Spectroscopic properties of fluoroquinolone antibiotics and nanosecond solvation dynamics in aerosol-OT reverse micelles

Photochemistry and Photobiology

Volumn 71, Issue 3, 2000, Pages 281-293

  Park, Hyoung Ryun ^a   Lee, Hyeong Chul ^a,c   Kim, Tae Heung ^b   Lee, Jin Ki ^b   Yang, Kiyull ^b   Bark, Ki Min ^b  

^a Chonnam National University   (South Korea)

^b Gyeongsang National University   (South Korea)

^c Department of Food and Nutrition   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DOCUSATE SODIUM; FLUMEQUINE; NITROGEN; NORFLOXACIN; OFLOXACIN; ORGANIC SOLVENT; PIPERAZINE DERIVATIVE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SODIUM 1,4 BIS(2 ETHYLHEXYL)SULFOSUCCINATE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANISOTROPY; ARTICLE; CALCULATION; REVERSE MICELLE; SOLVATION; SPECTROSCOPY; TEMPERATURE;

ANTI-INFECTIVE AGENTS; FLUOROQUINOLONES; MICELLES; NORFLOXACIN; OFLOXACIN; PHOTOCHEMISTRY; QUINOLIZINES; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY;

EID: 0034161205     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)071<0281:SPOFAA>2.0.CO;2     Document Type: Article

References (55)

