{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T04:04:34Z","timestamp":1791173074839,"version":"4.1.0"},"reference-count":37,"publisher":"Elsevier BV","issue":"6","license":[{"start":{"date-parts":[[2007,7,1]],"date-time":"2007-07-01T00:00:00Z","timestamp":1183248000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Life Sciences"],"published-print":{"date-parts":[[2007,7]]},"DOI":"10.1016\/j.lfs.2007.06.014","type":"journal-article","created":{"date-parts":[[2007,6,29]],"date-time":"2007-06-29T17:56:33Z","timestamp":1183139793000},"page":"458-467","source":"Crossref","is-referenced-by-count":7,"title":["Neurotoxicity studies with the monoamine oxidase B substrate 1-methyl-3-phenyl-3-pyrroline"],"prefix":"10.1016","volume":"81","author":[{"given":"Modupe O.","family":"Ogunrombi","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarel F.","family":"Malan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gisella","family":"Terre'Blanche","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kay","family":"Castagnoli","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"suffix":"Jr.","given":"Neal","family":"Castagnoli","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jacobus J.","family":"Bergh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jacobus P.","family":"Petzer","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.lfs.2007.06.014_bib1","doi-asserted-by":"crossref","first-page":"887","DOI":"10.1021\/ja01378a035","article-title":"Gamma-pyrrolidino- and gamma-pyrrolidinopropyl benzoates","volume":"51","author":"Andrews","year":"1929","journal-title":"Journal of the American Chemical Society"},{"key":"10.1016\/j.lfs.2007.06.014_bib2","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1016\/0003-2697(76)90527-3","article-title":"A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding","volume":"72","author":"Bradford","year":"1976","journal-title":"Analytical Biochemistry"},{"issue":"4","key":"10.1016\/j.lfs.2007.06.014_bib3","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1021\/tx970001d","article-title":"The neuronal nitric oxide synthase inhibitor 7-nitroindazole also inhibits the monoamine oxidase-B-catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine","volume":"10","author":"Castagnoli","year":"1997","journal-title":"Chemical Research in Toxicology"},{"issue":"5","key":"10.1016\/j.lfs.2007.06.014_bib4","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1021\/tx000224v","article-title":"Neuroprotection in the MPTP Parkinsonian C57BL\/6 mouse model by a compound isolated from tobacco","volume":"14","author":"Castagnoli","year":"2001","journal-title":"Chemical Research in Toxicology"},{"issue":"2","key":"10.1016\/j.lfs.2007.06.014_bib5","doi-asserted-by":"crossref","first-page":"574","DOI":"10.1016\/0006-291X(84)91293-2","article-title":"Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase","volume":"120","author":"Chiba","year":"1984","journal-title":"Biochemical and Biophysical Research Communications"},{"issue":"3","key":"10.1016\/j.lfs.2007.06.014_bib6","doi-asserted-by":"crossref","first-page":"1228","DOI":"10.1016\/0006-291X(85)91071-X","article-title":"Active uptake of MPP+, a metabolite of MPTP, by brain synaptosomes","volume":"128","author":"Chiba","year":"1985","journal-title":"Biochemical and Biophysical Research Communications"},{"issue":"4","key":"10.1016\/j.lfs.2007.06.014_bib7","doi-asserted-by":"crossref","first-page":"1771","DOI":"10.1046\/j.1471-4159.1997.69041771.x","article-title":"Inhibition of monoamine oxidase contributes to the protective effect of 7-nitroindazole against MPTP neurotoxicity","volume":"69","author":"Di Monte","year":"1997","journal-title":"Journal of Neurochemistry"},{"key":"10.1016\/j.lfs.2007.06.014_bib8","doi-asserted-by":"crossref","first-page":"3212","DOI":"10.1039\/p19900003212","article-title":"A regiospecific synthesis of 3-arylpyrroles","volume":"11","author":"Gallagher","year":"1990","journal-title":"Journal of the Chemical Society. Perkin Transactions 1"},{"issue":"5","key":"10.1016\/j.lfs.2007.06.014_bib9","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1016\/j.physbeh.2006.01.033","article-title":"Cortical\/hippocampal monoamines, HPA-axis changes and aversive behavior following stress and restress in an animal model of post-traumatic stress disorder","volume":"87","author":"Harvey","year":"2006","journal-title":"Physiology & Behavior"},{"issue":"4656","key":"10.1016\/j.lfs.2007.06.014_bib10","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1126\/science.6610213","article-title":"Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine in