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 shu

Primary Photochemical Properties of Difloxacin in Neutral Aqueous Solution

1.
1. Shanghai Institute of Applied Physics, Chinese Academy of Sciences, Shanghai 201800, P. R. China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received Date: 10 April 2014
Available Online: 16 September 2014
Fund Project: 国家自然科学基金(21173252)资助项目 (21173252)

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 (pK_a) 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 e_aq^- 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.
- Photochemical property,
- Laser flash photolysis,
- Pulse radiolysis,
- Difloxacin,
- Excited state
1. [1]
  
  (1) Condorelli, G.; De Guidi, G.; Giuffrida, S.; Sortino, S.; Chillemi, R.; Sciuto, S. Photochem. Photobiol. 1999, 70, 280.
2. [2]
  (2) Martinez, L.; Chignell, C. F. J. Photochem. Photobiol. B 1998, 45, 51. doi: 10.1016/S1011-1344(98)00160-2
3. [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]
  (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]
  (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]
  (6) Domagala, J. M. J. Antimicrob. Chemoth. 1994, 33, 685. doi: 10.1093/jac/33.4.685
7. [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]
  (8) Fasani, E.; Profumo, A.; Albini, A. Photochem. Photobiol. 1998, 68, 666. doi: 10.1111/php.1998.68.issue-5
9. [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. [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. [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. [12]
  (13) Ismail, M. Vet. Res. Commun. 2007, 31, 467. doi: 10.1007/ s11259-006-3464-4
13. [13]
  (14) Inui, T.; Taira, T.; Matsushita, T.; Endo, T. Xenobiotica 1998, 28, 887. doi: 10.1080/004982598239128
14. [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. [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. [16]
  (17) Drlica, K.; Zhao, X. L. Microbiol. Mol. Biol. Rev. 1997, 61, 377.
17. [17]
  (18) Walker, R. D. Aust. Vet. J. 2000, 78, 84. doi: 10.1111/j.1751-0813.2000.tb10528.x
18. [18]
  (19) Cao, H. P.; Zhang, H. X.; He, S.; Zheng,W. D.; Yang, X. L. Isr. J. Aquacult-Bamid 2013, 65, 896.
19. [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. [20]
  (21) Atef, M.; El-Banna, H. A.; Abd El-Aty, A. M.; udah, A. Deut. Tierarztl. Woch. 2002, 109, 320.
21. [21]
  (22) Heinen, E. J. Vet. Pharmacol. Ther. 2002, 25, 1. doi: 10.1046/j.1365-2885.2002.00381.x
22. [22]
  (23) Abd El-Aty, A. M.; udah, A.; Ismail, M.; Shimoda, M. Vet. Res. Commun. 2005, 29, 297.
23. [23]
  (24) Adams, A. R.; Haines, G. R.; Brown, M. P.; Gronwall, R.; Merritt, K. Can. J. Vet. Res. 2005, 69, 229.
24. [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. [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. [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. [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. [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. [29]
  (30) Sortino, S.; De Guidi, G.; Giuffrida, S.; Monti, S.; Velardita, A. Photochem. Photobiol. 1998, 67, 167.
30. [30]
  (31) Lorenzo, F.; Navaratnam, S.; Allen, N. S. J. Am. Chem. Soc. 2008, 130, 12238. doi: 10.1021/ja8044713
31. [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. [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. [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. [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. [35]
  (36) Martinez, L. J.; Scaiano, J. C. Photochem. Photobiol. 1998, 68, 646. doi: 10.1111/php.1998.68.issue-5
36. [36]
  (37) Sandros, K.; Backstrom, H. L. J. Acta Chim. Scand. 1962, 16, 958. doi: 10.3891/acta.chem.scand.16-0958
37. [37]
  (38) Sandros, K. Acta Chim. Scand. 1964, 18, 2355. doi: 10.3891/acta.chem.scand.18-2355
38. [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. [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. [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. [41]
  (42) Monti, S.; Sortino, S. Photochem. Photobiol. Sci. 2002, 1, 877.
42. [42]
  (43) Bensasson, R. V.; Gramain, J. C. J. Chem. Soc. Faraday Trans. 1980, 76, 1801. doi: 10.1039/f19807601801
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