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Nobilamides A-H, long-acting transient receptor potential vanilloid-1 (TRPV1) antagonists from mollusk-associated bacteria

Zhenjian Lin; Christopher A. Reilly; Rowena Antemano; Ronald W. Hughen; Lenny Marett; Gisela P. Concepcion; Margo G. Haygood; Baldomero M. Olivera; Alan Light; Eric W. Schmidt

(Profiled Author: Margo Haygood)

Journal of Medicinal Chemistry. 2011;54(11):3746-3755.


New compounds nobilamides A-H and related known compounds A-3302-A and A-3302-B were isolated based upon their suppression of capsaicin-induced calcium uptake in a mouse dorsal root ganglion primary cell culture assay. Two of these compounds, nobilamide B and A-3302-A, were shown to be long-acting antagonists of mouse and human TRPV1 channels, abolishing activity for >1 h after removal of drug presumably via a covalent attachment. Other derivatives also inhibited the TRPV1 channel, albeit with low potency, affording a structure-activity profile to support the proposed mechanism of action. While the activities were modest, we propose a new mechanism of action and a new site of binding for these inhibitors that may spur development of related analogues for treatment of pain. © 2011 American Chemical Society.

PMID: 21524089     PMCID: PMC3133741    

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