Citation:
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 Physico-Chimica Sinica,
;2014, 30(11): 2134-2141.
doi:
10.3866/PKU.WHXB201409161
-
The photochemical properties of difloxacin (DFX) were investigated in neutral aqueous solution. DFX aqueous solution showed intense absorption with one peak at 273 nm (molar absorption coefficient ε= 33000 dm3·mol-1·cm-1) and two other peaks at 323 and 335 nm (ε=15500 dm3·mol-1·cm-1) with the same molar absorption coefficient. Both the absorption and emission properties of DFX were pH-dependent. The acid dissociation constant (pKa) for the protonation equilibria of the ground state (5.9 and 9.8) were determined spectroscopically. DFX fluoresces weakly, and its maximum quantum yield for fluorescence emission was 0.06 at pH 3. Laser flash photolysis and pulse radiolysis studies were carried out to characterize the transient species of DFX aqueous solution. Triplet-triplet absorption reached a maximum at 620 nm with a molar absorption coefficient of 7900 dm3·mol-1·cm-1. The energy transfer method was used to estimate the triplet energy of DFX, which was 263.5 kJ·mol-1. The quantum yield of triplet formation was determined to be 0.21. Furthermore, DFX showed monophotonic photoionization with a quantum yield of 0.02. Pulse radiolysis indicated that DFX could react with eaq- and ·OH, and the bimolecular rate constants for these reactions were 1.72×1010 and 1.0×1010 dm3· mol-1 ·s-1, respectively. It is expected that this research may be helpful in determining the phototoxicity mechanism of DFX.
-
-
-
[1]
(1) Condorelli, G.; De Guidi, G.; Giuffrida, S.; Sortino, S.; Chillemi, R.; Sciuto, S. Photochem. Photobiol. 1999, 70, 280.
-
[2]
(2) Martinez, L.; Chignell, C. F. J. Photochem. Photobiol. B 1998, 45, 51. doi: 10.1016/S1011-1344(98)00160-2
-
[3]
(3) Klecak, G.; Urbach, F.; Urwyler, H. J. Photochem. Photobiol. B 1997, 37, 174. doi: 10.1016/S1011-1344(96)07424-6
-
[4]
(4) Martinez, L. J.; Sik, R. H.; Chignell, C. F. Photochem. Photobiol. 1998, 67, 399. doi: 10.1111/php.1998.67.issue-4
-
[5]
(5) Jechalke, S.; Focks, A.; Rosendahl, I.; Groeneweg, J.; Siemens, J.; Heuer, H.; Smalla, K. Fems Microbiol. Ecol. 2014, 87, 78. doi: 10.1111/1574-6941.12191
-
[6]
(6) Domagala, J. M. J. Antimicrob. Chemoth. 1994, 33, 685. doi: 10.1093/jac/33.4.685
-
[7]
(7) Matsumoto, M.; Kojima, K.; Nagano, H.; Matsubara, S.; Yokota, T. Antimicrob. Agents Chemother. 1992, 36, 1715. doi: 10.1128/AAC.36.8.1715
-
[8]
(8) Fasani, E.; Profumo, A.; Albini, A. Photochem. Photobiol. 1998, 68, 666. doi: 10.1111/php.1998.68.issue-5
-
[9]
(9) Monti, S.; Sortino, S.; Fasani, E.; Albini, A. Chem. Eur. J. 2001, 7, 2185.(10) Li, H. X.; Liu, Y. C.; Tang, R. Z.; Zhang, P.;Wang,W. F. Sci. China Chem. 2012, 55, 1358.
