TY - JOUR
T1 - Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains
AU - Wang, Shuxiang
AU - Li, Hongdong
AU - Chen, Chao
AU - Zhang, Jinchao
AU - Li, Shenghui
AU - Qin, Xinying
AU - Li, Xiaoliu
AU - Wang, Kerang
PY - 2012/10/15
Y1 - 2012/10/15
N2 - A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 106, 1.51 × 106 and 0.709 × 106 M-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.
AB - A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68 × 106, 1.51 × 106 and 0.709 × 106 M-1, respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.
KW - Binding property
KW - Cytotoxicity
KW - Phenanthrene imidazole derivatives
KW - Polyglycol side chain
UR - http://www.scopus.com/inward/record.url?scp=84866743325&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2012.08.079
DO - 10.1016/j.bmcl.2012.08.079
M3 - Article
SN - 0960-894X
VL - 22
SP - 6347
EP - 6351
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 20
ER -