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I Study of Β-Lactamase Inhibitory Potential of Synthesized Ketophosph(On)Ates and Phytochemicals from Apocynaceae and Compositae Families

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I Study of Β-Lactamase Inhibitory Potential of Synthesized Ketophosph(On)Ates and Phytochemicals from Apocynaceae and Compositae Families Study of β-Lactamase Inhibitory Potential of Synthesized Ketophosph(on)ates and Phytochemicals from Apocynaceae and Compositae Families. MUHAMMAD AKMAL KHAN SESSION (2008-2012) 19-Ph.D.-GCU-Chem-04 DEPARTMENT OF CHEMISTRY GOVERNMENT COLLEGE UNIVERSITY LAHORE. i Study of β-Lactamase Inhibitory Potential of Synthesized Ketophosph(on)ates and Phytochemicals from Apocynaceae and Compositae Families. Submitted to GC University, Lahore in partial fulfillment of the requirements for the award of degree of DOCTOR OF PHILOSOPHY IN CHEMISTRY By MUHAMMAD AKMAL KHAN SESSION (2008-2012) 19-Ph.D.-GCU-Chem-04 DEPARTMENT OF CHEMISTRY GOVERNMENT COLLEGE UNIVERSITY LAHORE. ii DECLARATION I, Muhammad Akmal Khan Roll No. 19-Ph.D.-GCU-Chem-04, student of Ph.D. in the subject of Chemistry, Session 2008-2012, hereby declare that the matter printed in the thesis titled “Study of beta-Lactamase Inhibitory Potential of Synthesized Ketophosph(on)ates and Phytochemicals from Apocynaceae and Compositae Families.” is my own research work and has not been printed, published and submitted as research work, thesis, publication or in any form in any University, Research Institution etc. in Pakistan or abroad. Dated:----------------------. ------------------------------------ Muhammad Akmal Khan iii RESEARCH COMPLETION CERTIFICATE Certified that the research work contained in this thesis; entitled “Study of β- Lactamase Inhibitory Potential of Synthesized Ketophosph(on)ates and Phytochemicals from Apocynaceae and Compositae Families” has been carried out and completed by Mr. Muhammad Akmal Khan; Roll No. 19-Ph.D.-GCU-Chem-04, under my supervision, during his Ph.D. (Chemistry) studies in the laboratories of the Department of Chemistry. Dated: --------------------- ---------------------------------- Supervisor Dr. Durre Shahwar Associate Professor, Department of Chemistry, Government College University, Lahore. Submitted through ------------------------------------- Prof. Dr. Islam Ullah Khan Chairman, Department of Chemistry, Government College University, Lahore. ---------------------------------- Controller of Examination, Government College University, Lahore. iv CERTIFICATE OF EXAMINERS Certified that the quantum and quality of the research work contained in this thesis entitled “Study of β-Lactamase Inhibitory Potential of Synthesized Ketophosph(on)ates and Phytochemicals from Apocynaceae and Compositae Families.” is adequate for the award of the degree of Doctor of Philosophy. -------------------------- Supervisor Dr. Durre Shahwar Associate Professor, Department of Chemistry, Government College University, Lahore. ----------------------------- External Examiner Prof. Dr. C. M. Ashraf, Pakistan Representative, The Royal Society of Chemistry, UK ------------------------------------- Prof. Dr. Islam Ullah Khan Chairman, Department of Chemistry, Government College University, Lahore. v Dedicated to All the Well-Wishers Of My Beloved Motherland “Islamic Republic of Pakistan” vi ACKNOWLEDGEMENTS All praises to Almighty Allah, Who induced the man with aptitude, knowledge, sight to observe and mind to think. Peace and blessings of Allah almighty be upon the Holy Prophet, Hazrat Muhammad (Peace be upon Him) who exhorted his followers to seek for knowledge from cradle to grave. My joy knows no bound to express my cordial gratitude to my learned research adviser Dr. Durre Shahwar, Associate Professor, Department of Chemistry, GC University, Lahore. Her keen interest, scholarly guidance and encouragement were a great help throughout the course of this research work. I feel great pleasure in expressing my sincere gratitude and thanks to the most respected, honorable, Prof. Dr. Islam Ullah Khan, Chairperson, & Prof. Dr. M. Akram Kashmiri, Ex-Chairperson, Department of Chemistry, GC University Lahore, for providing all facilities to undertake this research work. I am also thankful to Dr. Athar Abbasi & Dr. Ahmad Adnan for their kind support and help. My cordial prays are for my beloved Father and Mother (late) who always remember me in their prayers. Their everlasting love, guidance and encouraging passion will remain with me Insha Allah till my last breath. All my family members; wife, brother and sisters are always a source of inspiration to me. I am thankful to them for their full support, encouragement and sincere prayers for my success. My heart-felt thanks are due to all my teachers, friends and those who contributed in this research work in any way, especially Brother Naeem Ahmad, Sami Ullah, Saif Ullah, Muhammad Asam, Safiq- Ur-Rehman, M. Nadeem Arshad Qadri, and Hafiz Muhammad Shafiq. I am also