Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.
J Am Chem Soc. 2016 Oct 12;138(40):13353-13360. doi: 10.1021/jacs.6b07890. Epub 2016 Sep 30.
α-Boryl ethers, carbonates, and acetals, readily prepared from the corresponding alcohols that are accessed through ketone diboration, react rapidly with hydrogen peroxide to release alcohols, aldehydes, and ketones through the collapse of hemiacetal intermediates. Experiments with α-boryl acetals containing a latent fluorophore clearly demonstrate that cargo can be released inside cells in the presence of exogenous or endogenous hydrogen peroxide. These experiments show that this protocol can be used for drug activation in an oxidative environment without generating toxic byproducts.
α-硼醚、碳酸酯和缩醛可以很容易地从通过酮双硼化反应得到的相应醇制备得到，它们与过氧化氢迅速反应，通过半缩醛中间体的塌陷，释放出醇、醛和酮。含有潜伏荧光团的α-硼缩醛的实验清楚地表明，在存在外源性或内源性过氧化氢的情况下，可以将货物释放到细胞内。这些实验表明，该方案可用于在氧化环境中激活药物，而不会产生有毒副产物。
