메뉴 건너뛰기




Volumn 6867, Issue , 2008, Pages

Steady-state and time-resolved fluorescence investigation of 2-pyridone and 3-pyridone in solution and their specific binding to human serum albumin

Author keywords

2 pyridone; 3 pyridone; Biological probes; Human serum albumin; Hydroxypyridines; Protein ligand recognition; Resonance energy transfer; Tautomerization

Indexed keywords

ABSORPTION; BINARY MIXTURES; BINDING ENERGY; BINDING SITES; BIOCONVERSION; BODY FLUIDS; ENERGY STORAGE; ENERGY TRANSFER; ETHERS; FLUIDS; FLUORESCENCE; HYDROGEN; HYDROGEN BONDS; LIGHT EMISSION; LUMINESCENCE; MIXTURES; MOLECULAR STRUCTURE; MOLECULES; QUENCHING; RATE CONSTANTS; SOLVATION; SOLVENTS; WATER ANALYSIS;

EID: 42249111888     PISSN: 16057422     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.762218     Document Type: Conference Paper
Times cited : (7)

References (43)
  • 1
    • 33646918845 scopus 로고    scopus 로고
    • Probing protein folding and conformational transitions with fluorescence
    • C. A. Royer, "Probing protein folding and conformational transitions with fluorescence," Chem. Rev. 106, 1769-1784 (2006).
    • (2006) Chem. Rev , vol.106 , pp. 1769-1784
    • Royer, C.A.1
  • 2
    • 13144281510 scopus 로고    scopus 로고
    • 2-Naphthol-phosphatidylethanolamine: A fluorescent phospholipid analog for excited-state proton transfer studies in membranes
    • P. Neyroz, L. Franzoni, C. Menna, A. Spisni, and L. Masotti, "2-Naphthol-phosphatidylethanolamine: A fluorescent phospholipid analog for excited-state proton transfer studies in membranes," J. Fluorescence 6, 127-138 (1996).
    • (1996) J. Fluorescence , vol.6 , pp. 127-138
    • Neyroz, P.1    Franzoni, L.2    Menna, C.3    Spisni, A.4    Masotti, L.5
  • 3
    • 0028032854 scopus 로고
    • Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescence probes
    • A. Sytnik, D. Gormin, and M. Kasha, "Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescence probes," Proc. Natl. Acad. Sci. USA 91, 11968-11972 (1994).
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 11968-11972
    • Sytnik, A.1    Gormin, D.2    Kasha, M.3
  • 4
    • 0028133255 scopus 로고
    • Excited-state intramolecular protein transfer as a fluorescence probe for protein binding-site static polarity
    • A. Sytnik and M. Kasha, "Excited-state intramolecular protein transfer as a fluorescence probe for protein binding-site static polarity," Proc. Natl. Acad. Sci. USA 91, 8627-8630 (1994).
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 8627-8630
    • Sytnik, A.1    Kasha, M.2
  • 5
    • 0029804350 scopus 로고    scopus 로고
    • Energy transfer to a proton-transfer fluorescence probe: Tryptophan to a flavonol in human serum albumin
    • A. Sytnik and Y. Litvinyuk, "Energy transfer to a proton-transfer fluorescence probe: tryptophan to a flavonol in human serum albumin," Proc. Natl. Acad. Sci. USA 93, 12959-12963 (1996).
    • (1996) Proc. Natl. Acad. Sci. USA , vol.93 , pp. 12959-12963
    • Sytnik, A.1    Litvinyuk, Y.2
  • 6
    • 0023922561 scopus 로고
    • Microcalorimetric and chromatographic investigations of the binding of some pyridine derivatives to cyclodextrins
    • S. El Gezawi, N. Omar, N. El Rabbat, H. Ueda, and J. H. Perrin, "Microcalorimetric and chromatographic investigations of the binding of some pyridine derivatives to cyclodextrins," J. Pharm. Biomed. Anal. 6, 399-406 (1988).
