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Synthesis and Radioactive Labeling of Biologically Active Peptides, Peptide and Protein Fragments

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Synthesis and Radioactive Labeling of Biologically Active Peptides, Peptide and Protein Fragments Synthesis and radioactive labeling of biologically active peptides, peptide and protein fragments Ph.D. Thesis Erzsébet Szemenyei Institute of Biochemistry Biological Research Centre of the Hungarian Academy of Sciences Szeged 2008 1 LIST OF PUBLICATIONS RELATED TO THE THESIS I. Erzsébet Szemenyei , Géza Tóth; Tritium labelling and degradation studies of Dmt 1- endomorphin-2. Journal of Labelled Compounds and Radiopharmaceuticals, 50 : 1148- 1152, (2007). II. Veronica Gonzalez-Nuñez, Gemma Arsequell, Erzsébet Szemenyei , Géza Tóth, Gregorio Valencia, Raquel E. Rodriguez ; Binding profile of the endogenous novel heptapeptide Met-Enkephalin-Gly-Tyr in zebrafish and rat brain. The Journal of Pharmacology and Experimental Therapeutics , 314 : 862-867, (2005). III. András. Z. Rónai, Erzsébet Szemenyei , Erzsébet Kató, László Kocsis, György Orosz, Mahmoud Al-Khrasani, Géza Tóth; Endomorphin synthesis in rat brain from intracerebroventricularly injected [ 3H]-Tyr-Pro: A possible biosynthetic route for endomorphins. Regulatory Peptides, 134 (1): 54-60, (2006). IV. Erzsébet Szemenyei , István Barna, Zsuzsa Mergl, Attila Keresztes, Zsuzsanna Darula, Erzsébet Kató, Géza Tóth, András Z. Rónai; Detection of a novel immunoreactive endomorphin 2-like peptide in rat brain extracts. Regulatory Peptides , 148 : 54-61, (2008). V. Archana Mukherjee, Kanchan Kothari, Géza Tóth, Erzsébet Szemenyei , Hal Dhar Sarma, József Környei, Meera Venkatesh; 99m Tc-labeled annexin V fragments: a potential SPECT radiopharmaceutical for imaging cell death. Nuclear Medicine and Biology, 33 (5): 635- 643, (2006). 2 ACKNOWLEDGEMENTS I would like to thank my supervisor, Dr. Géza Tóth, for the opportunity to accomplish my PhD work in his laboratory and for all his support during this period. It is to thank to my university consultant, Dr. Éva Hajdú, and Prof. Botond Penke for all their help. Dr. András Z. Rónai and Dr. József Környei are entitled extra acknowledgement for their useful professional advices, kind instructions and stable support. My thanks are due to the members of the pharmacology group of the Semmelweis University, to Dr. Erzsébet Kató and Dr. Mahmoud Al-Khrasani, to Dr. Raquelle Rodriguez’s team from University of Salamanca for the biological characterization of my compounds. Special thanks to Dr. Zsuzsa Mergl for the immunization and Dr. István Barna for the radioimmunoassay. I am grateful to Dr. Kanchan Kothari and her group from Bhabha Atomic Research Centre for the biological measurements of the annexin V fragments. I am grateful to Dr. Zsuzsanna Darula, Emília Szájli and Dr. Zoltán Kele for the mass- spectrometric analysis of my peptides. At last but not least, thanks also to be expressed to my colleagues in our laboratory, to Dr. Judit Farkas, Éva Papp, Bencze Jánosné, Andrea Mosonyi, Attila Keresztes, Dr. Attila Borics, Dr. Csaba Tömböly and special thanks to Dr. Balázs Leitgeb. 3 TABLE OF CONTENTS 1. Introduction .............................................................................................................. 8 1.1. Radioactive isotopes as tracers .............................................................................. 8 Radioactive tracing................................................................................................... 8 Tritium and tritium labeling methods of peptides...................................................... 8 Technetium-99m and 99m Tc-labeling methods of peptides ...................................... 11 Iodine-125 and 125 I-labeling methods of peptides ................................................... 13 1.2. Endogenous opioids .............................................................................................. 15 Opioid receptors and endogenous opioid peptides .................................................. 15 Endomorphins ........................................................................................................ 17 Dmt-endomorphins ................................................................................................ 18 Zebrafish endogenous opioid peptide ..................................................................... 18 1.3. Role of Annexin V in apoptosis ............................................................................ 19 Apoptosis ............................................................................................................... 19 Annexin V.............................................................................................................. 19 2. Aims and Scopes ...................................................................................................... 21 3. Materials and Methods ........................................................................................... 23 Working with tritium .............................................................................................. 23 Working with 125 I and 99m Tc ................................................................................... 24 3.1. Synthesis and purification of peptides ................................................................. 24 Solid-phase peptide synthesis using Boc strategy ................................................... 25 Solid-phase peptide synthesis using Fmoc strategy ................................................. 26 Purification of peptides .......................................................................................... 26 3.2. Tritium labeling of peptides ................................................................................. 26 3.3. Characterization of tritiated peptides ................................................................. 27 Determination of specific activity ........................................................................... 27 Tritium distributions in labeled peptides ................................................................. 27 3.4. Methods for investigation of the metabolism of tritiated peptides ..................... 28 3.5. Peptide isolation methods from rat brain ............................................................ 28 Animals ................................................................................................................. 28 Peptide-extraction procedures from rat brain .......................................................... 28 125 I-labeling of peptides containing tyrosine ........................................................... 29 Preparation of endomorphin 2-keyhole limpet hemocyanin conjugate .................... 29 4 3.6. Tc-99m-labeling of annexin V fragments via nitrido intermediate .................... 30 Stability studies ...................................................................................................... 30 Synthesis of [ 99m TcN] 2+ intermediate ...................................................................... 30 Labeling of peptides via nitrido intermediate .......................................................... 30 Determination of the radiochemical purity .............................................................. 30 4. Results and Discussion ............................................................................................ 31 4.1. Synthesis and tritiation of endomorphin analogues ............................................ 31 Dmt 1-endomorphin 2 .............................................................................................. 31 Synthesis ......................................................................................................... 31 Tritiation ......................................................................................................... 31 Distribution ..................................................................................................... 32 Stability ........................................................................................................... 32 4.2. Synthesis and tritiation of peptide analogues from Zebrafish ............................ 34 Synthesis ................................................................................................................ 34 Tritiation ................................................................................................................ 34 Saturation binding assays ....................................................................................... 34 Results and discussion of competition binding assays ............................................. 35 4.3. Investigation of a possible endomorphin biosynthesis route .............................. 37 Synthesis ................................................................................................................ 37 Tritiation ................................................................................................................ 38 Results of the chromatographic procedure .............................................................. 38 Synthesis of 125 I-endomorphin 2 ............................................................................. 40 Results of radioimmunoassay ................................................................................. 40 Discussion of the investigation of a possible endomorphin biosynthetic route ........ 42 4.4. Synthesis and 99m Tc-labeling of annexin V fragments ........................................ 43 Synthesis ................................................................................................................ 43 Stability studies .....................................................................................................
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