) of 12.5 and 25 (So(Bg/mL, respectively, but were not cytotoxic in tumor cell assays under the conditions tested. Chapter 4 describes work performed to determine the molecular target of lasonolide A using affinity chromatography. The target of lasonolide A is of interest since lasonolide A is known to kill cancer cells in vitro through a unique mechanism., This chapter highlights the research performed to create an affinity matrix with immobilized lasonolide. A target has not been confirmed but there are a number of interesting hits that are being pursued. In Chapter 5, a liquid chromatography-mass spectrometry (LC-MS) screening method was established in order to rapidly identify the metabolites from numerous collections of Lyngbya spp. obtained from Broward and Lee County, Florida sites that may help marine ecologists assess the effects of Lyngbya spp. blooms on the environment. A link between the metabolites produced and nutrients from both the algal tissue and water column was also explored.
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Date Issued: 2009
PURL: http://purl.flvc.org/FAU/369392
Subject Headings: Natural products, Therapeutic use, Sponges, Ecology, Marine resources, Research, Marine biotechnology
Format: Document (PDF)

Title: The d(3,7) non-cubic ligand field spectrum and the electronic spectra of quadrate chromium (III) complexes.
Creator: Williams, Chamindra S., Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: In the first-part of this two-part study, the quadrate energy levels of the d3 configuration including spin-orbit interaction are derived in the rare-earth coupling scheme using ligand-field symmetry parameters Dq, Ds, and Dt, by the method of tensor-operators. Comparison is made to the strong field coupling scheme. In the second part of this study, interpretation of polarised single-crystal spectra of trans-[Cr(tmd)2F2]ClO4, trans-[Cr(en)2(dma)2](ClO4) 3, trans-[Cr(en)2(dmf)Br](ClO4) 2 and...
Show moreIn the first-part of this two-part study, the quadrate energy levels of the d3 configuration including spin-orbit interaction are derived in the rare-earth coupling scheme using ligand-field symmetry parameters Dq, Ds, and Dt, by the method of tensor-operators. Comparison is made to the strong field coupling scheme. In the second part of this study, interpretation of polarised single-crystal spectra of trans-[Cr(tmd)2F2]ClO4, trans-[Cr(en)2(dma)2](ClO4) 3, trans-[Cr(en)2(dmf)Br](ClO4) 2 and trans-[Cr(en)2(dmf)Cl](ClO4) 2 as well as unpolarised single-crystal spectrum of trans-[Cr(en) 2(dmf)2](ClO4)3 and solution spectra of trans-[Cr(pn)(en)F2]ClO4, trans-[Cr(en)2FCl]ClO4 and trans-[Cr(en) 2FBr]ClO4 is made using Gaussian analysis of the bands in both polarisations where possible. Ligand field parameters Dq, Ds, Dt and B are extracted from the spectra using energy matrices in the strong-field coupling scheme by fitting the quadrate components of the two lowest energy cubic quartet bands exactly. Discussion of these parameters and the translated AOM (angular overlap model) parameters, is presented. A thorough interpretation of the high-energy intraconfigurational doublet bands in a number of trans-diacidobis (ethylenediamine) chromium (111) complexes is made using quadrate energy matrices including spin-orbit interaction. Entire programming code for the energy matrices in the rare-earth coupling scheme is included, as are procedures for computing 3-j and 6-j symbols. The complete quadrate energy matrices for d3 configuration in the strong-field coupling scheme with spin-orbit perturbation as well quadrate energy matrices for d3 configuration in the rare-earth coupling scheme are included.
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Date Issued: 2005
PURL: http://purl.flvc.org/fcla/dt/12180
Subject Headings: Chemistry, Inorganic, Chemistry, Physical
Format: Document (PDF)

