{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T20:12:10Z","timestamp":1777493530157,"version":"3.51.4"},"reference-count":59,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2002,7,17]],"date-time":"2002-07-17T00:00:00Z","timestamp":1026864000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["European Journal of Biochemistry"],"published-print":{"date-parts":[[2002,8]]},"abstract":"<jats:p>Four substrate analogs, 4\u2010(2\u2010naphthyloxy)\u20102\u2010butyn\u20101\u2010amine (<jats:bold>1<\/jats:bold>), 1,4\u2010diamino\u20102\u2010chloro\u20102\u2010butene (<jats:bold>2<\/jats:bold>), 1,6\u2010diamino\u20102,4\u2010hexadiyne (<jats:bold>3<\/jats:bold>), and 2\u2010chloro\u20105\u2010phthalimidopentylamine (<jats:bold>4<\/jats:bold>) have been tested as inhibitors against mammalian, plant, bacterial, and fungal copper\u2010containing amine oxidases: bovine plasma amine oxidase (BPAO), equine plasma amine oxidase (EPAO), pea seedling amine oxidase (PSAO), <jats:italic>Arthrobacter globiformis<\/jats:italic> amine oxidase (AGAO), <jats:italic>Escherichia coli<\/jats:italic> amine oxidase (ECAO), and <jats:italic>Pichia pastoris<\/jats:italic> lysyl oxidase (PPLO). Reactions of 1,4\u2010diamino\u20102\u2010butyne with selected amine oxidases were also examined. Each substrate analog contains a functional group that chemical precedent suggests could produce mechanism\u2010based inactivation. Striking differences in selectivity and rates of inactivation were observed. For example, between two closely related plasma enzymes, BPAO is more sensitive than EPAO to <jats:bold>1<\/jats:bold> and <jats:bold>3<\/jats:bold>, while the reverse is true for <jats:bold>2<\/jats:bold> and <jats:bold>4<\/jats:bold>. In general, inactivation appears to arise in some cases from TPQ cofactor modification and in other cases from alkylation of protein residues in a manner that blocks access of substrate to the active site. Notably, <jats:bold>1<\/jats:bold> completely inhibits AGAO at stoichiometric concentrations and is not a substrate, but is an excellent substrate of PSAO and inhibition is observed only at very high concentrations. Structural models of <jats:bold>1<\/jats:bold> in Schiff base linkage to the TPQ cofactor in AGAO and PSAO (for which crystal structures are available) reveal substantial differences in the degree of interaction of bound <jats:bold>1<\/jats:bold> with side\u2010chain residues, consistent with the widely divergent activities. Collectively, these results suggest that the development of highly selective amine oxidase inhibitors is feasible.<\/jats:p>","DOI":"10.1046\/j.1432-1033.2002.03035.x","type":"journal-article","created":{"date-parts":[[2003,3,11]],"date-time":"2003-03-11T18:33:14Z","timestamp":1047407594000},"page":"3645-3658","source":"Crossref","is-referenced-by-count":36,"title":["Towards the development of selective amine oxidase inhibitors"],"prefix":"10.1111","volume":"269","author":[{"given":"Eric M.","family":"Shepard","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jennifer","family":"Smith","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bradley O.","family":"Elmore","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jason A.","family":"Kuchar","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lawrence M.","family":"Sayre","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David M.","family":"Dooley","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2002,7,17]]},"reference":[{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.2111581"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi9628836"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi9824994"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00190a019"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-5793(94)00884-1"},{"key":"e_1_2_8_7_2","doi-asserted-by":"crossref","first-page":"32039","DOI":"10.1016\/S0021-9258(18)31595-3","article-title":"Evidence for a self\u2010catalytic mechanism of 2,4,5\u2010 trihydroxyphenylalanine quinone biogenesis in yeast copper amine oxidase","volume":"269","author":"Cai D.","year":"1994","journal-title":"J. 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