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Chemical Compound Review

Phenoxazinone     phenoxazin-3-one

Synonyms: SureCN8067, CHEMBL147062, AG-E-40007, CTK0I2125, AR-1F3395, ...
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Disease relevance of Phenoxazinone


High impact information on Phenoxazinone


Biological context of Phenoxazinone

  • Prevention of growth of human lung carcinoma cells and induction of apoptosis by a novel phenoxazinone, 2-amino-4,4alpha-dihydro-4alpha,7-dimethyl-3H-phenoxazine-3-one [5].
  • The structure was confirmed by chemical synthesis through oxidative dimerization of ethyl 3-amino-4-hydroxybenzoate with 2-(N-methylamino)phenol and subsequent hydrolysis of the resultant phenoxazinone ester [6].

Associations of Phenoxazinone with other chemical compounds

  • Anti-tumor effects of a novel phenoxazinone, 2-amino-4,4-dihydro-4alpha,7-dimethyl-3H-phenoxazine-3-one (Phx), which was synthesized by the reaction of 2-amino-5-methylphenol with bovine hemoglobin, were studied in terms of suppression of the proliferation of human lung carcinoma cells and apoptosis induction [5].
  • Root colonizing microorganisms and the endophytic fungus Fusarium verticillioides participated in benzoxazolinone detoxification by converting the compound to 2-acetamidophenol (AAP) or O-hydroxyphenyl malonamic acid (OHPMA), a process accompanied by the appearance of phenoxazinone [7].

Gene context of Phenoxazinone

  • The strain containing the disrupted relA gene did not produce actinomycin and contained significantly lower levels of the enzyme phenoxazinone synthase than the wild-type strain [8].

Analytical, diagnostic and therapeutic context of Phenoxazinone


  1. A novel o-aminophenol oxidase responsible for formation of the phenoxazinone chromophore of grixazone. Suzuki, H., Furusho, Y., Higashi, T., Ohnishi, Y., Horinouchi, S. J. Biol. Chem. (2006) [Pubmed]
  2. Activation of phenoxazinone synthase expression in Streptomyces lividans by cloned DNA sequences from Streptomyces antibioticus. Jones, G.H., Hopwood, D.A. J. Biol. Chem. (1984) [Pubmed]
  3. Cell-free synthesis of the phenoxazinone synthetase subunit by polyribosomes from Streptomyces antibioticus. Jones, G.H. J. Biol. Chem. (1980) [Pubmed]
  4. Antitumor agents. 1. Synthesis, biological evaluation, and molecular modeling of 5H-pyrido[3,2-a]phenoxazin-5-one, a compound with potent antiproliferative activity. Bolognese, A., Correale, G., Manfra, M., Lavecchia, A., Mazzoni, O., Novellino, E., Barone, V., Pani, A., Tramontano, E., La Colla, P., Murgioni, C., Serra, I., Setzu, G., Loddo, R. J. Med. Chem. (2002) [Pubmed]
  5. Prevention of growth of human lung carcinoma cells and induction of apoptosis by a novel phenoxazinone, 2-amino-4,4alpha-dihydro-4alpha,7-dimethyl-3H-phenoxazine-3-one. Abe, A., Yamane, M., Tomoda, A. Anticancer Drugs (2001) [Pubmed]
  6. Structure and syntheses of texazone. 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid, an actinomycete metabolite. Gerber, N.N., Yale, H.L., Taber, W.A., Kurobane, I., Vining, L.C. J. Antibiot. (1983) [Pubmed]
  7. Zea mays: benzoxazolinone detoxification under sulfur deficiency conditions-a complex allelopathic alliance including endophytic fusarium verticillioides. Knop, M., Pacyna, S., Voloshchuk, N., Kant, S., Müllenborn, C., Steiner, U., Kirchmair, M., Scherer, H.W., Schulz, M. J. Chem. Ecol. (2007) [Pubmed]
  8. relA is required for actinomycin production in Streptomyces antibioticus. Hoyt, S., Jones, G.H. J. Bacteriol. (1999) [Pubmed]
  9. Molecular cloning and expression of the phenoxazinone synthase gene from Streptomyces antibioticus. Jones, G.H., Hopwood, D.A. J. Biol. Chem. (1984) [Pubmed]
  10. Actinomycin production persists in a strain of Streptomyces antibioticus lacking phenoxazinone synthase. Jones, G.H. Antimicrob. Agents Chemother. (2000) [Pubmed]
  11. Crystallization and initial X-ray analysis of phenoxazinone synthase from Streptomyces antibioticus. Smith, A.W., Camara-Artigas, A., Olea, C., Francisco, W.A., Allen, J.P. Acta Crystallogr. D Biol. Crystallogr. (2004) [Pubmed]
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