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Dr. A.A. El-Mohty Dr. Shoukar T.M. Atwa Benha University Faculty of Science Chemistry Department RADIOCHEMICAL STUDIES ON THE SEPARATION OF IODINE- 131 AND RADIOIODINATION OF SOME ORGANIC COMPOUNDS A Thesis Submitted by MAHMOUD ABBAS ISMAIL MOHAMED Isotopes and Radioactive Generators Dep., Hot Labs. Center Atomic Energy Authority To Faculty of Science – Benha University Presented as partial fulfillment of The Degree of M.Sc In chemistry Supervised by Prof .Dr .H .A. Dessouki Prof . Dr .S .A .El -Bayoumy Prof. of Inorganic and Prof. of Radiochemistry Analytical Chemistry Isot. and Radio Generators.Dept, Faculty of Science Benha Univ. Atomic Energy Authority Dr. Shoukar T.M. Atwa Dr. A.A. El-Mohty Lect. of Physical Chemistry Pro Ass it. Prof.of Radiochemistry Faculty of Science Benha Univ. Isot. and Radio Generators.Dept, Atomic Energy Authority 2010 آ ام اء درات آ إ اد- ١٣١و اآت ا د ا ر ــــد س ا ا واات ا – آ ا ارة ه ا ار ا آــ اــــ ــم – ــ ل در ا اء اـــــــــاف أ.د/ ا ا أ.د/ د اذ اء ا و ا أذ اــء اـــ آ ام - ـــ ا واات ا هــــ اـــ ارــــــــ د/ ر أ.م.د / أ ا رس اء ا أذ اــء اـــ آ ام - ـــ ا واات ا هــــ اـــ ارــــــــ ٢٠١٠ List of abbreviations Abbr. Referent CAT Chloramine-T H2O2 Hydrogen peroxide HPLC High performance liquid chromatography TLC Thin layer chromatography Temp. Temperature Conc. Concentration min Minute NCA No Carrier Added Rf Relative front Rt Retention time CNS Central nervous system Y-indole 4-[2-hydroxy-3- (isopentylamino)propoxy] indole Epidepride N-[(1-ethyl-2- pyrrolidyl)methyl]-2,3- dimethoxy-5-(tributylstannyl) benzamide SPECT Single Photon emission computed tomography PET Positron emission tomography HPGe High purity germanium cpm count per minute ETRR-2 The second Egyptain Research Reactor h Hour µ Micro β- Beta particles α Alpha particles γ Gamma emission d Day g gram Ci Curie (radioactivity unit) 131mTe Isotope in another energy state KeV kilo electron volt Av average a.m.u atomic mass unit EC Electron Capture (n,f) neutron fission reaction 123 IBZM [123 I]Iodine substituted benzamide At Astatine ICl Iodine monochloride MW Mega watt ACKNOWLEDGMENT This work was carried out in the laboratories of the Isotopes and Radioactive Generators Department, Isotope Production Division, Hot Labs. Center, Atomic Energy Authority, Inshas, Egypt. The author wishes to thank deeply Prof. Dr. Hassan Ali Dessouki, Professor of Inorganic and Analytical Chemistry, Faculty of Science, Benha University, for sponsoring this work and for his valuable and constant interest throughout these studies. I would like to express my deep gratitude and sincere appreciation to Prof. Dr. Sami Abu-Bakr El Bayoumy Isotopes and Radioactive Generators Department, Atomic Energy Authority, to whom I am greatly indebted for his great help, encouragement, valuable and sincere efforts in reviewing this thesis. The author would like to thank Prof. Dr. Ahmed Abd-El-Mohty Bayoumy, Head of Isotopes and Radioactive Generators Department, Atomic Energy Authority, for effective supervision advice, continuous encouragement through the whole work. My deep and profound gratitude to Dr. Shoukar Tawfik Faculty of Science, Benha University, for