| Identification | Back Directory | [Name]
3-aminophenoxazone | [CAS]
1916-59-2 | [Synonyms]
Phx-3
Questiomycin A
2-Aminophenoxazon
3-aminophenoxazone
2-AMino-3-phenoxazone
2-amino-1H-phenoxazin-3-one
2-Amino-3-oxo-3H-phenoxazine
3H-Phenoxazin-3-one, 2-aMino-
2-AMino-3H-phenoxazin-3-one, 2-AMinophenoxazone, AV Toxin C, NSC 94945 | [Molecular Formula]
C12H8N2O2 | [MDL Number]
MFCD00207317 | [MOL File]
1916-59-2.mol | [Molecular Weight]
212.2 |
| Chemical Properties | Back Directory | [Melting point ]
249-250 °C | [Boiling point ]
352.04°C (rough estimate) | [density ]
1.2399 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 2mg/mL; DMSO: 3mg/mL; DMSO:PBS (pH 7.2) (1:20): 0.04mg/mL | [form ]
A solid | [pka]
2.73±0.20(Predicted) | [color ]
Brown to black | [InChI]
InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2 | [InChIKey]
RDJXPXHQENRCNG-UHFFFAOYSA-N | [SMILES]
C1C2C(OC3=C(N=2)C=CC=C3)=CC(=O)C=1N |
| Hazard Information | Back Directory | [Description]
Questiomycin A is a phenoxazine and a chromophore that has been found in Streptomyces and has antibacterial and anticancer activities. It is active against M. scrofulaceum, M. marinum, and M. intracellulare (MICs = 2.8, 11.3, and 5.6 μg/ml, respectively) but not M. tuberculosis, M. smegmatis, M. kansasii, or M. fortuitum (MICs = >45 μg/ml). It is also inactive against E. coli, P. aeruginosa, S. tymphimurium, S. aureus, or L. monocytogenes. It is cytotoxic to a variety of cancer cells, including MCF-7, A549, MIA PaCa-2, and LoVo-1 cells (IC50s = 1.67, 5.48, 7.16, and 20.03 μM, respectively) as well as human umbilical vein endothelial cells (HUVECs) but not human embryonic lung fibroblast cells (HELs; IC50s = 16.06 and >50 μM, respectively). Questiomycin A reduces the increased intracellular pH in a variety of cancer cell lines, as well as in HUVECs and HELs. It prevents lung metastasis in a B16 mouse melanoma model of metastasis when administered at a dose of 0.5 mg/kg simultaneously with B16 cells or every three days. It is also a chromophore product of the reducing agent 2-aminophenol oxidation (as 2-amino-phenoxazine-3-one) and has been used as a readout in the study of catalytic oxidation of 2-aminophenol by various metal-containing complexes. It has an absorbance of 435 nm in methanol. | [Uses]
Questiomycin A is a natural antimicrobial agent produced by agriculturally important species such as maize, rye, and wheat. | [Uses]
Questiomycin A is a phenoxazine produced by several Streptomyces species and some fungi and bacteria. Questiomycin A is weakly active against bacteria, fungi, plants and tumour cell lines, and inhibits aromatase and sulfatases. Questiomycin, like other phenoxazines, stimulates cell growth and turnover in vitro, an activity possibly related to their ability to form stable free radicals. More recently, questiomycin A has been shown to inhibit pulmonary metastasis caused by mouse melanoma cells. Questiomycin A and related phenoxazines are important dereplication standards in discovery research to eliminate leads due to high amounts of weakly potent actives. | [Definition]
ChEBI:2-aminophenoxazin-3-one is a phenoxazine. | [in vivo]
Questiomycin A (10 mg/kg; i.p.; once a day for 8 days) enhances the antitumor effect of Sorafenib by stimulating the downregulation of GRP78 in vivo[1]. | Animal Model: | Nude mice (HepG2 cells xenograft model)[1]. | | Dosage: | 10 mg/kg | | Administration: | Intraperitoneal injection; once a day; 8 days. | | Result: | Stimulated Sorafenib-dependent antitumor activity. |
| [storage]
Store at -20°C | [References]
[1] K ANZAI. The new antibiotics, questiomycins A and B.[J]. Journal of Antibiotics, 1960, 13: 125-132.
[2] NARAYAN CH. JANA . Synthesis, structure and diverse coordination chemistry of cobalt(III) complexes derived from a Schiff base ligand and their biomimetic catalytic oxidation of o-aminophenols[J]. Polyhedron, 2019, 164: Pages 23-34. DOI: 10.1016/j.poly.2019.02.024
[3] SHIGETAKA SHIMIZU. Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non-tuberculosis mycobacteria.[J]. Tohoku Journal of Experimental Medicine, 2004, 203 1: 47-52. DOI: 10.1620/tjem.203.47
[4] XIAO-FANG CHE. 2-Aminophenoxazine-3-one and 2-amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazine-3-one cause cellular apoptosis by reducing higher intracellular pH in cancer cells.[J]. Proceedings of the Japan Academy. Series B, Physical and Biological Sciences, 2011, 87 4: 199-213. DOI: 10.2183/pjab.87.199
[5] TAKAYUKI HONGO . 2-Aminophenoxazine-3-one Prevents Pulmonary Metastasis of Mouse B16 Melanoma Cells in Mice[J]. Journal of pharmacological sciences, 2010, 114 1: Pages 63-68. DOI: 10.1254/jphs.10023fp
[6] CHANDAN MUKHERJEE. A Tetracopper(II)-Tetraradical Cuboidal Core and Its Reactivity as a Functional Model of Phenoxazinone Synthase?[J]. Inorganic Chemistry, 2007, 46 23: 9895-9905. DOI: 10.1021/ic7012599 |
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