磷酸基团在环丙沙星光敏损伤DNA中的作用

doi:10.3866/PKU.WHXB201211131

Abstract

Abstract:

Stable and transient spectroscopic studies were conducted to investigate the influence of DNA phosphate bases in the process of DNA damage photo-induced by ciprofloxacin (CPX). The results of UV-visible and fluorescence studies confirmed that the absorption and emission properties of CPX were affected by the concentration of phosphate buffer (PB), and these results indicated that there are interactions between CPX and the phosphate anion. To investigate the relationship between the phosphate base and CPX, a comparative experiment was conducted using guanosine (Gua), 2'-deoxyguanosine (dG), and 2'-deoxyguanosine-5'c-monophosphate (dGMP). By comparative experiments, we found that the type of spectrum of CPX triplet state was changed due to the phosphate base of dGMP, hence, we concluded that the photo-damage process was changed. The effects of phosphate base of dGMP on the CPX triplet state (³CPX^*) spectrum have been investigated by laser flash photolysis methods, and the results confirmed that there are hydrogen-bonding interactions between the phosphate base of dGMP and CPX. In this study, we found that CPX and dGMP are combined together by the hydrogen bond which changed the mode of DNA damage photo-induced by CPX. Finally, based on the results obtained in this study, a rational scheme to describe the role of phosphate base playing in the DNA damage process photo-induced by CPX is proposed.

Key words: Photo-induced damage, Phosphate base, Ciprofloxacin, dGMP, Laser flash photolysis, DNA damage

LIU Yan-Cheng, LI Hai-Xia, CUI Ron-Grong, XU Yu-Lie, WANG Wen-Feng. Phosphate Base Effect on DNA Damage Photo-Induced by Ciprofloxacin[J]. Acta Phys. -Chim. Sin. 2013, 29(01), 212-216. doi: 10.3866/PKU.WHXB201211131

