Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from streptomyces species, strain CNS284

Martin Conda-Sheridan, Laura Marler, Eun Jung Park, Tamara P. Kondratyuk, Katherine Jermihov, Andrew D. Mesecar, John M. Pezzuto, Ratnakar N. Asolkar, William Fenical, Mark Cushman

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Abstract

The isolation of 2-bromo-1-hydroxyphenazine from a marine Streptomyces species, strain CNS284, and its activity against NF-κB, suggested that a short and flexible route for the synthesis of this metabolite and a variety of phenazine analogues should be developed. Numerous phenazines were subsequently prepared and evaluated as inducers of quinone reductase 1 (QR1) and inhibitors of quinone reductase 2 (QR2), NF-κB, and inducible nitric oxide synthase (iNOS). Several of the active phenazine derivatives displayed IC50 values vs QR1 induction and QR2 inhibition in the nanomolar range, suggesting that they may find utility as cancer chemopreventive agents.

Original languageEnglish (US)
Pages (from-to)8688-8699
Number of pages12
JournalJournal of Medicinal Chemistry
Volume53
Issue number24
DOIs
StatePublished - Dec 23 2010

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ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

Conda-Sheridan, M., Marler, L., Park, E. J., Kondratyuk, T. P., Jermihov, K., Mesecar, A. D., Pezzuto, J. M., Asolkar, R. N., Fenical, W., & Cushman, M. (2010). Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from streptomyces species, strain CNS284. Journal of Medicinal Chemistry, 53(24), 8688-8699. https://doi.org/10.1021/jm1011066