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

Research output: Contribution to journalArticle

51 Citations (Scopus)

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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NAD(P)H Dehydrogenase (Quinone)
Streptomyces
Phenazines
Nitric Oxide Synthase Type II
Inhibitory Concentration 50
Lead
2-bromo-1-hydroxyphenazine
Neoplasms
phenazine

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from streptomyces species, strain CNS284. / Conda-Sheridan, Martin; Marler, Laura; Park, Eun Jung; Kondratyuk, Tamara P.; Jermihov, Katherine; Mesecar, Andrew D.; Pezzuto, John M.; Asolkar, Ratnakar N.; Fenical, William; Cushman, Mark.

In: Journal of Medicinal Chemistry, Vol. 53, No. 24, 23.12.2010, p. 8688-8699.

Research output: Contribution to journalArticle

Conda-Sheridan, M, Marler, L, Park, EJ, Kondratyuk, TP, Jermihov, K, Mesecar, AD, Pezzuto, JM, Asolkar, RN, 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, vol. 53, no. 24, pp. 8688-8699. https://doi.org/10.1021/jm1011066
Conda-Sheridan, Martin ; Marler, Laura ; Park, Eun Jung ; Kondratyuk, Tamara P. ; Jermihov, Katherine ; Mesecar, Andrew D. ; Pezzuto, John M. ; Asolkar, Ratnakar N. ; Fenical, William ; Cushman, Mark. / Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from streptomyces species, strain CNS284. In: Journal of Medicinal Chemistry. 2010 ; Vol. 53, No. 24. pp. 8688-8699.
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