    • (1988) J. Pharm. Biomed. Anal , vol.6 , pp. 399-406
    • El Gezawi, S.1    Omar, N.2    El Rabbat, N.3    Ueda, H.4    Perrin, J.H.5
  • 7
    • 33847088018 scopus 로고
    • Energies and alkylations of tautomeric heterocyclic compounds: Old problems-new answers
    • P. Beak, "Energies and alkylations of tautomeric heterocyclic compounds: old problems-new answers," Acc. Chem. Res. 10, 186-192 (1977).
    • (1977) Acc. Chem. Res , vol.10 , pp. 186-192
    • Beak, P.1
  • 8
    • 0001246344 scopus 로고
    • Electronic properties and π-π* absorption spectrum of 2-pyridone
    • A. Fujimoto, K. Inuzuka, and R. Shiba, "Electronic properties and π-π* absorption spectrum of 2-pyridone," Bull. Chem. Soc Jpn. 54, 2802-2806 (1981).
    • (1981) Bull. Chem. Soc Jpn , vol.54 , pp. 2802-2806
    • Fujimoto, A.1    Inuzuka, K.2    Shiba, R.3
  • 9
    • 0010427474 scopus 로고
    • Spectroscopy, structure, and proton dynamics of 2-hydroxypyridine and its clusters with water and ammonia
    • M. R. Nimlos, D. F. Kelley, and E. R. Bernstein, "Spectroscopy, structure, and proton dynamics of 2-hydroxypyridine and its clusters with water and ammonia," J. Phys. Chem. 93, 643-651 (1989).
    • (1989) J. Phys. Chem , vol.93 , pp. 643-651
    • Nimlos, M.R.1    Kelley, D.F.2    Bernstein, E.R.3
  • 10
    • 36449003365 scopus 로고
    • 0 electronic transition of 2-pyridone. A rotational Duschinsky effect. Structural and dynamical consequences
    • 0 electronic transition of 2-pyridone. A rotational Duschinsky effect. Structural and dynamical consequences," J. Chem. Phys. 95, 8732-8743 (1991).
    • (1991) J. Chem. Phys , vol.95 , pp. 8732-8743
    • Held, A.1    Champagne, B.B.2    Pratt, D.W.3
  • 12
    • 26444613371 scopus 로고    scopus 로고
    • Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C:O bands
    • Y. Matsuda, T. Ebata, and N. Mikami, "Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C:O bands," J. Chem. Phys. 110, 8397-8407 (1999).
    • (1999) J. Chem. Phys , vol.110 , pp. 8397-8407
    • Matsuda, Y.1    Ebata, T.2    Mikami, N.3
  • 14
    • 15544367204 scopus 로고    scopus 로고
    • Reaction paths of tautomerization between hydroxypyridines and pyridones
    • N. Tsuchida and S. Yamabe, "Reaction paths of tautomerization between hydroxypyridines and pyridones," J. Phys. Chem. A 109, 1974-1980 (2005).
    • (2005) J. Phys. Chem. A , vol.109 , pp. 1974-1980
    • Tsuchida, N.1    Yamabe, S.2
  • 15
    • 34547325782 scopus 로고    scopus 로고
    • Ab initio/DFT and AIM studies on dual hydrogen-bonded complexes of 2-hydroxypyridine/2-pyridone tautomerism
    • D. -L. Wu, L. Liu, G. -F. Liu, and D. -Z. Jia, "Ab initio/DFT and AIM studies on dual hydrogen-bonded complexes of 2-hydroxypyridine/2-pyridone tautomerism," J. Phys. Chem. A 111, 5244-5252 (2007).
    • (2007) J. Phys. Chem. A , vol.111 , pp. 5244-5252
    • Wu, D.-L.1    Liu, L.2    Liu, G.-F.3    Jia, D.-Z.4
  • 17
    • 0002587695 scopus 로고
    • Ionization constants of heterocyclic substances. II. Hydroxy-derivatives of nitrogenous six-membered ring-compounds
    • A. Albert and J. N. Phillips, "Ionization constants of heterocyclic substances. II. Hydroxy-derivatives of nitrogenous six-membered ring-compounds," J. Chem. Soc. 1294-1304 (1956).