Title: Effect of external pH on cyanobacterial pigment expression.
Creator: West, Maria., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Cyanobacteria are classified as alkalophiles despite their preferential uptake of the acidic form of dissolved inorganic carbon. Long term impacts of external pH on the expression of photosynthetic and structural pigments in Schizothrix calcicola were investigated as potential contributing factors to this phenomenon. More robust cell walls in S. calcicola at pH
Show moreCyanobacteria are classified as alkalophiles despite their preferential uptake of the acidic form of dissolved inorganic carbon. Long term impacts of external pH on the expression of photosynthetic and structural pigments in Schizothrix calcicola were investigated as potential contributing factors to this phenomenon. More robust cell walls in S. calcicola at pH <7 are suggested by significantly greater expression of myxoxanthophylls. Direct and indirect physiological costs of altering cell walls may contribute to S. calcicola's depressed growth at acidic pH. Comparison of chlorophylls expression suggests that alkaline rather than neutral external pH is only beneficial for S. calcicola growth in absence of nutrient limitation. While the cyanobacterial biomarker ratio of chlorophylls to echinenone was stable across the pertinent pH range of 6-8, other pigment ratios in S. calcicola were affected by pH with an approximately two week lag between the change of pH and the corresponding change of pigment expression.
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Date Issued: 2010
PURL: http://purl.flvc.org/FAU/2795335
Subject Headings: Environmental toxicology, Cyanobacteria, Environmental aspects, Ecosystem management, Vegetation dynamics
Format: Document (PDF)

Title: Isolation, Characterization and Synthesis of New Diterpenes from Pseudopterogorgia elisabethae.
Creator: Wan, Zhongliang, Florida Atlantic University, Kerr, Russell G., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Pseudopterogorgia elisabethae is a known source of structurally interesting bioactive metabolites. A detailed search for new, related compounds was undertaken in this study which resulted in the isolation and characterization of more than ten new diterpenes with serrulatane and ileabethane skeletons. Some of the new compounds isolated are closely related terpenes with significant biological activity and others are likely to be key biosynthetic intermediates. As a component of the development...
Show morePseudopterogorgia elisabethae is a known source of structurally interesting bioactive metabolites. A detailed search for new, related compounds was undertaken in this study which resulted in the isolation and characterization of more than ten new diterpenes with serrulatane and ileabethane skeletons. Some of the new compounds isolated are closely related terpenes with significant biological activity and others are likely to be key biosynthetic intermediates. As a component of the development of a production method of anti-inflammatory compounds such as seco-pseudopterosin and elisabethadione, a synthesis of a seco-pseudoperosin aglycone from elisabethatriene was developed.
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Date Issued: 2006
PURL: http://purl.flvc.org/fau/fd/FA00000883
Subject Headings: Biosynthesis, Diterpenes--Synthesis, Marine invertebrates, Anti-inflammatory agents
Format: Document (PDF)

