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Amine Oxidases: Function and Dysfunction: Proceedings of the 5th International Amine Oxidase Workshop, Galway, Ireland, August 22–25, 1992 PDF

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Preview Amine Oxidases: Function and Dysfunction: Proceedings of the 5th International Amine Oxidase Workshop, Galway, Ireland, August 22–25, 1992

Journal of Neural Transmission Suppiementum 41 K F. TIpton, M. B. H. Youdim, C. 1. BalWell~ B. A. Callingham, and G. A. Lyles (eds.) Amine Oxidases: FUnction and Dysfunction Proceedings of the 5th International Amine Oxidase Workshop, Galway, Ireland, August 22-25, 1992 Springer-Verlag Wien New York Prof. Dr. K. F. Tipton Biochemistry Department, Trinity College, Dublin, Ireland Prof. Dr. M. B. H. Youdim Department of Pharmacology, Technion, Haifa, Israel Dr. C. J. Barwell School of Pharmacy and Biomedical Sciences, University of Portsmouth, United Kingdom Prof. Dr. B. A. Callingham Department of Pharmacology, University of Cambridge, United Kingdom Dr. G. A. Lyles Department of Pharmacology and Clinical Pharmacology, University of Dundee, United Kingdom This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. © 1994 Springer-VeriagjWien Product Liability: The publisher can give no guarantee for information about drug dosage and application thereof contained in this book. In every individual case the respective user must check its accuracy by consulting other pharmaceutical literature. The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Typesetting: Best-set Typesetter Ltd, Hong Kong Printed on acid-free and chlorine-free bleached paper With 113 Figures Library of Congress Cataloging-in-Publication Data: International Amine Oxidases Workshop (5th: 1992: Galway, Ireland) Amino oxidases: form and dysfunction: proceedings of the 5th Interna- tional Amine Oxidases Workshop, Galway, Ireland, August 22-25, 1992 / K. F. Tipton ... [et al.], eds. p. cm. - (Journal of neural transmission. Supplementum; 41) ISBN 0-387-82521-5 1. Monoamine oxidase-Congresses. 2. Amine oxi- dase - Congresses. 3. Monoamine oxidase - Inhibitors - Congresses. I. Tipton, Keith F. II. Title. III. Series. QP603.M6I58 1992. 612.8'042 - dc20. 94-6714 CIP ISSN 0303-6995 ISBN-13:978-3-211-82521-1 e-ISBN-13 :978-3-7091-9324-2 DOl: 10.1007/978-3-7091-9324-2 Preface Amine Oxidase workshops are held in alternate years, and such is the pace of advance in this area that there is always a great deal of new and exciting material to report. New data on the structures of the monoamine oxidases and their promoter regions are presented in these proceedings along with unexpected discoveries about their behaviour, function, and dysfunction. Renewed interest in the design and operation of selective monoamine oxidase inhibitors has stemmed from suggestions that inhibitors of monoamine oxidase-B may be neuroprotective whereas reversible monoamine oxidase-A inhibitors are free of the "cheese effects" associated with irreversible inhibitors of that enzyme at doses where they are effective antidepressants. All these aspects and many more are discussed in this volume. The only thing still lacking is the X-ray crystal structure of the monoamine oxidases; membrane-bound proteins are so beastly! However, advances in other areas suggest that problem will eventually be solved, perhaps in time for the next Amine Oxidase workshop which is to be held in Saskatoon, Canada, in 1994. The semicarbazide-sensitive amino oxidases (SSAO) remain the Cinderella of this field, nevertheless, there were many Prince (and Princess) Charmings at this particular ball to flirt with her. Despite this there is still no clear indication of the physiological function(s) of this group of enzymes. Several possibilities are discussed here and the developments reported in the design of new and more specific inhibitors should eventually lead to a better understanding of these aspects. We would like to express our gratitude to ASTA Medica AG, Britania Pharmaceuticals, Chinoin, Ciba-Geigy (Basel), Convention Bureau of Ireland, Farmitalia Carlo Erba, Galway Regional Tourist Board, Hoffman-La Roche (Basel), International