    • (1956) J. Chem. Soc , pp. 1294-1304
    • Albert, A.1    Phillips, J.N.2
  • 18
    • 0000875265 scopus 로고
    • Proton magnetic resonance spectra of tautomeric substituted pyridines and their conjugate acids
    • R. H. Cox, A. A. Bothner-By, A. Aksel, "Proton magnetic resonance spectra of tautomeric substituted pyridines and their conjugate acids," J. Phys. Chem. 73, 2465-2468 (1969).
    • (1969) J. Phys. Chem , vol.73 , pp. 2465-2468
    • Cox, R.H.1    Bothner-By, A.A.2    Aksel, A.3
  • 19
    • 0016486606 scopus 로고
    • A fluorescence study of hydroxypyridines
    • A. Weisstuch, P. Neidig, and A. C. Testa, "A fluorescence study of hydroxypyridines," J. Lumin. 10, 137-144 (1975).
    • (1975) J. Lumin , vol.10 , pp. 137-144
    • Weisstuch, A.1    Neidig, P.2    Testa, A.C.3
  • 20
    • 0000216182 scopus 로고
    • Spectra and ionization constants of the vitamin B6 group and related 3-hydroxypyridine derivatives
    • D. Metzler and E. Snell, "Spectra and ionization constants of the vitamin B6 group and related 3-hydroxypyridine derivatives," J. Am. Chem. Soc 77, 2431-2437 (1955).
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 2431-2437
    • Metzler, D.1    Snell, E.2
  • 21
    • 2242462414 scopus 로고
    • Solvent effects on protomeric equilibriums: Quantitative correlation with an electrostatic hydrogen-bonding model
    • P. Beak and J. B. Convington, "Solvent effects on protomeric equilibriums: quantitative correlation with an electrostatic hydrogen-bonding model," J. Am. Chem. Soc. 100, 3961-3963 (1978).
    • (1978) J. Am. Chem. Soc , vol.100 , pp. 3961-3963
    • Beak, P.1    Convington, J.B.2
  • 22
    • 0002575639 scopus 로고
    • Enthalpies of combustion of the three hydroxypyridines and the four hydroxy-2- methylpyridines
    • S. Suradi, N. El Saiad, G. Pilcher, and H. A. Skinner, "Enthalpies of combustion of the three hydroxypyridines and the four hydroxy-2- methylpyridines," J. Chem.Theromodyn. 14, 45-50 (1982).
    • (1982) J. Chem.Theromodyn , vol.14 , pp. 45-50
    • Suradi, S.1    El Saiad, N.2    Pilcher, G.3    Skinner, H.A.4
  • 23
    • 37049106398 scopus 로고
    • Equilibrium and activation thermodynamic parameters of the tautomerism of 6-methoxy-2-pyridone in water
    • M. Chevrier, J. Guillerez, and J. E. Dubois, "Equilibrium and activation thermodynamic parameters of the tautomerism of 6-methoxy-2-pyridone in water," J. Chem. Soc., Perkin Trans. 2 979-982 (1983).
    • (1983) J. Chem. Soc., Perkin Trans , vol.2 , pp. 979-982
    • Chevrier, M.1    Guillerez, J.2    Dubois, J.E.3
  • 24
    • 0018413926 scopus 로고
    • Human serum albumin. Spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin
    • C. B. Berde, B. S. Hudson, R. D. Simon, and L. A. Sklar, "Human serum albumin. Spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin," J. Biol. Chem. 254, 391-400 (1979).
    • (1979) J. Biol. Chem , vol.254 , pp. 391-400
    • Berde, C.B.1    Hudson, B.S.2    Simon, R.D.3    Sklar, L.A.4
  • 25
    • 0026664548 scopus 로고
    • Atomic structure and chemistry of human serum albumin
    • X. M. He and D. C. Carter, "Atomic structure and chemistry of human serum albumin," Nature (London) 358, 209-215 (1992).
