Please use this identifier to cite or link to this item: https://doi.org/10.1002/cmdc.201000520
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dc.titleAurones as Modulators of ABCG2 and ABCB1: Synthesis and Structure-Activity Relationships
dc.contributor.authorSim, H.M.
dc.contributor.authorLoh, K.Y.
dc.contributor.authorYeo, W.K.
dc.contributor.authorLee, C.Y.
dc.contributor.authorGo, M.L.
dc.date.accessioned2014-10-29T01:49:18Z
dc.date.available2014-10-29T01:49:18Z
dc.date.issued2011-04-04
dc.identifier.citationSim, H.M., Loh, K.Y., Yeo, W.K., Lee, C.Y., Go, M.L. (2011-04-04). Aurones as Modulators of ABCG2 and ABCB1: Synthesis and Structure-Activity Relationships. ChemMedChem 6 (4) : 713-724. ScholarBank@NUS Repository. https://doi.org/10.1002/cmdc.201000520
dc.identifier.issn18607179
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/105694
dc.description.abstractThe ability of aurones to modulate the efflux activities of ABCG2 and ABCB1 was investigated by quantifying their effects on the accumulation of pheophorbideA (PhA) in ABCG2-overexpressing MDA-MB-231/R cells and calceinAM in ABCB1-overexpressing MDCKII/MDR1 cells. Key structural features for interactions at both ABCG2 and ABCB1 are a methoxylated ringA, an intact exocyclic double bond, and the location of the carbonyl bond on ringC. Modifications on ringsB and C were less critical and served primarily to moderate activity and selectivity for one or both transporters. These SAR trends were quantified by Free-Wilson analyses and are reflected in a pharmacophore model for PhA accumulation. Several compounds were found to be equipotent with fumitremorginC (FTC) in promoting PhA accumulation, and they also demonstrated strong affinities for ABCB1. These compounds were disubstituted on ringB with methoxy or a combination of methoxy and hydroxy groups. Taken together, our findings highlight the versatility of the aurone template as a lead scaffold for the design of dual-targeting ABCG2 and ABCB1 modulators. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1002/cmdc.201000520
dc.sourceScopus
dc.subjectABCB1
dc.subjectABCG2
dc.subjectAurones
dc.subjectFree-Wilson analysis
dc.subjectModulators
dc.subjectStructure-activity relationships
dc.typeArticle
dc.contributor.departmentPHARMACY
dc.description.doi10.1002/cmdc.201000520
dc.description.sourcetitleChemMedChem
dc.description.volume6
dc.description.issue4
dc.description.page713-724
dc.identifier.isiut000288814900017
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