thankful for the support of my junior fellows especially Miss Afifa Saeed, Asma Yasmeen, Uzma Sana , Misbah Naz, Tania Khan and Mr. Muhammad Mansha. I express my feelings of gratitude to all the members of non-teaching staff of the Department, especially Mr. Shahzad Khan, Mr. Ejaz, Mr. Rahmat, Mr. Manzoor Mr. Farasat and Mr. Khalil for their constant help. Thanks and gratitude are due to Mr. Abdul Waheed (Chief Librarian), Mr. Qaiser, Miss Samreen and Mr. Ghulam Murtaza among the Main-Library staff. My worthy thanks are due to Mr. Shafiq Mughal (Treasurer), Mr. Waseem Shahzad (Deputy Treasurer), Mr. Qaisar Khan and Mr. Mubashar. I am also thankful to HEC (Higher Education Commission) for financial support under Indigenous PhD Fellowship Program. Throughout the course of my Ph.D I have had help from numerous people. The space here does not allow to thank everybody by name, I’m sorry. It is not my forgetfulness: I do remember smiling face of each & every one. vii ABSTRACT Present work consists of study of β-Lactamase (BLase) inhibitory potential of phytochemicals from Apocynaceae & Compositae families and Ketophosph(on)ates. For this study; an easy, efficient & economical method was developed, used successfully and published. In this study, thirty two compounds were prepared and characterized by EIMS & 1H-NMR. These compounds comprise of: Diethyl (2-oxo-2-phenylethyl) phosphonate(1), Diethyl [(E)-1-benzoyl-2-phenylvinyl] phosphonate(2), Diethyl[(E)- 1-benzoyl-2-(2-hydroxyphenyl) vinyl] phosphonate(3), Diethyl [(1E,3E)-1-benzoyl-4- phenylbuta-1,3-dien-1-yl] phosphonate(4), Diethyl [(1E)-1-benzoyl-2-phenylprop-1- en-1-yl]phosphonate(5), Diethyl [(E)-1-benzoyl-2-(4-hydroxy-3-methoxyphenyl) vinyl] phosphonate(6), Diethyl benzyl phosphonate(7), Diethyl [2-(2-hydroxyphenyl)- 2-oxo-1-phenylethyl] phosphonate(8), Diethyl [(3E)-2-oxo-1,4-diphenylbut-3-en-1- yl] phosphonate(9), Diethyl(2-oxo-1,2-diphenylethyl) phosphonate(10), Diethyl (2,4- dioxo-1-phenylpentyl) phosphonate(11), Diethyl (2,4-dioxo-1,4-diphenylbutyl) phosphonate(12), Ethyl (diethoxyphosphoryl) acetate(13), Diethyl (oxiran-2- ylmethyl) phosphonate(14), Diethyl[2-(2-hydroxyphenyl)-1-oxiran-2-yl-2-oxoethyl] phosphonate(15), 6-Diethyl [(3E)-1-oxiran-2-yl-2-oxo-4-phenylbut-3-en-1-yl] phosphonate(16), Diethyl (1-oxiran-2-yl-2-oxo-2-phenylethyl) phosphonate(17), Diethyl (1-oxiran-2-yl-2,4-dioxopentyl) phosphonate(18), Diethyl (1-oxiran-2-yl-2,4- dioxo-4-phenylbutyl) phosphonate(19), Diethyl (2-nitrobenzyl) phosphonate(20), six derivatives (21-26) containing the Tetraethyl ethane-1,2-diylbis (phosphonate) motif, Diethyl methylphosphonate(27), Diethyl [2-(2-hydroxyphenyl)-2-oxoethyl] phosphonate(28), Diethyl [(3E)-2-oxo-4-phenylbut-3-en-1-yl] phosphonate(29), Diethyl (2-oxo-2-phenylethyl) phosphonate(30), Diethyl(2,4-dioxopentyl) phosphonate(31) and Diethyl (2,4-dioxo-4-phenylbutyl) phosphonate (32). Seventeen compounds showed BLase inhibition activity. The compounds 1, 12, 29 & 32 were found more active than Clavulanic acid (used as standard). Extraction and bioassay guided isolation of Cichorium intybus resulted in the purification and identification of ten compounds: [Lupeol (33), β-Sitosterol(34), p- hydroxy phenyl acetic acid(35), Isovanillic acid(36), Syringic acid(37), Vanillic acid(38), Esculetin(39), Scopoletin(40), Umbelliferone(41) and Kaempferol(42)]. Stigmasterol(43) was the only compound isolated from Ageratum conyzoides but six compounds: [Conessine(44), Kurchinin(45), Conimine(46), Kurchamine(47), Holaromine(48) & Kurchessine(49)] were extracted from Holarrhena antidysenterica. viii However two compounds: [Lupeol(32) & Campesterol(50)], were extracted from Carissa opaca while Quercetin(51) & Kaempferol(42) were isolated from Alstonia scholaris. β-Sitosterol(34), α-Amyrin(52) & Ursolic acid(53) came out of Calotropis procera. All the phytochemicals were subject to BLase inhibition study. In general these phytochemicals showed poor activity however Kurchamine(47), Holaromine(48) and Quercetine(51) were relatively more active in this respect. ix CONTENTS List of Tables (xv) List of Figures (xvi) List of Schemes (xvii) List of Abbreviations/acronyms (xviii) 1. Introduction 1-20 1.1. Antibiotics 1 Fig-1.1: Introductory Facts and Core structures of Lactam Antibiotics 1 Table-1.1:- Some Common Agents Used for Antimicrobial Chemotherapy 2 1.1.1:- Mechanism of β-Lactam Antibiotic Activity 3 Fig-1.2: A comparison between the structure of Penicillins with that of D-alanyl-D-alanine-Peptidoglycan 3 1.1.2:-Resistance towards Antibiotics 4 Fig1.3: Inactivation of Antibiotic Molecule through Hydrolysis by Enzyme 4 1.1.2.1:-Strategy To Combat Bacterial Resistance 5 1.1.2.2:-Classification of Beta-Lactamases (BLase) 5 Fig-1.4: Ambler’s classification of enzyme BLase. 6 Table 1.2- Bush Functional Grouping of BLase 8 1.1.2.2.1:-Extended Spectrum BLases (ESBLases) 9 1.1.2.2.2:- Class-C or group-1 (AmpC)-BLases 10 1.1.2.2.3:-Carbapenemases
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