Total synthesis and biological evaluation of the marine bromopyrrole alkaloid dispyrin: elucidation of discrete molecular targets with therapeutic potential.

Kennedy JP, Brogan JT, Lindsley CW
J Nat Prod. 2008 71 (10): 1783-6

PMID: 18800848 · DOI:10.1021/np800339e

The first total synthesis of dispyrin, a recently reported bromopyrrole alkaloid from Agelas dispar with an unprecedented bromopyrrole tyramine motif, was achieved in three steps on a gram scale (68.4% overall). No biological activity was reported for dispyrin, so we evaluated synthetic dispyrin against>200 discrete molecular targets in radioligand binding and functional assays. Unlike most marine natural products, dispyrin (1) possesses no antibacterial or anticancer activity, but was found to be a potent ligand and antagonist of several therapeutically relevant GPCRs, the alpha1D and alpha2A adrenergic receptors and the H2 and H3 histamine receptors.

MeSH Terms (13)

Adrenergic Agonists Agelas Alkaloids Animals Drug Screening Assays, Antitumor Histamine Agents Hydrocarbons, Brominated Ligands Marine Biology Microbial Sensitivity Tests Molecular Structure Pyrroles Receptors, G-Protein-Coupled

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