Abstract
The constrained photophysics of intramolecular charge transfer (ICT) probe 4-(dimethylamino)cinnamic acid (DMACA) was studied in different surfactant systems as well as in presence of model water soluble protein bovine serum albumin (BSA). Binding of the probe in ionic micelles like sodium dodecyl sulfate (SDS) and cetyl trimethyl ammonium bromide (CTAB) causes an increase in ICT fluorescence intensity, whereas, in non-ionic TritonX-100 (TX-100) the intensity decreases with a concomitant increase in emission from locally excited (LE) state. The observations were explained in terms of the different binding affinity, location of the probe and also the nature of specific hydrogen bonding interaction in the excited state nonradiative relaxation process of DMACA. The ICT fluorescence emission yield decreases in BSA due to the locking in of the probe buried in the hydrophobic pocket of the protein structure. SDS induced uncoiling of protein and massive cooperative binding between BSA and SDS is manifested by the release of probe molecules in relatively free aqueous environment.
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B. E. Cohen, T. B. McAnaney, E. S. Park, Y. N. Jan, S. G. Boxer, L. Y. Jan, Probing protein electrostatics with a synthetic fluorescent amino acid, Science, 2002, 296, 1700–1703.
K. Bhattacharyya, Solvation dynamics and proton transfer in supramolecular assemblies, Acc. Chem. Res., 2003, 36, 95–101.
D. Zhong, A. Douhal, A. H. Zewail, Femtosecond studies of protein-ligand hydrophobic binding and dynamics: human serum albumin, Proc. Natl. Acad. Sci. USA, 2000, 97, 14056–14061.
C. H. Evans, S. DeFeyter, L. Viaene, J. van Stam, F. C. DeSchryver, Biomolecular processes of α-Terthiophene in a ß-Cyclodextrin environment: An exploratory study, J. Phys. Chem., 1996, 100, 2129–2135.
P. P. Mishra, R. Adhikary, P. Lahiri, A. Dutta, Chlorin p6 as a fluorescent probe for the investigation of surfactant-cyclodextrin interactions, Photochem. Photobiol. Sci., 2006, 5, 741–747.
M. Vasilescu, D. F. Anghel, M. Almgren, P. Hansson, S. Saito, Fluorescence probe study of the interactions between nonionic poly(oxyethylenic) surfactants and poly(acrylic acid) in aqueous solutions, Langmuir, 1997, 13, 6951–6955.
J. M. Beechem, L. Brand, Time-resolved fluorescence of proteins, Ann. Rev. Biochem., 1985, 54, 43–71.
J. W. Petrich, M. C. Chang, D. B. McDonald, G. R. Fleming, On the origin of nonexponential fluorescence decay in tryptophan and its derivatives, J. Am. Chem. Soc., 1983, 105, 3824–3832.
J. H. Fendler, Membrane Mimetic Chemistry, Wiley-Interscience, New York, 1982.
Surfactants in Solution, ed. K. L. Mittal and B. Lindman, Plenum, New York, 1984, vol. 1 and 2.
Physics of Amphiphiles, Micelles, Vesicles and Microemulsions, ed. V. De Giorgio and M. Conti, North-Holland, Amsterdam, 1985.
S. Mishima, Y. Ono, Y. Araki, Y. Akao, Y. Nozawa, Two related cinnamic acid derivatives from Brazilian honey bee Propolis, Baccharin and Drupanin, induce growth inhibition in Allografted Sarcoma S-180 in Mice, Biol. Pharma. Bull., 2005, 28, 1025–1030.
A. R. Kroon, W. D. Hoff, H. P. M. Fennema, J. Gijzen, G.-J. Koomen, J. W. Verhoeven, W. Crielaard, K. J. Hellingwerf, Spectral tuning, fluorescence, and photoactivity in hybrids of photoactive yellow protein, reconstituted with native or modified chromophores, J. Biol. Chem., 1996, 271, 31949–31956.
P. R. Bangal, S. Chakravorti, Photophysics of 4-dimethylamino cinnamic acid in different environments, J. Photochem. Photobiol., A, 1998, 116, 191–202.
K. Rotkiewicz, K. H. Grellmann, Z. R. Grabowski, Reinterpretation of the anomalous fluorescence of p-N, N-dimethylamino-benzonitrile, Chem. Phys. Lett., 1973, 19, 315–318.
