Caffeine Mediated Dissociation of a Potential Mutagen from DNA Mimetics, DNA and Cellular Nuclei: Ultrafast Spectroscopic Studies
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We present femtosecond to nanosecond-resolved studies of the dynamics of aqueous solvation within self-assembled dimeric structure of caffeine molecules. We have extended our studies in various temperatures in order to explore structural evolution of the self assemblies and consequently the dynamics of solvation in the interior of the dimer. Furthermore, we report a systematic investigation of caffeine induced dissociation of ethidium (Et) cation, a potential mutagen from nucleic acids and biomimetic systems. Time-resolved fluorescence studies are consistent with a mechanism where caffeine-Et complex formation in bulk solution drives the dissociation of DNA-bound Et. Temperature dependent picosecond resolved studies show the caffeine-Et complex to be stable over a wide range of temperature, within and beyond the normal physiological limit. A combination of NMR spectroscopy and DLS experiments allowed us to propose a molecular model of caffeine-Et complex. Caffeine induced extraction of Et from whole cells were also performed on squamous epithelial cells collected from the inner lining of the human mouth, A549 (lung carcinoma), A375 (human skin), RAW (macrophage) and Vero (African green monkey kidney epithelium) cell lines. Interestingly, the efficiency of caffeine in extracting Et has been found to be dependent on cell types. Our steady state and picosecond resolved spectroscopic studies on the detachment of Et from various biomimicking micelles of different charges reveal the specificity of caffeine molecule for carrying out such dissociation. The picosecond resolved Förster resonance energy transfer (FRET) studies between a DNA minor groove binder dye Hoeschst 33258 (H258, donor) and Et (acceptor) have been employed to investigate the alteration in their association in presence of caffeine in the molecular level. Finally, our fluorescence micrographs of epithelial cells validate the alteration of FRET efficiency between the donor and the acceptor due to the caffeine mediated release of the latter. Our results both in-vitro as well as ex-vivo provide important clues about efficiency and role of caffeine as a potential anti-mutagenic therapeutic agent
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Selby, C. P., Sancar, A., Molecular mechanisms of DNA repair inhibition by caffeine, Proc. Natl. Acad. Sci., volume 87, (issue 9), May 1990, pages 3522-3525.
Larsen, R. W., Jasuja, R. et al., Spectroscopic and molecular modelling studies of caffeine complexes with DNA intercalators, Biophys. J., volume 70, (issue 1), January 1996 pages 443-452.
Davies, D. B., Veselkov, D. A. et al., Heteroassociation of caffeine and aromatic drugs and their competitive binding with a DNA oligomer., Eur Biophys J., volume 30, (issue 5), september 2001, pages 354-366.
McKelvey, V. J., McKenna, P. G., Enhanced synergism between caffeine and mitomycin C in the induction of cytogenetic aberrations in thymidine kinase-deficient Friend murine erythroleukaemia cells Mutagenesis, volume 1, (issue 3), May 1986, pages 173-178
Mourelatos, D., Dozi-Vassiliades, J. et al., Enhancement of Cytogenetic Damage and of Antineoplastic Effect by Caffeine in Ehrlich Ascites Tumor Cells Treated with Cyclophosphamide in Vivo, Cancer Res, volume 48, (issue 5), March 1988, pages 1129-1131.
Ross, W. E., Zwelling, L. A. et al., Relationship between cytotoxicity and dna strand break-age produced by adriamycin and other intercalating agents, Int. J. Radiat. Oncol. Biol. Phys., volume 5, (issue 6), August 1979, pages 1221-1224.
Iliakis, G., Nusse, M. et al., Differential reduction by caffeine of adriamycin induced cell killing and cell cycle delays in chinese hamster v79 cells, Int. J. Radiat. Oncol. Biol. Phys., volume 12, (issue 11), November 1986, pages 1987-1995.
Ganapathi, R., Grabowski, D. et al., Modulation of Adriamycin and N-Trifluoroacetyladriamycin-14-valerate Induced Effects on Cell Cycle Traverse and Cytotoxicity in P388 Mouse Leukemia Cells by Caffeine and the Calmodulin Inhibitor Trifluoperazine, Cancer Res., volume 46, (issue 11), November 1986, pages 5553-5557.
