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Progress in Radiopharmacology INIS-mf—11544 Proceedings of the Vth International Symposium on Radiopharmacology PROGRESS IN RADIOPHARMACOLOGY EDITORS A. E. A. MITTA R. A. CARO C. O. CANELLAS 986 BUENOS AIRES - REPUBLICA ARGENTINA 1987 & ,f<? 000 Y'{ Proceedings of the Vth International Symposium on Radiopharmacology PROGRESS IN RADIOPHARMACOLOGY EDITORS A. E. A. MITTA R. A. CARO C. O. CANELLAS 986 BUENOS AIRES - REPUBLICA ARGENTINA 1987 Proceedings of the Vth International Symposium on Radiopharmacology PROGRESS IN RADIOPHARMACOLOGY EDITORS A. E. A. MITTA Comision Nacional de Energia Atomica Buenos Aires, Republics Argentina R. A. CARO Facultad de Farmacia y Bioquimica Universidad de Buenos Aires, Republics Argentina C. O. CAIVIELLAS Comision Nacional de Energia Atomica Buenos Aires, Republica Argentina PREFACE This book contains most of the papers presented at the V International Symposium on Radiopharmacology held at Buenos Aires, Argentina, from the 29th to the 31st October, 1986. The papers were put into the same order as they were presented at the symposium. The V Simposium was sponsored by the Argentine Atomic Energy Commission, which allowed, among other things, the edition of this book. I want to acknowledge specially the cordial assistance of Profs.DlSiRicardo.A.Caro and Carlos. O.Canellas in the publication of the present book. PREFACE The Executive Committee of the V International Symposium on Radiopharmacology acknowledges deeply the participation of all those who presented their paper, discussed the results or simply assisted to the sympos ium. The proceedings we are publishing herewith are the result of the efforts of the authors who sent us the full papers, as well as the excellent work done by the Printing Department of the Argentine Atomic Energy Commission. We hope that this publication will steer the efforts towards an increasing knowledge and utilization of radiopharmacology, as a branch of science capable of a peaceful application of radioisotopes for the benefit of Mankind. The Editors TABLE OF CONTENTS BIOLOGICAL EVALUATION OF '9mTc cis-PLATINUM IMI NOD IACETIC ACID COMPLEXES AS TUMOR IMAGING AGENT 1 A . Awa1uddin, J.J.Jacobs, D.W.Bourne, D.D.Madda1ena, J.G. Wilson and R . E.Boyd. COMPUTED FUNCTIONAL ANALYSIS OF ""TC EHIDA KINETICS IN PATIENTS 22 V.Blaha, I.Cihak, F.Nicek and J.Horak SYNTHESIS AND BIODISTRIBUTION OF SOME RADIOIODINATED DIAMINES 32 A.V.Joshua, J.G.Sandford, J.R.Scott and S.N.Muddukrishna RADIOPHARMACOLOGY OF IMINOD[ACETIC ACID N-DERIVAT IVES ANALYSIS IN BIOLOGICAL MODEL AND COMPARISON TO HUMAN BEINGS 4 1 C.O.Canellas, M.G.ArgiieLles and A.E.A.Mitta THE INFLUENCE OF MONOFLUORMETHYLH1STIDINE (MFMH) ON THE MAMMARY ADENOCARCINOMA M-2 58 M.C.P.ubio, M.E.Landa, H.Targovnik, L.L.Colombo, A.J. Scolnik and R.A.Caro 1-131 METAIODOBENZYLGUANIDINE (MIBG.I-I31) KINETICS IN A CARCINOID TUMOR 64 R.Schiavo, G.Concolino, F.Fazi, P . Iannantuono , S.Li.Voti, A.Manzara and P.Pavoni. 