γ-Rubromycin isolated from Streptomyces sp. consists of a densely oxygenated naphthazarin ring and an isocoumarin moiety linked through a unique aromatic 5,6-sproketal ring system. The rubromycins exhibit a wide range of biological activity including antimicrobial and anticancer properties.
β-Rubromycin and γ-rubromycin display potent activity against human telomerase(IC50=3µm), the reverse transcriptase of HIV-1, and the moloney murine leukemia virus. α-Rubromycin, the only member of the group to lack the aryl spiroketal moiety, exhibits substantially decreased inhibitory potency towards telomerase(IC50>200µm), which suggests that the spiroketal core is an essential pharmacophore for the inhibition of telomerase. Purpuromycin, a potential topical agent for vaginal infections, and heliquinomycin, a selective inhibitor of DNA helicase are structurally related to the rubromycins.
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