Chemistry:Arabilin
From HandWiki
Arabilin is a chemical compound with the molecular formula C
28H
31NO
6. It was first isolated from the MK756-CF1 strain of Streptomyces in 2010.[1] Chemically, it contains a substituted γ-pyrone ring and a p-nitrophenyl group that is rarely found in nature.
Arabilin acts as an androgen antagonist,[1] and therefore has attracted research interest in its potential pharmacological use.[2][3] A laboratory synthesis of arabilin has been reported.[4][5]
Related compounds also isolated from Streptomyces include spectinabilin and SNF4435C.[1]
References
- ↑ 1.0 1.1 1.2 Kawamura, Tatsuro; Fujimaki, Takahiro; Hamanaka, Natsuki; Torii, Kentaro; Kobayashi, Hiroki; Takahashi, Yoshikazu; Igarashi, Masayuki; Kinoshita, Naoko et al. (2010). "Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1". The Journal of Antibiotics 63 (10): 601–605. doi:10.1038/ja.2010.98. PMID 20736953.
- ↑ Fujimaki, Takahiro; Saito, Shun; Imoto, Masaya (2017). "Arabilin overcomes resistance to AR-targeted therapy". The Journal of Antibiotics 70 (3): 328–330. doi:10.1038/ja.2016.162. PMID 28074047.
- ↑ Imoto, Masaya; Fujimaki, Takahiro; Saito, Shun; Tashiro, Etsu (2021). "Androgen receptor antagonists produced by Streptomyces overcome resistance to enzalutamide". The Journal of Antibiotics 74 (10): 706–716. doi:10.1038/s41429-021-00453-y. PMID 34282313.
- ↑ Lim, Hee Nam; Parker, Kathlyn A. (2011). "Total Synthesis of the Potent Androgen Receptor Antagonist (−)-Arabilin: A Strategic, Biomimetic [1,7]-Hydrogen Shift". Journal of the American Chemical Society 133 (50): 20149–20151. doi:10.1021/ja209459f. PMID 22085260. Bibcode: 2011JAChS.13320149L.
- ↑ "Synthesis of (–)-Arabilin". Synfacts 8 (3): 0242. 2012. doi:10.1055/s-0031-1290244.
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