UVA radiation induced ultrafast electron transfer from a food carcinogen benzo[a]pyrene to organic molecules, biological macromolecules, and inorganic nano structures

Journal of Physical Chemistry B

Volumn 117, Issue 14, 2013, Pages 3726-3737

  Banerjee, Soma ^a   Sarkar, Soumik ^a   Lakshman, Karthik ^b   Dutta, Joydeep ^b   Pal, Samir Kumar ^a  

^a S N BOSE NATIONAL CENTRE FOR BASIC SCIENCES   (India)

^b SULTAN QABOOS UNIVERSITY   (Oman)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGENS; DNA; ELECTRON TRANSITIONS; FLUORESCENCE SPECTROSCOPY; MOLECULES; NANORODS; PYRENE; ZINC OXIDE;

BIOLOGICAL MACROMOLECULE; EFFECT OF TEMPERATURE; ELECTRON DONATING PROPERTIES; FLUORESCENCE LIFETIMES; HUMAN SERUM ALBUMINS; REACTIVE OXYGEN SPECIES; TEMPERATURE DEPENDENT; ULTRAFAST ELECTRON TRANSFER;

ASSOCIATION REACTIONS;

EID: 84876255191     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp312536x     Document Type: Article

References (44)

1. Phillips, D. H. Fifty Years of Benzo(a)pyrene Nature 1983, 303, 468-472
2. Phillips, D. H. Polycyclic Aromatic Hydrocarbons in the Diet Mutat. Res. 1999, 443, 139-147
3. Ling, H.; Sayer, J. M.; Plosky, B. S.; Yagi, H.; Boudsocq, F.; Woodgate, R.; Jerina, D. M.; Yang, W. Crystal Structure of a Benzo[a]pyrene Diol Epoxide Adduct in a Ternary Complex with a DNA Polymerase Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 2265-2269
4. Alam, S.; Conway, M. J.; Chen, H. S.; Meyers, C. The Cigarette Smoke Carcinogen Benzo[a]pyrene Enhances Human Papillomavirus Synthesis J. Virol. 2008, 82, 1053-1058
5. Dutta, K.; Ghosh, D.; Nazmi, A.; Kumawat, K. L.; Basu, A. A Common Carcinogen Benzo[a]pyrene Causes Neuronal Death in Mouse via Microglial Activation PloS One 2010, 5, 1-14
6. Shimizu, Y.; Nakatsuru, Y.; Ichinose, M.; Takahashi, Y.; Kume, H.; Mimura, J.; Kuriyama, Y. F.; Ishikawa, T. Benzo[a]pyrene Carcinogenicity is Lost in Mice Lacking the Aryl Hydrocarbon Receptor Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 779-782
7. Denissenko, M. F.; Pao, A.; Tang, M. S.; Pfeifer, G. P. Preferential Formation of Benzo[a]pyrene Adducts at Lung Cancer Mutational Hotspots in P53 Science 1996, 274, 430-432
8. Kapitulnik, J.; Levin, W.; Conney, A. H.; Yagi, H.; Jerina, D. M. Benzo[a]pyrene 7,8-dihydrodiol is More Carcinogenic than Benzo[a]pyrene in New Born Mice Nature 1977, 266, 378-380
9. Eling, T. E.; Thompson, D. C.; Foureman, G. L.; Curtis, J. F.; Hughes, M. F. Prostaglandin H Synthase and Xenobiotic Oxidation Annu. Rev. Pharmacol. Toxicol. 1990, 30, 1-45
10. Wilk, M.; Girke, W. Reactions Between Benzo[a]pyrene and Nucleo bases by One-Electron Oxidation J. Natl. Cancer Inst. 1972, 49, 1585-5197
11. Wan, C.; Fiebig, T.; Kelley, S. O.; Treadway, C. R.; Barton, J. K.; Zewail, A. H. Femtosecond Dynamics of DNA-Mediated Electron Transfer Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6014-6019
12. Nguyena, J.; Maa, Y.; Luoa, T.; Bristowb, R. G.; Jaffrayc, D. A.; Lua, Q. B. Direct Observation of Ultrafast-Electron-Transfer Reactions Unravels High Effectiveness of Reductive DNA Damage Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 11778-11783
