Questiomycin A | CAS# 1916-59-2 | Chromophore

MedKoo Cat#: 573980 | Name: Questiomycin A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Questiomycin A

CAS#1916-59-2

Theoretical Analysis

MedKoo Cat#: 573980

Name: Questiomycin A

CAS#: 1916-59-2

Chemical Formula: C12H8N2O2

Exact Mass: 212.0586

Molecular Weight: 212.21

Elemental Analysis: C, 67.92; H, 3.80; N, 13.20; O, 15.08

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 475.00
1g	USD 1,050.00

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Related CAS #

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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

Product Data

Instruction

View handling instruction

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

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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

In vivo protocol:

TBD

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