K. A. Zachariasse, M. Grobys, Th. von der Haar, A. Hebecker, Yu. V. Il’ichev, O. Morawski, I. Rückert, W. Kühnle, Photo-induced intramolecular charge transfer and internal conversion in molecules with a small energy gap between S1 and S2. Dynamics and structure, J. Photochem. Photobiol., A, 1997, 105, 373–383.
A. MacIejewski, J. Kubicki, K. Dobek, Different sources of 4-aminophthalimide solvation dynamics retardation inside micellar systems, J. Colloid Interface Sci., 2006, 295, 255–263.
P. P. Mishra, A. L. Koner, A. Datta, Interaction of lucifer yellow with cetyltrimethyl ammonium bromide micelles and the consequent suppression of its non-radiative processes, Chem. Phys. Lett., 2004, 400, 128–132.
A. Mallick, B. Haldar, N. Chattopadhyay, Intramolecular charge transfer in organized assemblies: Fluorescence of 3-acetyl-4-oxo-6,7-dihydro-12 H indolo-[2,3-a] quimolizine in reverse micelles, J. Surface Sci. Technol., 2004, 20, 255–265.
P. Hazra, D. Chakrabarty, A. Chakraborty, N. Sarkar, Effect of hydrogen bonding on intramolecular charge transfer in aqueous and non-aqueous reverse micelles, J. Photochem. Photobiol., A, 2004, 167, 23–30.
Y. Hirose, H. Yui, T. Sawada, The ultrafast relaxation dynamics of a viscosity probe molecule in an AOT-reversed micelle: Contribution of the specific interactions with the local environment, J. Phys. Chem. B, 2004, 108, 9070–9076.
T. A. Fayed, Probing of micellar and biological systems using 2-(p-dimethylaminostyryl)benzoxazole: An intramolecular charge transfer fluorescent probe, Colloids Surfaces A: Physicochem. Eng. Aspects, 2004, 236, 171–177.
R. Das, D. Guha, S. Mitra, S. Kar, S. Lahiri, S. Mukherjee, Intramolecular charge transfer as probing reaction: Fluorescence monitoring of protein-surfactant interaction, J. Phys. Chem. A, 1997, 101, 4042–4047.
E. B. Tada, O. A. El Seoud, Solvatochromism in organized assemblies: effects of the sphere-to-rod micellar transition, Prog. Colloid Polymer Sci., 2002, 121, 101–109.
G. Cojocariu, A. Natansohn, Intramolecular Complexation in Aqueous Solutions of an End-Capped Poly(Ethylene Glycol), J. Phys. Chem. B, 2002, 106, 11737–11745.
A. K. Singh, M. Darshi, Fluorescence probe properties of intramolecular charge transfer diphenylbutadienes in micelles and vesicles, Biochim. Biophys. Acta-Biomembranes, 2002, 1563, 35–44.
H.-R. Park, T. H. Kim, K.-M. Bark, Physicochemical properties of quinolone antibiotics in various environments, Eur. J. Med. Chem., 2002, 37, 443.
M. Viard, J. Gallay, M. Vincent, M. Paternostre, Origin of Laurdan Sensitivity to the Vesicle-to-Micelle Transition of Phospholipid-Octylglucoside System: A Time-Resolved Fluorescence Study, Biophys. J., 2001, 80, 347–359.
P. A. Adams, M. C. Berman, Kinetics and mechanism of the interaction between human serum albumin and monomeric haemin, Biochem. J., 1980, 191, 95–102.
L. Savu, C. Benassasyag, G. Vallette, N. Christeff, E. Nuney, Mouse a1-Fetoprotein and Albumin, J. Biol. Chem., 1981, 256, 9414–9418.
A. Roda, G. Cappeleri, R. Aldini, E. Roda, L. Barbara, Quantitative aspects of the interaction of bile acids with human serum albumin, J. Lipid Res., 1982, 23, 490–495.
J. S. Stamler, D. J. Singel, J. Loscalzo, Biochemistry of nitric oxide and its redox-activated forms, Science, 1992, 258, 1898–1902.
H. Bian, H. Zhang, Q. Yu, Z. Chen, H. Liang, Studies on the interaction of cinnamic acid with bovine serum albumin, Chem. Pharm. Bull., 2007, 55, 871–875.
L. Liu, W. R. Hudgins, S. Shack, M. Q. Yin, D. Samid, Cinnamic acid: A natural product with potential use in cancer intervention, Int. J. Cancer, 1995, 62, 345–350.
