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

LAUR Repository

Show simple item record

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.date.issued 2019-04-15
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

Files in this item

Files Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record

Search LAUR

Advanced Search


My Account