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Peptide Targeting of Platinum Anti-Cancer Drug and Synthesis of Water Soluble Monofunctional Pt(II) Complexes Useful for Biological Labeling Margaret W

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Peptide Targeting of Platinum Anti-Cancer Drug and Synthesis of Water Soluble Monofunctional Pt(II) Complexes Useful for Biological Labeling Margaret W Louisiana State University LSU Digital Commons LSU Doctoral Dissertations Graduate School 2009 Peptide Targeting of Platinum Anti-Cancer Drug and Synthesis of Water Soluble Monofunctional Pt(II) Complexes Useful for Biological Labeling Margaret W. Ndinguri Louisiana State University and Agricultural and Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_dissertations Part of the Chemistry Commons Recommended Citation Ndinguri, Margaret W., "Peptide Targeting of Platinum Anti-Cancer Drug and Synthesis of Water Soluble Monofunctional Pt(II) Complexes Useful for Biological Labeling" (2009). LSU Doctoral Dissertations. 541. https://digitalcommons.lsu.edu/gradschool_dissertations/541 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Doctoral Dissertations by an authorized graduate school editor of LSU Digital Commons. For more information, please [email protected]. PEPTIDE TARGETING OF PLATINUM ANTI-CANCER DRUG AND SYNTHESIS OF WATER SOLUBLE MONOFUNCTIONAL Pt (II) COMPLEXES USEFUL FOR BIOLOGICAL LABELING A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry. By Margaret W. Ndinguri B. S., Jomo Kenyatta University of Agriculture and Technology, 2001 August, 2009 DEDICATION To my parents Simon and Phyllis Ndinguri, my husband Anthony Ndirangu and children Chealsea and Chris Gachagua ii ACKNOWLEDGEMENTS I wish to express my gratitude to the following people who have been instrumental in the completion of this work. I thank the almighty God for his faithfulness, mercy and grace. I have drawn strength and inspiration from Psalms 23 My advisor, Dr. Robert Hammer for his mentorship advice, patience and support through out this project. He made my research experience challenging and rewarding. Committee members Dr. William Crowe, Dr. Brian Hales, Dr. Bin Chen, and external representative Dr. Inder Sehgal. Dr. Sita Aggarwal from Pennington Biomedical Research Institute, Martha Juban of protein facility and Dr. Azeem Hasaan of mass spectrometry for their help in their respective facilities. Dr. Isaah Warner, Dr. Alfonso Davila, Dr. Steve Watkins and Sheridan Wilkes for their special help and guidance whenever I was in need. You were God sent to me in times of need and I will always be grateful for your kind deeds. Dr. Hammer’s group for their support and friendship. Special thanks to Cyrus and Marcus. My mother Phyllis Ndinguri and father Simon Ndinguri for their unconditional love, confidence in me, prayers, encouragement, and unwavering support during my years of study. To you I will always be indebted. My mother in law Virginia Ndirangu and my mom for the great help in taking care of the little ones Chealsea and Chris while I was in school. Your love and support are priceless. To my sibling, Elizabeth Ndinguri, Monicah Ndinguri, Leah Ndinguri, and Erastus Ndinguri for their words of encouragement. iii Last but not least, an immeasurable amount of gratitude to my husband, Anthony Ndirangu for his love, sacrifice and constant support. My children Chealsea and Chris Gachagua, who are two bundles of joy, that give me a reason to live and to forget my worries. They are the best thing that happened to me in graduate school! To all my friends and relatives who have supported me all the way. Thank you! iv TABLE OF CONTENTS DEDICATION ................................................................................................................................ ii ACKNOWLEDGEMENTS ........................................................................................................... iii ABSTRACT ................................................................................................................................... ix CHAPTER 1. INTRODUCTION ................................................................................................... 1 1.1 Platinum Complexes ............................................................................................................. 1 1.2 Curcumin............................................................................................................................... 2 1.3 Polyamine Analogues ........................................................................................................... 3 1.4 Targeted Chemotherapeutic Agents ...................................................................................... 4 1.5 References ............................................................................................................................. 5 CHAPTER 2. PEPTIDE TARGETING OF PLATINUM ANTI-CANCER DRUGS ................... 8 2.1 Introduction ........................................................................................................................... 8 2.2 Experimental Section .......................................................................................................... 10 2.3 Results and Discussion ....................................................................................................... 18 2.4 Conclusion .......................................................................................................................... 31 2.6 References ........................................................................................................................... 32 CHAPTER 3. PEPTIDE TARGETING OF PLATINUM ANTICANCER DRUG AND CURCUMIN USING LHRH MOTIF .......................................................................................... 37 3.1 Introduction ......................................................................................................................... 37 3.2 Experiment Section ............................................................................................................. 39 3.3 Results and Discussion ....................................................................................................... 44 3.4 Conclusion .......................................................................................................................... 51 3.5 References ........................................................................................................................... 51 CHAPTER 4. EXPLORING WATER SOLUBLE N-TRIDENTATE Pt(II) COMPLEXES USEFUL FOR SPECTROSCOPIC AND BIOLOGICAL LABELING ...................................... 53 4.1 Introduction ......................................................................................................................... 53 4.2 Experimental Section .......................................................................................................... 55 4.3 Results and Discussion ....................................................................................................... 61 4.4 Conclusion .......................................................................................................................... 76 4.6 References ........................................................................................................................... 77 CHAPTER 5. CONCLUSIONS ................................................................................................... 81 APPENDIX. ONGOING WORK AND FUTURE STUDIES ..................................................... 83 A.1 Synthesis of Targeted Phthalocyanines .............................................................................. 83 A.2 Results ................................................................................................................................ 83 A.3 References .......................................................................................................................... 85 VITA ............................................................................................................................................. 98 v LIST OF ABBREVIATIONS Atfcdien N′-[7-(acetamido)-4-(trifluoromethyl)coumarin] diethylenetriamine acdien 2-(bis(2-aminoethyl)amino)acetic acid atfc 7-amino-4-(trifluoromethyl)coumarin Arg arginine Asn asparagine Acm acetamidomethyl AgNO3 silver nitrate Bocdien N,N′′-bis(tert-butyloxycarbonyl)diethylenetriamine Bocdienatfc N,N′′-bis(tert-butyloxycarbonyl)diethylenetriaminly-N′-[7- (acetamido)-4-(trifluoromethyl)coumarin] Bocdienac N,N′′-bis(tert-butyloxycarbonyl)diethylenetriaminly-N′-glycine Cys cysteine Dien diethyltriamine DBU 1,8-diazobicyclo[4.50] undec-7-ene DIPEA diisopropylethylamine DMF dimethylformamide vi Et2O diethyl ether EtOH ethanol Fmoc 9-fluorenylmethoxycarbonyl Gly glycine HPLC high performance liquid chromatography NaH sodium hydride NMR nuclear magnetic resonance Pbf 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl mPEG oligoethylene glycol group PYAOP 7-azabenzotriazolyoxytris(pyrrolidino) phosphonium hexafluorophosphate. TFA trifluoroacetic acid THF tetrahydrofuran Trt trityl m multiplet MALDI matrix assisted laser desorption ionization min minute µM micromolar vii mM millimolar mmol millimole MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide NaOH sodium hydroxide NMR nuclear magnetic resonance MeCN acetonitile PDT photodynamic therapy Pip piperidine PyAOP 7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate TIPS triisopropylsilane TMS tetramethylsilane viii ABSTRACT Platinum has been used as an inorganic medicinal
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