Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Bioorg Med Chem. 2010 Dec 15;18(24):8630-41. doi: 10.1016/j.bmc.2010.10.004. Epub 2010 Oct 16.
The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an α,β-unsaturated γ-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria.
荧光标记索拉明（一种抗肿瘤番荔枝内酯）的汇聚合成通过 2,5-二醛基四氢呋喃与带有荧光基团的炔烃和另一个带有α,β-不饱和γ-内酯的炔烃的两次不对称炔基化反应完成。对人癌细胞系生长抑制活性的测定表明，末端带有荧光基团的探针可能具有与天然生物堿相同的作用模式。丹磺酰基标记的索拉明和 MitoTracker Red 的合并荧光表明，番荔枝内酯定位于线粒体中。