9 9m A SIMPLE METHOD FOR THE PREPARATION OF DIFFICULT Tc COMPLEXES USING SURFACE ADSORBED STANNOUS IONS 75 D.J.Madda1ena, G.M.Snowdon, A.Awaluddin and P.M.Pojer BLOOD CELLS RADIOLABELING ACHIEVEMENTS, CHALLENGES AND PROSPECTS 86 J.Weininger and J.Trumper THE SYNTHESIS AND PROPERTIES OF 1 -(4 -IODO-5-NITROIMIDA ZOLYD-2-HYDROXY-3-METHOXYPROPANE A NOVEL RAD IOSENS IT IZER FOR USE AS AN HYPOX1C CELL MARKER 107 L.I.Wiebe, D.C.Jette, J.R.Mercer, B.Samuel, R.J.Flanagan J.Lee, B.E.Meeker and J . D.Chapmann. SPECIFIC ACTIVITY DETERMINATION OF 1-125 LABELED PROLACTIN BY RECEPTOR AND RADIOINMUNOLOGICAL SELF-DISPLACEMENT METHODS 129 E.S.Rivera, G.A.Coiuccia, A.Venturino, S.Malkischer and R.A.Caro. STRUCTURE-ACTIVITY STUDIES ON Tc PHENOLIC AMINOCARB£ XYLLIC ACID HEPATOBILIARY AGENTS 135 D.J.Maddalena, J.G.Wilson and G.M.Snowdon IN VIVO STABILITY AND INERTNESS OF VARIOUS DIRECT LABELED AND CHELATE-TARGET PROTEIN 157 Gy.A.Janoki, L.Korosi, G.KLievnyi and B.Spett ] 8 h BJODISTRIBUCION Y ESTIMACION DOSIMETR1CA DEL Re HEDP 165 M.G.Noto y A.Manzini METODOLOGIA PARA LA EVALUACION DE FARMACOS DECONTAMINANTES EN SISTEMAS "IN VITRO" 170 C.Fernandez Degiorgi, D.Dubner y I.Gomez Parada PREPARACION Y CONTROL DE CALIDAD DE COMPUESTOS DE i86Re 184 M.G.Noto, R.A.Amor, D.A.Cavig1ia, M.T.Ratner, A.M.Schroder, J.C.Rocco y A.Manzini DIISOPROPIL-IDA, MEBROFENIN E IODOFENIN MARCADOS CON n Q Tc "SU EVALUACION EN VARIOS MODELOS BIOLOGICOS" 188 M.G.Argue 1les, A.S.Leon, E.S.Verdera, E.Leon, C.O.Caftellas y A.E.A.Mitta QQ PREPARACION Y CONTROL DE CALIDAD DE FIBRINOGENO Tc 202 M.G.Noto, G.Rabiller, C.Garrie Faget, C.Fisman y A.Manzini LIST OF PARTICIPANTS 2O7 BIOLOGICAL EVALUATION 0^ qpMTc cis-PLATINl!M IMINOFJIACETIC ACID AGENTS. A.AWALUDDIN*, J.J. JACOBS**, ^.'/.B O.J.MADDALENA***^ .I.fi.WILSON*** AND R.E.BOYD * ISOTOPE HEPT^ UNIT TENAPA "IUKLEAR^ COMPLEX PUSPATI, BANGI, MALAYSIA. ** PHARMACY DEPT,, UNIVERSITY OF QUEENSLAND^ ST. LUCIA^ OLD^ AUSTRALIA, *** ISOTOPE HIVISION^ AUSTRALIAN ATOMIC F.NERRY COMMISSION^ LUCAS HEIRHTS RESEARCH LABORATORIES^ PRIVATE ^AIL BAG NRO I, 'IENAI, »!S'.^ ?23'I ^EPUBLICA ARGENTINA BIOLOGICAL EVALUATION OP 99mTc cis-PLATINUM IMINODIACETIC ACID COMPLEXES AS TUMOUR IMAGING AGENTS A. Awaluddin1, J.J. Jacobs2, D.W. Bourne2, D.J. Maddalena3, J.G. Wilson3 and R.E. Boyd3 Isotope Dept,- Unit Tenaga Nuklear, Komplex Puspati, Bangi, Malaysia 2 Pharmacy Dept, University of Queensland, St Lucia, Qld, Australia Isotope Division, Australian Atomic Energy Commission, Lucas Heights Research Laboratories, Private Mail Bag No. 1, Menai, NSW, 2234, Australia. ABSTRACT The biodistributions of three new "mTc labelled cis-platinum bifunctional tumour imaging agents were examined in mice bearing the EMT6 sarcoma between 15 minutes and 24 hours post injection. The three complexes were excreted primarily via the renal pathway into the urine but at quite different rates. All complexes had some affinity for the tumour, but complex TTI had the greatest, with tumour to blood and tumour to muscle ratios at 24 hours in excess of 10:1 and 18:1. Keywords Tumour Imaging agents; 99raTc; EMT6 sarcoma mice; cisplatin; cis-diammineplichloroplatinuin (II); iminodiacetic acid — 3 — INTRODUCTION In recent years, considerable attention has been focused on the development of radiopharmaceuticals for diagnostic scintigraphic imaging of tumours. In a survey of 12 specialist journals issued between 1976 and 1981,.Weibe (1983) found more than 160 papers describing studies in animals on potential tumour imaging agents utilising a wide variety of radionuclides. Many more have been published since, but very