Society for Neurochemistry, Marian Merrell Dow, Med- labs, Merk Sharp and Dohme Research Laboratories U.S.A., Millipore, Phar- moa, Sandoz Pharmaceutical, Sanofi Winthrop, Somerset and Synthelab6- L.E.R.S., whose generous support made the meeting possible. Although the workshop organisers were officially listed as Keith Tipton and Moussa Y oudim, the acutal work, was of course done by others and we are particularly grateful to Mary Anderson, Melina Lawless, John McCrodden, Gemma Tipton, and Gill Tipton for making everything happen. Perhaps a special word of praise is also due to the Irish weather over the period of the Meeting which ensured that most of those attending remained at the sessions rather than experiencing the delights of Western Ireland. VI Preface The 5th Amine Oxidase Workshop and these proceedings are dedicated to Irv Kopin. An appreciation of his contributions is published elsewhere in this volume and it is probably sufficient to say that on behalf of so many working in this field, we are proud to honour a man who has contributed so much to our understanding of the functions and metabolism of the biogenic amines. Dublin, April 1994 K. F. TIPTON M. B. H. Y OUDIM C. J. BARWELL B. A. CALLINGHAM G. A. LYLES Irwin J. Kopin, M.D. Irwin Kopin ("Irv") is one of the major contributors to understanding the function and metabolism of catecholamines. His research spans the whole spec- trum of the field, from biosynthesis, release, and metabolism of the biogenic amines, to detailed pharmacology of the drugs affecting the system, metabolism of the endogenous compounds in laboratory animals and man, and their role in cardiovascular and mental disease. It is particularly appropriate that he should be honoured at the Galway meeting on MAO and trace amines, since he has made basic contributions to both areas. In a series of classical papers in the 1960s, he described the role of MAO in the metabolism of endogenous nor- adrenaline, and also demonstrated the accumulation and release of octopamine following MAO inhibition. More recently, he was a major force behind the unravelling of the MPTP story at NIH, which spawned so much excitement and renewed interest in selective neurotoxicity, with particular application to the role of MAO-B. Irv Kopin was born (1929) in New York, and acquired an early interest in applied chemistry working in his father's mirror silvering factory. When he finally succeeded in making a really clean mirror (he relates), his father said: VIII Irwin J. Kopin, M.D. "Now you can go to college". Chemistry, however, is not the only of his strong basic sciences. His first of many awards, while at the College of the City of New York, was for excellence in pure and applied calculus. His mathematical ability is immediately evident in the logical approach he brings to a variety of scientific problems, and has enabled him to unravel complex problems of me- tabolite distribution in the body. He obtained both his B.Sc. (biochemistry) and M.D. degrees at McGill University, Montreal, and joined the National Institutes of Health (Laboratory of Clinical Science), Bethesda, in 1957. There, as is now well known, he joined forces with Julius Axelrod. The dingy 2D corridor, deep in the labyrinth of the Clinical Center, seems an inappropriate place for such a scintillating team as Kopin and Axelrod, but the results of this combination, as well as with many other associates, are now history. Since joining NIH, he has left the Bethesda campus for only one year, to complete his medical residency at Columbia, New York. The medical back- ground has played an important role in his ability to apply basic science to the study and treatment of human illness, and is also evident in the comprehen- siveness of his physiological knowledge. The application of his work to mental illness earned him the Anna -M onika Award for Research on Depression (twice). He is unrelenting in his pursuit of basic research, despite the rigors of a senior administrative appointment in the US Government (currently, he is Director ofIntramural Research, National Institute of Neurological Disorders). Despite his heavy administrative load, he is readily