Chapter 3 Multiparametric Probing of Microenvironment with Solvatochromic Fluorescent Dyes

Methods in Enzymology

Volumn 450, Issue , 2008, Pages 37-58

  Klymchenko, Andrey S ^a,b   Demchenko, Alexander P ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b PALLADIN INSTITUTE OF BIOCHEMISTRY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYFLAVONE; FLUORESCENT DYE; 3-HYDROXYFLAVONE; FLAVONOID; PROTEIN;

BINDING SITE; HYDROGEN BOND; LIPID BILAYER; MICROENVIRONMENT; MOLECULAR PROBE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN BINDING; PROTON TRANSPORT; REVIEW; SPECTROSCOPY; ALGORITHM; ARTICLE; CHEMISTRY; METABOLISM; METHODOLOGY; SOLUBILITY; SPECTROFLUOROMETRY;

ALGORITHMS; BINDING SITES; FLAVONOIDS; FLUORESCENT DYES; HYDROGEN BONDING; LIPID BILAYERS; PROTEINS; SOLUBILITY; SPECTROMETRY, FLUORESCENCE;

EID: 58249094517     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(08)03403-4     Document Type: Review

References (42)

1. Abraham M.H. Hydrogen bonding. 31. Construction of a scale of solute effective or summation hydrogen-bond basicity. J. Phys. Org. Chem. 6 (1993) 660
2. Abraham M.H., Chadha H.S., Whiting G.S., and Mitchell R.C. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of Seiler. J. Pharm. Sci. 83 (1994) 1085
3. Bakhshiev N.G. Spectroscopy of Intermolecular Interactions (1972), Nauka, Leningrad
4. Bhattacharya A.A., Curry S., and Franks N.P. Binding of the general anesthetics propofol and halothane to human serum albumin: High resolution crystal structures. J. Biol. Chem. 275 (2000) 38731
5. y, S′, and SPP empirical scales as descriptors of nonspecific solvent effects. J. Org. Chem. 62 (1997) 8231
6. Catalan J., Perez P., and Blanco F.G. Analysis of the solvent effect on the photophysics properties of 6-propionyl-2-(dimethylamino)naphthalene (PRODAN). J. Fluorescence 1 (1991) 215
7. Chou P.-T., Martinez M.L., and Clements J.H. Reversal of excitation behavior of proton-transfer vs. charge-transfer by dielectric perturbation of electronic manifolds. J. Phys. Chem. 97 (1993) 2618
8. Chou P.-T., Pu S.-C., Cheng Y.-M., Yu W.-S., Yu Y.-C., Hung F.-T., and Hu W.-P. Femtosecond dynamics on excited-state proton/ charge-transfer reaction in 4′-N,N-diethylamino-3-hydroxyflavone. The role of dipolar vectors in constructing a rational mechanism. J. Phys. Chem. A 109 (2005) 3777
9. Demchenko A.P. Protein fluorescence, dynamics and function: Exploration of analogy between electronically excited and biocatalytic transition states. Biochim. Biophys. Acta 1209 (1994) 149
10. Demchenko A.P., Klymchenko A.S., Pivovarenko V.G., Ercelen S., Duportail G., and Mely Y. Multiparametric color-changing fluorescence probes. J. Fluorescence 13 (2003) 291
11. Demchenko A.P. Site-selective red-edge effects. Methods in Enzymology 450 R21 (2008) 59 (This volume)
12. Ercelen S., Klymchenko A.S., and Demchenko A.P. Ultrasensitive fluorescent probe for the hydrophobic range of solvent polarities. Anal. Chim. Acta 464 (2002) 273
13. Ercelen S., Klymchenko A.S., and Demchenko A.P. Novel two-color fluorescence probe with extreme specificity to Bovine Serum Albumin. FEBS Lett. 538 (2003) 25
14. Formosinho S.J., and Arnaut L.G. Excited-state proton transfer reactions II. Intramolecular reactions. J. Photochem. Photobiol. A: Chem. 75 (1993) 21
15. Kasha M. Proton-transfer spectroscopy. Perturbation of the tautomerization potential. J. Chem. Soc. Faraday Trans. 2 82 (1986) 2379
16. Klymchenko A.S., and Demchenko A.P. Probing AOT reverse micelles with two-color fluorescence dyes based on 3-hydroxychromone. Langmuir 18 (2002) 5637
17. Klymchenko A.S., and Demchenko A.P. Electrochromic modulation of excited-state intramolecular proton transfer: The new principle in design of fluorescence sensors. J. Am. Chem. Soc. 124 (2002) 12372
18. Klymchenko A.S., and Demchenko A.P. Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer. Phys. Chem. Chem. Phys. 5 (2003) 461
19. Klymchenko A.S., Duportail G., Ozturk T., Pivovarenko V.G., Mely Y., and Demchenko A.P. Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. Chem. Biol. 9 (2002) 1199