Traganos, F., Kaminska-Eddy, B. et al., Caffeine reverses the cytotoxic and cell kinetic effects of Novantrone (mitoxantrone), Cell Prolif., volume 24, (issue 3), May 1991, pages 305-319.
Johansson, B., Halldner, L. et al., Hyperalgesia, anxiety, and decreased hypoxic neuroprotection in mice lacking the adenosine A 1 receptor, Proc. Natl. Acad. Sci., volume 98, (issue 16), July 2001, pages 9407-9412.
Danilov, V. I., Shestopalova, A. V., Hydrophobic effect in Biological Associates: A Monte Carlo Simulation of Caffeine Molecules Stacking, Int. J. Quantum Chem, volume 35, (issue 1), January 1989, pages 103-112.
Wong, E. L. S., Gooding, J. J., The Electrochemical Monitoring of the Perturbation of Charge Transfer through DNA by Cisplatin, J. Am. Chem. Soc., volume 129, (issue 29), June 2007, pages 8950-8951.
Řeha, D., Kabelá, M. et al., Intercalators. 1. Nature of Stacking Interactions between Intercalators (Ethidium, Daunomycin, Ellipticine, and 4‘,6-Diaminide-2-phenylindole) and DNA Base Pairs. Ab Initio Quantum Chemical, Density Functional Theory, and Empirical Potential Study, J. Am. Chem. Soc., volume 124, (issue 13), March 2002, pages 3366-3376.
Rips, I., Jortner, J., Dynamic solvent effects on outer‐sphere electron transfer, J. Chem. Phys, volume 87, (issue 4), August 1987, pages 2090-2104.
Hynes, J. T., Outer-sphere electron-transfer reactions and frequency-dependent friction, J. Phys. Chem., volume 90, (issue 16), July 1986, pages 3701-3706.
Traganos, F., Kapuscinski, J. et al., Caffeine modulates the effects of DNA-intercalating drugs in vitro: a flow cytometric and spectrophotometric analysis of caffeine interaction with novantrone, doxorubicin, ellipticine, and the doxorubicin analogue AD198, Cancer Res., volume 51, (issue 14), July 1991, pages 3682-3689.
Mahler, H. R., Perlman, P. S., Effects of mutagenic treatment by ethidium bromide on cellular and mitochondrial phenotype, Arch. Biochem. Biophys., volume 148, (issue 1), January 1972, pages 115-129.
Johnson, I. M., Kumar, S. G. B. et al., De-intercalation of Ethidium Bromide and Acridine Orange by Xanthine Derivatives and Their Modulatory Effect on Anticancer Agents: A study of DNA-directed Toxicity Enlightened by Time Correlated Single Photon Counting, J. Biomol. Struct. Dyn., volume 20, (issue 5), May 2003, pages 677-685.
Kapuscinski, J., Kimmel, M., Thermodynamic model of mixed aggregation of intercalators with caffeine in aqueous solution, Biophys.Chem., volume 46, (issue 2), April 1993, pages 153-163.
Davies, D. B., Veselkov, D. A. et al., Hetero-association of caffeine and aromatic drugs and their competitive binding with a DNA oligomer, Eur. Biophys. J., volume 30, (issue 5), September 2001, pages 354–366.
Piosik, J., Zdunek, M. et al., The modulation by xanthines of the DNA-damaging effect of polycyclic aromatic agents: Part II. The stacking complexes of caffeine with doxorubicin and mitoxantrone, Biochemical Pharmacology,, volume 63, (issue 4), February 2002, pages 635-646.
Banerjee, S., Bhowmik, D. et al., Ultrafast Spectroscopic Study on Caffeine Mediated Dissociation of Mutagenic Ethidium from Synthetic DNA and Various Cell Nuclei, J. Phys. Chem. B., volume 115, (issue 49), October 2011, pages 14776-14783.
Turro, N. J., Grätzel, M. et al., Photophysical and Photochemical Processes in Micellar Systems, Angew. Chem. Intern. Ed., volume 19, (issue 9), September 1980, pages 675-696.
Zhong, D., Pal, S. K. et al., Femtosecond Studies of Protein -DNA Binding and Dynamics: Histone I, Chem Phys Chem, volume 2, (issue 4), April 2001, pages 219 -227.