Title: Chemical Studies of Caribbean Marine Organisms.
Creator: Vansach, Tifanie, West, Lyndon M., Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The projects described in this dissertation concentrated on investigating Caribbean species for qualitative and quantitative chemical differences. Chapter one includes a brief update on the status of natural products as drugs, a discussion of the biodiversity of Caribbean marine organisms as well as a discussion about the chemistry of algae and sponges. In chapter two, an experiment to test for possible effects of warmer, more acidic water and how that will impact coral reef organisms was...
Show moreThe projects described in this dissertation concentrated on investigating Caribbean species for qualitative and quantitative chemical differences. Chapter one includes a brief update on the status of natural products as drugs, a discussion of the biodiversity of Caribbean marine organisms as well as a discussion about the chemistry of algae and sponges. In chapter two, an experiment to test for possible effects of warmer, more acidic water and how that will impact coral reef organisms was conducted. Six common Caribbean coral reef sponge species were grown in seawater for 24 days ranging from values experienced at summer-maxima (temperature = 28 ºC; pH = 8.1) to those predicted for the year 2100 (T = 31 ºC; pH = 7.8). For each species, attachment rates, growth, and survival were similar between temperature and pH levels. Only two metabolite concentrations varied significantly between treatments but were similar to baseline levels. In chapter three, a chemical survey of Florida Keys algae was performed using MeOH extraction and HP-20 SPE with varying Me2CO:H2O solutions. 1H NMR spectra were collected for each fraction and analyzed for interesting signals. A Laurencia sp. was extracted and found to contain the known compound isodactylyne (61) with the structure determined using spectroscopic analyses. In chapter four, a Laurencia obtusa specimen was investigated to determine the compound causing oxygenated signals between 4.50 – 4.80 ppm in the 1H NMR spectra observed in chapter three. A large scale extraction and fractionation was performed and the compound was determined to be 1-O-palmitoyl-2-O-myristoyl-3-O-(6-sulfo-α- D-quinovo-pyranosyl)-glycerol (63). In chapter five, the isolation and structural elucidation of a new compound, furocaespitanenone (64) and two known compounds (10R)- and (10S)-10-O-methylfurocaespitanelactol 65 and 66, from a Laurencia sp. collected off of the Florida Keys using MeOH extraction and HP-20 column chromatography is described. A potential biosynthesis of 64 from furocaepsitane (68) is proposed.
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Date Issued: 2019
PURL: http://purl.flvc.org/fau/fd/FA00013274
Subject Headings: Marine organisms, Caribbean, Algae--chemistry, Sponges--Caribbean Sea, Chemistry
Format: Document (PDF)

Title: THE FORMATION OF DIHALOACETONITRILES BY CHLORINATION OF NATURAL WATER.
Creator: TREHY, MICHAEL LEE., Florida Atlantic University, Bieber, Theodore I., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: Dihaloacetonitriles (DHANs) are shown to be produced by the chlorination of natural water, thus joining the ranks of the trihalomethanes (THMs) likewise produced by chlorination. Certain amino acids such as aspartic acid, tryptophan, and tyrosine are implicated as precursor substances for the DHANs and also to some extent for the THMs. The degradation of DHANs by hydrolysis and by thiosulfate was studied. Various methods of analysis are evaluated with respect to their ability to determine...
Show moreDihaloacetonitriles (DHANs) are shown to be produced by the chlorination of natural water, thus joining the ranks of the trihalomethanes (THMs) likewise produced by chlorination. Certain amino acids such as aspartic acid, tryptophan, and tyrosine are implicated as precursor substances for the DHANs and also to some extent for the THMs. The degradation of DHANs by hydrolysis and by thiosulfate was studied. Various methods of analysis are evaluated with respect to their ability to determine DHANs and THMs. The dilemma faced by water plants in dealing with the dual problem of DHANs and THMs is discussed. The role of hydrolysis in the formation of THMs has also been evaluated.
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Date Issued: 1980
PURL: http://purl.flvc.org/fcla/dt/14011
Subject Headings: Water--Purification--Chlorination
Format: Document (PDF)

