title: Unciaphenol, an Oxygenated Analogue of the Bergman Cyclization Product of Uncialamycin Exhibits Anti-HIV Activity.
abstract: Unciaphenol (2), an oxygenated analogue of the Bergman cyclization product of the enediyne uncialamycin (1), has been isolated along with 1 from cultures of the actinomycete Streptomyces uncialis. It is proposed that the C-22 OH substituent in 2 might arise from the attack of a nucleophilic oxygen species on the p-benzyne diradical intermediate IA in the Bergman cyclization of 1. 2 shows in vitro anti-HIV activity against viral strains that are resistant to clinically utilized anti-retroviral therapies.
authors.affiliation: Departments of Chemistry and Earth & Ocean Sciences, University of British Columbia , Vancouver, BC, Canada V6T 1Z1.
authors.forename: David E
authors.initials: DE
authors.lastname: Williams
authors.affiliation: Departments of Chemistry and Earth & Ocean Sciences, University of British Columbia , Vancouver, BC, Canada V6T 1Z1.
authors.forename: Helen
authors.initials: H
authors.lastname: Bottriell
authors.affiliation: Life Sciences Institute, Department of Microbiology and Immunology, University of British Columbia , Vancouver, BC, Canada V6T 1Z3.
authors.forename: Julian
authors.initials: J
authors.lastname: Davies
authors.affiliation: Faculty of Health Sciences and Department of Molecular Biology and Biochemistry, Simon Fraser University , Burnaby, BC, Canada V5A 1S6.
authors.forename: Ian
authors.initials: I
authors.lastname: Tietjen
authors.affiliation: Faculty of Health Sciences and Department of Molecular Biology and Biochemistry, Simon Fraser University , Burnaby, BC, Canada V5A 1S6.|British Columbia Centre for Excellence in HIV/AIDS, St. Paul's Hospital , Vancouver, BC, Canada V6Z 1Y6.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Brockman
authors.affiliation: Departments of Chemistry and Earth & Ocean Sciences, University of British Columbia , Vancouver, BC, Canada V6T 1Z1.
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
mesh_terms: D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003500:Cyclization; D024882:Drug Resistance, Viral; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents; D001688:Biological Products; C512009:uncialamycin; C000605681:unciaphenol