1. Smith, J. T. and C. S. Lewin (1988) The Quinolones (Edited by V. T. Andriole), pp. 23-82. Academic Press, New York.
2. Kang, J. S., T. H. Kim, K. B. Park, B. H. Chung and J. I. Youn (1993) Enoxacin photosensitivity. Photodermatol. Photoimmunol. Photomed. 9, 159-161.
3. Cho, Y. H., T. H. Kim, H. B. Park, C. K. Park and K. M. Park (1995) Evaluation of the phototoxic potential of some quinolone antibiotics. Kor. J. Dermatol. 33, 1021-1028.
4. Wong, M., J. K. Thomas and M. Gratzel (1976) Fluorescence probing of inverted micelles. The state of solubilized water clusters in alkane/diisooctyl sulfosuccinate (aerosol OT) solution. J. Am. Chem. Soc. 98, 2391-2397.
5. Menger, F. M. and G. Saito (1977) Adsorption, displacement, and ionization in water pool. J. Am. Chem. Soc. 100, 4376-4379.
6. Zhang, J. and F. V. Bright (1991) Nanosecond reorganization of water within the interior of reverse micelles revealed by frequency-domain fluorescence spectroscopy. J. Phys. Chem. 95, 7900-7907.
7. Jain, T. K., M. Varshney and A. Maitra (1989) Structural studies of aerosol OT reverse micellar aggregates by FT-IR spectroscopy. J. Phys. Chem. 93, 7409-7416.
8. Karukstis, K. K., A. A. Frazier, D. S. Martula and J. A. Whiles (1996) Characterization of the microenvironments in AOT reversed micelles using multidimensional spectral analysis. J. Phys. Chem. 100, 11133-11138.
9. Grieser, F. and C. J. Drummond (1988) The physicochemical properties of self-assembled surfactant aggregates as determined by some molecular spectroscopic probe techniques. J. Phys. Chem. 92, 5580-5593.
10. Fletcher, P. D. I., A. M. Howe and B. H. Robinson (1987) The kinetics of solubilizate exchange between water droplets of a water-in-oil microemulsion. J. Chem. Soc. Faraday Trans. I 83, 985-1006.
11. Halle, B., T. Andersson, S. E. Forsen and B. Lindman (1981) Protein hydration from water. Oxygen-17 magnetic relaxation. J. Am. Chem. Soc. 103, 500-508.
12. Thompson, K. F. and L. M. Gierasch (1984) Conformation of a peptide solubilizate in a reversed micelle water pool. J. Am. Chem. Soc. 106, 3648-3652.
13. Grigolini, P. and M. Maestro (1986) A two-state statistic model for the dynamics of constrained water in reversed micelles. Chem. Phys. Lett. 127, 248-252.
14. Kim, V., G. Y. Frolov, V. I. Ermakov and S. E. Pak (1987) Interaction between the solvating power of the medium and the solubilization of water in reverse-micellar solutions of sodium di-2-ethylhexyl sulfosucinate. Kolloidn. Zh. 49, 1067-1069.
15. D'Aprano, A., A. Lizzio, V. Turco Liveri, F. Aliotta, C. Vasi and P. Migliardo (1988) Aggregation states of water in reversed AOT micelles: Raman evidence. J. Phys. Chem. 92, 4436-4439.
16. Riter, R. E., E. P. Undiks and N. E. Levinger (1998) Impact of counterion on water motion in aerosol OT reverse micelles. J. Am. Chem. Soc. 120, 6062-6067.
17. Riter, R. E., D. M. Willard and N. E. Levinger (1998) Water immobilization at surfactant interfaces in reverse micelles. J. Phys. Chem. B 102, 2705-2714.
18. Fendler, J. H. (1982) Membrane mimetic chemistry: Characterization and Applications of Micelles. Microemulsions. Monolayers. Bilayers, Vesicles, Host-Guest Systems, and Polyions, chapter 3, p. 522. Wiley, New York.
19. Barbara, P. F. and W. Jarzeba (1990) Ultrafast fluorescence measurements in chemistry. Adv. Photochem. 15, 78-88.
20. Maroncelli, M. (1993) Excited-state proton transfer and hydrogen-bonding dynamics in n-azaindol: time-resolved fluorescence and computer simulation. J. Mol. Liq. 57, 624-625.
21. Politi, M. J., O. Brandt and J. H. Fendler (1985) Ground- and excited-state proton transfers in reversed micelles. Polarity restrictions and isotope effects. J. Phys. Chem. 89, 2345-2354.
22. 2O in reversed micelles. 3. J. Am. Chem. Soc. 99, 4730-4736.
23. Bark, K. M., and R. K. Force (1993) Fluorescence properties of fluoranthene as a function of temperature and environment. Spectrochim. Acta 49A, 1605-1611.
24. Eaton, D. F. (1987) Reference Compounds for Fluorescence Measurement. IUPAC Organic Chem. Division, 1-11. Wilmington, Delaware.
25. Demas, J. N. and G. A. Grosby (1971) Evaluation of photoluminescence lifetimes. J. Phys. Chem. 75, 2463-2466.
26. Lakowicz, J. R., G. Lackzo, I. Gryczynski, H. Szmacinski and W. Wiczk (1988) Gigahertz frequency-domain fluorometry: resolution of complex decay, picosecond processes and future developments. J. Photochem. Photobiol. B Biol. 2, 295-311.
27. Jameson, D. M., E. Gratton and R. D. Hall (1984) Multifrequency phase and modulation fluorometry. Appl. Spectrosc. Rev. 20, 105-124.
28. Easter, J. M., R. P. DeToma and L. Brand (1976) Nanosecond time-resolved emission spectroscopy of a fluorescence probe adsorbed to 1-α-egg lecithin vesicles. Biophys. J. 16, 571-583.
