Hydrolysis-Sensitive Dithiolethione Prodrug Micelles

Urara Hasegawa, Naoya Tateishi, Hiroshi Uyama, André J. Van Der Vlies

Research output: Contribution to journalArticlepeer-review

Abstract

Prodrug micelles carrying 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OH), a compound possessing chemopreventive properties, are prepared from amphiphilic block copolymers linking ADT-OH via an ester bond using glycine (PAM-PGlyADT) and isoleucine linkers (PAM-PIleADT). The release of ADT-OH from the PAM-PIleADT micelles is much slower than the PAM-PGlyADT micelles. The PAM-PGlyADT micelles show comparable toxicity with ADT-OH in different cancer cell lines, whereas the PAM-PIleADT micelles are not toxic up to 400μM. This ADT-ester prodrug micelle approach enables to modulate the release rate of ADT-OH and thus might find application in cancer therapy and prevention. Hydrolysis-sensitive micellar prodrugs of desmethyl anethole dithiolethione (ADTOH), a chemopreventive agent, are prepared from amphiphilic block copolymers composed of a hydrophilic poly(N-acryloyl morpholine) block and a hydrophobic block linking ADT-OH via an ester bond using glycine and isoleucine linkers. This ADT-ester approach enables to modulate the release rate of ADT-OH and thus might find potential application in cancer therapy and prevention.

Original languageEnglish (US)
Pages (from-to)1512-1522
Number of pages11
JournalMacromolecular Bioscience
Volume15
Issue number11
DOIs
StatePublished - Nov 1 2015

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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