available to a large group of post- doctoral fellows and other research workers, and revels in bringing scientific order to a chaotic problem, such as understanding the meaning of a complex PET scan, or the intricacies of CNS dopamine release. In spite of responsibilities to a variety of scientific committees, editorial boards, international congresses and currently serving as President of the Amer- ican Society of Neuropsychopharmacology, he maintains his regular swimming practice (was intercollegiate champion). At his home in Bethesda he is happy to show a visitor his collection of stamps and postcards from all over the world. With his wife Rita, whom he met at McGill, he has two daughters and a son, Alan, who has started his career in medical research with important publications on the molecular biology of gastro-intestinal hormones. Rita runs a center for Hebrew teachers, and is particularly proud of her innovative resource depart- ment. Few researchers in the life sciences possess such diverse skills in chemistry, mathematics, and physiology as Irv Kopin. Still fewer, who possess such skills, are able to put them to such valuable use in their chosen branch of science; but only a very small number are capable of instilling as much appreciation for science in those around him, a quality for which many of us are indebted. J. P. M. FINBERG Contents Monoamine oxidase: structure Weyler, W.: Functional expression of C-terminally truncated human monoamine oxidase type A in Saccharomyces cerevisiae ................................ 3 Ramsay, R. R., Tan, A. K., Weyler, W.: Kinetic properties of cloned human liver monoamine oxidase A .................................................. 17 Shih, J. c., Zhu, Q.-S., Grimsby, J., Chen, K.: Identification of human monoamine oxidase (MAO) A and B gene promoters .................................. 27 Barwell, C. J., Ebrahimi, S. A.: Some problems associated with measuring monoamine oxidase activity in the presence of sodium azide ............................ 35 Barwell, C. J., Ebrahimi, S. A.: Some kinetic properties of guinea pig liver monoamine oxidase ............................................................... 41 Anderson, M. C., Tipton, K. F.: Estimation of monoamine oxidase concentrations in soluble and membrane-bound preparations by inhibitor binding .............. 47 Monoamine oxidase: functions Kopin, I. J.: Monoamine oxidase and catecholamine metabolism. . . . . . . . . . . . . . . .. 57 May, T., Rommelspacher, H.: Monoamine oxidase (MAO; E.C. 1.4.3.4) characteristics of platelets influenced by in vitro and in vivo ethanol on alcoholics and on control subjects .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 69 Della Corte, L., Bianchi, L., Colivicchi, A., Kennedy, N. P., Tipton, K. F.: The effects of ethanol on rat brain monoamine oxidase activities. . . . . . . . . . . . . . . . . . . . . . .. 75 Strolin Benedetti, M., Thomassin, J., Tocchetti, P., Dostert, P., Kettler, R., Da Prada, M.: Species differences in changes of heart monoamine oxidase activities with age 83 Saura, J., Richards, J. G., Mahy, N.: Age-related changes on MAO in BIIC 57 mouse tissues: a quantitative radioautographic study .............................. 89 Fogel, W. A., Maslinski, c.: The FAD dependent amine oxidases in relation to de- velopmental state of enterocyte . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 95 Fernandes, M. H., Soares-da-Silva, P.: Role of monoamine oxidase and cathecol-O- methyltransferase in the metabolism of renal dopamine ...................... 101 Lavian, G., Finberg, J. P. M., Youdim, M. B. H.: Comparison of the effect ofreversible and irreversible MAO inhibitors of renal nerve activity in the anesthetized rat .. 107 McKenna, K. F., McManus, D. J., Baker, G. B., Coutts, R. T.: Chronic administration of the antidepressant phenelzine and its N-acetyl analogue: effects on GABAergic function .............................................................. 115 Finberg, J. P. M., Pacak, K., Goldstein, D. S., Kopin, I. J.: Modification of cerebral cortical noradrenaline release by chronic inhibition of MAO-A ............... 