Structure-activity relationships in the induction of single-strand breakage in plasmid pBR322 DNA by amino sugars and derivatives.
Structure-activity relationships in the induction of strand breakage in plasmid pBR322 DNA by amino sugars and their derivatives were investigated using agarose gel electrophoresis. The coexistence of a potential free aldehyde group at the C-1 position and a free amino group at the C-2 position in the molecules was indispensable for the display of DNA strand-breaking activity in both mono- and oligo-aminosaccharides. The activity was increased by the introduction of an acidic group, especially a phosphate group, at the C-6 position. The activity was also increased by the addition of Cu2+. The order of activity of the amino monosaccharides tested was D-isoglucosamine > D-mannosamine > D-galactosamine > D-glucosamine, and it is suggested that this order is correlated with the portion of acyclic (aldehydo) form in the solution of each sugar. The possible chemical basis for DNA strand breakage by amino sugars is discussed.
Kashige
N
N
Faculty of Pharmaceutical Sciences, Fukuoka University, Japan.
Yamaguchi
T
T
Ohtakara
A
A
Mitsutomi
M
M
Brimacombe
J S
JS
Miake
F
F
Watanabe
K
K
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004249:DNA Damage; D004269:DNA, Bacterial / Q000187:drug effects* / Q000302:isolation & purification; D004587:Electrophoresis, Agar Gel; D006595:Hexosamines / Q000494:pharmacology*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000494:pharmacology*; D010957:Plasmids / Q000187:drug effects; D013329:Structure-Activity Relationship
D004269:DNA, Bacterial; D006595:Hexosamines; D009844:Oligosaccharides