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Effects of Cisplatin Analog Size on the Reaction with DNA Bases Swathi Nandala Western Kentucky University, [email protected]

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Effects of Cisplatin Analog Size on the Reaction with DNA Bases Swathi Nandala Western Kentucky University, Swathi.5055@Gmail.Com Western Kentucky University TopSCHOLAR® Masters Theses & Specialist Projects Graduate School 5-2013 Effects of Cisplatin Analog Size on the Reaction with DNA Bases Swathi Nandala Western Kentucky University, [email protected] Follow this and additional works at: http://digitalcommons.wku.edu/theses Part of the Medicinal-Pharmaceutical Chemistry Commons, and the Organic Chemistry Commons Recommended Citation Nandala, Swathi, "Effects of Cisplatin Analog Size on the Reaction with DNA Bases" (2013). Masters Theses & Specialist Projects. Paper 1256. http://digitalcommons.wku.edu/theses/1256 This Thesis is brought to you for free and open access by TopSCHOLAR®. It has been accepted for inclusion in Masters Theses & Specialist Projects by an authorized administrator of TopSCHOLAR®. For more information, please contact [email protected]. EFFECTS OF CISPLATIN ANALOG SIZE ON THE REACTION WITH DNA BASES A Thesis Presented to The Faculty of the Department of Chemistry Western Kentucky University Bowling Green, Kentucky In Partial Fulfillment Of the Requirements for the Degree Master of Science By Swathi Nandala May 2013 I would like to dedicate this thesis to my Research Advisor, Dr. Kevin Williams, who stood by me in each and every aspect of my research and lead me to complete it successfully. I also dedicate this work to my parents, who encouraged me to study at Western Kentucky University and to my friends who built immense confidence in me and helped me in many ways to complete my thesis. ACKNOWLEDGMENTS First of all, I would like to express my sincere gratitude to my Research Advisor Dr. Kevin M. Williams, for his patience, motivation, enthusiasm, and immense knowledge. Without his guidance and persistent help this thesis would not have been possible. I would like to thank my thesis committee members, Dr. Hemali Rathnayake and Dr. Bangbo Yan, who have given their invaluable time towards my defense. I would like to express my deepest gratitude to Dr. Cathleen Webb, Head of the department for providing financial means and laboratory facilities. I take this opportunity to express my sincere thanks to all faculty members of Department of Chemistry for guiding me throughout the period of study at the facility. My deepest thanks to my parents, N. Sudharshan and Madhavi, for their endless love, encouragement and for their support both mentally and financially. Special thanks to all my friends who have willingly helped me a lot with their abilities and also for building enthusiasm and confidence in me. Last but not least, my heartful thanks to God for blessing me with good health and support throughout my life. iv TABLE OF CONTENTS 1. INTRODUCTION ...................................................................................................... 1 1.1 Causes of Cancer......................................................................................................... 1 1.2 Discovery of cisplatin as an anticancer agent ............................................................. 3 1.3 Chemistry of Cisplatin ................................................................................................ 5 1.4 Synthesis of cisplatin .................................................................................................. 8 1.5 Mechanism of Action .................................................................................................. 9 1.6 Role of Ctr1 in cellular accumulation of Cisplatin ................................................... 12 1.7 Cisplatin Resistance .................................................................................................. 14 1.8 Binding of Cisplatin to DNA Bases .......................................................................... 16 1.9 Cisplatin binds more preferably to guanine than adenine. Why? ............................. 16 1.10 Previous Research ..................................................................................................... 18 1.11 Our Approach............................................................................................................ 18 2. EXPERIMENTAL SECTION .................................................................................. 20 2.1 Reagents used............................................................................................................ 20 2.2 Synthesis of platinum diethylenetriamine dinitrate or [Pt(dien)(NO 3)]NO 3 ............. 20 v 2.3 Synthesis of platinum pentamethyldiethylene triaminedinitrate or [Pt(Me 5dien)(NO 3)]NO 3 ................................................................................................... 