title: Identification of Pyridinium with Three Indole Moieties as an Antimicrobial Agent.
abstract: A novel pyridinium with three indole moieties, tricepyridinium, was obtained from the culture of an Escherichia coli clone incorporating metagenomic libraries from the marine sponge Discodermia calyx. For the important structural elements of tricepyridinium to be investigated for antibacterial activity, tricepyridinium and its analogues were chemically synthesized. Tricepyridinium had antimicrobial activity, but not against E. coli, and cytotoxicity against P388 cells. Additional bioassays with its synthetic analogues revealed that the intriguing combination of the indole moieties, most likely derived from three tryptamines, as well as the pyridinium moiety were chiefly responsible for its potent biological activities.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Okada
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Tomotoshi
authors.initials: T
authors.lastname: Sugita
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Chin Piow
authors.initials: CP
authors.lastname: Wong
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Toshiyuki
authors.identifier: 0000-0003-2917-1797
authors.initials: T
authors.lastname: Wakimoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Ikuro
authors.identifier: 0000-0002-3640-888X
authors.initials: I
authors.lastname: Abe
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000737:chemistry / Q000187:drug effects; D007211:Indoles / Q000737:chemistry*; D007941:Leukemia P388; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry / Q000302:isolation & purification*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D007211:Indoles; D011726:Pyridinium Compounds; C000621481:tricepyridinium