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

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

  • Bioorg Med Chem Lett. 2014 Jan 1;24(1):382-5. doi: 10.1016/j.bmcl.2013.10.064.
Myeong Seop Kim 1,  Yooran Ki 1,  Song Yeon Ahn 1,  Suyoung Yoon 1,  Sung-Eun Kim 1,  Hyeung-Geun Park 1,  Wei Sun 2,  Karam Son 3,  Minghua Cui 3,  Sun Choi 3,  Larry V Pearce 4,  Timothy E Esch 4,  Ian A Deandrea-Lazarus 4,  Peter M Blumberg 4,  Jeewoo Lee 5
Affiliations

Affiliations

  • 1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea.
  • 2 Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.
  • 3 National Leading Research Lab of Molecular Modeling & Drug Design, College of Pharmacy, Graduate School of Pharmaceutical Sciences and Global Top 5 Research Program, Ewha Womans University, Seoul 120-750, Republic of Korea.
  • 4 Laboratory of Cancer Biology and Genetics, Center for Cancer Research, National Cancer Institute, NIH, Bethesda, MD 20892, USA.
  • 5 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea. Electronic address: jeewoo@snu.ac.kr.
PMID: 24321344 DOI: 10.1016/j.bmcl.2013.10.064
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.

Keywords

Capsaicin; Molecular modeling; Resiniferatoxin; TRPV1 antagonist; Vanilloid receptor 1.

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