21 2.4 Preparation of Stock Solutions.................................................................................. 22 2.5 Methods..................................................................................................................... 23 3. RESULTS ................................................................................................................. 25 3.1 Reaction of [Pt(Me 5dien)(NO 3)]NO 3 and 5’-AMP ................................................... 25 3.2 Reaction of [Pt(Me 5dien)(NO 3)]NO 3 and 5’-AMP at different temperatures ........... 29 3.3 Reaction of [Pt(Me5dien)(NO 3)]NO 3 and 5’-GMP .................................................. 30 3.4 Reaction of [Pt(dien)(NO) 3]NO 3 and 5’-AMP ......................................................... 33 3.5 Reaction of [Pt(dien)(NO 3)]NO 3 and 5’-GMP ......................................................... 36 4. DISCUSSION ........................................................................................................... 40 REFERENCES ................................................................................................................. 45 vi LIST OF FIGURES Figure 1: Structure of Cisplatin or cis -DDP. (Wiltshaw & Kroner, 1976) ......................... 4 Figure 2: Schematic diagram showing various binding sites available for cisplatin (Lippert, 1999). ................................................................................................................... 6 Figure 3: Structures of Carboplatin & Oxaliplatin (Wiltshaw & Kroner, 1976). ............... 8 Figure 4: Synthetic scheme for the Dhara synthesis of cisplatin (Dhara, 1970). ................ 9 Figure 5: Cytotoxic pathway of cisplatin (Lippert, 1999). ............................................... 11 Figure 6: Adducts formed after binding of cisplatin to DNA (Cepeda et al, 2007). ........ 12 Figure 7: Schematic illustration of the trimeric pore of CTR1 (Howell, Safaei, Larson, & Sailor, 2010). ..................................................................................................................... 14 Figure 8: Structures of [Pt(Me 5dien)(NO 3)]NO 3 and [Pt(dien)(NO 3)]NO 3 ...................... 19 Figure 9: Structures of 5’- Adenosine monophosphate & 5’-Guanosine monophosphate. ........................................................................................................................................... 19 Figure 10: (C) is the product formed by the coordination of [Pt(Me 5dien)(NO 3)]NO 3 complex (A) at N 7 position of (B)..................................................................................... 25 Figure 11: (C) is the product formed by the coordination of [Pt(Me 5dien)(NO 3)]NO 3 complex (A) at N 1 position of (B)..................................................................................... 26 Figure 12: Partial NMR spectra of the reaction of Pt(Me 5dien) and 5’-AMP on day 1 & 12....................................................................................................................................... 27 Figure 13: Partial NMR spectra showing the reaction of Pt(Me 5dien) and AMP at temperatures of 25, 40, 60, and 80 ºC. .............................................................................. 30 Figure 14: (C) is the product formed by the coordination of [Pt(Me 5dien)(NO 3)NO 3] ’ complex (A) at N 7 position of 5 -GMP (B). ...................................................................... 31 vii Figure 15: Partial NMR spectrum of reaction of [Pt(Me 5dien)(NO 3)]NO 3 and GMP at 10, 70 & 120 min interval. ...................................................................................................... 32 Figure 16: (C) is the product formed by the coordination of [Pt(dien)(NO 3)]NO 3 (A) at N 7 position of AMP (B). ........................................................................................................ 34 Figure 17: Partial NMR spectrum of reaction of [Pt(dien)(NO 3)]NO 3 and AMP at 10, 20 & 80 min interval. ............................................................................................................. 35 Figure 18: (C) is the product formed by the coordination of [Pt(dien)(NO 3)]NO 3 (A) at N 7 position of GMP (B). ....................................................................................................... 37 ’ Figure 19: Partial NMR spectrum of reaction of [Pt(dien)(NO 3)]NO 3 and 5 -GMP at 10, 35 & 60 min interval. ........................................................................................................ 38 viii LIST OF TABLES Table 1: Rate constants of cisplatin analogs with nucleotide bases. ................................. 39 ix EFFECTS OF CISPLATIN ANALOG SIZE ON THE REACTION WITH DNA BASES Swathi Nandala May 2013 49 Pages Directed by: Kevin Williams, Hemali Rathnayake, and Bangbo Yan Department of Chemistry Western Kentucky University Cancer is the second leading
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