Azinomycin B | CAS# 106486-76-4 | antitumor

MedKoo Cat#: 412417 | Name: Azinomycin B

Description:

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

Azinomycin B is an antitumor antibiotic produced by Streptomyces sahachiroi.

Chemical Structure

Azinomycin B

CAS#106486-76-4

Theoretical Analysis

MedKoo Cat#: 412417

Name: Azinomycin B

CAS#: 106486-76-4

Chemical Formula: C31H33N3O11

Exact Mass: 623.2115

Molecular Weight: 623.62

Elemental Analysis: C, 59.71; H, 5.33; N, 6.74; O, 28.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Azinomycin B; NSC20088; NSC-20088; NSC 20088

IUPAC/Chemical Name

1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1S)-2-(((1E)-1-((3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-(((1Z)-1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-((2S)-2-methyloxiranyl)-2-oxoethyl ester

InChi Key

QIKVYJOCQXXRSJ-PKDLRSQSSA-N

InChi Code

InChI=1S/C31H33N3O11/c1-14-7-6-8-18-19(14)9-17(42-5)10-20(18)30(41)45-27(31(4)13-43-31)29(40)33-23(28(39)32-21(12-35)15(2)36)24-26(44-16(3)37)25(38)22-11-34(22)24/h6-10,12,22,25-27,35,38H,11,13H2,1-5H3,(H,32,39)(H,33,40)/b21-12-,24-23+/t22-,25+,26+,27+,31-,34?/m0/s1

SMILES Code

O=C(C1=C2C=CC=C(C)C2=CC(OC)=C1)O[C@@H]([C@@]3(C)OC3)C(N/C(C(N/C(C(C)=O)=C\O)=O)=C4N5C[C@@]5([H])[C@@H](O)[C@@H]/4OC(C)=O)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 623.62 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

1: Balazy M, Fausto A, Voskanian C, Chavez B, Panesar H, Minehan TG. Dimeric and trimeric derivatives of the azinomycin B chromophore show enhanced DNA binding. Org Biomol Chem. 2017 May 31;15(21):4522-4526. doi: 10.1039/c7ob00944e. PMID: 28513737; PMCID: PMC5513485. 2: Senthilnathan D, Kalaiselvan A, Venuvanalingam P. Sequence selectivity of azinomycin B in DNA alkylation and cross-linking: a QM/MM study. J Mol Model. 2013 Jan;19(1):383-90. doi: 10.1007/s00894-012-1557-2. Epub 2012 Aug 24. PMID: 22930355. 3: Wang S, Liu K, Xiao L, Yang L, Li H, Zhang F, Lei L, Li S, Feng X, Li A, He J. Characterization of a novel DNA glycosylase from S. sahachiroi involved in the reduction and repair of azinomycin B induced DNA damage. Nucleic Acids Res. 2016 Jan 8;44(1):187-97. doi: 10.1093/nar/gkv949. Epub 2015 Sep 22. PMID: 26400161; PMCID: PMC4705692. 4: Zhao Q, He Q, Ding W, Tang M, Kang Q, Yu Y, Deng W, Zhang Q, Fang J, Tang G, Liu W. Characterization of the azinomycin B biosynthetic gene cluster revealing a different iterative type I polyketide synthase for naphthoate biosynthesis. Chem Biol. 2008 Jul 21;15(7):693-705. doi: 10.1016/j.chembiol.2008.05.021. PMID: 18635006. 5: Liu C, Kelly GT, Watanabe CM. In vitro biosynthesis of the antitumor agent azinomycin B. Org Lett. 2006 Mar 16;8(6):1065-8. doi: 10.1021/ol052987l. PMID: 16524269. 6: Foulke-Abel J, Kelly GT, Zhang H, Watanabe CM. Characterization of AziR, a resistance protein of the DNA cross-linking agent azinomycin B. Mol Biosyst. 2011 Sep;7(9):2563-70. doi: 10.1039/c1mb05136a. Epub 2011 Jul 21. PMID: 21776524. 7: Zang H, Gates KS. DNA binding and alkylation by the "left half" of azinomycin B. Biochemistry. 2000 Dec 5;39(48):14968-75. doi: 10.1021/bi001998d. PMID: 11101313. 8: Wang S, Zhao R, Liu K, Zhu M, Li A, He J. Essential role of an unknown gene aziU3 in the production of antitumor antibiotic azinomycin B verified by utilizing optimized genetic manipulation systems for Streptomyces sahachiroi. FEMS Microbiol Lett. 2012 Dec;337(2):147-54. doi: 10.1111/1574-6968.12020. Epub 2012 Nov 2. PMID: 23039858. 9: Kelly GT, Liu C, Smith R 3rd, Coleman RS, Watanabe CM. Cellular effects induced by the antitumor agent azinomycin B. Chem Biol. 2006 May;13(5):485-92. doi: 10.1016/j.chembiol.2006.02.015. PMID: 16720269. 10: Ding W, Deng W, Tang M, Zhang Q, Tang G, Bi Y, Liu W. Biosynthesis of 3-methoxy-5-methyl naphthoic acid and its incorporation into the antitumor antibiotic azinomycin B. Mol Biosyst. 2010 Jun;6(6):1071-81. doi: 10.1039/b926358f. Epub 2010 Mar 16. PMID: 20485749.