Pal, S. K., Peon, J. et al., Biological water at the protein surface:Dynamical solvation probed directly with femtosecond resolution, Proc. Natl. Acad. Sci., volume 99, (issue 4), February 2002, pages 1763-1768.
Mitra, R. K., Sinha, S. S. et al., Interactions of Nile Blue with Micelles, Reverse Micelles and a Genomic DNA, J. Fluoresc., volume 18, (issue 2), March 2008, pages 423-432.
Banerjee, D., Pal, S. K., Ultrafast charge transfer and solvation of DNA minor groove binder: Hoechst 33258 in restricted environments, Chem. Phys. Lett., volume 432, (issue 2006, pages 257-262.
Sitkowski, J., Stefaniak, L. et al., Complete assignments of the 1H, 13C and 15N NMR spectra of caffeine, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., volume 51, (issue 5), May 1995, pages 839-841.
Connor, D. V. O., Philips, D. Time Correlated Single Photon Counting, 1984.
Philips, L. A., Webb, S. P. et al., High-pressure studies of rotational reorientation dynamics: The role of dielectric friction, J. Chem. Phys., volume 83, (issue 11), December 1985, pages 5810-5821.
Kalman, B., Clarke, N. et al., Dynamics of a new fluorescent probe, 2,5,8,11-tetra-tert-butylperylene in solution, cubic lyotropic liquid crystals, and model membranes, J. Phys. Chem., volume 93, (issue 11), January 1989, pages 4608-4615.
Kapusta, P., Erdmann, R. et al., Time-Resolved Fluorescence Anisotropy Measurements Made Simple, J. Fluoresc., volume 13, (issue 2), March 2003, pages 179-183.
Bockris, J. O. M., Saluja, P. P. S., Ionic Solvation Numbers from Compressibilities and Ionic Vibration Potentials Measurements;, J. Phys. Chem, volume 76, (issue 15), July 1972, pages 2140-2151.
Lakowicz, J. R. Principles of fluorescence spectroscopy; Kluwer Academic/Plenum: New York, 1999.
Banerjee, D., Pal, S. K., Simultaneous Binding of Minor Groove Binder and Intercalator to Dodecamer DNA: Importance of Relative Orientation of Donor and Acceptor in FRET, J. Phys. Chem. B. (Letter), volume 111, (issue 19), April 2007, pages 5047-5052.
Banerjee, S., Verma, P. K. et al., Probing the interior of Self-assembled Caffeine Dimer at various Temperatures, J Fluoresc, volume 22, (issue 2), March 2012, pages 753-769.
Carlucci, L., Gavezzotti, A., Molecular Recognition and Crystal Energy Landscapes: An X-ray and Computational Study of Caffeine and Other Methylxanthines, Chem. Eur. J., volume 11, (issue 1), December 2005, pages 271 - 279.
Jahagirdar, D. V., Arbad, B. R. et al., Studies in Partial Molar Volumes, Partial Molar Compressibilities and Viscosity B-Coefficients of Caffeine in Water at Four Temperatures., J. Mol. Liq., volume 85, (issue 3), May 2000, pages 361-373.
Maevsky, A. A., Sukhorukov, B. I., IR study of base stacking interactions Nucl. Acids Res. , volume 8, (issue 13), July 1980, pages 3029-3042.
Millero, F. J., Surdo, A. L. et al., The apparent molal volumes and adiabatic compressibilities of aqueous amino acids at 25.degree.C, J. Phys. Chem., volume 82, (issue 7), April 1978, pages 784-792.
Benz, R., Some Thermodynamic Properties Of The System PuCl3—KCl From Electromotive force data, J. Phys. Chem., volume 65, (issue 1), January 1961, pages 81-84.
Pal, S. K., Sukul, D. et al., Solvation Dynamics of DCM in Micelles, Chem. Phys. Lett., volume 327, (issue 1-2), September 2000, pages 91-96.
Sarkar, R., Shaw, A. K. et al., Ultrafast photoinduced deligation and ligation dynamics: DCM in micelle and micelle-enzyme complex, J. Photochem. Photobiol. B, volume 83, (issue 3), June 2006, pages 213-222.