Title: MONITORING COLLAGENOLYSIS UTILIZING TRIPLE HELICAL PEPTIDE PROBES.
Creator: Tokmina-Roszyk, Michal, Fields, Gregg B., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Collagen is the major structural scaffold in the body and serves as barrier between tissues, and thus its turnover is tightly regulated. Collagen triple-helical structure renders it resistant to general proteolysis. Several proteases are capable of cleaving the triplehelical regions of collagen, including several mammalian matrix metalloproteinases (MMPs) and bacterial collagenases. MMP-mediated collagenolysis is associated with numerous diseases and some bacterial collagenases have found...
Show moreCollagen is the major structural scaffold in the body and serves as barrier between tissues, and thus its turnover is tightly regulated. Collagen triple-helical structure renders it resistant to general proteolysis. Several proteases are capable of cleaving the triplehelical regions of collagen, including several mammalian matrix metalloproteinases (MMPs) and bacterial collagenases. MMP-mediated collagenolysis is associated with numerous diseases and some bacterial collagenases have found clinical application use due to their efficiency in the hydrolysis of the collagen triple-helix. A selective Förster resonance energy transfer triple-helical peptide (fTHP) probe for monitoring the activity of Clostridial collagenase has been developed. The fTHP [sequence: Gly-mep-Flp-(Glyvi Pro-Hyp)4-Gly-Lys(Mca)-Thr-Gly-Pro-Leu-Gly-Pro-Pro-Gly-Lys(Dnp)-Ser-(Gly-Pro-Hyp)4-NH2] was stable at 37 °C and was efficiently hydrolyzed by bacterial collagenase (kcat/KM = 25,000 s -1 M-1) but not by clostripain, trypsin, neutral protease, thermolysin, or elastase. The bacterial collagenase fTHP assay can be utilized in applications where specific activity towards triple-helical collagen needs to be evaluated, such as isolation of cells from various tissues. An fTHP scaffold was also utilized to evaluate the sequence preferences of eight MMPs. Residues spanning from P3 to P11 investigated using a positional scanning synthetic combinatorial library. Deconvolution of the library data revealed distinct motifs for several MMPs and discrimination among closely related MMPs. The results of this study show that the P10 11 substrate play an important role in the collagenase-substrate interactions and that modifying these residues can drastically affect the affinity of MMPs towards THP substrates. The identified sequence preferences of MMPs will enable the design of selective triple-helical MMP probes that could be used for monitoring in vivo enzyme activity and enzyme-facilitated drug delivery.
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Date Issued: 2019
PURL: http://purl.flvc.org/fau/fd/FA00013422
Subject Headings: Collagen, Peptides, Matrix Metalloproteinases, Microbial Collagenase, Molecular Probes
Format: Document (PDF)

Title: THE ROLE OF MATRIX METALLOPROTEINASE-28 IN HEALTH AND DISEASE.
Creator: Tokmina-Roszyk, Dorota, Fields, Gregg B., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Matrix Metalloproteinase-28 (MMP-28) is the newest and least characterized member of MMP family. To date several potential substrate candidates for MMP-28 have been proposed but no in vivo substrates for this enzyme were confirmed. In the central nervous system (CNS) MMP-28 is believed to be important factor during myelination of the developing nervous system as well as during remyelination that follows neuronal injury. On the other hand, MMP-28 has been found in actively demyelinating...
Show moreMatrix Metalloproteinase-28 (MMP-28) is the newest and least characterized member of MMP family. To date several potential substrate candidates for MMP-28 have been proposed but no in vivo substrates for this enzyme were confirmed. In the central nervous system (CNS) MMP-28 is believed to be important factor during myelination of the developing nervous system as well as during remyelination that follows neuronal injury. On the other hand, MMP-28 has been found in actively demyelinating lesions in both experimental autoimmune encephalopathy (EAE) and multiple sclerosis patients suggesting its possible role in pathological events associated with autoimmune neurodegenerative processes. In addition, MMP-28 has been linked to modulation of immune response and activation of macrophages which presents another role of this enzyme in autoimmune pathologies. In the study described herein, MMP-28 has been shown to affect myelin composition and appearance, mitochondrial protein content, and vesicular transport proteins. Moreover, the decrease in myelin basic protein quantity observed in healthy MMP-28KO animals affected the myelin staining intensity in various brain regions including corpus callous. Cellular energetic studies did not reveal differences in mitochondrial function in MMP-28KO animals and no difference in reactive oxygen species was observed. In the EAE model, MMP-28 deletion increased the occurrence of atypical form of EAE characterized by increased inflammation of arbor vitae of the brain. In addition, MMP-28 deletion decreased the inflammatory infiltrates present in brains obtained from EAE animals. Lastly, MMP-28 has been shown to affect cellular energetics and activation of bone marrow derived macrophages during the initial stages and after 24 h activation. In addition, MMP-28 deletion increased proinflammatory cytokines and receptors CD86 and iNOS found in M1 polarized macrophages.
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Date Issued: 2020
PURL: http://purl.flvc.org/fau/fd/FA00013601
Subject Headings: Matrix Metalloproteinases, Multiple sclerosis, Neurodegenerative disease
Format: Document (PDF)

