Intramolecular H-Bond Formation Mediated De-Excitation of Curcuminoids: A Time-Resolved Fluorescence Study
Luca Nardo
University of Insubria, Department of Physics and Mathematics and C.N.I.S.M.-C.N.R., U.d.R. Como Via Valleggio 11, 22100 Como, Italy
Search for more papers by this authorAlessandra Andreoni
University of Insubria, Department of Physics and Mathematics and C.N.I.S.M.-C.N.R., U.d.R. Como Via Valleggio 11, 22100 Como, Italy
Search for more papers by this authorHanne Hjorth Tønnesen
School of Pharmacy, University of Oslo, P.O. Box 1068 Blindern, 0316 Oslo, Norway
Search for more papers by this authorLuca Nardo
University of Insubria, Department of Physics and Mathematics and C.N.I.S.M.-C.N.R., U.d.R. Como Via Valleggio 11, 22100 Como, Italy
Search for more papers by this authorAlessandra Andreoni
University of Insubria, Department of Physics and Mathematics and C.N.I.S.M.-C.N.R., U.d.R. Como Via Valleggio 11, 22100 Como, Italy
Search for more papers by this authorHanne Hjorth Tønnesen
School of Pharmacy, University of Oslo, P.O. Box 1068 Blindern, 0316 Oslo, Norway
Search for more papers by this authorKe-Li Han
State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China
Search for more papers by this authorGuang-Jiu Zhao
State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China
Search for more papers by this authorSummary
This chapter contains sections titled:
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Introduction
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Experimental Set-Up and Data Analysis Methods
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Results and Discussion
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Conclusions
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References
References
- H. H. Tønnesen, Int. J. Pharm., 225, 1 (2001).
- B. C. Wilson and M. S. Patterson, Phys. Med. Biol., 31, 327 (1986).
- S. J. Formosan and L. G. Arnaut, J. Photochem. Photobiol. A: Chem., 75, 21 (1993).
- L. G. Arnaut and S. J. Formosinho, J. Photochem. Photobiol. A: Chem., 75, 1 (1993).
- A. Weller, Naturwiss., 42, 175 (1955).
- G. Gilli and V. Bertolasi, in The Chemistry of Enols, ed. by Z. Rappoport. John Wiley & Sons, Inc., New York, NY, pp. 713–764 (1990).
- A. C. Weedon, in The Chemistry of Enols, ed. by Z. Rappoport. John Wiley & Sons, Inc., New York, NY, pp. 591–638 (1990).
- P. Nikolov, F. Fratev, I. Petkov and P. Markov, Chem. Phys. Lett., 83, 170 (1981).
- K. Balasubramanian, J. Agric. Food Chem., 54, 3512 (2006).
- J. T. Mague, W. L. Alworth and F. L. Payton, Acta Cryst. C, 60, 608 (2004).
- S. M. Khopde, K. I. Priyadarsini, D. K. Palit and T. Mukherjee, Photochem. Photobiol., 72, 625 (2000).
- A. A. Gorman, I. Hamblett, V. S. Srinivasan and P. D. Wood, Photochem. Photobiol., 59, 389 (1994).
- T. A. Dahl, P. Bilski, K. J. Reszka and C. F. Chignell, Photochem. Photobiol., 59, 290 (1994).
- C. F. Chignell, P. Bilski, K. J. Reszka et al., Photochem. Photobiol., 59, 295 (1994).
- R. N. Chopra, I. C. Chopra, K. L. Honada and L. D. Kapur, Indigenous Drugs of India, 2nd edition. Duhr, Calcutta, India (1958).
- K. M. Nadkarni (ed.), In India Material Medica. Popular Prakashan, Mumbai, India, pp. 414–416 (1976).
- A. Krishnamoorthy, The Wealth of India: a Dictionary of Indian Raw Materials and Industrial Products, Vol. 2. CSIR, New Delhi, India, p. 402 (1950).
- A. Mukhopadhyay, N. Basu, N. Ghatak and P. K. Gujzal, Agents Actions, 12, 508 (1982).
- R. C. Srimal and B. N. Dhawan, J. Pharm. Pharmacol., 25, 447 (1973).
- T. Rao, N. Basu, N. Ghatak and P. K. Gujral, Indian J. Med. Res., 75, 574 (1982).
- S. Fujisawa, T. Atsumi, M. Ishihara and Y. Kadoma, Anticancer Res., 24, 563 (2004).
- S. V. Jovanovic, S. Steenken, C. W. Boone and M. G. Simic, J. Am. Chem. Soc., 121, 9677 (1999).
- O. P. Sharma, Biochem. Pharmacol., 25, 1811 (1976).