    • (1992) Nature (London) , vol.358 , pp. 209-215
    • He, X.M.1    Carter, D.C.2
  • 26
    • 0034624021 scopus 로고    scopus 로고
    • Binding of the general anesthetics propofol and halothane to human serum albumin
    • A. A. Bhattacharya, S. Curry, and N. P. Franks, "Binding of the general anesthetics propofol and halothane to human serum albumin," J. Biol. Chem. 275, 38731-38738 (2000).
    • (2000) J. Biol. Chem , vol.275 , pp. 38731-38738
    • Bhattacharya, A.A.1    Curry, S.2    Franks, N.P.3
  • 27
    • 0000686383 scopus 로고    scopus 로고
    • Molecular recognition
    • Ed
    • H. S. Gellman, Ed., "Molecular recognition," Chem. Rev. 97, 1231-1734 (1997).
    • (1997) Chem. Rev , vol.97 , pp. 1231-1734
  • 28
    • 0015935434 scopus 로고
    • Reversible denaturation of human serum albumin by pH, temperature, and guanidine hydrochloride followed by optical rotation
    • K. Wallevik, "Reversible denaturation of human serum albumin by pH, temperature, and guanidine hydrochloride followed by optical rotation," J. Biol. Chem. 248, 2650-2655 (1973).
    • (1973) J. Biol. Chem , vol.248 , pp. 2650-2655
    • Wallevik, K.1
  • 29
    • 0033512054 scopus 로고    scopus 로고
    • Spectroscopic properties of 2-hydroxypyridine and excited state anion formaion
    • G. Will, E. Waghorne, D. Fitzmaurice, D. Guha, A. Mondal, and S. Mukherjee, "Spectroscopic properties of 2-hydroxypyridine and excited state anion formaion," Ind. J. Chem. 38A, 753-759 (1999).
    • (1999) Ind. J. Chem , vol.38 A , pp. 753-759
    • Will, G.1    Waghorne, E.2    Fitzmaurice, D.3    Guha, D.4    Mondal, A.5    Mukherjee, S.6
  • 30
    • 33751554526 scopus 로고
    • Polarity of AOT micellar interfaces: Use of the preferential solvation concepts in the evaluation of the effective dielectric constants
    • M. Belletête, M. Lachapelle, and G. Durocher, "Polarity of AOT micellar interfaces: use of the preferential solvation concepts in the evaluation of the effective dielectric constants," J. Phys. Chem. 94, 5337-5341 (1990).
    • (1990) J. Phys. Chem , vol.94 , pp. 5337-5341
    • Belletête, M.1    Lachapelle, M.2    Durocher, G.3
  • 31
    • 33746361826 scopus 로고    scopus 로고
    • Examining [2,2'-bipyridyl]-3,3'-diol as a possible DNA model base pair
    • O. K. Abou-Zied, "Examining [2,2'-bipyridyl]-3,3'-diol as a possible DNA model base pair," J. Photochem. Photobiol. A 182, 192-201 (2006).
    • (2006) J. Photochem. Photobiol. A , vol.182 , pp. 192-201
    • Abou-Zied, O.K.1
  • 32
    • 34547861268 scopus 로고    scopus 로고
    • The role of water in solvating the hydrogen bonding center of 2-(2'-hydroxyphenyl)benzoxazole
    • O. K. Abou-Zied, "The role of water in solvating the hydrogen bonding center of 2-(2'-hydroxyphenyl)benzoxazole," Chem. Phys. 337, 1-10 (2007).
    • (2007) Chem. Phys , vol.337 , pp. 1-10
    • Abou-Zied, O.K.1
  • 33
    • 0033568839 scopus 로고    scopus 로고
    • Hydrogen bonding effects in the photophysics of a drug, Piroxicam, in homogeneous media and dioxane-water mixtures
    • S. M. Andrade, M. B. Costa, "Hydrogen bonding effects in the photophysics of a drug, Piroxicam, in homogeneous media and dioxane-water mixtures," Phys. Chem. Chem. Phys. 1, 4213-4218 (1999).