few have been shown to be clinically useful. Gallium-67 citrate is considered the agent of choice, but its use in diagnosis and the staging of tumour types has proved unsatis- factory since not all tumour sites or types are detectable. Other limitations are that it only reliably detects tumours greater than 1 cm in diameter; it localises in a variety of non- cancerous inflammatory lesions and scintigraphic imaging must be carried out after 24 to 48 hours due to high body backgrounds. Gallium-67 citrate also has poor physical properties which make it ill-suited to scintigraphic imaging with a gamma camera (Lentle, 1986). Consequently, there is a great need for new and better tumour imaging agents preferably based on Technetium, or some other radionuclide with near optimal physical characteristics for gamma imaging. One approach is to label drugs such as cancer chemotherapy drugs, which localise in certain tumours, with radionuclides and hope that the resultant complex does not lose its tumour specificity. -4- Bleomycin labelled with Co localises well in a number of tumour types and in some comparisons has been shown to be more sensitive than fa Gallium citrate (Poulose et al., 1974; Grove et al., 1974), but owing to its long physical half-life and poor imaging characteristics it has not gained widespread use. Attempts at replacing the b7Co with 111In or "mTc have not been success- ful (Lentle, 1986). Even before its clinical studies had been completed (DeConti et al. , 1973), Lange et al. (1972) had examined the possibility of using cisplatin, the first of a widely used group of platinum coordination complexes with anti-tumour activity, as a tumour imaging agent, by replacing some of the platinum in the complex with the radionuclide, 193mPt. In subsequent studies, cisplatin has been labelled with othar platinum radionuclides, including Pt (Wolf et al., 1973; Smith et al., 1974), i9xPt (Baer et al., 1985) and its nitrogen has been replaced with X"N (Haber et al., 1985). Although these compounds localise in some tumours, the physical properties of the radionuclides are less than ideal and complex syntheses with radioactive materials are required in their preparation. A less obvious but more useful approach would be to synthesise a bifunctional chelate where the cisplatin acting as a tumour binding moiety was joined to a ligand capable of forming a stable complex with a variety of radionuclides. -5- This paper describes the initial biological studies on a series of three new organo-platinum complexes (figure 1) containing the cis-dichloroplatinvtm moiety for tumour binding with benzylimino- diacetic acids as tha chelating groups for Tc. MATERIALS AND METHODS Formulation of the Complexes The syntheses of organo-platinum compounds I, II and III have been described elsewhere (Awaluddin et al. , 1987). The "mTc complexes of the three compounds were prepared using a sodium borohydride reduction method. Five milligrams of compound I, II or III was dissolved in isotonic saline (1.0 mL) and sodium hydroxide (0.1 mL, 1.0 M) in a 10 mL vial. The pH was adjusted to 7 with 1.0 M HC1, generator-derived sodium pertechnetate (20 MBq, 0.1 mL) was added and the resultant solution diluted to 3.0 mL with isotonic saline.
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