| 光谱学与光谱分析 |
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| Synthesis and DNA-Binding Properties of Three Compouds Containing Pyridinecarboxamide |
| LIN Qiu-yue1,2,LU Xiao-hong1,CHEN Jian-rong1,2,LI Liang-chao1,2,HE Xin-qian1 |
1. College of Chemical and Life Science, Zhejiang Normal University, Jinhua 321004, China
2. Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces，Zhejiang Normal University, Jinhua 321004，China |
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Abstract N,N’-bis(2-pyridinecarboxamide)-1,2-ethane(H2L1), N, N’-bis(2-pyridinecarboxamide)-1,2-beneze(H2L2) and N-phenylpyridine-2-carboxamide(HL3) were synthesized, and characterized by elemental analysis, IR and HNMR spectra. UV-visible (UV-Vis) spectra, fluorescence spectra and SERS spectra to study the interaction of the three ligands with calf thymus DNA. UV-visible (UV-Vis) spectra show that with the incremental addition of DNA, the bands of H2L1, H2L2 and HL3 all show Hypochromism. Meanwhile fluorescence spectra show that the addition of the three ligands to DNA pretreated with EB causes an appreciable reduction in fluorescence intensity，indicating that the ligands compete with ethidium bromide in binding to DNA, and free ethidium bromide increases. The addition of DNA causes the SERS signals of the ligands to weakened and some bands to disappeared. Based on the above experimental results, we conclude that the three ligands bind to DNA mainly through the intercalation mode. The binding constant of the three compouds Kb was calculated, 1.20×104 for H2L1, 1.33×104 for H2L2 and is 1.52×104 for HL3. Kr was also calculated to be 0.67, 1.52 and 1.73 for H2L1, H2L2 and HL3, respectively. The value indicates that the binding of HL3 to DNA is stronger than that of H2L1 and H2L2, as HL3 has proper planar structure, smaller molecular volume and less steric hindrance. The three ligands can all induce the cleavage of plasmid pBR322 DNA. An increase in H2L1, H2L2 and HL3 concentrations causes more transformation of plasmid DNA from closed circular conformations to nicked conformations. But linear conformations have not been observed. The cleavage of plasmid pBR322 DNA caused by the three ligands is not selective.
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Received: 2006-10-29
Accepted: 2007-02-09
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Corresponding Authors:
LIN Qiu-yue
E-mail: sky51@zjnu.cn
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[1] Kurosaki H, Sharma R K, Aoki S, et al. J. Chem. Soc. Dalton Trams, 2001, (4)：441.
[2] LU Xiao-hong, LIN Qiu-yue, HU Rui-ding, et al(陆晓红，林秋月，胡瑞定，等). Spectroscopy and Spectral Analysis(光谱学与光谱分析)，2007，27(6)：1176.
[3] ZHANG Jun-yong, LIN Qin, DUAN Chun-ying, et al. J. Chem. Soc. Dalton Trans., 2002, (4): 591.
[4] Leung W H, Ma J X, Yam V W W, et al. J. Chem. Soc. Dalton Trans., 1991, (4)：1071.
[5] Trost B M, Hachiya I. J. Am. Chem. Soc., 1998, 120(5): 1104.
[6] Huc Ivan, Krische Michael J, Funeriu Daniel P, et al. J. Inorg. Chem, 1999, (38)：1415.
[7] KE Wei-zhong, YU Duo-wei, CHEN Wan-rong, et al(柯惟中, 余多慰, 陈婉蓉, 等). Journal of Nanjing Normal University(Natural Science)(南京师大学报·自然科学版), 1995, 18(3): 55.
[8] QI Jian-ying, MA Hong-xia, YANG Qi-yun, et al(戚建英, 马红霞, 杨启云, 等). Journal of Sichuan University(Natural Science)(四川大学学报·自然科学版), 2000, 37(3): 414.
[9] Ray Manabendra, Mukherjee Rabindranath, Richardson Jhon F, et al. J. Chem. Soc. Dalton Trans., 1994, (7): 965.
[10] LIU Jie, ZHANG Ti-xiang, LU Tong-bu, et al. J. Inorg. Biochem., 2002, 91：269.
[11] Barton Jacqueline K, Danishefsky Avis, Goldberg Jonathan. J. Am. Chem. Soc., 1984, 106： 2172.
[12] WANG Ping-hong, ZHANG Qi, WANG Liu-fang, et al(王平红, 张 岐, 王流芳, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2006, 26(5): 941.
[13] Lakowicz Joseph R, Weber Gregorio. Biochem., 1973, 12: 4161.
[14] PAN Jia-lai(潘家来). Application of Raman Spectra in Organic Chemistry(激光拉曼光谱在有机化学中的应用). Beijing: Chemical Industry Press(北京: 化学工业出版社), 1986. 68.
[15] WANG Shu-ling, YU Jun-sheng(王树玲, 于俊生). Chemical Journal of Chinese Universities(高等化学学报), 2002, 23(9): 1676.
[16] Igor Nabiev, Alexandre Baranov, Igor Chourpa, et al. J. Phys. Chem., 1995, 99(5): 1608.
[17] HU Rui-ding, LIN Qiu-yue, HUANG Wei, et al(胡瑞定, 林秋月, 黄 炜, 等). Journal of the Chinese Rare Earths Soceity(中国稀土学报), 2005, 23(3): 372.
[18] WANG Ping-hong, ZHANG Qi, YUAN Wen-bing, et al(王平红, 张 岐, 袁文兵, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2006, 26(7): 1298.
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