mice","volume":"224","author":"Heikkila","year":"1984","journal-title":"Science"},{"issue":"5985","key":"10.1016\/j.lfs.2007.06.014_bib11","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1038\/311467a0","article-title":"Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors","volume":"311","author":"Heikkila","year":"1984","journal-title":"Nature"},{"key":"10.1016\/j.lfs.2007.06.014_bib12","doi-asserted-by":"crossref","first-page":"4015","DOI":"10.1016\/S0040-4039(01)89727-6","article-title":"Pyrrolidine as a common contaminant of \u03943-pyrroline: correct structure of the product from isatin and \u03943-pyrroline","volume":"41","author":"Hudson","year":"1967","journal-title":"Tetrahedron Letters"},{"issue":"2","key":"10.1016\/j.lfs.2007.06.014_bib13","doi-asserted-by":"crossref","first-page":"856","DOI":"10.1016\/S0022-3565(24)35176-6","article-title":"Species-dependent differences in monoamine oxidase A and B-catalyzed oxidation of various C4 substituted 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl derivatives","volume":"291","author":"Inoue","year":"1999","journal-title":"Journal of Pharmacology and Experimental Therapeutics"},{"issue":"2","key":"10.1016\/j.lfs.2007.06.014_bib14","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1016\/0014-2999(84)90740-4","article-title":"Uptake of MPP+ by dopamine neurons explains selectivity of parkinsonism-inducing neurotoxin, MPTP","volume":"106","author":"Javitch","year":"1984","journal-title":"European Journal of Pharmacology"},{"key":"10.1016\/j.lfs.2007.06.014_bib15","doi-asserted-by":"crossref","first-page":"2301","DOI":"10.1002\/cber.19691020719","article-title":"\u00dcber die umsetzung von phenalen mit vinylogen farmamidinium-salzen: Synthese substituierter pyrene und des azuleno[5,6,7-cd]phenalens","volume":"102","author":"Jutz","year":"1969","journal-title":"Chemische Berichte"},{"issue":"22","key":"10.1016\/j.lfs.2007.06.014_bib16","doi-asserted-by":"crossref","first-page":"4165","DOI":"10.1021\/jm00100a023","article-title":"Synthesis of novel MPTP analogs as potential monoamine oxidase B (MAO-B) inhibitors","volume":"35","author":"Kalgutkar","year":"1992","journal-title":"Journal of Medicinal Chemistry"},{"key":"10.1016\/j.lfs.2007.06.014_bib17","doi-asserted-by":"crossref","first-page":"1423","DOI":"10.1002\/cber.19560890609","article-title":"Neue synthese von b-pyrrolidonen; Darstellung von dl-g-oxo-prolin, dl-allo-hydroxy-prolin und 4-\u00e4thoxy-pyrrol-carbons\u00e4ure-(2)","volume":"89","author":"Kuhn","year":"1956","journal-title":"Chemische Berichte"},{"issue":"41","key":"10.1016\/j.lfs.2007.06.014_bib18","doi-asserted-by":"crossref","first-page":"12135","DOI":"10.1021\/ja0205434","article-title":"3-Pyrrolines are mechanism-based inactivators of the quinone-dependent amine oxidases but only substrates of the flavin-dependent amine oxidases","volume":"124","author":"Lee","year":"2002","journal-title":"Journal of the American Chemical Society"},{"issue":"5958","key":"10.1016\/j.lfs.2007.06.014_bib19","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1038\/311464a0","article-title":"Intraneuronal generation of a pyridinium metabolite may cause drug-induced parkinsonism","volume":"311","author":"Markey","year":"1984","journal-title":"Nature"},{"issue":"26","key":"10.1016\/j.lfs.2007.06.014_bib20","doi-asserted-by":"crossref","first-page":"2503","DOI":"10.1016\/0024-3205(85)90146-8","article-title":"Inhibition of NADH-linked oxidation in brain mitochondria by 1-methyl-4-phenyl-pyridine, a metabolite of the neurotoxin, 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine","volume":"36","author":"Nicklas","year":"1985","journal-title":"Life Sciences"},{"issue":"1","key":"10.1016\/j.lfs.2007.06.014_bib21","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/0304-3940(87)90076-0","article-title":"4-Phenylpyridine and three other analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lack dopaminergic nigrostriatal neurotoxicity in mice and marmosets","volume":"75","author":"Perry","year":"1987","journal-title":"Neuroscience Letters"},{"issue":"7","key":"10.1016\/j.lfs.2007.06.014_bib22","doi-asserted-by":"crossref","first-page":"1299","DOI":"10.1016\/S0968-0896(02)00648-X","article-title":"Inhibition of monoamine oxidase B by selective adenosine A2A receptor antagonists","volume":"11","author":"Petzer","year":"2003","journal-title":"Bioorganic & Medicinal Chemistry"},{"issue":"6","key":"10.1016\/j.lfs.2007.06.014_bib23","doi-asserted-by":"crossref","first-page":"829","DOI":"10.1021\/jo00805a022","article-title":"The formic acid-formaldehyde methylation of amines","volume":"36","author":"Pine","year":"1971","journal-title":"Journal of Organic Chemistry"},{"key":"10.1016\/j.lfs.2007.06.014_bib24","series-title":"MPTP: A Neurotoxin Producing a Parkinsonian Syndrome","first-page":"703","article-title":"Recommended practices for the safe handling of MPTP","author":"Pitts","year":"1986"},{"issue":"4","key":"10.1016\/j.lfs.2007.06.014_bib25","doi-asserted-by":"crossref","first-page":"1184","DOI":"10.1111\/j.1471-4159.1991.tb11409.x","article-title":"Interaction of 