Title: Synthesis and Bioactivity Investigation of Bridged Bicyclic Compounds and a Mechanistic Investigation of a Propargyl Hydrazine Cycloaddition Catalyzed by an Ammonium Salt.
Creator: St.Germain, Elijah, Lepore, Salvatore D., Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: We report the development of a general route to the synthesis of [4.3.1], [3.3.1], an especially [3.2.1] bicyclic compounds structurally related to vitisinol D, a natural product. This allows for diastereoselective synthesis of bicyclic compounds with five adjacent chiral centers. This route was employed in a preliminary SAR investigation into the neuroprotectant effect of small molecules in an in vivo experiment measuring the degree of restorative effect of synaptic transmission in the...
Show moreWe report the development of a general route to the synthesis of [4.3.1], [3.3.1], an especially [3.2.1] bicyclic compounds structurally related to vitisinol D, a natural product. This allows for diastereoselective synthesis of bicyclic compounds with five adjacent chiral centers. This route was employed in a preliminary SAR investigation into the neuroprotectant effect of small molecules in an in vivo experiment measuring the degree of restorative effect of synaptic transmission in the neuromuscular junction of Drosophila melanogaster larvae under acute oxidative stress. One of the compounds exhibited intriguing potential as a neuroprotectant and outperformed resveratrol in restoring synaptic function under oxidative stress. The hypothesis that bridged bicyclic compounds may hold promise as drug scaffolds due to their conformational rigidity and ability to orient functional appendages in unique orientations is developed. The second focus is a mechanistic investigation into a tetrabutylammoniumcatalyzed cycloaddition as evidence of a novel ammonium-alkyne interaction. A carbamate nitrogen adds to a non-conjugated carbon–carbon triple bond under the action of an ammonium catalyst leading to a cyclic product. Studies in homogeneous systems suggest that the ammonium agent facilitates cyclitive nitrogen–carbon bond formation through a cation–π interaction with the alkyne unit. Using Raman spectroscopy, this cation–π interaction is directly observed for the first time. DFT modeling elucidated the mechanistic factors in this cycloaddition. A teaching experiment was developed based on this mechanistic investigation. Control experiments were employed to demonstrate the testing of two alternative mechanistic hypotheses. Cyclization reactions were performed with a soluble base (sodium phenoxide) with and without tetrabutylammonium bromide under homogeneous conditions. Students observed that ammonium salt accelerates the reaction. They were encouraged to develop a testable hypothesis for the role of the ammonium salt in the cyclization mechanism: typical phase transfer or other. IR spectroscopy was used to directly observe a dose dependent shift of the alkyne stretching mode due to a cation−π interaction. Undergraduates were able to employ the scientific method on a contemporary system and see how data are generated and interpreted to adjudicate between rival hypotheses in a way that emulates authentic and current research in a lab setting.
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Date Issued: 2018
PURL: http://purl.flvc.org/fau/fd/FA00013100
Subject Headings: Bicyclic compounds., Ammonium salts., Cycloaddition Reaction.
Format: Document (PDF)

Title: Synthesis and Characterization of Organotin Polyamine Esters from Diglycine.
Creator: Slawek, Paul Peter, Carraher, Charles E., Haky, Jerome E., Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: This research is part of a long-term project aimed at elucidating important structural features, of both ligands and metals, that are needed to produce effective anti-cancer agents. The specific goal is the synthesis of organotin polymers containing amino acids, in this case the diamino acid diglycine. The desired materials were synthesized with percent yields ranging from 32-99%. The products were synthesized employing the interfacial polymerization technique. The polymers were then...
Show moreThis research is part of a long-term project aimed at elucidating important structural features, of both ligands and metals, that are needed to produce effective anti-cancer agents. The specific goal is the synthesis of organotin polymers containing amino acids, in this case the diamino acid diglycine. The desired materials were synthesized with percent yields ranging from 32-99%. The products were synthesized employing the interfacial polymerization technique. The polymers were then characterized utilizing the following physical characterization techniques: light scattering photometry (LS), Infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and matrix assisted laser desorption mass spectroscopy (MALDI). Physical characterization showed evidence of formation of desired adducts in addition to data that was consistent with the formation of materials containing multiple repeat units. The materials were then analyzed for biological activity. The synthesized materials displayed the ability to inhibit tested cancer cell lines.
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Date Issued: 2018
PURL: http://purl.flvc.org/fau/fd/FA00013158
Subject Headings: Organotin Compounds, Glycylglycine, Antineoplastic agents--Development
Format: Document (PDF)

