# Azinomycin B

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**Azinomycin B** is a [natural product](/source/Natural_product) that contains densely assembled functionalities with potent [antitumor](/source/Antitumor) activity.[1] It is isolated from *[Streptomyces sahachiroi](/source/Streptomyces_sahachiroi)*[2] which is reisolated from *[S. griseofuscus](/source/Streptomyces_griseofuscus)* along with its [analog](/source/Structural_analog) azinomycin A.[3] Azinomycin B can bind within the major groove of [DNA](/source/DNA) and forms covalent [interstrand crosslinks](/source/Interstrand_crosslinks) (ISCs) with the [purine](/source/Purine) bases.[4][5][6][7] The DNA alkylation and crosslinking by azinomycin B suggests its potent antitumor activity.[8]

## Biosynthesis

The biosynthesis of azinomycin B includes a type 1 [polyketide synthase](/source/Polyketide_synthase) and several [nonribosomal peptide synthetases](/source/Nonribosomal_peptide_synthetase).[9]

## References

1. Zhao, Qunfei, Qingli He, Wei Ding, Mancheng Tang, Qianjin Kang, Yi Yu, Wei Deng, Qi Zhang, Jie Fang, Gongli Tang, and Wen Liu. "Characterization of the Azinomycin B Biosynthetic Gene Cluster Revealing a Different Iterative Type I Polyketide Synthase for Naphthoate Biosynthesis." Chemistry & Biology 15.7 (2008): 693-705. Web.

1. Hata, T., Koga, F., Sano, Y., Kanamori, K., Matsumae, A., Sunagawa, R., Hoshi, T., Shima, T., Ito, S., and Tomizawa, S. (1954). Carzinophilin, a new tumor inhibitory substance produced by Streptomyces. I. J. Antibiot. 7A, 107–112.

1. Yokoi, K., Nagaoka, K., and Nakashima, T. (1986). Azinomycins A and B, new antitumor antibiotics. II. Chemical structures. Chem. Pharm. Bull. (Tokyo) 34, 4554–4561.

1. Armstrong, R.W., Salvati, M.E., and Nguyen, M. (1992). Novel interstrand cross-links induced by the antitumor antibiotic carzinophillin/azinomycin B. J. Am. Chem. Soc. 114, 3144–3145.

1. Hartley, J.A., Hazrati, A., Kelland, L.R., Khanim, R., Shipman, M., Suzenet, F., and Walker, L.F. (2000). A synthetic azinomycin analogue with demonstrated DNA cross-linking activity: Insights into the mechanism of action of this class of antitumor agent. Angew. Chem. Int. Ed. Engl. 39, 3467–3470.

1. Coleman, R.S., Perez, R.J., Burk, C.H., and Navarro, A. (2002). Studies on the mechanism of action of azinomycin B: definition of regioselectivity and sequence selectivity of DNA cross-link formation and clarification of the role of the naphthoate. J. Am. Chem. Soc. 124, 13008–13017.

1. LePla, R.C., Landreau, C.A.S., Shipman, M., and Jones, G.D. (2005). On the origin of the DNA sequence selectivity of the azinomycins. Org. Biomol. Chem. 3, 1174–1175.

1. Kelly, G.T., Liu, C., Smith, R., III, Coleman, R.S., and Watanabe, C.M.H. (2006). Cellular effects induced by the antitumor agent azinomycin B. Chem. Biol. 13, 485–492.

1. Zhao, Qunfei, Qingli He, Wei Ding, Mancheng Tang, Qianjin Kang, Yi Yu, Wei Deng, Qi Zhang, Jie Fang, Gongli Tang, and Wen Liu. "Characterization of the Azinomycin B Biosynthetic Gene Cluster Revealing a Different Iterative Type I Polyketide Synthase for Naphthoate Biosynthesis." Chemistry & Biology 15.7 (2008): 693-705. Web.

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