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Bioorg Med Chem Lett. 2014 Aug 15;24(16):3736-8. doi: 10.1016/j.bmcl.2014.07.002. Epub 2014 Jul 14.

Short oligonucleotide prodrug having 5-fluoro and 5-iodouracil inhibits the proliferation of cancer cells in a photo-responsive manner.

Author information

1
School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahi-dai, Nomi, Ishikawa 923-1292, Japan; Research Center for Bio-Architecture, Japan Advanced Institute of Science and Technology, 1-1 Asahi-dai, Nomi, Ishikawa 923-1292, Japan. Electronic address: kenzo@jaist.ac.jp.
2
School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahi-dai, Nomi, Ishikawa 923-1292, Japan.

Abstract

Photo-induced C1' hydrogen abstraction of 5-fluoro-2'-deoxyuridine was adopted as the key reaction for releasing 5-fluorouracil (5-FU) anticancer drug from oligonucleotide strands. After photoirradiation following 5-FU release, anticancer activity was expected. We demonstrated that oligonucleotide tetramer, d(A(F)U(I)UA), can release 5-FU under physiological conditions in a photo-responsive manner thorough photo-induced C1' hydrogen abstraction, and that the 5-FU released from d(A(F)U(I)UA) having a phosphorothioate backbone clearly suppresses the proliferation of HeLa cells in a photo-responsive manner.

KEYWORDS:

5-Fluorouracil; Cancer cells; Photoirradiation; Prodrug

PMID:
25080163
DOI:
10.1016/j.bmcl.2014.07.002
[Indexed for MEDLINE]

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