Title: MULTIVALENT PROTEIN GLYCOSYLATION: A DRIVING FORCE OF CANCER PROGRESSION AND ALZHEIMER’S DISEASE PATHOGENESIS.
Creator: Singh, YashoNandini, Cudic, Maré, Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Glycosylation is a frequent and heterogeneous post-translational protein modification occurring in all domains of life. Aberrant cell-surface glycosylation is shown to mediate several processes involved in tumor cell proliferation, adhesion, and metastasis. Recent findings linked altered protein glycosylation to Alzheimer’s disease (AD) pathogenesis. One key obstacle in studying functional consequences of glycosylation has been the lack of structurally defined glycopeptide or protein model...
Show moreGlycosylation is a frequent and heterogeneous post-translational protein modification occurring in all domains of life. Aberrant cell-surface glycosylation is shown to mediate several processes involved in tumor cell proliferation, adhesion, and metastasis. Recent findings linked altered protein glycosylation to Alzheimer’s disease (AD) pathogenesis. One key obstacle in studying functional consequences of glycosylation has been the lack of structurally defined glycopeptide or protein model compounds for biochemical studies at the molecular level. For tumor progression, studies are crucial towards understanding the glycan-lectin recognition process tied to deciphering the information contained in glycan structures and for AD, foundational studies are necessary for understanding the role of O-glycosylation in protein processing and its fate toward the amyloid pathway. In chapter 1, a highly O-glycosylated transmembrane and cancer-associated mucin protein, MUC1, is used as a model for designing synthetic tools for exploring its role in metastasis via association with lectins and specificity of anti-MUC1 antibodies. This dissertation for the first time presents a MUC1-based positional scanning synthetic glycopeptide combinatorial library that varies in the number and location of tumor-associated Tn antigen. The importance of defined structural complexity for evaluating glycan density and glycosylation patterns for binding to Tn-specific plant lectins and anti-MUC1 (mouse) monoclonal antibodies was revealed using an enzyme-linked lectin assay (ELLA). Chapter 2 addressed the growing significance of peptide lectinomimics for recognizing tumor-specific glycans. Fluorescently labelled alanine scan analogues of odorranalectin (OL), a cyclic peptide that exhibits lectin like properties, were screened for binding BSA-conjugated monosaccharides using ELLA. Results revealed that Lys5, Phe7, Tyr9, Gly12, Leu14, and Thr17 were crucial for binding BSA-L-fucose, BSA-Dgalactose and BSA-N-acetyl-D-galactosamine. The thermodynamics of binding of the selected alanine analogues was evaluated by isothermal titration calorimetry. The thermodynamic profile of interactions with asialofetuin exhibits shift to an entropy-driven mechanism compared to fucoidan, which displayed an enthalpy-entropy compensation, typically associated with the carbohydrate-lectin recognition process. Chapter 3 focused on amyloid-precursor protein (APP) O-glycosylation and its role in AD pathogenesis. We synthesized native and Swedish-mutated (glyco)peptides with O-GalNAc moiety on Thr663 and/or Ser667 or Tyr681 to explore the role of glycosylation on conformation, secretase activity, and aggregation kinetics of Aβ40. Our results show that conformation is strongly dependent on external conditions such as buffer ions and solvent polarity as well as internal modifications of (glyco)peptides such as length, O-glycosylation, and Swedish mutation (Lys670Asn/Met671Leu). Furthermore, the level of β-secretase activity significantly increased for the glycopeptides containing the Swedish mutation compared to their nonglycosylated and native counterparts. Lastly, glycopeptides impacted the kinetics of Aβ40 aggregation by significantly increasing the lag phase and delaying aggregation onset, however, this effect was less pronounced for its Swedish-mutated counterparts.
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Date Issued: 2022
PURL: http://purl.flvc.org/fau/fd/FA00013949
Subject Headings: Glycosylation, Alzheimer Disease, Lectins
Format: Document (PDF)

