A Cationic Micelle as In Vivo Catalyst for Tumor-Localized Cleavage Chemistry

Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19750-19758. doi: 10.1002/anie.202106526. Epub 2021 Jul 1.

Abstract

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.

Keywords: controlled release; desilylation; in vivo chemistry; micellar catalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzothiazoles / chemistry*
  • Catalysis
  • Cations / chemistry
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Carriers / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Mice
  • Micelles
  • Molecular Structure
  • Neoplasms, Experimental / drug therapy
  • Neoplasms, Experimental / pathology

Substances

  • Antineoplastic Agents
  • Benzothiazoles
  • Cations
  • Drug Carriers
  • Micelles
  • benzothiazole