Literature DB >> 24321344

Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands.

Myeong Seop Kim1, Yooran Ki1, Song Yeon Ahn1, Suyoung Yoon1, Sung-Eun Kim1, Hyeung-Geun Park1, Wei Sun2, Karam Son3, Minghua Cui3, Sun Choi3, Larry V Pearce4, Timothy E Esch4, Ian A Deandrea-Lazarus4, Peter M Blumberg4, Jeewoo Lee5.   

Abstract

The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Capsaicin; Molecular modeling; Resiniferatoxin; TRPV1 antagonist; Vanilloid receptor 1

Mesh：

Substances：

Year:  2013        PMID： 24321344      PMCID： PMC6957263          DOI： 10.1016/j.bmcl.2013.10.064

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  17 in total

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Journal:  Bioorg Med Chem       Date:  2001-01       Impact factor: 3.641

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Authors:  A Szallasi; P M Blumberg
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5.  The cloned capsaicin receptor integrates multiple pain-producing stimuli.

Authors:  M Tominaga; M J Caterina; A B Malmberg; T A Rosen; H Gilbert; K Skinner; B E Raumann; A I Basbaum; D Julius
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Review 8.  Euphorbium: modern research on its active principle, resiniferatoxin, revives an ancient medicine.

Authors:  G Appendino; A Szallasi
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10.  Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper.

Authors:  A Szallasi; P M Blumberg
Journal:  Neuroscience       Date:  1989       Impact factor: 3.590
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  7 in total

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Journal:  Bioorg Med Chem Lett       Date:  2014-04-23       Impact factor: 2.823

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