Characterization of a novel gastropod toxin (6-bromo-2-mercaptotryptamine) that inhibits shaker K channel activity

Wayne P. Kelley, Andrew M. Wolters, Jon T Sack, Rebecca A. Jockusch, John C. Jurchen, Evan R. Williams, Jonathan V. Sweedler, William F. Gilly

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


A novel potassium channel antagonist has been purified from the defensive mucus secreted by Calliostoma canaliculatum, a marine snail found in the temperate coastal waters of the western Pacific. The toxin is expelled from the hypobranchial gland as part of a defensive response and is contained within a viscous matrix that minimizes dilution and degradation. The active compound was isolated by multistage microbore HPLC separations followed by bioactivity assays. Nuclear magnetic resonance, combined with electrospray ionization Fourier-transform ion cyclotron resonance and electrospray ionization ion trap mass spectrometry indicate that the active component is a heretofore unknown indole-derivative, a disulfide-linked dimer of 6-bromo-2-mercaptotryptamine (BrMT). Exudates from the hypobranchial glands of various marine mollusks have been sources for dye compounds such as 6-6 dibromoindigo, the ancient dye Tyrian purple. BrMT represents the first correlation of a hypobranchial gland exudate with a molecular response. Voltage clamp experiments with a number of K channel subtypes indicate that BrMT inhibits certain voltage-gated K channels of the Kv1 subfamily.

Original languageEnglish (US)
Pages (from-to)34934-34942
Number of pages9
JournalJournal of Biological Chemistry
Issue number37
StatePublished - Sep 12 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry


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