Pal, S. K., Mandal, D. et al., Solvation dynamics of 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM) in a microemulsion, Chem. Phys. Lett., volume 312, (issue 2-4), October 1999, pages 178-184.
Wu, M., Gu, W. et al., Preparation and characterization of ultrafine zinc sulfide particles of quantum confinement, Chem Phys Lett, volume 224, (issue 5-6), July 1994, pages 557-562.
Meulen, P. v. d., Zhang, H. et al., Subpicosecond Solvation Relaxation of 4-(Dicyanomethylene)-2-methyl-6-(p-(dimethylamino)styryl)-4H-pyran in Polar Liquids, J. Phys. Chem., volume 100, (issue 13), March 1996, pages 5367-5373.
Drake, J. M., Lesiecki, M. L. et al., Photophysics and Cis_Trans Isomerization of DCM, Chem Phys Lett, volume 113, (issue 1985, pages 530-534.
Zhang, H., Jonkman, A. M. et al., Femtosecond studies of charge separation in photo-excited DCM in liquid solution, Chem Phys Lett, volume 224, (issue 5-6), July 1994, pages 551-556.
Easter, D. C., Baronavski, A. P., Ultrafast relaxation in the fluorescent state of the laser dye DCM, Chem Phys Lett, volume 201, (issue 1-4), January 1993, pages 153-158.
Zana, R., Microviscosity of Aqueous Surfactant Micelles: Effect of Various Parameters, J. Phys. Chem. B., volume 103, (issue 43), July 1999, pages 9117-9125.
Fee, R. S., Maroncelli, M., Estimating the time-zero spectrum in time-resolved emmsion measurements of solvation dynamics, Chem Phys., volume 183, (issue 2-3), June 1994, pages 235-247.
Jimenez, R., Fleming, G. R. et al., Femtosecond solvation dynamics of water, Nature, volume 369, (issue 6480), June 1994, pages 471 - 473.
Riter, R. E., Willard, D. W. et al., Water Immobilization at Surfactant Interfaces in Reverse Micelles, J. Phys. Chem. B., volume 102, (issue 15), March 1998, pages 2705-2714.
Corbeil, E. M., Levinger, N. E., Dynamics of Polar Solvation in Quaternary Microemulsions, Langmuir, volume 19, (issue 18), July 2003, pages 7264-7270.
Hirose, K., A Practical Guide for the Determination of Binding Constants, J. Incl. Phenom. Macrocycl. Chem., volume 39, (issue 3-4), April 2001, pages 193-209.
Datta, A., Mandal, D. et al., Interaction of Triton X-100 with cyclodextrins. A fluorescence study, J. Chem. Soc., Faraday Trans., volume 94, (issue 23), 1998, pages 3471-3475.
Chang, T. L., Cheung, H. C., A model for molecules with twisted intramolecular charge transfer characteristics: solvent polarity effect on the nonradiative rates of dyes in a series of water-ethanol mixed solvents, Chem. Phys. Lett., volume 173, (issue 4), october 1990, pages 343-348.
Bhattacharyya, K., Chowdhury, M., Environmental and magnetic field effects on exciplex and twisted charge transfer emission, Chem. Rev., volume 93, (issue 1), January 1993, pages 507–535.
Sarkar, N., Das, K. et al., Interaction of urea with fluorophores bound to cyclodextrins. Fluorescence of p-toluidino naphthalene sulphonate, Chem. Phys. Lett., volume 196, (issue 5), August 1992, pages 491-496.
Nakamura, A., Saitoh, K. et al., Fluctuation in structure of inclusion complexes of cyclodextrins with fluorescent probes, Chem. Phys. Lett., volume 187, (issue 1-2), November 1991, pages 110-115.
Sarkar, N., Das, K. et al., Salt effect on the hydrophobic binding of p-toluidino naphthalene sulphonate with cyclodextrins, Chem. Phys. Lett., volume 218, (issue 5-6), February 1994, pages 492-498.
Almgren, M., Grieser, F. et al., Dynamic and static aspects of solubilization of neutral arenes in ionic micellar solutions, J. Am. Chem. Soc., volume 101, (issue 2), January 1979, pages 279–291.