her sincere efforts during the experimental work and revision of this thesis. The author expresses his gratitude and sincere appreciation to Dr. Ahmed Ali Abd-El-Sadek, Isotopes and Radioactive Generators Department, Atomic Energy Authority, for his helpful and valuable guidance during the experimental work. The author would like to thank Dr. Mahmoud Hamdi Mahmoud Sanad, Labeled Compounds Department, Atomic Energy Authority, for continuous help. To My parents My wife My sons ( Mennh, Tasneem) My best friends Approved Sheet Title: RADIOCHEMICAL STUDIES ON THE SEPARATION OF IODINE-131 AND RADIOIODINATION OF SOME ORGANIC COMPOUNDS Name : MAHMOUD ABBAS ISMAIL MOHAMED Isotopes and Radioactive Generators Dep., Hot Labs. Center Atomic Energy Authority Supervisors : Name Position Signature Prof. Dr .H .A. Dessouki Prof. of Inorganic and Analytical Chemistry Faculty of Science- Benha Univ. Prof . Dr .S.A. El-Bayoumy Prof. Prof. of Radiochemistry Isot. and Radio Generators.Dept, Atomic Energy Authority Dr. A.A. El-Mohty Assis. Prof.of Radiochemistry Isot. and Radio Generators.Dept, Atomic Energy Authority Dr. Shoukar T.M. Atwa Lect. of Physical Chemistry Faculty of Science- Benha Univ. Head of Chemistry Department Prof. Dr. S.G. Donia 2010 ا ا د س ا ان ا درات آ ا اد- ١٣١ و اآت ا د ا ار ا اء ا « ﻟﺠﻟﻟﺠﺠﻟﺠــــﻨﻨﻨﻨ ــــــ ﺔﺔﺔ ﺍﻹﺍﺍﻹﻹ ﺷﺷﺷ ــــــ ﺮﺍﻑ » ا ا ا ا.د/ د اذ اء ا - آام- ا.د / أ ا اذ اء ا- ه ا ار ا.د / أ ا اذ اء ا - ه ا ار د/ آر رس اء ا آ ام - ر اء (ا.د/ ل د) ٢٠١٠ ا ا د س ا ان ا درات آ ا اد- ١٣١ و اآت ا د ا ار ا اء ا « ﻟﺠﻟﻟﺠﺠﻟﺠــــﻨﻨﻨﻨ ــــــ ﺔ ﺍﻟﻤﻨ ـــ ﺎﻗﺸﺔ » ا ا ا ا.د/ رأ د اذ اء ا- ر او م ا ا.د/ اذ اء ا- ه ا ار ا.د/ د اذ اء ا - آام- ا.د / أ ا اذ اء ا- ه ا ار ر اء (ا.د/ ل د) ٢٠١٠ Contents Page Chapter I I. Introduction.………………..………………………….………..…...…...1 I.1. General Considerations ……………….…………………….........…...1 I.2 Physical and Chemical Properties of Tellurium……...........................3 I.3 Physical and Chemical Properties of Iodine........................….............3 I.4. Radiochemistry of Iodine……………….…………………..….……...6 I.5 Production of 131 I………………………………………………..……..10 I.6 Types of nuclear reactions…………………………………….......….11 I.6.1 (n,γγγ) reactions.…………………………………………………..…...11 I.6.2 Multistage "double neutron" (2n,γγγ) reactions…...……………..….12 I.6.3 (n,p) reactions………………………………………………………..13 I.6.4 (n,ααα) Reactions..…………………………………………………..…13 I.6.5 Fission reactions………………………………...…………………...13 I.7 Definition of the labeled compound .…………………..…………...…14 I.8 Types of labeling .…………………………………………………..…..14 I.9 Methods of labeling Pharmaceutical compounds………………...…14 I.9.1 Chemical synthesis…..…….………………………………………...14 I.9.2 Biosynthesis…..…...…………………………………………………15 I.9.3 Recoil labeling……….………………………………….……......….15 I.9.4 Excitation labeling….………………………….…………………....16 I.9.5 Bifunctional chelates labeling.…….………………..…………........16 I.9.6 Isotopic exchange reactions…….……………….…………….........16 I.10 Radiopharmaceuticals.………………………..…….….……....…....17 I.11 Radionuclides used for diagnostic nuclear medicine….………...…18 i I.11.1 Single photon emission computed tomography (SPECT)……….18 I.11.2 Dual and triple head camera…………………………...…………19 I.11.3 Positron emission tomography (PET)……………………….