Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.ejmech.2010.03.023
DC FieldValue
dc.titleFunctionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
dc.contributor.authorLee, C.-Y.
dc.contributor.authorChew, E.-H.
dc.contributor.authorGo, M.-L.
dc.date.accessioned2014-10-29T01:53:11Z
dc.date.available2014-10-29T01:53:11Z
dc.date.issued2010-07
dc.identifier.citationLee, C.-Y., Chew, E.-H., Go, M.-L. (2010-07). Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR. European Journal of Medicinal Chemistry 45 (7) : 2957-2971. ScholarBank@NUS Repository. https://doi.org/10.1016/j.ejmech.2010.03.023
dc.identifier.issn02235234
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/105973
dc.description.abstractThe chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. © 2010 Elsevier Masson SAS.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.ejmech.2010.03.023
dc.sourceScopus
dc.subjectAurones
dc.subjectChemoprevention
dc.subjectNAD(P)H:quinone oxidoreductase 1
dc.subjectPhase II enzyme inducers
dc.typeArticle
dc.contributor.departmentPHARMACY
dc.description.doi10.1016/j.ejmech.2010.03.023
dc.description.sourcetitleEuropean Journal of Medicinal Chemistry
dc.description.volume45
dc.description.issue7
dc.description.page2957-2971
dc.description.codenEJMCA
dc.identifier.isiut000278626400032
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