Design of a Thiol-Responsive, Traceless Prodrug with Rapid Self-Immolation for Cancer Chemotherapy

ACS Appl Bio Mater. 2021 Jun 21;4(6):4982-4989. doi: 10.1021/acsabm.1c00247. Epub 2021 May 21.

Abstract

Prodrugs can be formed by chemical modification of the existing active pharmaceutical ingredients (APIs); however, this often sacrifices their functional efficacy. Self-immolative linkers have recently attracted attention, as they can be designed to release pristine APIs. Herein, we report a strategy to generate a self-immolative prodrug (SIP) that can release pristine doxorubicin (DOX). Compared to conventional linkers, the key SIP DOX (KSIP-DOX) developed here can rapidly and quantitatively release the API due to its strong leaving group after reduction by thiol groups, which are present in tumors. KSIP-DOX has enhanced cellular uptake and improved anticancer efficacy, demonstrating its utility for cancer treatment.

Keywords: antitumor; cross-linker; doxorubicin; drug release; self-immolation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic* / administration & dosage
  • Antibiotics, Antineoplastic* / chemistry
  • Antibiotics, Antineoplastic* / toxicity
  • Cell Line, Tumor
  • Doxorubicin* / administration & dosage
  • Doxorubicin* / chemistry
  • Doxorubicin* / pharmacokinetics
  • Doxorubicin* / toxicity
  • Drug Design
  • Drug Liberation
  • Female
  • Glutathione / metabolism
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Neoplasms / drug therapy
  • Prodrugs* / administration & dosage
  • Prodrugs* / chemistry
  • Prodrugs* / pharmacokinetics
  • Prodrugs* / toxicity

Substances

  • Antibiotics, Antineoplastic
  • Prodrugs
  • Doxorubicin
  • Glutathione