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Reversed Phase HPLC Isolation and Characterization of Novel Conopeptides from Conus nux By Rani Elizabeth Ramlakhan A Thesis Submitted to the Faculty of The Charles E. Schmidt College of Science In Partial Fulfillment of the Requirements for the Degree of Master of Science Florida Atlantic University Boca Raton, FL December 2002 Isolation and Characterization of Novel Conopeptides from Conus nux By Rani Elizabeth Ramlakhan This thesis was prepared under the direction of the candidate's thesis advisor, Dr. Frank Mari, Department of Chemistry and Biochemistry and has been approved by the members of her supervisory committee. It was submitted to the faculty of the Charles E. Schmidt College of Science and was accepted in partial fulfillment of the requirements for the degree of Master of Science. SUPERVISORY COMM TTEE: / ~~(} partment of Chemistry and Biochemistry hmidt College of Science ~w~ Vice Provost Date 11 AKNOWLEDGEMENTS Special thanks to Dr. Frank Mari for the opportunity ofjoining and becoming a member of his research team. I would also like to thank Florida Sea Grant College Fund for providing funding for this research. I would like to thank Dr. Gregg Fields and Dr. Craig Byrdwell for all their help and support over the past few years. It was my pleasure working with Fred Pfleuger, Herminsul Cano, Aldo Franco, David Mora, Husam Abbasi, Carolina Moller and all the rest of the members of this research team. I thank and wish each of them success in finding new scientific breakthroughs in this field of research. Finally, I would like to thank my parents, Harry and Surnintra Ramlakhan, and my brothers, Enrick, Michael, and David, for all their support in all my educational endeavors over the past few years. ill ABSTRACT Author: Rani Elizabeth Ramlakhan Title: Isolation and Characterization ofNovel Conopeptides from Conus nux Institution: Florida Atlantic University Thesis Advisor: Dr. Frank Mari Degree: Master of Science Year: 2002 Cone snails are marme gastropods belonging to the genus Conus that inhabit in tropical habitats throughout the world. They are predators that paralyze their prey by injection of venom, containing a complex mixture of conopeptides. The venom of cone snails has been found to be a valuable source of specific drugs for disorders ranging from stroke to chronic pain. For this work, the venom of Conus nux, a Panarnic cone snail species, was extracted and analyzed. Components of the venom were isolated using Size Exclusion Chromatography (SEC) and Reversed Phase High Performance Liquid Chromatography techniques. A novel conopeptide sequence, determined by Edman Degradation is reported. The arrangement of the cysteines residues within this sequence suggest that it member of the M-superfarnily of conotoxins. lV TABLE OF CONTENTS LIST OF TABLES ........................................................................................................ vii LIST OF FIGURES ........................................................................................................ ix 1. INTRODUCTION ..................................................................................................... 1 1.1 General Background .................................................................................................. 1 1.2 Cone Snail Venom Apparatus .................................................................................... 2 1.3 Venom Composition .................................................................................................. 3 1.4 Conotoxins ................................................................................................................ 4 1.5 Conus Peptides as Drugs ............................................................................................ 7 1.6 Objectives ............................................................................................................... 10 2. MATERIALS AND METHODS ............................................................................. 11 2.1 Cone Snail Description and Collection ..................................................................... 1 I 2.2 Crude Venom Extraction ......................................................................................... 13 2.3 Peptide Isolation ...................................................................................................... 16 2.4 Reversed Phase HPLC ............................................................................................. 18 2.5 Size Exclusion Chromatography .............................................................................. 20 2.6 Analytical Reversed Phase HPLC ............................................................................ 22 2. 7 Reduction/ Alkylation ............................................................................................... 23 3. RESULTS AND DISCUSSION .............................................................................. 24 v 3.1 Chromatographic Analysis ofVenom ...................................................................... 24 3.2 Peptide Sequencing ................................................................................................. 51 3.3 M-superfamily ......................................................................................................... 53 4. CONCLUSIONS ..................................................................................................... 62 5. REFERENCES ........................................................................................................ 64 Vl LIST OF TABLES Table 1.4a Classification of Co no toxins (II) ............................................................... 6 Table I.4b Structural Classification of Conotoxins (23) ................................................ 7 Table I.5 Potential Therapeutics of Conopeptides ....................................................... 9 Table 2.2 List of Crude Venom Batches of Conus nux .............................................. I6 Table 2.4 Fluorescent Indicator Dyes ........................................................................ 20 Table 3.Ia Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions I-I8 ............................................................................................ 26 Table 3.Ib Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions I9-33 .......................................................................................... 29 Table 3.Ic Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions 34-47 .......................................................................................... 30 Table 3.Id Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions 48-63 .......................................................................................... 3I Table 3.Ie Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions 64-81 .......................................................................................... 32 Table 3.I f Retention times, MW, and Bioassays results for Conus nux (NUX_A) fractions 82-103 ........................................................................................ 33 Table 3.1g Molecular Weight (Da) vs. Retention Time (min) for Conus nux (NUX_A) ................................................................................................. 34 Table 3.Ih Molecular Weight (Da) vs. Retention Time (min) for Conus nux (NUX_A) and Conus jaspideus, an Atlantic cone snail species .................................. 34 Vll Table 3.li Retention times of the fractions collected from NUX Ea .......................... 37 Table 3.1j Retention times of the fractions collected from NUX Eb .......................... 37 Table 3.1k Retention times and Intensity of fractions collected from NUX_E01 ........ .40 Table 3.11 Retention times and Intensity of fractions collected from NUX_E02 ........ .40 Table 3.1m Retention times and Intensity offractions collected from NUX_E03 ........ .41 Table 3.1n Retention times and Intensity offractions collected from NUX_E04 ........ .42 Table 3.1o Retention times, Intensity, and MW offractions collected from NUX E05 ................................................................................................. 43 Table 3.lp Retention times, Intensity, and MW offractions collected from NUX E06 ................................................................................................. 44 Table 3.1q Retention times, Intensity, and MW offractions collected from NUX E07 ................................................................................................. 45 Table 3.1 r Retention times, Intensity, and MW of fractions collected from NUX E08 ................................................................................................. 46 Table 3.1 s Retention times and Intensity of fractions collected from NUX_E09 ........ .47 Table 3.1t Retention times and Intensity of fractions collected from NUX_El 0 ........ .48 Table 3.1u Retention times and Intensity of fractions collected from NUX_E11 ........ .49 Table 3.1 v Retention times, Intensity and MW of fractions collected from NUX E12 ................................................................................................. 50 Table 3.2 Peptide Sequence of fraction NUX_E0905 (nux-1) ................................... 52 Table 3.3a Comparison of the sequence ofnux-1 and published J..~.-conotoxins ............ 54 Table 3.3b Table of J.!-conotoxins (Patent W0021 07678) ..........................................
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