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.
Copyright © 2014 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Cell Proliferation / drug effects
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Fluorouracil / chemistry
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Fluorouracil / pharmacology*
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HeLa Cells
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Humans
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Molecular Structure
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Oligonucleotides / chemical synthesis
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Oligonucleotides / chemistry
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Oligonucleotides / pharmacology*
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Photochemical Processes
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Prodrugs / chemical synthesis
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Prodrugs / chemistry
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Prodrugs / pharmacology*
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Structure-Activity Relationship
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Uracil / analogs & derivatives*
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Uracil / chemistry
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Uracil / pharmacology
Substances
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Antineoplastic Agents
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Oligonucleotides
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Prodrugs
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Uracil
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5-iodouracil
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Fluorouracil