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A one-pot synthesis and biological activity of ageladine A and analogues

Shengule, Sudhir; Loa-Kum-Cheung, Wendy; Blairvacq, Melina; Meijer, Laurent; Nakao, Yoichi; Karuso, Peter; Parish, Christopher

Description

A one-pot synthesis of ageladine A and analogues is reported. The key Pictet-Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found...[Show more]

dc.contributor.authorShengule, Sudhir
dc.contributor.authorLoa-Kum-Cheung, Wendy
dc.contributor.authorBlairvacq, Melina
dc.contributor.authorMeijer, Laurent
dc.contributor.authorNakao, Yoichi
dc.contributor.authorKaruso, Peter
dc.contributor.authorParish, Christopher
dc.date.accessioned2015-12-10T23:30:59Z
dc.identifier.issn0022-2623
dc.identifier.urihttp://hdl.handle.net/1885/68419
dc.description.abstractA one-pot synthesis of ageladine A and analogues is reported. The key Pictet-Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found to be highly active in an antiangiogenic screen, suggesting that the angiogenic activity of ageladine A is not associated with MMP inhibition but rather kinase inhibitory activity. Cytotoxicity was excluded as a mode of action by the assay of ageladine A and an analogue against 60 human cell lines.
dc.publisherAmerican Chemical Society
dc.sourceJournal of Medicinal Chemistry
dc.subjectKeywords: ageladine a; ageladine a derivative; aldehyde derivative; antineoplastic agent; matrix metalloproteinase; natural product; phosphotransferase; unclassified drug; antiangiogenic activity; article; controlled study; drug activity; drug structure; enzyme act
dc.titleA one-pot synthesis and biological activity of ageladine A and analogues
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume54
dc.date.issued2011
local.identifier.absfor030402 - Biomolecular Modelling and Design
local.identifier.ariespublicationf2965xPUB1707
local.type.statusPublished Version
local.contributor.affiliationShengule, Sudhir, Macquarie University
local.contributor.affiliationLoa-Kum-Cheung, Wendy, Macquarie University
local.contributor.affiliationParish, Christopher, College of Medicine, Biology and Environment, ANU
local.contributor.affiliationBlairvacq, Melina, CNRS
local.contributor.affiliationMeijer, Laurent, CNRS
local.contributor.affiliationNakao, Yoichi, Waseda University
local.contributor.affiliationKaruso, Peter, Macquarie University
local.description.embargo2037-12-31
local.bibliographicCitation.issue7
local.bibliographicCitation.startpage2492
local.bibliographicCitation.lastpage2503
local.identifier.doi10.1021/jm200039m
local.identifier.absseo920102 - Cancer and Related Disorders
dc.date.updated2016-02-24T08:16:21Z
local.identifier.scopusID2-s2.0-79953767989
local.identifier.thomsonID000289215700044
CollectionsANU Research Publications

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