WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H573980
CAS#: 1916-59-2
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. It is cytotoxic to a variety of cancer cells, including MCF-7, A549, MIA PaCa-2, and LoVo-1 cells as well as human umbilical vein endothelial cells (HUVECs) but not human embryonic lung fibroblast cells. 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.
Hodoodo Cat#: H573980
Name: Questiomycin A
CAS#: 1916-59-2
Chemical Formula: C12H8N2O2
Exact Mass: 212.06
Molecular Weight: 212.208
Elemental Analysis: C, 67.92; H, 3.80; N, 13.20; O, 15.08
Synonym: Questiomycin A
IUPAC/Chemical Name: 2-amino-3H-phenoxazin-3-one
InChi Key: RDJXPXHQENRCNG-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: NC1=CC2=NC3=CC=CC=C3OC2=CC1=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
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The following data is based on the product molecular weight 212.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1. Anzai, K., Isono, K., Okuma, K., et al. New antibiotics, questiomycins A and B. Rikagaku Kenkyusho Hokoku 36, 577-583 (1960).
2. Jana, N.C., Patra, M., Brandão, P., et al. Synthesis, structure and diverse coordination chemistry of cobalt(III) complexes derived from a Schiff base ligand and their biomimetic catalytic oxidation of o-aminophenols. Polyhedron 164, 23-34 (2019).
3. Shimizu, S., Suzuki, M., Tomoda, A., et al. Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non-tuberculosis mycobacteria. Tohoku J. Exp. Med. 203(1), 47-52 (2004).
4. Che, X.-F., Zheng, C.-L., Akiyama, S.-I., et al. 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. Proc. Jpn. Acad. Ser. B Phys. Biol. Sci. 87(4), 199-213 (2011).
5. Hongo, T., Miyano-Kurosaki, N., Kurosaki, K., et al. 2-Aminophenoxazine-3-one prevents pulmonary metastasis of mouse B16 melanoma cells in mice. J. Pharmacol. Sci. 114(1), 63-68 (2010).
6. Mukherjee, C., Weyhermüller, T., Bothe, E., et al. A tetracopper(II)-tetraradical cuboidal core and its reactivity as a functional model of phenoxazinone synthase. Inorg. Chem. 46(23), 9895-9905 (2007).
