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Mar. Drugs 2017, 15(4), 87;

Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya Street, 16/10, Moscow 117997, Russia
G.B. Elyakov Pacific Institute of Bioorganic Chemistry (PIBOC), Russian Academy of Sciences, Prospect 100 let Vladivostoku, 159, Vladivostok 690022, Russia
Sechenov First Moscow State Medical University, Institute of Molecular Medicine, Trubetskaya str.8, bld. 2, Moscow 119991, Russia
Korea Institute of Ocean Science & Technology, Marine Natural Products Laboratory, Ansan 426-744, Korea
Author to whom correspondence should be addressed.
Academic Editor: Kirsten Benkendorff
Received: 16 January 2017 / Revised: 28 February 2017 / Accepted: 20 March 2017 / Published: 23 March 2017
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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Marine sponges contain a variety of low-molecular-weight compounds including guanidine alkaloids possessing different biological activities. Monanchomycalin B and urupocidin A were isolated from the marine sponge Monanchora pulchra. We found that they act as inhibitors of the TRPV1, TRPV2, and TRPV3 channels, but are inactive against the TRPA1 receptor. Monanchomycalin B is the most active among all published marine alkaloids (EC50 6.02, 2.84, and 3.25 μM for TRPV1, TRPV2, and TRPV3, correspondingly). Moreover, monanchomycalin B and urupocidin A are the first samples of marine alkaloids affecting the TRPV2 receptor. Two semi-synthetic urupocidin A derivatives were also obtained and tested against TRP (Transient Receptor Potential) receptors that allowed us to collect some data concerning the structure-activity relationship in this series of compounds. We showed that the removal of one of three side chains or double bonds in the other side chains in urupocidin A led to a decrease of the inhibitory activities. New ligands specific to the TRPV subfamily may be useful for the design of medicines as in the study of TRP channels biology. View Full-Text
Keywords: guanidine alkaloids; sponge; Monanchora pulchra; TRPV1; TRPV2; TRPV3; TRPA1 guanidine alkaloids; sponge; Monanchora pulchra; TRPV1; TRPV2; TRPV3; TRPA1

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Korolkova, Y.; Makarieva, T.; Tabakmakher, K.; Shubina, L.; Kudryashova, E.; Andreev, Y.; Mosharova, I.; Lee, H.-S.; Lee, Y.-J.; Kozlov, S. Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors. Mar. Drugs 2017, 15, 87.

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