The oxidative damage of plasmid DNA by ascorbic acid derivatives in vitro: the first research on the relationship between the structure of ascorbic acid and the oxidative damage of plasmid DNA.
To study the structure-function relationship of the oxidative-damage effect of ascorbic acid, we have focused on the interaction between plasmid DNA pUC19 and a series of ascorbic acid derivatives modified on different OH groups in the presence of transition metal ions. Some ascorbic acid derivatives can selectively cleave plasmid DNA from Form I to Form II in the presence of low concentration of Cu2+ just like ascorbic acid itself, while other derivatives oxidatively damage plasmid DNA slightly. We found that those derivatives with unattached 2-OH and 3-OH groups retain the ability to cleave the plasmid DNA. The derivatives that have been methylated on 2-OH or 3-OH can only cleave plasmid DNA softly, and those derivatives that have been protected on both 2-OH and 3-OH can hardly exert an oxidative damage on plasmid DNA under the same condition. Form these results, we can draw the conclusion that 2-OH and 3-OH groups of the ascorbic acid molecule contribute most to this biological activity.
Liu
Pei-Yan
PY
Department of Chemistry, Key Laboratory of Green Chemistry and Technology, Ministry of Education, Sichuan University, Chengdu, Sichuan 610064, P.R. China.
Jiang
Ning
N
Zhang
Ji
J
Wei
Xi
X
Lin
Hong-Hui
HH
Yu
Xiao-Qi
XQ
D001205:Ascorbic Acid / Q000009:adverse effects / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004249:DNA Damage; D017665:Hydroxyl Radical / Q000032:analysis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010957:Plasmids / Q000187:drug effects / Q000235:genetics*; D013329:Structure-Activity Relationship
D017665:Hydroxyl Radical; D001205:Ascorbic Acid