Citation: GAO Yun-Yan, CAO Lu, OU Zhi-Ze, CHEN Chen, LI Yi, WANG Xue-Song. Synthesis and Characterization of a Cu(I) Complex of Dipyrido[3,2-a：2’,3’-c]-7-aza-phenazine and Its Interaction with DNA[J]. Acta Physico-Chimica Sinica, ;2013, 29(10): 2162-2172. doi: 10.3866/PKU.WHXB201308152 shu

Synthesis and Characterization of a Cu(I) Complex of Dipyrido[3,2-a：2’,3’-c]-7-aza-phenazine and Its Interaction with DNA

GAO Yun-Yan ^1, ,
CAO Lu ¹ ,
OU Zhi-Ze ^1, ,
CHEN Chen ¹ ,
LI Yi ² ,
WANG Xue-Song ²

1.
1 Key Laboratory of Space Applied Physics and Chemistry of the Ministry of Education, School of Science, Northwestern Polytechnical University, Xi'an 710072, P. R. China;
2 Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China

Received Date: 20 June 2013
Available Online: 15 August 2013
Fund Project: 国家自然科学基金(21073143) (21073143)基金(Z2009-1-71002, Z2009-1-71006) (Z2009-1-71002, Z2009-1-71006)西北工业大学基础研究基金(JC200822, JC20100239) (JC200822, JC20100239)

A 1,10-phenanthroline dipyrido[3,2-a:2',3'-c]-7-aza-phenazine derivative (dpapz) and its Cu(I) complex [Cu(dpapz)₂]PF₆ are prepared and characterized by proton nuclear magnetic resonance spectroscopy (¹H NMR), Fourier transform infrared spectroscopy (FTIR), and high resolution electrospray ionization mass spectrometry (HR ESI-MS). The interactions of dpapz and [Cu(dpapz)₂]PF₆ with calf thymus DNA (CT DNA) are studied by ultraviolet-visible spectroscopy (UV-Vis), fluorescence spectroscopy, DNA melting temperature, and cyclic voltammetry. When the ligand dpapz interacts with DNA, there is no red shift of the absorption peak and only a small hypochromic (<30%) effect on the absorption spectra. In addition, the interaction leads to a slight increase in the melting temperature of DNA (ΔT_m=7.8 ℃). All the results indicate that groove binding is the primary interaction of dpapz with CT DNA. However, when [Cu(dpapz)₂]PF₆ interacts with DNA, there is a red shift of the absorption peak (2-3 nm), a large hypochromic effect on the absorption spectrum (>50%), and a significant increase in the melting temperature of DNA (ΔT_m=11.1 ℃), indicating that [Cu(dpapz)₂]PF₆ electrostatically associates with DNA in a partial intercalation manner. The complexes of dpapz and [Cu(dpapz)₂]PF₆ with DNA are further confirmed by ethidium bromide (EB) fluorescence assays and cyclic voltammetry. The association constants for dpapz and [Cu(dpapz)₂]PF₆ with CT DNA are 2.88×10⁵ and 5.32×10⁵ mol·L^-1, respectively. The yield of singlet oxygen produced by [Cu(dpapz)₂]PF₆ is similar to that of dpapz, while the yield of superoxide anion radical for [Cu(dpapz)₂]PF₆ is lower than that of dpapz. Active oxygen quencher experiments indicate that singlet oxygen, superoxide anion radicals, and hydrogen radicals all take part in the photocleavage of DNA by [Cu(dpapz)₂]PF₆ and dpapz. However, [Cu(dpapz)₂]PF₆ causes more photodamage of plasmid DNA than does dpapz, most likely because of its higher affinity for DNA.
- Phenanthroline derivative,
- Cu(I) complex,
- Photocleavage of DNA,
- Active oxygen,
- Mode of DNAinteraction
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