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New Developments in Cyclized Arsenic and Antimony Thiolates

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New Developments in Cyclized Arsenic and Antimony Thiolates University of Kentucky UKnowledge University of Kentucky Doctoral Dissertations Graduate School 2007 NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES Taimur A. Shaikh University of Kentucky, [email protected] Right click to open a feedback form in a new tab to let us know how this document benefits ou.y Recommended Citation Shaikh, Taimur A., "NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES" (2007). University of Kentucky Doctoral Dissertations. 494. https://uknowledge.uky.edu/gradschool_diss/494 This Dissertation is brought to you for free and open access by the Graduate School at UKnowledge. It has been accepted for inclusion in University of Kentucky Doctoral Dissertations by an authorized administrator of UKnowledge. For more information, please contact [email protected]. ABSTRACT OF DISSERTATION Taimur A. Shaikh The Graduate School University of Kentucky 2007 NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES ___________________________________ ABSTRACT OF DISSERTATION ___________________________________ A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the College of Arts and Sciences at the University of Kentucky By Taimur A. Shaikh Lexington, Kentucky Director: Dr. David A. Atwood, Associate Professor of Chemistry Lexington, Kentucky Copyright © Taimur Shaikh 2007 ABSTRACT OF DISSERTATION NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES There is a continued interest in the properties of arsenic thiolate compounds for both industrial and biological uses. Recent discoveries in the medicinal properties of such compounds have resulted in a sustained need for the synthesis of new dithiarsolane compounds for research as anti-leukemic compounds. Close analogues of the 2-halo arsenic dithiolates, namely those with an arsenic-carbon bond instead of an arsenic-halide bond, have recently been shown to have some efficacy towards leukemia cells. Based on the hydrolytic character and the active role of glutathione with arsenic in vivo, the compounds reported here may also have such activity. Arsenic compounds have demonstrated biological activity in the literature, thus the hypothesis of this thesis is cyclized arsenic thiolates can be synthesized with the appropriate characteristics as to be potentially useful medicinal agents as well as provide new structural and reaction information. A series of arsenic and antimony di- and trithiolates has been synthesized and characterized. Those compounds include 2-chloro-1,3,2-dithiarsolane, 2-bromo- 1,3,2-dithiarsolane, 2-iodo-1,3,2-dithiarsolane, 2-chloro-1,3,2-dithiarsenane, 2-bromo- 1,3,2-dithiarsenane, 2-iodo-1,3,2-dithiarsenane, 3-chloro-4H,7H-5,6-benz-1,3,2- dithiarsepine, 2-chloro-benzo-1,3,2-dithiarsole, 1,2-bis-dithiarsolan-2-ylmercapto-ethane, tris-(pentafluorophenylthio)-arsen, bis(2-(1,3,2-benzodithiarsol-2ylsulfanyl)- benzenesulfide), 2-chloro-benzo-1,3,2-dithiastibole, and bis(2-(1,3,2-benzodithistibol)- 1,2-benzenedithiol. Elucidation of the pH characteristics of arsenic dithiolates within the human toxicity reaction pathway is an area of interest. It has been shown that the aqueous arsenic dithiolate stability depends on the size of the ring. 2-Chloro-1,3,2-dithiarsolane has been shown to be somewhat stable at both low and high pH as well as neutral pH. 1,2-bis- Dithiarsolan-2-ylmercapto-ethane is completely stable in a neutral aqueous solution. Glutathione does not permanently bind to arsenic even in overwhelming excess. In particular, these fully characterized compounds determine how reactive the As–S and As–Cl linkages are under environmental and biological conditions, and provide a source of new reagents to examine in medical applications. Future applications may include the incorporation of the reported compounds in filtration and remediation technologies with further modification. KEYWORDS: Arsenic, Antimony, Dithiol, Leukemia, X-ray structure Taimur A, Shaikh January 18, 2007 NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES By Taimur A. Shaikh David A. Atwood, Ph.D. Director of Dissertation Robert B. Grossman, Ph.D. Director of Graduate Studies January 18, 2007 Date RULES FOR THE USE OF DISSERTATIONS Unpublished dissertations submitted for the Doctor's degree and deposited in the University of Kentucky Library are as a rule open for inspection, but are to be used only with due regard to the rights of the authors. Bibliographical references may be noted, but quotations or summaries of parts may be published only with the permission of the author, and with the usual scholarly acknowledgments. Extensive copying or publication of the dissertation in whole or in part also