References

(1) Domagala, J. M.; Hanna, L. D.; Heifetz, C. L.; Hutt, M. P.;Mich, T. F.; Sanchez, J. P.; Solomon, M. J. Med. Chem. 1986, 29 (3), 394. doi: 10.1021/jm00153a015
(2) Van Doorslaer, X.; Demeestere, K.; Heynderickx, P. M.; VanLangenhove, H.; Dewulf, J. Appl. Catal. B-Environ. 2011, 101 (3-4), 540. doi: 10.1016/j.apcatb.2010.10.027
(3) Cuquerella, M. C.; Bosca, F.; Miranda, M. A.; Belvedere, A.;Catalfo, A.; de Guidi, G. Chem. Res. Toxicol. 2003, 16 (4), 562.doi: 10.1021/tx034006o
(4) Lorenzo, F.; Navaratnam, S.; Edge, R.; Allen, N. S. Photochem. Photobiol. 2008, 84 (5), 1118. doi: 10.1111/php.2008.84.issue-5
(5) Lorenzo, F.; Navaratnam, S.; Edge, R.; Allen, N. S. Photochem. Photobiol. 2009, 85 (4), 886. doi: 10.1111/php.2009.85.issue-4
(6) Martinez, L. J.; Sik, R. H.; Chignell, C. F. Photochem. Photobiol. 1998, 67 (4), 399.
(7) Gurbay, A.; Gonthier, B.; Signorini-Allibe, N.; Barret, L.;Favier, A.; Hincal, F. Neurotoxicology 2006, 27 (1), 6. doi: 10.1016/j.neuro.2005.05.007
(8) Belvedere, A.; Bosca, F.; Catalfo, A.; Cuquerella, M.; Guidi, G.;Ma, M. Chem. Res. Toxicol. 2002, 15 (9), 1142. doi: 10.1021/tx025530i
(9) Hartmann, A.; Golet, E. M.; Gartiser, S.; Alder, A. C.; Koller, T.;Widmer, R. M. Arch. Environ. Con. Tox. 1999, 36 (2), 115. doi: 10.1007/s002449900449
(10) Fasani, E.; Negra, F. F. B.; Mella, M.; Monti, S.; Albini, A.J. Org. Chem. 1999, 64 (15), 5388. doi: 10.1021/jo982456t
(11) Vasconcelos, T. G.; Henriques, D. M.; Konig, A.; Martins, A. F.Chemosphere 2009, 76 (4), 487. doi: 10.1016/j.chemosphere.2009.03.022
(12) Paul, T.; Dodd, M. C.; Strathmann, T. J. Water Res. 2010, 44 (10), 3121. doi: 10.1016/j.watres.2010.03.002
(13) Sortino, S.; Condorelli, G. New J. Chem. 2001, 26 (1), 250.
(14) Pascual-Reguera, M. I.; Parras, G. P.; Diaz, A. M. Microchem. J. 2004, 77 (1), 79. doi: 10.1016/j.microc.2004.01.003
(15) Shang, Z. C.; Yi, P. G.; Yu, Q. S.; Lin, R. S. Acta Phys. -Chim. Sin. 2001, 17 (1), 48. [商志才, 易平贵, 俞庆森, 林瑞森. 物理化学学报, 2001, 17 (1), 48. ] doi: 10.3866/PKU.WHXB20010110
(16) Cui, L.; Ren, B.; Tian, Z. Q. Acta Phys. -Chim. Sin. 2010, 26 (2), 397. [崔丽, 任斌, 田中群. 物理化学学报, 2010, 26 (2), 397.] doi: 10.3866/PKU.WHXB20100136
(17) Mella, M.; Fasani, E.; Albini, A. Helv. Chim. Acta 2001, 84 (9),2508. doi: 10.1002/1522-2675(20010919)84:9<2508::AID-HLCA2508>3.0.CO;2-Y
(18) Joshi, H. C.; Bridhkoti, J. P.; Mishra, H.; Pant, S. Spectrochim. Acta A 2011, 79 (3), 412. doi: 10.1016/j.saa.2011.02.044
(19) Albini, A.; Monti, S. Chem. Soc. Rev. 2003, 32 (4), 238. doi: 10.1039/b209220b
(20) Spratt, T. E.; Schultz, S. S.; Levy, D. E.; Chen, D.; Schluter, G.;Williams, G. M. Chem. Res. Toxicol. 1999, 12 (9), 809.
(21) Wasielewski, M. R. Chem. Rev. 1992, 92 (3), 435. doi: 10.1021/cr00011a005
(22) Ferguson, J.; Johnson, B. E. Brit. J. Dermatol. 1990, 123 (1), 9.doi: 10.1111/bjd.1990.123.issue-1
(23) Monti, S.; Sortino, S.; Fasani, E.; Albini, A. Chem. -Eur. J.2001, 7 (10), 2185.
(24) Chen, J.W.; Ge, L. K.;Wei, X. X.; Zhang, S. Y.; Qiao, X. L.;Cai, X. Y.; Xie, Q. Environ. Sci. Technol. 2010, 44 (7), 2400.doi: 10.1021/es902852v
(25) Takacsnovak, K.; Noszal, B.; Hermecz, I.; Kereszturi, G.;Podanyi, B.; Szasz, G. J. Pharm. Sci.-Us. 1990, 79 (11), 1023.
(26) Liu, Y. C.; Zhang, P.; Li, H. X.;Wang,W. F. Photochem. Photobiol. 2012, 88 (3), 639. doi: 10.1111/php.2012.88.issue-3

