ChemInform Abstract: Synthesis and γ-Radiolysis of 2′-Deoxy-5-fluorouridine and 5- Fluorouridine Derivatives
Autor: | Hiroshi Nishikawa, Yoshio Otsuji, Tokuyuki Kuroda, Makoto Morimoto, Tadashi Ashizawa, Koji Hisamura, Ikuo Matsukuma, Nobuhiro Nakamizo |
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Rok vydání: | 2010 |
Předmět: | |
Zdroj: | ChemInform. 24 |
ISSN: | 0931-7597 |
DOI: | 10.1002/chin.199308278 |
Popis: | Seventeen compounds having a variety of substituents at the 3- and 5′-positions of 2′-deoxy-5-fluorouridine (5-FUdR) and 5-fluorouridine (5-FUR) were synthesized, and their γ-radiolysis in aqueous solutions were studied. The compounds having thioureido (RNHCSNH, R H, PhCH2, acyl) and thiocarbonylamino (XCSNH, X PhCH2S, PhO) groups at the 3-position of 5-FUdR were efficiently cleaved to give 5-FUdR with high G values upon γ-irradiation of their aqueous solutions. The active species for these cleavage reactions were hydrated electron (e− aq), H• and HO•. However, the compounds having a dimethylsulfoxyimino group at 3-position of 5-FUdR and 5-FUR afforded 5-FUdR and 5-FUR only under the radiolysis conditions where e− aq becomes a principal active species. The compound having a 2-benzoylthiazoylthiocarbonylamino group at the 3-position of 5-FUdR showed the highest reactivity toward HO.. The mechanisms of these γ-radiolysis reactions are discussed. The examination of anticellular activities of γ-irradiated compounds having a thiocarbonylamino group at the 3-position of 5-FUdR toward murine Sarcoma 180 cells revealed that these compounds may be utilized as a candidate for a radiation-induced drug (RID). |
Databáze: | OpenAIRE |
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