-
[10]
(11) Liu, Y. C.; Zhang, P.; Li, H. X.; Tang, R. Z.; Cui, R. R.;Wang, W. J. Photochem. Photobiol. B 2013, 118, 58. doi: 10.1016/j. jphotobiol.2012.11.002
-
[11]
(12) Li, H. X.; Zhang, P.; Liu, Y. C.; Tang, R. Z.; Xing, Z. G.; Yao, S. D.; Fu, H. Y.;Wang,W. F. Rad. Phys. Chem. 2012, 81, 40. doi: 10.1016/j.radphyschem.2011.09.005
-
[12]
(13) Ismail, M. Vet. Res. Commun. 2007, 31, 467. doi: 10.1007/ s11259-006-3464-4
-
[13]
(14) Inui, T.; Taira, T.; Matsushita, T.; Endo, T. Xenobiotica 1998, 28, 887. doi: 10.1080/004982598239128
-
[14]
(15) Guo, J. B.; Ostermann, A.; Siemens, J.; Dong, R. J.; Clemens, J. Waste Manage. 2012, 32, 131. doi: 10.1016/j. wasman.2011.07.031
-
[15]
(16) Sun, M.; Li, J.; Gai, C. L.; Chang, Z. Q.; Li, J. T.; Zhao, F. Z. J. Vet. Pharmacol. Ther. 2014, 37, 186. doi: 10.1111/ jvp.2014.37.issue-2
-
[16]
(17) Drlica, K.; Zhao, X. L. Microbiol. Mol. Biol. Rev. 1997, 61, 377.
-
[17]
(18) Walker, R. D. Aust. Vet. J. 2000, 78, 84. doi: 10.1111/j.1751-0813.2000.tb10528.x
-
[18]
(19) Cao, H. P.; Zhang, H. X.; He, S.; Zheng,W. D.; Yang, X. L. Isr. J. Aquacult-Bamid 2013, 65, 896.
-
[19]
(20) Frazier, D. L.; Thompson, L.; Trettien, A.; Evans, E. I. J. Vet. Pharmacol. Ther. 2000, 23, 293. doi: 10.1046/j.1365-2885.2000.00285.x
-
[20]
(21) Atef, M.; El-Banna, H. A.; Abd El-Aty, A. M.; udah, A. Deut. Tierarztl. Woch. 2002, 109, 320.
-
[21]
(22) Heinen, E. J. Vet. Pharmacol. Ther. 2002, 25, 1. doi: 10.1046/j.1365-2885.2002.00381.x
-
[22]
(23) Abd El-Aty, A. M.; udah, A.; Ismail, M.; Shimoda, M. Vet. Res. Commun. 2005, 29, 297.
-
[23]
(24) Adams, A. R.; Haines, G. R.; Brown, M. P.; Gronwall, R.; Merritt, K. Can. J. Vet. Res. 2005, 69, 229.
-
[24]
(25) Ding, F. K.; Cao, J. Y.; Ma, L. B.; Pan, Q. S.; Fang, Z. P.; Lu, X. C. Aquaculture 2006, 256, 121.
-
[25]
(26) Lian, N.; Zhao, H. C.; Sun, C. Y.; Jin, L. P.; Zhang, Z. L.; Zheng, Y. Z. Chem. J. Chin. Univ. 2002, 23, 564. [连宁, 赵慧春, 孙春燕, 金林培, 张仲伦, 郑雁珍. 高等学校化学学报, 2002, 23, 564.]
-
[26]
(27) Zuo, Z. H.; Yao, S. D.; Luo, J. A.;Wang,W. F.; Zhang, J. S.; Lin, N. Y. J. Photochem. Photobiol. B 1992, 15, 215. doi: 10.1016/1011-1344(92)85125-E
-
[27]
(28) Yao, S. D.; Sheng, S. G.; Cai, J. H.; Zhang, J. S.; Lin, N. Y. Radiat. Phys. Chem. 1995, 46, 105. doi: 10.1016/0969-806X(94)00120-9
-
[28]
(29) Navaratnam, S.; Claridge, J. Photochem. Photobiol. 2000, 72, 283. doi: 10.1562/0031-8655(2000)072<0283:PPPOO>2.0.CO;2
-
[29]
(30) Sortino, S.; De Guidi, G.; Giuffrida, S.; Monti, S.; Velardita, A. Photochem. Photobiol. 1998, 67, 167.