[1]	Jintao Dong, Sainan Ji, Yi Zhang, Mengxia Ji, Bin Wang, Yingjie Li, Zhigang Chen, Jiexiang Xia, Huaming Li. Construction of Z-Scheme MnO₂/BiOBr Heterojunction for Photocatalytic Ciprofloxacin Removal and CO₂ Reduction [J]. Acta Phys. -Chim. Sin., 2023, 39(11): 2212011-.
[2]	Xiaoqing Jia, Xiaoyu Bai, Zhezhe Ji, Yi Li, Yan Sun, Xueyue Mi, Sihui Zhan. Insight into the Effective Removal of Ciprofloxacin Using a Two-Dimensional Layered NiO/g-C₃N₄ Composite in Fe-Free Photo-Electro-Fenton System [J]. Acta Phys. -Chim. Sin., 2021, 37(8): 2010042-.
[3]	Hai-Xia LI,Yan-Cheng LIU,Rui-Zhi TANG,Peng ZHANG,Liu-Kui MA,Chi-Yuan WEI,Wen-Feng WANG. Reactions of Triplet-State Difloxacin with Amino Acids and dGMP: A Laser Flash Photolysis Study [J]. Acta Phys. -Chim. Sin., 2017, 33(5): 1051-1056.
[4]	LI Hai-Xia, ZHOU Bao-Chang, LIU Yan-Cheng, TANG Rui-Zhi, ZHANG Peng, LI Jing-Ye, WANG Wen-Feng. Primary Photochemical Properties of Difloxacin in Neutral Aqueous Solution [J]. Acta Phys. -Chim. Sin., 2014, 30(11): 2134-2141.
[5]	YUAN Hai-Xia, PAN Hu-Xiang, WU Yan-Lin, ZHAO Jian-Feng, DONG Wen-Bo. Laser Flash Photolysis Mechanism of Pyrenetetrasulfonate in Aqueous Solution [J]. Acta Phys. -Chim. Sin., 2012, 28(04): 957-962.
[6]	TANG Rui-Zhi, LI Hai-Xia, LIU Yan-Cheng, ZHANG Peng, CAO Xi-Yan, WANG Wen-Feng. Laser Flash Photolysis Study on Electron Transfer Oxidation Reaction of Tryptophan or Tyrosine with Triplet State Vitamin K₃ [J]. Acta Phys. -Chim. Sin., 2012, 28(01): 213-216.
[7]	ZHANG Feng, WANG Hong-Yan, LIN Yue-Xia. Effects of Cu²⁺ on Proton Transfer Processes in an Adenine-Thymine Anion Base Pair [J]. Acta Phys. -Chim. Sin., 2011, 27(12): 2799-2804.
[8]	ZHU Hui, WANG Mei, CHENG Ling-Li, ZHU Rong-Rong, SUN Xiao-Yu, YAO Si-De, WU Qing-Sheng, WANG Shi-Long. Photoionization and Photoexcitation Mechanisms of Salicylic Acid [J]. Acta Phys. -Chim. Sin., 2010, 26(01): 87-93.
[9]	LI Xian-Wen, ZHOU He, XU Yan, HU Yi-Qiao. Phase Conversion between Anhydrous and Hydrated Ciprofloxacin [J]. Acta Phys. -Chim. Sin., 2010, 26(01): 1-6.
[10]	QIN Yan; HUANG Li; DONG Wen-Bo; FANG Hao-Jie; HOU Hui-Qi. Cross-Reaction Mechanism between HNO₂ and C₆H₅Br in Aqueous Solution under Irradiation at 355 nm [J]. Acta Phys. -Chim. Sin., 2007, 23(11): 1677-1682.
[11]	LIU Rui-Li; ZHAO Hong-Wei; ZHANG Zhao-Xia; YAO Si-De; LI Qing-Nuan; LI Wen-Xin. Laser Flash Photolysis of C₆₀-dexamethasone [J]. Acta Phys. -Chim. Sin., 2007, 23(07): 1127-1130.
[12]	ZHANG Ren-Xi;HUANG Li;FANG Hao-Jie;DONG Wen-Bo;HOU Hui-Qi. Reaction Mechanism of C₆F₆-HNO₂ Aqueous Solution under Irradiation at 355 nm [J]. Acta Phys. -Chim. Sin., 2007, 23(02): 152-156.
[13]	ZHU Cheng-Zhu; ZHAGN Ren-Xi; FANG Hao-Jie; ZHAO Qing-Xiang; HOU Hui-Qi. Study on the Reaction Mechanism of Chlorobenzene with Nitrous Acid in Atmospheric Aqueous Phases Initiated by Irradiation of 355 nm UV Light [J]. Acta Phys. -Chim. Sin., 2005, 21(04): 367-371.
[14]	Zhu Cheng-Zhu;Zhang Ren-Xi;Zheng Guang-Ming;Ouyang Bin;Zhao Qing-Xiang;Hou Hui-Qi. Reaction Mechanism of Aqueous Benzene with Hydrogen Peroxide by Transient Absorbance Spectra [J]. Acta Phys. -Chim. Sin., 2004, 20(09): 1112-1117.
[15]	Shang Zhi-Cai;Yi Ping-Gui;Yu Qing-Sen;Lin Rui-Sen. Reaction Mechanism between Ciprofloxacin Hydrochloride and Bovine Serum Albumin [J]. Acta Phys. -Chim. Sin., 2001, 17(01): 48-52.

Phosphate Base Effect on DNA Damage Photo-Induced by Ciprofloxacin

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0