123 Goodnough, D. B., Baker, G. B.: Comparisons of the actions of high and low doses of the MAO inhibitor tranylcypromine on 5-HT2 binding sites in rat cortex .... 127 Reuss, S., Requintina, P. J., Riemann, R., Oxenkrug, G. F.: Clorgyline effect on pineal melatonin biosynthesis in adrenalectomized rats pretreated with 6-hydroxydopa- mine ................................................................. 135 Requintina, P. J., Oxenkrug, G. F., Yuwiler, A., Oxenkrug, A. G.: Synergistic sedative effect of selective MAO-A, but not MAO-B, inhibitors and melatonin in frogs .. 141 x Contents Requintina, P. J., Driscoll, P., Oxenkrug, G. F.: Clorgyline effect on pineal melatonin biosynthesis in roman high- and low-avoidance rats ......................... 145 Dostert, P., Castelli, M. G., Cicioni, P., Strolln Benedetti, M.: Reboxetine prevents the tranylcypromine-induced increase in tyramine levels in rat heart .............. 149 Sherry-McKenna, R. L., Wong, J. T. F., Paetsch, P. R., Baker, G. B., Mousseau, D. D., McKenna, K. F., Coutts, R. T., Greenshaw, A. J.: Monoamine oxidase inhibitors: effects on tryptophan concentrations in rat brain ........................... 155 Deprenyl, MAO-B and neurodegenerative conditions Magyar, K.: Behaviour of (- )-deprenyl and its analogues ...................... 167 Gerlach, M., Youdim, M. B. H., Riederer, P.: Is selegiline neuroprotective in Parkinson's disease? ........ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 177 Chiueh, C. c., Huang, S.-J., Murphy, D. L.: Suppression of hydroxyl radical formation by MAO inhibitors: a novel possible neuroprotective mechanism in dopaminergic neurotoxicity .......................................................... 189 Naoi, M., Maruyama, W., Niwa, T., Nagatsu, T.: Novel toxins and Parkinson's disease: N-methylation and oxidation as metabolic bioactivation of neurotoxin ........ 197 Sziniki, I., Kardos, V., Patthy, M., Patfalusi, M., Gaal, J., Solti, M., Kollar, E., Singer, J.: Amphetamine-metabolites of deprenyl involved in protection against neuro- toxicity induced by MPTP and 2'-methyl-MPTP ............................ 207 Lai, C. T., Zuo, D. M., Yu, P. H.: Is brain superoxide dismutase activity increased following chronic treatment with l-deprenyl? ............................... 221 Freisleben, H.-J., Lehr, F., Fuchs, J.: Lifespan of immunosuppressed NMRI-mice is increased by deprenyl ................................................... 231 Jossan, S. S., Ekblom, J., Gudjonsson, 0., Hagbarth, K.-E., AquiIonius, S.-M.: Double blind cross over trial with deprenyl in amyotrophic lateral sclerosis ............ 237 Jossan, S. S., Ekblom, J., AquiIonius, S.-M., Oreland, L.: Monoamine oxidase-B in motor cortex and spinal cord in amyotrophic lateral sclerosis studied by quantitative autoradiography ....................................................... 243 Oxenkrug, G. F., Requintina, P. J., Correa, R. M., Yuwiler, A.: The effect of 6-months l-deprenyl administration on pineal MAO-A and MAO-B activity and on the content of melatonin and related indoles in aged female Fisher 344N rats ...... 249 Ekblom, J., Jossan, S. S., Oreland, L., Walum, E., Aquilonius, S.-M.: Reactive gliosis and monoamine oxidase B .............................................. 253 Delumeau, J. c., Bentue-Ferrer, D., Gandon, J. M., Amrein, R., Belliard, S., Allain, H.: Monoamine oxidase inhibitors, cognitive functions and neurodegenerative dis- eases ................................................................. 259 Newer monoamine oxidase inhibitors Dostert, P.: Can our knowledge of monoamine oxidase (MAO) help in the design of better MAO inhibitors? ................................................. 269 Balsa, D., Perez, V., Fernandez-Alvarez, E., Unzeta, M.: Kinetic behaviour of some acetylenic indolalkylamine derivatives and their corresponding parent amines '" 281 Fernandez-Garcia, c., Marco, J. L., Fernandez-Alvarez, E.: Acetylenic and allenic derivatives of 2-(5-methoxy-l-methylindolyl)alkylamines as selective inhibitors of MAO-A and MAO-B ................................................... 287 Valoti, M., Costanzo, M., Perez, V., Unzeta, M., Sgaragli, G. P.: Interactions between substituted tryptamine analogues, MAO inhibitors and cytochrome P-450 ...... 