DNA binding property and antitumor evaluation of xanthone with dimethylamine side chain.
In this work, a xanthone derivative was obtained by cationic modification of the free hydroxyl group of xanthone with dimethylamine group of high pKa value. The interactions of xanthones with DNA were investigated by spectroscopic methods, electrophoretic migration assay and polymerase chain reaction test. Results indicate that xanthones can intercalate into the DNA base pairs by the hydrophobic plane and the xanthone with dimethylamine side chain may also bind the DNA phosphate framework by the basic amine alkyl chain, thus showing a better DNA binding ability than the xanthone. Furthermore, inhibition on tumor cells (ECA109, SGC7901, GLC-82) proliferation of xanthones were evaluated by MTT method. Analysis results show that the xanthone with dimethylamine side chain exhibits more effective inhibition activity against three cancer cells than the xanthone. The effects on the inhibition of tumor cells in vitro agree with the studies of DNA binding. It means that the amine alkyl chain would play an important role in its antitumor activity and DNA binding property.
College of Pharmaceutical Sciences, Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Hebei University, Baoding, 071002, People's Republic of China, shenr05@126.com.
Rui
R
Shen
Weihua
W
Wang
Gengliang
G
Yang
D001667:Binding, Competitive; D049109:Cell Proliferation; D002942:Circular Dichroism; D004247:DNA / Q000378:metabolism*; D004123:Dimethylamines / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy* / Q000473:pathology; D013050:Spectrometry, Fluorescence; D014407:Tumor Cells, Cultured; D044004:Xanthones / Q000737:chemistry / Q000494:pharmacology*
D004123:Dimethylamines; D044004:Xanthones; D004247:DNA; C009689:xanthone; C034516:dimethylamine