1-methyl-4-phenylpyridinium ion (MPP+) and its analogs with the rotenone\/piericidin binding site of NADH dehydrogenase","volume":"56","author":"Ramsay","year":"1991","journal-title":"Journal of Neurochemistry"},{"issue":"8","key":"10.1016\/j.lfs.2007.06.014_bib26","doi-asserted-by":"crossref","first-page":"2221","DOI":"10.1021\/jm00170a029","article-title":"In vivo intracerebral microdialysis studies in rats of MPP+ analogues and related charged species","volume":"33","author":"Rollema","year":"1990","journal-title":"Journal of Medicinal Chemistry"},{"key":"10.1016\/j.lfs.2007.06.014_bib27","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1016\/S0076-6879(87)42075-2","article-title":"Preparation of the flavin-containing aromatic amine oxidases of human placenta and beef liver","volume":"142","author":"Salach","year":"1987","journal-title":"Methods in Enzymology"},{"issue":"2","key":"10.1016\/j.lfs.2007.06.014_bib28","doi-asserted-by":"crossref","first-page":"274","DOI":"10.1016\/0003-9861(90)90330-2","article-title":"Inhibition of mitochondrial respiration by analogues of the dopaminergic neurotoxin 1-methyl-4-phenylpyridinium: structural requirements for accumulation-dependent enhanced inhibitory potency on intact mitochondria","volume":"280","author":"Sayre","year":"1990","journal-title":"Archives of Biochemistry and Biophysics"},{"issue":"11","key":"10.1016\/j.lfs.2007.06.014_bib29","doi-asserted-by":"crossref","first-page":"1263","DOI":"10.1007\/s007020100004","article-title":"Neurochemical findings in the MPTP model of Parkinson's disease","volume":"108","author":"Schmidt","year":"2001","journal-title":"Journal of Neural Transmission"},{"issue":"1","key":"10.1016\/j.lfs.2007.06.014_bib30","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/0300-483X(88)90169-2","article-title":"Mechanism of the neurotoxicity of 1-methyl-4-phenylpyridinium (MPP+), the toxic bioactivation product of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)","volume":"49","author":"Singer","year":"1988","journal-title":"Toxicology"},{"issue":"1","key":"10.1016\/j.lfs.2007.06.014_bib31","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.molbrainres.2004.09.017","article-title":"The MPTP model of Parkinson's disease","volume":"134","author":"Smeyne","year":"2005","journal-title":"Brain Research. Molecular Brain Research"},{"issue":"1","key":"10.1016\/j.lfs.2007.06.014_bib32","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0006-8993(90)90308-X","article-title":"Astroglial ablation prevents MPTP-induced nigrostriatal neuronal death","volume":"509","author":"Takada","year":"1990","journal-title":"Brain Research"},{"issue":"10","key":"10.1016\/j.lfs.2007.06.014_bib33","doi-asserted-by":"crossref","first-page":"3512","DOI":"10.1016\/j.bmc.2006.01.011","article-title":"Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC)","volume":"14","author":"Vlok","year":"2006","journal-title":"Bioorganic & Medicinal Chemistry"},{"issue":"2","key":"10.1016\/j.lfs.2007.06.014_bib34","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/S0968-0896(97)10020-7","article-title":"1-Methyl-3-pyrrolines and 2-methylisoindolines: new classes of cyclic tertiary amine monoamine oxidase B substrates","volume":"6","author":"Wang","year":"1998","journal-title":"Bioorganic & Medicinal Chemistry"},{"issue":"Pt 1","key":"10.1016\/j.lfs.2007.06.014_bib35","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1042\/bj3360063","article-title":"Mechanism-based inhibition of monoamine oxidase by 3-aryl-\u03943-pyrrolines","volume":"336","author":"Williams","year":"1998","journal-title":"Biochemical Journal"},{"key":"10.1016\/j.lfs.2007.06.014_bib36","first-page":"225","article-title":"The behaviour of aryl pyrrolines with monoamine oxidase","volume":"7","author":"Williams","year":"1999","journal-title":"Neurobiology (Budapest)"},{"key":"10.1016\/j.lfs.2007.06.014_bib37","doi-asserted-by":"crossref","first-page":"752","DOI":"10.1021\/jm01239a007","article-title":"Pyrrolidines. VII. 3-Hydroxy-1-pyrrolidinecarboxylic acid esters","volume":"5","author":"Wu","year":"1962","journal-title":"Journal of Medicinal and Pharmaceutical Chemistry"}],"container-title":["Life Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0024320507004729?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0024320507004729?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,1,18]],"date-time":"2025-01-18T00:23:01Z","timestamp":1737159781000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0024320507004729"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,7]]},"references-count":37,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2007,7]]}},"alternative-id":["S0024320507004729"],"URL":"https:\/\/doi.org\/10.1016\/j.lfs.2007.06.014","relation":{},"ISSN":["0024-3205"],"issn-type":[{"value":"0024-3205","type":"print"}],"subject":[],"published":{"date-parts":[[2007,7]]}}}