- S. Toda, T. Miyasi, H. Arichi et al., Chem. Pharm. Bull., 33, 1725 (1985).
- N. Sreejayan, T. P. A. Devasagayam, K. I. Priyadarsini and M. N. A. Rao, Int. J. Pharmacol., 151, 127 (1997).
- N. Sreejayan and M. N. A. Rao, J. Pharm. Pharmacol., 46, 1013 (1994).
- N. Sreejayan and M. N. A. Rao, Int. J. Pharmacol., 100, 93 (1993).
- K. I. Priyadarsini, Free Radic. Biol. Med., 23, 838 (1997).
- S. M. Khopde, K. I. Priyadarsini, P. Venkatesan and M. N. A. Rao, Biophys. Chem., 80, 85 (1999).
- A. Khafif, S. P. Schantz, T. C. Chou et al., Carcinogenesis, 19, 419 (1998).
- T. H. Leu and M. C. Maa, Curr. Med. Chem., 2, 357 (2002).
- Y. J. Surh, Nat. Rev. Cancer, 3, 768 (2003).
- A. H. Conney, Cancer Res., 63, 7005 (2003).
- M. Nagabhushan and S. V. Bhide, Nutr. Cancer, 8, 201 (1986).
- P. E. Hartman and D. M. Shankel, Environ. Mol. Mutagen., 15, 145 (1990).
- M. Nagabhushan and S. V. Bhide, J. Am. Coll. Nutr., 11, 192 (1992).
- M. T. Huang, R. C. Smart, C. Q. Wong and A. H. Conney, Cancer Res., 48, 5941 (1988).
- J. Woo, Y. Kim, Y. Choi et al., Carcinogenesis, 24, 1199 (2003).
- P. J. Moos, K. Edes, J. Mullally and J. Fitzpatrick, Carcinogenesis, 9, 1611 (2004).
- R. Rashmi, S. Kumar and D. Karunagaran, Carcinogenesis, 26, 713 (2005).
- M. J. Van Erk, E. Teuling, Y. C. M. Staal et al., J. Carcinogen., 3, 1 (2004).
- S. E. Lee, B. C. Campbell, R. J. Molyneux et al., J. Agric. Food Chem., 49, 5171 (2001).
- J. S. Shim, J. H. Kim, H. Y. Cho et al., J. Chem. Biol., 10, 695 (2003).
- D. L. Flynn and M. F. Rafferty, Prostaglandins Leukotrienes Med. 22, 357 (1986).
- M. T. Huang, T. Lysz, T. Ferraro et al., Cancer Res., 51, 813 (1991).
- H. M. Wortelboer, M. Usta, A. E. van der Velde et al., Chem. Res. Toxicol., 16, 1642 (2003).
- F. Yang, G. P. Lim, A. N. Begum et al., J. Biol. Chem., 280, 5892 (2004).
- M. E. Egan, M. Pearson, S. A. Weiner et al., Science, 304, 600 (2004).
- B. B. Aggrawal, C. Sundaram, N. Malani and H. Ichikawa, Adv. Exp. Med. Biol., 595, 1 (2007).
- A. Mazumder, N. Neamati, S. Sunder et al., J. Med. Chem., 40, 3057 (1997).
- Z. Sui, R. Salto, J. Li et al., Bioorg. Med. Chem., 1, 415 (1993).
- F. Zsila, Z. Bikàdi and M. Simonyi, Tetrahedron: Asymmetry, 14, 2433 (2003).
- W. Au and T. C. Hsu, Environ. Mutagen., 1, 27 (1979).
- B. Vijayalaxami, Mutat. Res., 79, 125 (1980).
- V. Ravindranath and N. Chandrasekhara, Toxicology, 22, 337 (1982).
- S. Abraham, S. K. Abraham and G. Radhamony, Cytologia, 41, 591 (1976).
- T. N. B. Shankar, N. V. Shanta, H. P. Ramesh et al., Ind. J. Exp. Biol., 18, 73 (1980).
- S. D. Deodhar, R. Sethi and R. C. Srimal, Ind. J. Med. Res., 71, 632 (1980).
- T. N. B. Shankar and I. A. S. Murthy, Ind. J. Exp. Biol., 17, 1363 (1978).
- T. A. Dahl, W. M. Mcgowan, M. A. Shand and V. S. Srinivasan, Arch. Microbiol., 151, 183 (1989).
- H. H. Tonnesen, H. de Vries, J. Karlsen and G. B. van Henegouwen, J. Pharm. Sci., 76, 371 (1987).
- E. Bruzell, E. Morisbak and H. H. Tønnesen, Photochem. Photobiol. Sci., 4, 523 (2005).
