Pitucamycin: structural merger of a phenoxazinone with an epoxyquinone antibiotic

J Nat Prod. 2010 Sep 24;73(9):1461-4. doi: 10.1021/np100344u.

Abstract

Chemical profiling of a Streptomyces griseus strain isolated from an old building with moisture damage led to the discovery of two novel phenoxazinones, chandrananimycin D and pitucamycin , along with the known grixazone B. Pitucamycin represents an unprecedented hybrid molecule composed of a phenoxazinone and an enaminomycin-like epoxyquinone moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Bacillus subtilis / drug effects
  • Basidiomycota / drug effects
  • Candida albicans / drug effects
  • Drug Screening Assays, Antitumor
  • Enterococcus faecalis / drug effects
  • Escherichia coli / drug effects
  • HeLa Cells
  • Humans
  • K562 Cells
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Mycobacterium / drug effects
  • Oxazines* / chemistry
  • Oxazines* / isolation & purification
  • Oxazines* / pharmacology
  • Penicillium chrysogenum / drug effects
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects
  • Streptomyces griseus / chemistry*

Substances

  • 1-((2-(acetylamino)-2-carboxyethyl)thio)-2-amino-3-oxo-8-carboxyl-3H-phenoxiazine
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Oxazines
  • chandrananimycin D
  • pitucamycin
  • phenoxazinone