29. Klamt, A. and G. Schüürmann (1993) COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans. 2, pp. 799-805.
30. Stewart, J. J. P. (1993) MOPAC 93. Fujitsu Limited, Tokyo, Japan.
31. Barbosa, J., R. Bergés, I. Toro and V. Sanz-Nebot (1997) Dissociation constants and preferential solvation of fluoroquinolones in hydroorganic mixtures used in LC. Int. J. Pharm. 149, 213-225.
32. Sanz-Nebot, V., I. Valls, D. Barber and J. Barbosa (1997) Acid-base behavior of quinolones in aqueous acetonitrile mixtures. Acta Chem. Scand. 51, 896-903.
33. Weber, G., and F. J. Farris (1979) Limited rotational motion: recognition by differential phase fluorometry. Biochemistry 18, 3075-3081.
34. Prendergast, F. G., G. I. Meyer, S. I. Carlson and J. D. Potter (1983) Synthesis, spectral properties, and use of 6-acryloyl-2-dimethylaminonaphthalene (Acrylodan). J. Biol. Chem. 258, 7541-7544.
35. Anstead, G. M., K. J. Hwang and J. A. Katzenellenbogen (1993) Characterization of the spectroscopic properties of a tetrahydrochrysene system containing a rigidified hydroxynitrostilbene chromophore: an inherently fluorescent ligand designed for the estrogen receptor. Photochem. Photobiol. 57, 616-628.
36. De, T. K. and A. Maitra (1995) Solution behaviour of aerosol OT in nonpolar solvents. Adv. Colloid Interface Sci. 59, 95-193.
37. Lee, H. C. (1999) Studies on the physicochemical properties of quinolone antibiotics. Ph.D Thesis, Chonnam National University, Korea.
38. Lakowicz, J. R. and H. Cherek (1985) Resolution of an excited-state reaction using frequency-domain fluorometry. Chem. Phys. Lett. 122, 380-384.
39. Lakowicz, J. R., E. Gratton, H. Cherek, B. P. Maliwal and G. Laczko (1984) Determination of time-resolved fuorescence emission spectra and anisotropies of a fluorophore-protein complex using frequency-domain phase-modulation fluorometry. J. Biol. Chem. 259, 10967-10972.
40. Kosower, E. M. and H. J. Dudiuk (1978) Intramolecular donor-acceptor systems. 5. Heavy atom effects on excited states of 6-N-arylamino-2-naphthalenesulfonate derivatives. J. Phys. Chem. 82, 2012-2015.
41. Seliskar, C. J. and L. Brand (1971) Electronic spectra of 2-aminonaphthalene-6-sulfonate and related molecules I. General properties and excited-state reactions. J. Am. Chem. Soc. 93, 5405-5414.
42. Grellman, K. H. and U. Schmitt (1982) Reactivity and decay pathways of photoexcited anilinonaphthalenes. J. Am. Chem. Soc. 104, 6267-6272.
43. Seliskar, C. J. and L. Brand (1971) Solvent dependence of the luminescence of N-arylaminonaphthalenesulfonates. Science 171, 799-800.
44. Cramer, F., W. Saenger and H.-C. Spatz (1967) Inclusion compounds. XIX. The formation of inclusion compound of α-cyclodextrin in aqueous solutions. J. Am. Chem. Soc. 89, 14-20.
45. Kosower, E. M., H. Kanety, H. Dodiuk, O. Striker, T. Jovin, H. Boni and D. Huppert (1983) Intramolecular donor-acceptor system 7. Solvent dielectric relaxation effects on the photophysics of 6-(phenylamino)-N,N-dimethyl-2-naphthalenesulfonamides. J. Phys. Chem. 87, 2479-2484.
46. Catena, G. C. and F. V. Bright (1989) Thermodynamic study on the effects of β-cyclodextrin inclusion with anilinonaphthalenesulfonates. Anal. Chem. 61, 905-909.
47. Bright, F. V., G. C. Catena and J. Huang (1990) Evidence for lifetime distributions in cyclodextrin inclusion complexes. J. Am. Chem. Soc. 112, 1343-1346.
48. Huang, J. and F. V. Bright (1990) Unimodal Lorentzian lifetime distributions for the 2-anilinonaphthalene-6-sulfonate-β-cyclodextrin inclusion complex recovered by multifrequency phase-modulation fluorometry. J. Phys. Chem. 94, 8457-8463.
49. Ebberson, T. W. and C. A. Ghiron (1989) Role of specific solvation in the fluorescence sensitivity of 1,8-ANS to water. J. Phys. Chem. 93, 7139-7143.
50. Kosower, E. M. (1985) Mechanism of fast intramolecular electron-transfer reactions. J. Am. Chem. Soc. 107, 1114-1118.
51. Timmers, K. and R. Sternglanz (1978) Ionization and divalent cation dissociation constants of nalidixic and oxolinic acids. Bioinorg. Chem. 9, 145-155.
52. Lakowicz, J. R. (1983) Principles of Fluorescence Spectroscopy, pp. 217-255. Plenum Press, New York.
53. Veselova, T. V., L. A. Limareva, A. S. Cherkasov and V. I. Shirokov (1965) A fluorometric determination of the lifetime of the excited dimers (excimers) in anthracene derivatives. Opt. Spectrosc. 19, 354-356.
54. Sarkar, N., K. Das, A. Datta, S. Das and K. Bhattacharyya (1996) Solvation dynamics of coumarin 480 in reversed micelles. Slow relaxation of water molecules. J. Phys. Chem. 100, 10523-10527.
55. Sarkar, N., A. Datta, S. Das and K. Bhattacharyya (1996) Solvation dynamics of coumarin 480 in micelles. J. Phys. Chem. 100, 15483-15486.