918658-19-2Relevant academic research and scientific papers
A Cationic Micelle as In Vivo Catalyst for Tumor-Localized Cleavage Chemistry
Chen, Mengqi,Ding, Zexuan,Hong, Hanyu,Li, Zi-Chen,Liu, Zhibo,Qi, Jianyuan,Rui, Yuchen,Wang, Chunhong
supporting information, p. 19750 - 19758 (2021/07/12)
The emerging strategies of accelerating the cleavage reaction in tumors through locally enriching the reactants is promising. Yet, the applications are limited due to the lack of the tumor-selectivity for most of the reactants. Here we explored an alternative approach to leverage the rate constant by locally inducing an in vivo catalyst. We found that the desilylation-induced cleavage chemistry could be catalyzed in vivo by cationic micelles, and accelerated over 1400-fold under physiological condition. This micelle-catalyzed controlled release platform is demonstrated by the release of a 6-hydroxyl-quinoline-2-benzothiazole derivative (HQB) in two cancer cell lines and a NIR dye in mouse tumor xenografts. Through intravenous injection of a pH-sensitive polymer micelles, we successfully applied this strategy to a prodrug activation of hydroxyl camptothecin (OH-CPT) in tumors. Its “decaging” efficiency is 42-fold to that without cationic micelles-mediated catalysis. This micelle-catalyzed desilylation strategy unveils the potential that micelle may act beyond a carrier but a catalyst for local perturbing or activation.
TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines
Huang, Chunhui,Gevorgyan, Vladimir
supporting information; experimental part, p. 10844 - 10845 (2009/12/04)
(Chemical Equation Presented) It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.