D. C. Carter, J. X. Ho, Structure of Serum Albumin, Adv. Protein Chem., 1994, 45, 153–203.
T. S. Singh, S. Mitra, Fluorescence behavior of intramolecular charge transfer state in trans-ethyl p-(dimethylamino)cinamate, J. Lumin., 2007, 127, 508–514.
P. R. Bangal, S. Panja, S. Chakravorti, Excited state photodynamics of 4-N,N-dimethylamino cinnamaldehyde: A solvent dependent competition of TICT and intermolecular hydrogen bonding, J. Photochem. Photobiol., A, 2001, 139, 5–16.
A. Cahkraborty, S. Kar, N. Guchhait, Photoinduced intramolecular charge transfer (ICT) reaction in trans-methyl p-(dimethylamino) cinnamate: A combined fluorescence measurement and quantum chemical calculations, Chem. Phys., 2006, 320, 75–83.
S. Panja, P. Chowdhury, S. Chakravravorti, Exploring the location and orientation of 4-(N,N-dimethylamino) cinnamaldehyde in anionic, cationic and non-ionic micelles, Chem. Phys. Lett., 2003, 368, 654–662.
T. S. Singh, S. Mitra, Fluorescence behavior of intramolecular charge transfer probe in anionic, cationic, and nonionic micelles, J. Colloid Interface Sci., 2007, 311, 128–134.
K. Bhattacharyya, M. Chowdhury, Environmental and magnetic field effects on exciplex and twisted charge transfer emission, Chem. Rev., 1993, 93, 507–535.
W. Verbouwe, L. Viaene, M. Van der Auweraer, F. C. De Schryver, H. Masuhara, R. Pansu, J. Faure, Photoinduced intramolecular charge transfer in diphenylamino-substituted triphenylbenzene, biphenyl, and fluorine, J. Phys. Chem. A, 1997, 101, 8157–8165.
Y. H. Kim, D. W. Cho, M. Yoon, D. Kim, Observation of hydrogen bonding effects on twisted intramolecular charge transfer of p-(N,N-dimethylamino)benzoic acid in aqueous cyclodextrin solutions, J. Phys. Chem., 1996, 100, 15670–15676.
M. Józefowich, K. A. Kozyra, J. R. Heldt, J. Heldt, Effect of hydrogen bonding on the intramolecular charge transfer fluorescence of 6-dodecanoyl-2-dimethylaminonaphtalene, Chem. Phys., 2005, 320, 45–53.
Y. Hirata, T. Okada, T. Nomoto, Significant quenching of the photoinduced charge separated state of aminophenyl(phenyl)acetylene and N,N-dimethyl aminophenyl(phenyl)acetylene in protic solvents, J. Phys. Chem. A, 1998, 102, 6585–6589.
Y. Moroi, Micelles, Plenum, NY, 1992.
C. Hirose, L. Sepulveda, Transfer free energies of p-alkyl-substituted benzene derivatives, benzene, and toluene from water to cationic and anionic micelles and to n-heptane, J. Phys. Chem., 1981, 85, 3689–3694.
The Plasma Proteins: Structure, Function and Genetic Control, ed. F. W. Putnam, Academic Press, New York, 2nd edn, 1975, vol. 1, pp. 141 and 147.
K. Hirayama, S. Akashi, M. Furuya, K. Fukuhara, Rapid confirmation and revision of the primary structure of bovine serum albumin by ESIMS and Frit-FAB LC/MS, Biochem. Biophys. Res. Commun., 1990, 173, 639–646.
K. Aoki, H. Okabayashi, S. Maezawa, T. Mizumo, M. Murata, K. Hiramatsu, Raman studies of Bovine Serum Albumin-ionic detergent-complexes and conformational change of albumin molecule induced by detergent binding, Biochem. Biophys. Acta, 1982, 703, 11–16.
M. N. Jones, A theoretical approach to the binding of the amphipathic molecules to globular proteins, Biochem. J., 1975, 151, 109–114.
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Singh, T.S., Mitra, S. Fluorimetric studies on the binding of 4-(dimethylamino)cinnamic acid with micelles and bovine serum albumin. Photochem Photobiol Sci 7, 1063–1070 (2008). https://doi.org/10.1039/b717475f
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DOI: https://doi.org/10.1039/b717475f