    • (1999) Phys. Chem. Chem. Phys , vol.1 , pp. 4213-4218
    • Andrade, S.M.1    Costa, M.B.2
  • 34
    • 34249834925 scopus 로고
    • Solvatochromic parameters for binary mixtures and a correlation with equilibrium constants. Parti. Dioxane-water mixtures
    • E. Casassas, G. Fonrodona, A. De Juan, " Solvatochromic parameters for binary mixtures and a correlation with equilibrium constants. Parti. Dioxane-water mixtures," J. Solution Chem. 21, 147-162 (1992).
    • (1992) J. Solution Chem , vol.21 , pp. 147-162
    • Casassas, E.1    Fonrodona, G.2    De Juan, A.3
  • 35
    • 33845280632 scopus 로고
    • Kamlet-Taft π * polarizability/dipolarity of mixtures of water with various organic solvents
    • W. J. Cheong, P. W. Carr, "Kamlet-Taft π * polarizability/dipolarity of mixtures of water with various organic solvents," Anal. Chem. 60, 820-826 (1988).
    • (1988) Anal. Chem , vol.60 , pp. 820-826
    • Cheong, W.J.1    Carr, P.W.2
  • 36
    • 0037739659 scopus 로고    scopus 로고
    • Study of the interaction between daunorubicin and human serum albumin, and the determination of daunorubicin in blood serum samples
    • C. Q. Jiang, M. X. Gao, X. Z. Meng, "Study of the interaction between daunorubicin and human serum albumin, and the determination of daunorubicin in blood serum samples," Spectrochim. Acta A 59, 1605-1610 (2003).
    • (2003) Spectrochim. Acta A , vol.59 , pp. 1605-1610
    • Jiang, C.Q.1    Gao, M.X.2    Meng, X.Z.3
  • 37
    • 0037009311 scopus 로고    scopus 로고
    • Interaction of drugs with bovine and human serum Albumin
    • A. Sulkowska, "Interaction of drugs with bovine and human serum Albumin," J. Mol. Struc 614, 227-232 (2002).
    • (2002) J. Mol. Struc , vol.614 , pp. 227-232
    • Sulkowska, A.1
  • 38
    • 0016801988 scopus 로고
    • The characterization of two specific drug binding sites on human serum albumin
    • G. Sudlow, D. J. Birkett, and D. N. Wade, "The characterization of two specific drug binding sites on human serum albumin," Mol. Pharm. 11, 824-832 (1975).
    • (1975) Mol. Pharm , vol.11 , pp. 824-832
    • Sudlow, G.1    Birkett, D.J.2    Wade, D.N.3
  • 39
    • 0003468776 scopus 로고    scopus 로고
    • T. Förster and O. Sinanoglu Eds, Academic Press, New York
    • T. Förster and O. Sinanoglu (Eds.), Modern Quantum Chemistry, Vol. 3, Academic Press, New York (1996).
    • (1996) Modern Quantum Chemistry , vol.3
  • 40
    • 27744599888 scopus 로고
    • Transfer mechanisms of electronic excitation
    • T. Förster, "Transfer mechanisms of electronic excitation," Discuss. Faraday Soc. 27, 7-17 (1959).
    • (1959) Discuss. Faraday Soc , vol.27 , pp. 7-17
    • Förster, T.1
  • 41
    • 0042358821 scopus 로고    scopus 로고
    • A study of the interaction between a new reagent and serum albumin by fluorescence spectroscopy
    • F. L. Cui, J. Fan, D.-L. Ma, M.-C. Liu, X.-G. Chen, Z.-D. Hu, "A study of the interaction between a new reagent and serum albumin by fluorescence spectroscopy," Anal. Lett. 36, 2151-2166 (2003).
    • (2003) Anal. Lett , vol.36 , pp. 2151-2166
    • Cui, F.L.1    Fan, J.2    Ma, D.-L.3    Liu, M.-C.4    Chen, X.-G.5    Hu, Z.-D.6
  • 42
    • 1842426864 scopus 로고
    • Oxygen quenching of fluorescence in solution: An experimental study of the diffusion process
    • W. R. Ware, "Oxygen quenching of fluorescence in solution: an experimental study of the diffusion process," J. Phys. Chem. 66, 455-458 (1962).
    • (1962) J. Phys. Chem , vol.66 , pp. 455-458
    • Ware, W.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.