……19 I.12 Preparation of radioiodinated compounds…………….………..….21 I.12.1 Electrophilic Substitution………….………...……….…………...22 I.12.1.1 Chloramine-T (CAT) method………….…..………..…………..22 I.12.1.2 Iodogen method…………………………..………………….…...23 I.12.1.3 Enzymatic method…………………………..…………….……..24 I.12.1.4 Electrolytic method………………………………………………25 I.12.2 Nucleophilic substitution…………………………………….….…25 I.12.2.1 Exchange in solvent………………...…………………………....26 I.12.2.2 Exchange in melt…………………………………………………26 I.12.2.3 Exchange for bromine………………….………………………..27 I.12.2.4 Catalyzed exchange …………...………………………………...28 I.13 Purification of radioiodinated compounds........................................28 I.14 Quality control ....................................................................................29 I.14.1 Chemical purity ………………………………..……………….…30 I.14.2 Radionuclidic purity ………….…………………………………...30 I.14.3 Radiochemical purity………………………………….…….…….31 I.15 Apyrogenicity, Toxicity and Biological distribution…….….…….. 32 Chapter II II.Experimental…...…………………………………….…………..…….33 II.1 Materials……….…..…………………………………………………33 II.2 Equipment…..…..…..……………………………….………………..33 II.3 Preparation and irradiation of target………………………………36 ii II.4. Factor affecting the production of 131 I……………………..……….36 II.4.1 Effect of oven temperature on the releasing 131 I activity.………..36 II.4.2 Effect of distillation time on the releasing 131 I activity and the concentration of tellurium in the separated radioiodine….…37 II.4.3 Sodium hydroxide concentration……..…..……………………….37 II.5 Quality control on the released 131 I.……………………………...….37 II.5.1 Chemical Purity…………………………………...………………..37 II.5.2 Radionuclidic Purity………….……...……………...………..……39 II.5.3 Radiochemical purity….………………...…………………………39 II.6 Iodination of 4-[2-hydroxy-3-(isopentylamino) propoxy] indole (Y-indole)..............................................................................................40 II.6.1 Cold iodination of Y-indole………………………………………40 II.6.1.1 Chloramine-T method………………………………………..….40 II.6.1.2 Iodogen method…….……...……………………………….….....41 II.6.2 Radioiodination of Y-indole…………………………………………..41 II.6.2.1 Chloramine-T method………………………………………………41 II.6.2.2 Iodogen method……………………………………………………...42 II.7 Iodination of [(1-ethyl-2-pyrrolidyl) methyl] -2,3-dimethoxy-5-(tributylstannyl) benzamide (Epidepride)….….42 II.7.1 Cold iodination of (Epidepride)………………………………….43 II.7.1.1 Chloramine-T method……...………………………....................43 II.7.1.2 Hydrogen peroxide method...…………….…………….......…..44 II.7.2 Radioiodination of epidepride……………..………….…………...44 II.7.2.1 Chloramine-T method…………………………..……………….44 II.7.2.2 Hydrogen peroxide method………………………….………….44 II.8 Biological distribution of the labeled compound in mice..............45 iii Chapter III III.Results and Discussion………………………...….…………………..46 III.1 Irradiation of target material………………………………………46 III.2 Dry distillation method………………….………………………….49 III.2.1 Effect of oven temperature on the releasing 131 I activity……….49 III.2.2 Effect of distillation time on the releasing 131 I activity and on the tellurium concentration in the separated radioiodine .…….49 III.2.3 Effect
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