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

426 Pages·1994·8.6 MB·English

by  Dr. W. Weyler (auth.), Prof. Dr. K. F. Tipton, Prof. Dr. M. B. H. Youdim, Dr. C. J. Barwell, Prof. Dr. B. A. Callingham, Dr. G. A. Lyles (eds.)

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
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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