291 O'Brien, E. M., Tipton, K. F., Meroni, M., Dostert, P.: Inhibition of monoamine oxidase by clorgyline analogues ................................................. 295 Contents XI Mullan, E. L., Williams, C. H.: Kinetics of inhibition ofMAO-B by N-(2-aminoethyl)- p-chlorobenzamide (Ro 16-6491) and analogues ............................ 307 Wouters, J., Moureau, F., Vercauteren, D. P., Evrard, G., Durant, F., Koenig, J. J., Ducrey, F., Jarreau, F. X.: Experimental and theoretical study of reversible mono- amine oxidase inhibitors: structural approach of the active site of the enzyme . . . 313 Henriot, S., Kuhn, C., Kettler, R., Da Prada, M.: Lazabemide (Ro 19-6327), a reversible and highly sensitive MAO-B inhibitor: preclinical and clinical findings ......... 321 Maruyama, W., Ota, A., Takahashi, A., Nagatsu, T., Naoi, M.: Food-derived hetero- cyclic amines, 3-amino-l,4-dimethyl-5H-pyrido[4,3-b]indole and related amines, as inhibitors of monoamine metabolism ................................... 327 Oxenkrug, G. F., Requintina, P. J., White, K., Yuwiler, A.: Chronopharmacological study of moc1obemide effect on the rat pineal melatonin biosynthesis .......... 335 Rovei, V., CaiUe, D., Curet, 0., Ego, D., Jarreau, F.-X.: Biochemical pharmacology of befloxatone (MD 370503), a new potent reversible MAO-A inhibitor ...... " 339 Curet, 0., Damoiseau, G., Labaune, J.-P., Rovel, V., Jarreau, F.-X.: Effects of be- floxatone, a new potent reversible MAO-A inhibitor, on cortex and striatum mono- amines in freely moving rats ............................................. 349 Celada, P., Bel, N., Artigas, F.: The effects of brofaromine, a reversible MAO-A inhibitor, on extracellular serotonin in the raphe nuclei and frontal cortex of freely moving rats ........................................................... 357 Vieira-Coelho, M. A., Helena Fernandes, M., Soares-da-Silva, P.: In vivo effects of the monoamine oxidase inhibitors R041-1049 and Ro 19-6327 on the production and fate of renal dopamine .................................................. 365 Hinze, C., Kaschube, M., Hardenberg, J.: Pharmacodynamics ofMDL 72974A: absence of effect on the pressor response to oral tyramine ........................... 371 Oxenkrug, G. F., Requintina, P. J., Yuwiler, A., Palfreyman, M. G.: The acute effect of the bioprecursor of the selective brain MAO-A inhibitor, MDL 72392, on rat pineal melatonin biosynthesis ............................................ 377 Oxenkrug, G. F., Requintina, P. J., McIntyre, I. M., White, K.: Chronic effect of the irreversible and reversible selective MAO-A inhibitors on rat pineal melatonin biosynthesis ........................................................... 381 Semicarbazide-sensitive amine oxidases Lyles, G. A.: Properties of mammalian tissue-bound semicarbazide-sensitive amine oxidase: possible clues to its physiological function? . . . . . . . . . . . . . . . . . . . . . . . . . 387 Yu, P. H., Davis, B. A., Boulton, A. A., Zuo, D. M.: Deamination of aliphatic amines by type B monoamine oxidase and semicarbazide-sensitive amine oxidase; phar- macological implications ................................................ 397 Palfreyman, M. G., McDonald, I. A., Bey, P., Danzin, C., Zreika, M., Cremer, G.: Haloallylamine inhibitors of MAO and SSAO and their therapeutic potential ... 407 Lizcano, J. M., Fernandez de Arriba, A., Lyles, G. A., Unzeta, M.: Several aspects on the amino oxidation by semicarbazide-sensitive amine oxidase (SSAO) from bovine lung .................................................................. 415 Buffoni, F., Cambi, S., Banchelli, G., Ignesti, G., Pirisino, R., Raimondi, L.: Semicar- bazide-sensitive amine oxidase activity of guinea pig dorsal skin .............. 421 Crosbie, A. E., Callingham, B. A.: Semicarbazide-sensitive amine oxidases in sheep plasma: interactions with some substrates and inhibitors ..................... 427 Holt, A., Callingham, B. A.: Location of the active site of rat vascular semicarbazide- sensitive amine oxidase ................................................. 433

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