13. Geacintov, N. E.; Prusik, T.; Khosrofian, J. M. Properties of Benzopyrene-DNA Complexes Investigated by Fluorescence and Triplet Flash Photolysis Techniques J. Am. Chem. Soc. 1976, 98, 6444-6452
14. Skipper, P. L.; Tannenbaum, S. R. Protein Adducts in the Molecular Dosimetry of Chemical Carcinogens Carcinogenesis 1990, 11, 507-518
15. Kure, E. H.; Andreassen, A.; Ovrebo, S.; Grzybowska, E.; Fiala, Z.; Strozyk, M.; Chorazy, M.; Haugen, A. Benzo(a)pyrene-Albumin Adducts in Humans Exposed to Polycyclic Aromatic Hydrocarbons in an Industrial Area of Poland Occup. Environ. Med. 1997, 54, 662-666
16. Srinivasan, B. N.; Fujimori, E. Benzo[a]pyrene-Serum: Albumin/cysteine Interactions: Fluorescene and Electron Spin Resonance Studies Chem. Biol. Interact. 1979, 28, 1-15
17. Brenner, D. J.; Doll, R.; Goodhead, D. T.; Hall, E. J.; Land, C. E.; Little, J. B.; Lubin, J. H.; Preston, D. L.; Preston, R. J.; Puskin, J. S.; Ron, E.; Sachs, R. K.; Samet, J. M.; Setlow, R. B.; Zaider, M. Cancer Risks Attributable to Low doses of Ionizing radiation: Assessing What We Really Know Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 13761-13766
18. Land, C. E.; Boice, J. D.; Shore, R. E.; Norman, J. E.; Tokunaga, M. Breast Cancer Risk From Low-Dose Exposures to Ionizing Radiation: Results of Parallel Analysis of Three Exposed Populations of Women J. Natl. Cancer Inst. 1980, 65, 353-376
19. Kawanishi, S.; Hiraku, Y.; Oikawa, S. Mechanism of Guanine-Specific DNA Damage by Oxidative Stress and its Role in Carcinogenesis and Aging Mutat. Res. Rev. Mutat. 2001, 488, 65-76
20. Toyooka, T.; Ibuki, Y.; Koike, M.; Ohashi, N.; Takahashi, S.; Goto, R. Coexposure to Benzo[a]pyrene Plus UVA Induced DNA Double Strand Breaks: Visualization of Ku Assembly in the Nucleus Having DNA Lesions Biochem. Biophys. Res. Commun. 2004, 322, 631-636
21. Toyooka, T.; Ibuki, Y.; Takabayashi, F.; Goto, R. Coexposure to Benzo[a]pyrene and UVA Induces DNA Damage: First proof of Double-Strand Breaks in a Cell-Free System Environ. Mol. Mutagen. 2006, 47, 38-47
22. Kang, Q.; Chen, Y.; Li, C.; Cai, Q.; Yao, S.; Grimes, C. A.; Calabresi, P. A Photoelectrochemical Immunosensor for Benzo[a]pyrene Detection Amplified by Bifunctional Gold Nanoparticles Chem. Commun. 2011, 47, 12509-12511
23. Atal, N.; Saradhi, P. P.; Mohanty, P. Inhibition of the Chloroplast Photochemical Reactions by Treatment of Wheat Seedlings with Low Concentrations of Cadmium: Analysis of Electron Transport Activities and Changes in Fluorescence Yield Plant Cell Physiol. 1991, 32, 943-951
24. Douki, T. Effect of Denaturation on the Photochemistry of Pyrimidine Bases in Isolated DNA J. Photochem. Photobiol. B 2006, 82, 45-52
25. Pal, S. K.; Zhao, L.; Zewail, A. H. Water at DNA Surfaces: Ultrafast Dynamics in Minor Groove Recognition Proc. Natl. Acad. Sci U.S.A.. 2003, 100, 8113-8118
26. Khan, S. N.; Islam, B.; Khan, A. U. Probing Midazoan Interaction with Human Serum Albumin and its Effect on Structural State of Protein IJIB 2007, 1, 102-112
27. Sarkar, S.; Makhal, A.; Bora, T.; Lakshman, K.; Singha, A.; Dutta, J.; Pal, S. K. Hematoporphyrin-ZnO Nanohybrids: Twin Applications in Efficient Visible-Light Photocatalysis and Dye-Sensitized Solar Cells ACS Appl. Mater. Interfaces 2012, 4, 7027-7035
