614717-88-3Relevant articles and documents
Effects of ligand planarity on the interaction of polypyridyl Ru(II) complexes with DNA
Xu, Hong,Zheng, Kang-Cheng,Chen, Yao,Li, Yi-Zhi,Lin, Li-Jun,Li, Hong,Zhang, Pei-Xin,Ji, Liang-Nian
, p. 2260 - 2268 (2003)
Two new polypyridyl ligands containing substituent Br at different positions in the phenyl ring, OBIP {OBIP = 2-(2-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline}, PBIP {PBIP = 2-(4-bromophenyl)imidazo[4,5-f]-1,10-phenanthroline} and their Ru(II) complexes, [Ru(dmp)2(OBIP)]2+ 1 and [Ru(dmp)2(PBIP)]2+ 2 (dmp = 2,9-dimethyl-1,10-phenanthroline), have been synthesized and charactrized. The binding of the two complexes to calf thymus DNA (CT DNA) has been investigated by spectrophotometric methods, viscosity measurements, as well as equilibrium dialysis and circular dichroism spectroscopy. Theoretical calculations for the two complexes were also carried out applying the density functional theory (DFT) method. The structure of complex 1 has been determined by single-crystal X-ray diffraction techniques. The imidazo[4,5-f]-1,10-phenanthroline moiety is not coplanar with the 2-bromophenyl ring, having a dihedral angle of 48.6 degrees in the OBIP ligand. The twisted conformation has been further confirmed by theoretical calculations, in which this dihedral angle is 48.2 degrees. The theoretical calculations also suggest that the PBIP ligand in complex 2 is essentially planar (dihedral angle is 0.4 degrees). The experimental results show that while complex bonds to CT DNA via a semi-intercalative mode, complex 2 strongly binds to CT DNA than through intercalation. Complex 2 is thus a much better candidate as an enantioselective binder to CT DNA complex 1. Some experimental regularities or trends have been reasonably explained by the theoretical results. These suggest that the planarity of the intercalated ligand has significant effects on the spectral properties and the DNA-binding behavior of the complexes, and that the DFT method can be used effectively to explain and predict some regularities or trends in the interaction of polypyridyl Ru(II) complexes with DNA.
Microwave-assisted synthesis of phenanthroimidazole derivatives as stabilizer of c-myc G-quadruplex DNA
Liao, Siyan,Zhang, Zhao,Wu, Qiong,Wang, Xicheng,Mei, Wenjie
, p. 6503 - 6508 (2015/01/09)
c-myc G-quadruplex DNA, which plays a central role in tumor progression and resistance, has been extensively investigated as potential target of antitumor drugs. In this paper, a series of phenanthroimidazole derives have been synthesized under irradiation of microwave in yields of 51-80%. The antitumor activity of these compounds against various tumor cells has been evaluated, and the results show that these compounds exhibit great inhibition to MDA-MB-231, MCF-7 and Hela cells, especially 5 inhibit the growth of MDA-MB-231 cells with IC50 about 3.6 μM. The further studies show that 5 can bind and stabilize c-myc G4 DNA in π-π stacking mode, which confirmed by the hypochromise in the electronic spectra of 5 with the increasing of c-myc G4 DNA. When dealt with 5, the strength of CD signal attributed to c-myc G4 DNA is decreased and the FRET melting point of c-myc G4 DNA is increased. Moreover, the molecule docking calculation was conducted to show that 5 suitably stack onto the 5′ G-quartet surface, and parallels to the surfaces of the G5 and G-quartet consisting of G7, G11, G16, and G20. As a result, the replication of c-myc oligomers is blocked by 5. In a word, this type of phenanthroimidazole derives can act as potential inhibitor against breast cancer cells by binding and stabilizing c-myc G4 DNA through π-π stacking.
