Synthesis and anti-cancer activity of C-ring-functionalized prodigiosin analogues
Synthesis and anti-cancer activity of C-ring-functionalized prodigiosin analogues
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DOI：
10.1021/jm061088f
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发表时间：
2007-04-05
影响因子：
7.3
通讯作者：
Thompson, Alison
中科院分区：
文献类型：
--
作者：
Regourd, Jasmine;Ali, Adeeb Al-Sheikh;Thompson, Alison
灵菌红素是天然产物4-甲氧基吡咯基二吡咯亚甲基家族的母体成员，以其抗癌活性而闻名。合成了一系列新的类似物，在C-环上引入侧链功能酯和β-羰基取代基。β-羰基基团允许灵菌烯的容易分离，并且侧基酯允许进一步衍生化。该新型灵菌红素通常保留灵菌红素在衍生自9种癌细胞类型的60种人细胞系中的抗癌活性，其中共轭的β-羰基（作为酮或酯）和侧基酯均不显著降低核心骨架的抗癌活性。
Prodigiosin is the parent member of the 4-methoxypyrrolyldipyrromethene family of natural products and is known for its anti-cancer activity. A new series of analogues was synthesized, incorporating pendent functional esters and beta-carbonyl substituents on the C-ring. The beta-carbonyl group allowed for the facile isolation of the prodigiosenes, and the pendent esters allow for further derivatization. The novel prodigiosenes generally retain the anti-cancer activity of prodigiosin in 60 human cell lines derived from nine cancer cell types, with neither the conjugated beta-carbonyl group, as either ketone or ester, nor the pendent ester significantly reducing the anti-cancer activity of the core skeleton.