-
[30]
(31) Lorenzo, F.; Navaratnam, S.; Allen, N. S. J. Am. Chem. Soc. 2008, 130, 12238. doi: 10.1021/ja8044713
-
[31]
(32) Lorenzo, F.; Navaratnam, S.; Edge, R.; Allen, N. S. Photochem. Photobiol. 2008, 84, 1118. doi: 10.1111/php.2008.84.issue-5
-
[32]
(33) Fasani, E.; Negra, F. F. B.; Mella, M.; Monti, S.; Albini, A. J. Org. Chem. 1999, 64, 5388. doi: 10.1021/jo982456t
-
[33]
(34) Zhang, P.; Li, H. X.; Yao, S. D.;Wang,W. F. Sci. China Chem. 2014, 57, 409. doi: 10.1007/s11426-013-4986-6
-
[34]
(35) Buxton, G. V.; Greenstock, C. L.; Helman,W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513. doi: 10.1063/1.555805
-
[35]
(36) Martinez, L. J.; Scaiano, J. C. Photochem. Photobiol. 1998, 68, 646. doi: 10.1111/php.1998.68.issue-5
-
[36]
(37) Sandros, K.; Backstrom, H. L. J. Acta Chim. Scand. 1962, 16, 958. doi: 10.3891/acta.chem.scand.16-0958
-
[37]
(38) Sandros, K. Acta Chim. Scand. 1964, 18, 2355. doi: 10.3891/acta.chem.scand.18-2355
-
[38]
(39) rman, A. A.; Hamblett, I.; Jensen, N. H. Chem. Phys. Lett. 1984, 111, 293. doi: 10.1016/0009-2614(84)85509-8
-
[39]
(40) Lhiaubet-Vallet, V.; Cuquerella, M. C.; Castell, J. V.; Bosca, F.; Miranda, M. A. J. Phys. Chem. B 2007, 111, 7409. doi: 10.1021/jp070167f
-
[40]
(41) Lorenzo, F.; Navaratnam, S.; Edge, R.; Allen, N. S. Photochem. Photobiol. 2009, 85, 886. doi: 10.1111/php.2009.85.issue-4
-
[41]
(42) Monti, S.; Sortino, S. Photochem. Photobiol. Sci. 2002, 1, 877.
-
[42]
(43) Bensasson, R. V.; Gramain, J. C. J. Chem. Soc. Faraday Trans. 1980, 76, 1801. doi: 10.1039/f19807601801
-
[1]
-
-
-
[1]
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
-
[2]
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
-
[3]
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
-
[4]
Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
-
[5]
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
-
[6]
Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
-
[7]
Lianghong Ye , Junqing Ni , Zhongyi Yan , Zhanming Zhang , Can Zhu , Mo Sun . Chemical Fuel-Driven Non-Equilibrium Color Change. University Chemistry, 2025, 40(3): 349-354. doi: 10.12461/PKU.DXHX202406109
-
[8]
Runhua Chen , Qiong Wu , Jingchen Luo , Xiaolong Zu , Shan Zhu , Yongfu Sun . 缺陷态二维超薄材料用于光/电催化CO2还原的基础与展望. Acta Physico-Chimica Sinica, 2025, 41(3): 2308052-. doi: 10.3866/PKU.WHXB202308052
-
[9]
Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO2 with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
-
[10]
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
-
[11]
Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064
-
[12]
Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
-
[13]
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
-
[14]
Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
-
[15]
Zhenlin Zhou , Siyuan Chen , Yi Liu , Chengguo Hu , Faqiong Zhao . A New Program of Voltammetry Experiment Teaching Based on Laser-Scribed Graphene Electrode. University Chemistry, 2024, 39(2): 358-370. doi: 10.3866/PKU.DXHX202308049
-
[16]
Tianlong Zhang , Jiajun Zhou , Hongsheng Tang , Xiaohui Ning , Yan Li , Hua Li . Virtual Simulation Experiment for Laser-Induced Breakdown Spectroscopy (LIBS) Analysis. University Chemistry, 2024, 39(6): 295-302. doi: 10.3866/PKU.DXHX202312049
-
[17]
Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
-
[18]
Zhiliang Li . An Overview of Research on the History of Catalysis Science in China. University Chemistry, 2024, 39(7): 398-404. doi: 10.3866/PKU.DXHX202310101
-
[19]
Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
-
[20]
Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111
-
[1]
Metrics
- PDF Downloads(297)
- Abstract views(1012)
- HTML views(79)