The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids.
The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two beta-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation.
Toshima
Kazunobu
K
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. toshima@applc.keio.ac.jp
Ozawa
Tomohiro
T
Kimura
Tomonori
T
Matsumura
Shuichi
S
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002236:Carbohydrate Conformation; D004249:DNA Damage / Q000187:drug effects* / Q000528:radiation effects; D004187:Disaccharides / Q000737:chemistry* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D010782:Photolysis; D011810:Quinoxalines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014466:Ultraviolet Rays
D000970:Antineoplastic Agents; D004187:Disaccharides; D011810:Quinoxalines