- E. Kunchandy and M. N. A. Rao, Int. J. Pharm., 58, 237 (1990).
- E. Kunchandy and M. N. A. Rao, Int. J. Pharm., 57, 173 (1989).
- L. Nardo, R. Paderno, A. Andreoni et al., Spectroscopy, 22, 187 (2008).
- K. M. Schaich, C. Fisher and R. King, in Phytochemicals for Cancer Prevention II, ed. by C. T. Ho, T. Osava, M.-T. Huangand R. T. Gosen. ACS Symp. Ser. 547, American Chemical Society, Washington, DC, pp. 204–221 (1994).
- H. H. Tønnesen and J. Karlsen, Z. Lebensm. Unters. Forsch., 180, 402 (1985).
- H. H. Tønnesen and J. Karlsen, Z. Lebensm. Unters. Forsch., 180, 132 (1985).
- D. E. Moore, in Photostability of Drugs and Drug Formulations, 2nd edition, ed. by H. H. Tønnesen. CRC Press, Boca Raton, FL, pp. 49–53 (2004).
- S. R. Flom and P. F. Barbara, J. Phys. Chem., 89, 4489 (1985).
- A. J. G. Strandjord, S. H. Courtney, D. M. Friedrich and P. F. Barbara, J. Phys. Chem., 87, 1125 (1983).
- S. Mitra and S. Mukherjee, J. Luminesc., 118, 1 (2006).
- P. H. Bong, Bull. Korean Chem. Soc., 21, 81 (2000).
- H. H. Tønnesen, J. Karlsen and G. B. van Henegouwen, Z. Lebensm. Unters. Forsch., 183, 116 (1986).
- G. Weber, J. Chem. Phys., 66, 4081 (1977).
- E. Gratton, M. Limkeman, J. R. Lakowicz et al., Biophys. J., 46, 479 (1984).
- M. G. Badea and L. Brand, Methods Enzymol., 61, 378 (1979).
- K. M. Yoo and R. R. Alfano, Opt. Lett., 15, 320 (1990).
- W. Becker, The bh TCSPC Handbook. Becker & Hickl GmbH, Berlin, Germany (2006).
- A. Abbotto, G. Baldini, L. Baverina et al., Biophys. Chem., 114, 35 (2005).
- I. Rech, G. Luo, M. Ghioni et al., IEEE J. Sel. Top. Quant., 10, 788 (2004).
- A. Spinelli, M. Ghioni, S. Cova and L. M. Davis, IEEE J. Quant. Elect., 34, 817 (1998).
- A. Spinelli, L. M. Davis and H. Dautet, Rev. Sci. Instrum., 67, 55 (1995).
- A. Lacaita, S. Cova, M. Ghioni and F. Zappa, IEEE Elect. Device Lett., 14, 360 (1993).
- A. Lacaita, M. Ghioni and S. Cova, Electron. Lett., 25, 841 (1989).
- S. Cova, A. Longoni, A. Andreoni and R. Cubeddu, IEEE J. Quant. Elect., 19, 630 (1983).
- L. Nardo, A. Andreoni, M. Bondani et al., J. Photochem. Photobiol. Sci. B: Biol., 97, 77–86 (2009).
- H. H. Tønnesen, J. Karlsen and A. Mostad, Acta Chem. Scand. B, 36, 475 (1982).
- A. Mostad, U. Pedersen, P. B. Rasmussen and S. O. Lawesson, Acta Chem. Scand. B, 37, 901 (1983).
- A. Andreoni, L. Nardo, A. Brega and M. Bondani, J. Appl. Phys., 101, 024921 (2007).
- A. Andreoni, M. Bondani, A. Brega et al., Appl. Phys. Lett., 84, 2457 (2004).
- L. Nardo, M. Bondani and A. Andreoni, Photochem. Photobiol., 84, 101 (2008).
- L. Nardo, A. Brega, M. Bondani and A. Andreoni, Appl. Opt., 47, 2477 (2008).
- J. Emsley, in Structure and Bonding, ed. by M. J. Clarke, J. B. Goodenough, J. A. Ibers et al.. Springer-Verlag, Berlin, Germany, pp. 148–191 (1984).
-
U. Pedersen, P. B. Rasmussen and S. O. Lawesson, Liebigs Ann. Chem., 1985, 1557 (1985).
10.1002/jlac.198519850805 Google Scholar
- F. Ortica and M. A. J. Rodgers, Photochem. Photobiol., 76, 745 (2001).
- J. Toullec, in The Chemistry of Enols, ed. by Z. Rappoport. John Wiley & Sons, Inc., New York, NY, pp. 324–398 (1990).