Title: Isolation and Biomimetic Synthesis of Marine Natural Products from the Gorgonian Briareum Asbestinum.
Creator: Simpson, Johnathon, West, Lyndon M., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Throughout history, natural products have produced a plethora of biologically active compounds that have established applications in medicine, biology, and pharmacy. The exploration for improved cytotoxic agents has continued to be a crucial path in natural products drug discovery. The focal point of this thesis sheds light on the biosynthetic relationship between the two distinct classes of briarane diterpenoids, the γ-lactone briarane and the briareolate esters. Additionally, this study...
Show moreThroughout history, natural products have produced a plethora of biologically active compounds that have established applications in medicine, biology, and pharmacy. The exploration for improved cytotoxic agents has continued to be a crucial path in natural products drug discovery. The focal point of this thesis sheds light on the biosynthetic relationship between the two distinct classes of briarane diterpenoids, the γ-lactone briarane and the briareolate esters. Additionally, this study elaborates on the discovery and elucidation of structurally unique secondary metabolites from the gorgonian coral Briareum asbestinum. The first chapter of this thesis provides a review of the development and discovery of diverse secondary metabolites. In addition, this chapter describes the role of natural products in drug discovery and summarizes the research progress in marine natural product chemistry in conjunction with a detailed overview of the current marine-derived pharmaceuticals.
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Date Issued: 2021
PURL: http://purl.flvc.org/fau/fd/FA00013857
Subject Headings: Marine natural products, Diterpenoids, Biomimetics, Soft corals
Format: Document (PDF)

Title: The electronic structures of dimolybdenum compounds; detailed electronic absorption and electrochemical studies of dimolybdenum BAII complexes.
Creator: Shih, Keng-Yu., Florida Atlantic University, Baird, Donald M., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The complexes Mo2(OAc)3(BAII), where BAII is 1,3-bis(arylimino)isoindoline, have been synthesized. A detailed interpretation of their 1H-NMR spectra has been made. The structure of the bis(pyridylimino)isoindoline derivative has been determined by X-ray analysis to facilitate the assignment of the resonance lines in the spectra. It has been found that there are trends in energies and intensities of the delta-->delta* transition in these compounds. Electron withdrawing substituents on the...
Show moreThe complexes Mo2(OAc)3(BAII), where BAII is 1,3-bis(arylimino)isoindoline, have been synthesized. A detailed interpretation of their 1H-NMR spectra has been made. The structure of the bis(pyridylimino)isoindoline derivative has been determined by X-ray analysis to facilitate the assignment of the resonance lines in the spectra. It has been found that there are trends in energies and intensities of the delta-->delta* transition in these compounds. Electron withdrawing substituents on the aromatic nitrogen heterocycles in BAII shift the delta-->delta* transition to a lower energy and a higher intensity as compared to electron releasing substituents. These trends suggest that mixing of M-->L charge transfer transitions with the delta-->delta* transitions is occurring in these compounds which is consistent with the results of electrochemical trends in oxidation potentials. The complexes which are hardest to oxidize in general have the lowest delta-->delta* transition.
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Date Issued: 1989
PURL: http://purl.flvc.org/fcla/dt/14516
Subject Headings: Chemistry, Inorganic
Format: Document (PDF)

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