requires the consent of the Dean of the Graduate School of the University of Kentucky. DISSERTATION Taimur A. Shaikh The Graduate School University of Kentucky 2007 NEW DEVELOPMENTS IN CYCLIZED ARSENIC AND ANTIMONY THIOLATES ___________________________________ DISSERTATION ___________________________________ A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the College of Arts and Sciences at the University of Kentucky By Taimur A. Shaikh Lexington, Kentucky Director: Dr. David A. Atwood, Professor of Chemistry Lexington, Kentucky Copyright © Taimur Shaikh 2007 Acknowledgements I would like to acknowledge and give thanks to the people that have given me guidance and support which made this dissertation possible. I would like to thank my advisor, Dr. David Atwood, for giving me an opportunity to do research in his lab. I want to thank the members of my committee for their input and motivation during my graduate school career: Drs. Jack Selegue, Bert Lynn, and Gail Brion. I especially want to thank Dr. Sean Parkin for his knowledge and help with the X-ray diffraction and John Layton for all his help with the NMR equipment. I want to thank the entire Atwood research group for their support in the lab. Thank you to all of the office staff for their assistance. An undergraduate, Ron Bakus II, was very helpful in this research. Namely, he synthesized the iodo-arsenic dithiolates and reproduced several of the compounds in this dissertation. I want to thank my wife, Marcy, for all her support and understanding while pursuing my degree. Without her love and support, this dissertation would not be possible. I want to thank my family for enabling me to write this dissertation. Finally, I want to thank God and Jesus Christ, my Lord and Savior for His love, provision and guidance in my life. iii TABLE OF CONTENTS Acknowledgments………………………………………………………………………..iii List of Tables…………………………………………………………...……………….viii List of Figures and Schemes..………………………………………………...……….......x Chapter One: Introduction 1.1 Overview……………………………………………………………………....1 1.1.1 Cancer Treatment with As2O3 and Other Arsenic-containing Compounds………………………………………………………………………….2 1.2 Fundamental Properties of Arsenic………………………………………..…..5 1.3 Chemical and Physical Properties of Arsenic………………………………....5 1.4 Geochemistry………………………………………………………………… 6 1.5 Sources of Arsenic in the Environment..……………………………………...6 1.5.1 Natural………………………………………………………………….6 1.5.2 Anthropogenic………………………………………………………….7 1.6 Current EPA Policy and Methods for Drinking Water Treatment………...….8 1.7 Historical Notes on Arsenic…………………………………………………...8 1.7.1 Cadet and Bunsen…………………………………………………...8 1.7.2 BAL, British Anti-Lewisite………………………………………....9 1.8 Industrial Uses……………………………………………………………….11 iv 1.8.1 Laser Windows and Hall Devices…………………………………….11 1.8.2 Pesticides……………………………………………………………...11 1.8.3 CCA Wood Treatment………………………………………………...12 1.9 Biological Chemistry of Arsenic…………………………………………….12 1.9.1 Oxidation-Reduction…………………………………………………..12 1.9.2 Methylation……………………………………………………………15 1.9.3 Dealkylation...…………………………………………………………16 1.9.4 Arsenic Resistance……………………………………………….........16 1.10 Human Arsenic Toxicology………………………………………………...17 1.11 ADP-Arsenate……………………………………………………………....21 1.12 Conclusion………………………………………………………………….23 Chapter Two: Halo-Arsenic Dithiolates and Trithiolates 2.1 Overview………………………………………………….………………….25 2.2 Background……….………………………………………………………….26 2.3 Experimental Section...…………………………………………………...….32 2.3.1 General………………………………………………………………...32 2.4 Results……………………………………………………………...………...39 2.4.1 Spectroscopy……………………………………………………….….39 2.4.2 Structure……………………………………………………………….42 2.5 Aqueous Stability…………………………………………………………….61 2.5.1 Method Employed…………………………………………………….64 2.5.2 Results…………………………………………………………………64 v 2.6 Conclusion…………………………………………………………………68 Chapter Three: Antimony Dithiolates and Trithiolates 3.1 Overview……………………………………………………………………..72 3.1.1 Fundamental Properties of Antimony.………………………………...72 3.1.2 Chemical and Physical Properties of Antimony……………………....73 3.1.3 Geochemistry of Antimony…………………………………………...73 3.1.4 Biological Activity of Antimony……………………………………...73 3.1.4.1 Biomethylation of Antimony………………………………....74 3.2 Antimony Trithiolates………………………………………………………..74 3.3 Experimental Section...……………………………………………………....75 3.3.1 General………………………………………………………………...75 3.4 Results……..…………………………………………………………………77 3.4.1 Synthesis and Spectroscopy…………………………………………...77 3.4.2 Structure………………………………………………………….........80 3.5 Conclusion…………………………………………………………………...83 Chapter Four: Conclusions and Future Research 4.1 Conclusions…………………………………………………………………..84 4.2 Future Research……………………………………………………………...87 4.2.1 Arsenic Thiolate Interactions in Blood Serum………………………..87 4.2.2 Environmental Applications…………………………………………..88
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