Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 최선 | * |
dc.date.accessioned | 2016-08-28T12:08:57Z | - |
dc.date.available | 2016-08-28T12:08:57Z | - |
dc.date.issued | 2011 | * |
dc.identifier.issn | 0960-894X | * |
dc.identifier.other | OAK-7169 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/221258 | - |
dc.description.abstract | A series of 5′-halogenated resiniferatoxin analogs have been investigated in order to examine the effect of halogenation in the A-region on their binding and the functional pattern of agonism/antagonism for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Halogenation at the 5-position in the A-region of RTX and of 4-amino RTX shifted the agonism of parent compounds toward antagonism. The extent of antagonism was greater as the size of the halogen increased (I > Br > Cl > F) while the binding affinities were similar, as previously observed for our potent agonists. In this series, 5-bromo-4-amino RTX (39) showed very potent antagonism with K i (ant) = 2.81 nM, which was thus 4.5-fold more potent than 5′-iodo RTX, previously reported as a potent TRPV1 antagonist. Molecular modeling analyses with selected agonists and the corresponding halogenated antagonists revealed a striking conformational difference. The 3-methoxy of the A-region in the agonists remained free to interact with the receptor whereas in the case of the antagonists, the compounds assumed a bent conformation, permitting the 3-methoxy to instead form an internal hydrogen bond with the C4-hydroxyl of the diterpene. © 2010 Elsevier Ltd. All rights reserved. | * |
dc.language | English | * |
dc.title | Receptor activity and conformational analysis of 5′-halogenated resiniferatoxin analogs as TRPV1 ligands | * |
dc.type | Article | * |
dc.relation.issue | 1 | * |
dc.relation.volume | 21 | * |
dc.relation.index | SCI | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 299 | * |
dc.relation.lastpage | 302 | * |
dc.relation.journaltitle | Bioorganic and Medicinal Chemistry Letters | * |
dc.identifier.doi | 10.1016/j.bmcl.2010.11.012 | * |
dc.identifier.wosid | WOS:000285544400059 | * |
dc.identifier.scopusid | 2-s2.0-78650511215 | * |
dc.author.google | Lim K.S. | * |
dc.author.google | Kang D.W. | * |
dc.author.google | Kim Y.S. | * |
dc.author.google | Kim M.S. | * |
dc.author.google | Park S.-G. | * |
dc.author.google | Choi S. | * |
dc.author.google | Pearce L.V. | * |
dc.author.google | Blumberg P.M. | * |
dc.author.google | Lee J. | * |
dc.contributor.scopusid | 최선(8659831000) | * |
dc.date.modifydate | 20240305081003 | * |