28. Sarkar, S.; Makhal, A.; Lakshman, K.; Bora, T.; Dutta, J.; Pal, S. K. Dual-Sensitization via Electron and Energy Harvesting in CdTe Quantum Dots Decorated ZnO Nanorod-Based Dye-Sensitized Solar Cells J. Phys. Chem. C 2012, 116, 14248-14256
29. O'Connor, D. V.; Philips, D. Time Correlated Single Photon Counting; Academic Press: London, 1984.
30. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum: New York, 1999.
31. Cooper, C. D.; Naff, W. T.; Compton, R. N. Negative Ion Properties of p-Benzoquinone: Electron Affinity and Compound States J. Chem. Phys. 1975, 63, 2752-2757
32. Beck, S. C.; Cramb, D. T. Condensed Phase Dispersive Interactions of Benzo[ a ]pyrene with Various Solvents and with DNA: A Twist on Solvatochromism J. Phys. Chem. B 2000, 104, 2767-2774
33. Wells, T. A.; Losi, A.; Dai, R.; Scott, P.; Park, S. M.; Golbeck, J.; Song, P. S. Electron Transfer Quenching and Photoinduced EPR of Hypericin and the Ciliate Photoreceptor Stentorin J. Phys. Chem. A 1997, 101, 366-372
34. Leland, B. A.; Joran, A. D.; Felker, P. M.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. Picosecond Fluorescence Studies on Intramolecular Photochemical Electron Transfer in Porphyrins Linked to Quinones at Two Different Fixed Distances J. Phys. Chem. 1985, 89, 5571-5573
35. Chen, G.; Cooks, R. G. Electron Affinities of Polycyclic Aromatic Hydrocarbons Determined by the Kinetic Method J. Mass. Spectrom. 1995, 30, 1167-1173
36. Sutherland, J. C.; Griffin, K. P. Absorption Spectrum of DNA for Wavelengths Greater than 300 nm Radiat. Res. 1981, 86, 399-410
37. Banerjee, D.; Pal, S. K. Direct Observation of Essential DNA Dynamics: Melting and Reformation of the DNA Minor Groove J. Phys. Chem. B 2007, 111, 10833-10838
38. Yeow, E. K. L.; Ghiggino, K. P.; Reek, J. N. H.; Crossley, M. J.; Bosman, A. W.; Schenning, A. P. H. J.; Meijer, E. W. The Dynamics of Electronic Energy Transfer in Novel Multiporphyrin Functionalized Dendrimers: A Time-Resolved Fluorescence Anisotropy Study J. Phys. Chem. B 2000, 104, 2596-2606
39. Banerjee, S.; Bhowmik, D.; Verma, P. K.; Mitra, R. K.; Sidhhanta, A.; Basu, G.; Pal, S. K. Ultrafast Spectroscopic Study on Caffeine Mediated Dissociation of Mutagenic Ethidium from Synthetic DNA and Various Cell Nuclei J. Phys. Chem. B 2011, 115, 14776-14783
40. Ketterer, B. Interactions Between Carcinogens and Proteins Br. Med. Bull. 1980, 36, 71-78
41. Marme, N.; Knemeyer, J. P.; Sauer, M.; Wolfrum, J. Inter- and Intramolecular Fluorescence Quenching of Organic Dyes by Tryptophan Bioconjugate Chem. 2003, 14, 1133-1139
42. Keskin, E.; YardIm, Y.; Senturk, Z. Voltammetry of Benzo[a]pyrene in Aqueous and Nonaqueous Media: Adsorptive Stripping Voltammetric Determination at Pencil Graphite Electrode Electroanalysis 2010, 22, 1191-1199
43. Sinha, S. S.; Mitra, R. K.; Pal, S. K. Temperature-Dependent Simultaneous Ligand Binding in Human Serum Albumin J. Phys. Chem. B 2008, 112, 4884-4891
44. Larsen, J. S.; Waluk, J.; Eriksson, S.; Thulstrup, E. W. Electronic States of Benzo[a]pyrene. Linear and Magnetic Circular Dichroism, Polarized Fluorescence, and Quantum Chemical Calculations J. Am. Chem. Soc. 1992, 114, 1942-1949