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Hydrolysis‐Sensitive Dithiolethione Prodrug Micelles
Author(s) -
Hasegawa Urara,
Tateishi Naoya,
Uyama Hiroshi,
van der Vlies André J.
Publication year - 2015
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201500156
Subject(s) - micelle , prodrug , chemistry , amphiphile , hydrolysis , copolymer , combinatorial chemistry , organic chemistry , biochemistry , polymer , aqueous solution
Prodrug micelles carrying 5‐(4‐hydroxyphenyl)‐3 H ‐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 400 µM. 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.