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Design and synthesis of 18F-labeled neurotoxic analogs of MPTP

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dc.contributor.author Riachi, Naji J.
dc.contributor.author Berridge, Marc S.
dc.contributor.author Sayre, Lawrence M.
dc.contributor.author Arora, Pramod K.
dc.contributor.author Terris, Andrew H.
dc.contributor.author Harik, Sami I.
dc.date.accessioned 2019-04-15T11:00:33Z
dc.date.available 2019-04-15T11:00:33Z
dc.date.copyright 1993 en_US
dc.identifier.issn 1520-4804 en_US
dc.identifier.uri http://hdl.handle.net/10725/10438
dc.description.abstract We report on the synthesis of two fluorine-18 labeled analogs of l-methyl-4-phenyl-1, 2, 3, 6- tetrahydropyridine (MPTP). A piperidyl triazene was fluorinated to produce [18F]-l-methyl-4- (2-fluorophenyl)-l, 2, 3, 6-tetrahydropyridine (2'-F-MPTP, 12) in very low yield, and l-methyl-4-[2-(fluoromethyl) phenyl]-1, 2, 3, 6-tetrahydropyridine (2'-FCH2-MPTP, 11) was labeled with 18F by nucleophilic displacement of the corresponding chloride in 60% yield. The biodistribution in mice of the latter radiotracer and its oxidation to l-methyl-4-[2-(fluoromethyl)phenyl]pyridinium (2'-FCH2-MPP+, 6) is also reported. The kinetics of oxidation of 2'-FCH2-MPTP and its solvolysis products (the corresponding 2'-hydroxymethyl and 2'-chloromethyl analogs) by rat liver monoamine oxidase were investigated. 2'-FCH2-MPTP accumulated to a useful degree in the brain, was oxidized by monoamine oxidase in vitro, was converted to the oxidation product in brain in vivo, and had a neurotoxic potency similar to that of MPTP. We feel it may be useful as an 18F-labeled radiopharmaceutical for positron tomographic studies of the mechanisms of MPTP toxicity. en_US
dc.language.iso en en_US
dc.title Design and synthesis of 18F-labeled neurotoxic analogs of MPTP en_US
dc.type Article en_US
dc.description.version Published en_US
dc.author.school SOM en_US
dc.author.idnumber 200902731 en_US
dc.author.department N/A en_US
dc.description.embargo N/A en_US
dc.relation.journal Journal of Medical Chemistry en_US
dc.journal.volume 36 en_US
dc.journal.issue 9 en_US
dc.article.pages 1284-1290 en_US
dc.identifier.doi http://dx.doi.org/10.1021/jm00061a021 en_US
dc.identifier.ctation Berridge, M. S., Sayre, L. M., Arora, P. K., Terris, A. H., Riachi, N. J., & Harik, S. I. (1993). Design and synthesis of 18F-labeled neurotoxic analogs of MPTP. Journal of medicinal chemistry, 36(9), 1284-1290. en_US
dc.author.email naji.riachi@lau.edu.lb en_US
dc.identifier.tou http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php en_US
dc.identifier.url https://pubs.acs.org/doi/abs/10.1021/jm00061a021?journalCode=jmcmar en_US
dc.orcid.id https://orcid.org/0000-0002-8652-9698 en_US
dc.author.affiliation Lebanese American University en_US


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