20. Klymchenko A.S., Duportail G., Mely Y., and Demchenko A.P. Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes. Proc. Natl. Acad. Sci. USA 100 (2003) 11219
21. Klymchenko A.S., Pivovarenko V.G., and Demchenko A.P. Elimination of hydrogen bonding effect on solvatochromism of 3-hydroxyflavones. J. Phys. Chem. A 107 (2003) 4211-4216
22. Klymchenko A.S., Pivovarenko V.G., Ozturk T., and Demchenko A.P. Modulation of solvent-dependent dual emission in 3-hydroxychromones by chemical substituents. New J. Chem. 27 (2003) 1336
23. Klymchenko A.S., Avilov S.V., and Demchenko A.P. Resolution of Cys and Lys labeling of alpha-crystallin with site-sensitive fluorescent 3-hydroxyflavone dye. Anal. Biochem. 329 (2004) 43
24. Klymchenko A.S., Duportail G., Demchenko A.P., and Mely Y. Bimodal distribution and fluorescence response of environment-sensitive probes in lipid bilayers. Biophys. J. 86 (2004) 2929
25. Klymchenko A.S., Stoeckel H., Takeda K., and Mely Y. Fluorescent probe based on intramolecular proton transfer for fast ratiometric measurement of cellular transmembrane potential. J. Phys. Chem. B 110 (2006) 13624
26. Kragh-Hansen U., Hellec F., de Foresta B., le Maire M., and Moller J.V. Detergents as probes of hydrophobic binding cavities in serum albumin and other water-soluble proteins. Biophys. J. 80 (2001) 2898
27. Lippert E.L. Laser-spectroscopic studies of reorientation and other relaxation processes in solution. In: Birks J.B. (Ed). Organic Molecular Photophysics Vol. 2 (1975), Wiley, New York 1-31
28. Liu W., Wang Y., Jin W., Shen G., and Yu R. Solvatochromogenic flavone dyes for the detection of water in acetone. Anal. Chim. Acta 383 (1999) 299
29. Mandal P.K., and Samanta A. Evidence of ground-state proton-transfer reaction of 3-hydroxyflavone in neutral alcoholic solvents. J. Phys. Chem. A 107 (2003) 6334
30. Mataga N., and Kubata T. Molecular interactions and electronic spectra (1970), Marcel Dekker, New York
31. Oncul S., and Demchenko A.P. The effects of thermal quenching on the excited-state intramolecular proton transfer reaction in 3-hydroxyflavones. Spectrochim. Acta A 65 (2006) 179
32. Reichardt C. Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 94 (1994) 2319
33. 2+ complexes. J. Phys. Chem. 102 (1998) 5907
34. Shynkar V.V., Mely Y., Duportail G., Piemont E., Klymchenko A.S., and Demchenko A.P. Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(dialkylamino)-3-hydroxyflavones. J. Phys. Chem. A 107 (2003) 9522
35. Shynkar V.V., Klymchenko A.S., Mely Y., Duportail G., and Pivovarenko V.G. Anion formation of 4′-(dimethylamino)-3-hydroxyflavone in phosphatidylglycerol vesicles induced by hepes buffer: A steady-state and time-resolved fluorescence investigation. J. Phys. Chem. B 108 (2004) 18750
36. Shynkar V., Klymchenko A.S., Piemont E., Demchenko A.P., and Mely Y. Dynamics of intermolecular hydrogen bonds in the excited states of 4′-dialkylamino-3-hydroxyflavones. on the pathway to an ideal fluorescent hydrogen bonding sensor. J. Phys. Chem. A 108 (2004) 8151
37. Shynkar V.V., Klymchenko A.S., Duportail G., Demchenko A.P., and Mely Y. Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes. Biochim. Biophys. Acta 1712 (2005) 128
38. Shynkar V.V., Klymchenko A.S., Kunzelmann C., Duportail G., Muller C.D., Demchenko A.P., Freyssinet J.-M., and Mely Y. Fluorescent biomembrane probe for ratiometric detection of apoptosis. J. Am. Chem. Soc. 129 (2007) 2187
39. Suppan P., and Ghoneim N. Solvatochromism (1997), The Royal Society of Chemistry, Cambridge, UK
40. Swinney T.C., and Kelley F.D. Proton transfer dynamics in substituted 3-hydroxyflavones: Solvent polarization effects. J. Chem. Phys. 99 (1993) 211
41. Tomin V.I., Oncul S., Smolarczyk G., and Demchenko A.P. Dynamic quenching as a simple test for the mechanism of excited-state reaction. Chem. Phys. 342 (2007) 126
42. Yesylevskyy S.O., Klymchenko A.S., and Demchenko A.P. Semi-empirical study of two-color fluorescent dyes based on 3-hydroxychromone. J. Mol. Struct.: Theochem. 755 (2005) 229