Synthesis of N-acetylglucosamine-modified ara-C and its effect on ovarian cancer cells.
1-beta-D-Arabinofuranosylcytosine (ara-C) was modified by reaction of tetra-N-acetylchitotetraose ((GlcNAc)4) using the transglycosylation activity of thermostable chitinase (EC 3.2.1.14) from Bacillus licheniformis X-7u. The structure of the modified ara-C was determined to be either beta 1-3'- or beta 1-5'-linked GlcNAc-ara-C or (GlcNAc)2-ara-C. The total yield of these glycosylated ara-Cs was about 10%. GlcNAc-ara-C and (GlcNAc)2-ara-C depressed the growth of G-401 cancer cells, while 5-O-beta-D-galactopyranosyl-beta-D-arabinofuranosylcytosine (Gal-ara-C) had no effect on G-401 cells.
Fujimoto
H
H
Meiji Institute of Health Science, Odawara, Japan.
Takayanagi
T
T
Ajisaka
K
K
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001407:Bacillus / Q000201:enzymology; D002455:Cell Division / Q000187:drug effects; D002688:Chitinases / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003561:Cytarabine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D005260:Female; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D010051:Ovarian Neoplasms / Q000473:pathology*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D003561:Cytarabine; D002688:Chitinases