Trachycladindoles A-G: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer.
A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a panel of human cancer cell lines and their structures were assigned on the basis of detailed spectroscopic analysis. Preliminary structure activity relationship (SAR) investigations by co-metabolite defined structural features key to the trachycladindole pharmacophore, highlighting an unusual bioactive molecular motif deserving of future investigation.
Capon
Robert J
RJ
Institute for Molecular Bioscience, The University of Queensland, St Lucia, Queensland, Australia. r.capon@imb.uq.ed.au
Peng
Chongsheng
C
Dooms
Cedric
C
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001315:Australia; D001943:Breast Neoplasms / Q000188:drug therapy*; D045744:Cell Line, Tumor; D015179:Colorectal Neoplasms / Q000188:drug therapy*; D004354:Drug Screening Assays, Antitumor; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008175:Lung Neoplasms / Q000188:drug therapy*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D007211:Indoles; C531585:trachycladindole A; C531586:trachycladindole B; C532241:trachycladindole C