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Please use this identifier to cite or link to this item: https://ir.swu.ac.th/jspui/handle/123456789/14351
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dc.contributor.authorSanphanya K.
dc.contributor.authorWattanapitayakul S.K.
dc.contributor.authorPrangsaengtong O.
dc.contributor.authorJo M.
dc.contributor.authorKoizumi K.
dc.contributor.authorShibahara N.
dc.contributor.authorPriprem A.
dc.contributor.authorFokin V.V.
dc.contributor.authorVajragupta O.
dc.date.accessioned2021-04-05T03:34:20Z-
dc.date.available2021-04-05T03:34:20Z-
dc.date.issued2012
dc.identifier.issn0960894X
dc.identifier.other2-s2.0-84859445159
dc.identifier.urihttps://ir.swu.ac.th/jspui/handle/123456789/14351-
dc.identifier.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84859445159&doi=10.1016%2fj.bmcl.2012.02.029&partnerID=40&md5=34a7bad30c6025cd626fb50305c64ffc
dc.description.abstractNovel urea derivatives of alkynes have been designed, synthesized, and evaluated as potential cancer therapeutics leads. The most active 1-((3-chloromethyl)phenyl)-3-prop-2-ynylurea (1) exhibited cytotoxic effect against HELA and MCF-7 cell lines with IC 50 values of 1.55 μM and 1.48 μM, respectively. Further investigation on tube formation assay in human vein umbilical cells (HUVEC) demonstrated that 1 and methyl 4-(3-(3-ethynylureido)benzyloxy) benzoate (6) possess antiangiogenic activity, with minimum effective dose of 25 nM (for 1) and 6.25 μM (for 6). The ED 50 of 1 and 6 were found to be 0.26 μM and 17.52 μM, respectively. The results from in vitro tyrosine kinase assay indicated the EGFR inhibition of 1 over other kinases (VEGFR2, FGFR1 and PDGFRβ). The cytotoxicity of 1 against EGFR overexpressing cell line A431 (IC 50 36 nM) was comparable to that of erlotinib. The binding mode of 1 from docking simulation in the EGFR active site revealed that the urea motif formed hydrogen bonding with Lys745, Thr854 and Asp855 in hydrophobic pocket of EGFR. Compound 1 is considered as a potential lead for further optimization. © 2012 Elsevier Ltd. All rights reserved.
dc.subject1 [(3 chloromethyl)phenyl] 3 prop 2 ynylurea
dc.subject3 prop 2 ynylurea
dc.subject4 (3 (3 ethynylureido)benzyloxy) benzoate
dc.subjectangiogenesis inhibitor
dc.subjectantineoplastic agent
dc.subjectepidermal growth factor receptor
dc.subjecterlotinib
dc.subjectprotein tyrosine kinase
dc.subjectunclassified drug
dc.subjectvasculotropin receptor 2
dc.subjectarticle
dc.subjectcell strain MCF 7
dc.subjectcytotoxicity
dc.subjectdrug screening
dc.subjectdrug synthesis
dc.subjectHeLa cell
dc.subjecthuman
dc.subjecthuman cell
dc.subjecthydrogen bond
dc.subjecthydrophobicity
dc.subjectin vitro study
dc.subjectAngiogenesis Inhibitors
dc.subjectBinding Sites
dc.subjectBreast Neoplasms
dc.subjectCell Line, Tumor
dc.subjectCell Proliferation
dc.subjectFemale
dc.subjectHeLa Cells
dc.subjectHumans
dc.subjectInhibitory Concentration 50
dc.subjectModels, Molecular
dc.subjectUrea
dc.titleSynthesis and evaluation of 1-(substituted)-3-prop-2-ynylureas as antiangiogenic agents
dc.typeArticle
dc.rights.holderScopus
dc.identifier.bibliograpycitationBioorganic and Medicinal Chemistry Letters. Vol 22, No.8 (2012), p.3001-3005
dc.identifier.doi10.1016/j.bmcl.2012.02.029
Appears in Collections:Scopus 1983-2021

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