Jobe, D. J., Verrall, R. E. et al., Fluorescence and Conductometric Studies of Potassium 2-(p-Toluidinyl)naphthalene-6-sulfonate/Cyclodextrin/Surfactant Systems, J. Phys. Chem., volume 92, (issue 12), June 1988, pages 3582-3586.
Catena., G. C., Bright., F. V., Thermodynamic Study on the Effects of P-Cyclodextrin Inclusion with Anilinonaphthalenesulfonates, Anal. Chem., volume 61, (issue 8), April 1989, pages 905-909.
Sen, P., Mukherjee, S. et al., Temperature dependence of solvation dynamics in a micelle. 4-Aminophthalimide in Triton X-100, Chem. Phys. Lett., volume 385, (issue 5-6), February 2004, pages 357-361.
Sarkar, R., Pal, S. K., Ligand-DNA Interaction in a Nanocage of Reverse Micelle, Biopolymers, volume 83, (issue 6), December 2006, pages 675-686.
Baranovsky, S. F., Bolotin, P. A. et al., Interaction of Ethidium Bromide and Caffeine with DNA in Aqueous Solution, J. Appl. Spectrosc., volume 76, (issue 1), January 2009, pages 132-139.
Falk, M., Chew, W. et al., Molecular modelling and NMR studies of the caffeine dimer, Can. J. Chem., volume 76, (issue 1), 1998, pages 48-56.
Ortega, A., Amoros, D. et al., Prediction of hydrodynamic and other solution properties of rigid proteins from atomic and residue-level models, Biophys. J., volume 101, (issue 4), August 2011, pages 892-898.
Lai, J. S., Herr, W., Ethidium bromide provides a simple tool for identifying genuine DNA-independent protein associations, Proc. Natl. Acad. Sci., volume 89, (issue 15), August 1992, pages 6958-6962.
Banerjee, S., Tachiya, M. et al., Caffeine-Mediated Detachment of Mutagenic Ethidium from Various Nanoscopic Micelles: An Ultrafast Förster Resonance Energy Transfer Study, J. Phys. Chem. B., volume 116, (issue 2012, pages 7841−7848.
Shaw, A. K., Sarkar, R. et al., Direct observation of DNA condensation in a nano-cage by using a molecular ruler, Chem. Phys. Lett., volume 408, (issue 4-6), June 2005, pages 366-370.
Pal, S. K., Mandal, D. et al., Photophysical Processes of Ethidium Bromide in Micelles and Reverse Micelles, J. Phys. Chem. B., volume 102, (issue 52), December 1998, pages 11017-11023.
Tachiya, M., Application of a generating function to reaction kinetics in micelles. Kinetics of quenching of luminescent probes in micelles, Chem. Phys. Lett., volume 33, (issue 2), June 1975, pages 289-292.
Infelta, P. P., Gratzel, M. et al., Luminescence Decay of Hydrophobic Molecules Solubilized in Aqueous Micellar Systems. A Kinetic Model, J. Phys. Chem., volume 78, (issue 2), January 1974, pages 190-195.
Tachiya, M., Kinetics of quenching of luminescent probes in micellar systems. II, J. Chem. Phys., volume 76, (issue 1), 1982, pages 340-348.
Sadhu, S., Halder, K. K. et al., Size Dependent Resonance Energy Transfer between Semiconductor Quantum Dots and Dye Using FRET and Kinetic Model, J. Phys. Chem. C, volume 114, (issue 9), February 2010, pages 3891-3897.
Gehlen, M. H., Auweraer, M. V. et al., Fluorescence Quenching in Micellar Microdomains. Analysis of an Approximate Solution to the Fluorescence Decay Including Exchange of Probe and Quencher, Langmuir, volume 8, (issue 1), January 1992, pages 64-67.
Sarkar, R., Pal, S. K., Interaction of Hoechst 33258 and Ethidium with Histone1-DNA Condensates, Biomacromolecules, volume 8, (issue 11), September 2007, pages 3332-3339.
Chen, T. R., In situ detection of mycoplasma contamination in cell cultures by fluorescent Hoechst 33258 stain, Experimental Cell Research, volume 104, (issue 2), February 1977, pages 255-262.
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