Questiomycin A
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MedKoo CAT#: 573980

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.


Chemical Structure

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Questiomycin A
CAS# 1916-59-2

Theoretical Analysis

MedKoo Cat#: 573980
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

Price and Availability

Size Price Availability Quantity
250mg USD 360
1g USD 900
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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:

Product Data:
Biological target: Questiomycin A 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). Questiomycin A reduces the increased intracellular pH in a variety of cancer cell lines, as well as in HUVECs and HELs.
In vitro activity: Questiomycin A has been elucidated to share the same biosynthesis process with PCA by gene deletion and in vitro assays. Through rational metabolic engineering, heterologous phenoxazinone synthase introduction, and medium optimization, the titer reached 589.78 mg/L in P. chlororaphis, the highest production reported to date. This work contributes to a better understanding of Questiomycin A biosynthesis and demonstrates a promising approach to developing a new antibacterial biopesticide in Pseudomonas. Reference: J Agric Food Chem. 2022 Jun 29;70(25):7742-7750. https://pubmed.ncbi.nlm.nih.gov/35708224/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 2.0 9.42
DMSO 3.0 14.14
DMSO:PBS (pH 7.2) (1:20) 0.0 0.19

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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: 1. Guo S, Hu H, Wang W, Bilal M, Zhang X. Production of Antibacterial Questiomycin A in Metabolically Engineered Pseudomonas chlororaphis HT66. J Agric Food Chem. 2022 Jun 29;70(25):7742-7750. doi: 10.1021/acs.jafc.2c03216. Epub 2022 Jun 15. PMID: 35708224. 2. Igarashi Y, Takagi K, Kajiura T, Furumai T, Oki T. Glucosylquestiomycin, a novel antibiotic from Microbispora sp. TP-A0184: fermentation, isolation, structure determination, synthesis and biological activities. J Antibiot (Tokyo). 1998 Oct;51(10):915-20. doi: 10.7164/antibiotics.51.915. PMID: 9917004.
In vitro protocol: 1. Guo S, Hu H, Wang W, Bilal M, Zhang X. Production of Antibacterial Questiomycin A in Metabolically Engineered Pseudomonas chlororaphis HT66. J Agric Food Chem. 2022 Jun 29;70(25):7742-7750. doi: 10.1021/acs.jafc.2c03216. Epub 2022 Jun 15. PMID: 35708224. 2. Igarashi Y, Takagi K, Kajiura T, Furumai T, Oki T. Glucosylquestiomycin, a novel antibiotic from Microbispora sp. TP-A0184: fermentation, isolation, structure determination, synthesis and biological activities. J Antibiot (Tokyo). 1998 Oct;51(10):915-20. doi: 10.7164/antibiotics.51.915. PMID: 9917004.
In vivo protocol: TBD

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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).