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  • Title: Cytotoxicity of N4-behenoyl-1-beta-D-arabinofuranosylcytosine through gradual conversion to 1-beta-D-arabinofuranosylcytosine in HeLa cells.
    Author: Maehara Y, Kusumoto T, Sakaguchi Y, Kusumoto H, Anai H, Sugimachi K.
    Journal: Anticancer Res; 1989; 9(1):41-4. PubMed ID: 2705754.
    Abstract:
    The metabolism of 1-beta-D-arabinofuranosylcytosine (ara-C) and N4-behenoyl-1-beta-D-arabinofuranosylcytosine (BH-AC) was studied in Hela cells. After the cells were exposed to ara-C at a concentration of 20 micrograms/ml or BH-AC at 46.5 micrograms/ml for 1, 3, 6, 12 or 24 hr, the level of ara-C was determined using the radioimmunoassay method, and the level of BH-AC and 1-beta-D-arabinofuranosyluracil (ara-U), using high-performance liquid chromatography. In the ara-C-treated cells, the intracellular ara-C increased to 1.26 micrograms/g cells after exposure for 6 hr, and ara-C was rapidly changed to ara-U in the cells and in the medium. In the BH-AC-treated cells, the intracellular BH-AC increased after exposure for 24 hr and BH-AC was gradually converted to ara-C in the cells: the intracellular level of ara-C was only 15% of that of BH-AC after exposure for 24 hr. BH-AC level in the medium persisted for 24 hr, at the initial concentration. Our findings show that BH-AC is stable compared to ara-C and gradually converts to ara-C. This conversion is presumably a critical step in the antineoplastic effect of BH-AC.
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