Diastereoselectivity and site dependency in the photochemistry of ketoprofen in the bovine serum albumin matrix

Photochemistry and Photobiology

Volumn 82, Issue 1, 2006, Pages 13-19

  Monti, Sandra ^a   Manet, Ilse ^a   Manoli, Francesco ^a   Morrone, Raffaele ^b   Nicolosi, Giovanni ^b   Sortino, Salvatore ^c  

^a Istituto per la Sintesi Organica e la Fotoreattività   (Italy)

^b Istituto di Chimica Biomolecolare   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINAE;

EID: 33644777908     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-07-11-RA-608     Document Type: Conference Paper

References (31)

1. Bosca, F., M. L. Marin and M. A. Miranda (2001) Photoreactivity of the nonsteroidal anti-inflammatory 2-arylpropionic acids with photosensitizing side effects. Photochem. Photobiol. 74, 637-655.
2. Bosca, F., M. A. Miranda, G. Carganico and D. Mauleon (1994) Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophore. Photochem. Photobiol. 60, 96-101.
3. Costanzo, L. L., G. De Guidi, G. Condorelli, A. Cambria and M. Fama (1989) Molecular mechanism of drug photosensitization. II - Photohemolysis sensitized by ketoprofen. Photochem. Photobiol. 50, 359-365.
4. Monti, S., S. Sortino, G. De Guidi and G. Marconi (1997) Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen). A picosecond and nanosecond time resolved study in aqueous solution. J. Chem. Soc. Faraday Trans. 93, 2269-2275.
5. Martinez, L. J. and J. C. Scaiano (1997) Transient intermediates in the laser flash photolysis of ketoprofen in aqueous solutions. Unusual photochemistry for the benzophenone chromophore. J. Am. Chem. Soc. 119, 11066-11070.
6. Borsarelli, C. D., S. E. Braslavsky, S. Sortino, G. Marconi and S. Monti (2000) Photodecarboxylation of ketoprofen in aqueous solution. A time resolved laser-induced optoacoustic study. Photochem. Photobiol. 72, 163-171.
7. Monti, S., S. Sortino, G. De Guidi and G. Marconi (1998) Supramolecular photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen). A study in the β-cyclodextrin cavity. New J. Chem. 599-604.
8. Dormán, G. and G. Prestwich (1994) Benzophenone photophores in biochemistry. Biochemistry 33, 5661-5673.
9. Chuang, V. T. G., A. Kuniyasu, H. Nakayama, Y. Matsushita, S. Hirono and M. Otagiri (1999) Helix 6 of subdomain IIIA of human serum albumin is the region primarily photolabeled by ketoprofen, an arylpropionic acid NSAID containing a benzophenone moiety. Biochim. Biophys. Acta 1434, 18-30.
10. Moser, J., Z. Sarabia, H. Minter, W. W. Lovell and G. M. J. Beijersbergen van Henegouwen (2000) Photobinding of ketoprofen in vitro and ex vivo. J. Photochem. Photobiol. B 58, 37-45.
11. Lahoz, A., D. Hernandez, M. A. Miranda, J. Perez-Prieto, I. M. Morera and J. Castell. (2001) Antibodies directed to drug epitopes to investigate the structure of drug-protein photoadducts. Recognition of a common photobound substructure in tiaprofenic acid/ketoprofen cross-photoreactivity. Chem. Res. Toxicol. 14, 1486-1491.
12. Hutt, A. J. and J. Caldwell (1984) The importance of stereochemistry in the clinical pharmacokinetics of the 2-arylpropionic acid non steroidal anti-inflammatory drugs. Clin. Pharmacokinet. 9, 371-373.
13. Festa, C., N. Levi-Minzi and M. Zandomeneghi (1996) Photochemistry in biological matrices: binding site photoreactivity of ketoprofen in serum albumins and chiral discrimination. Gazz. Chim. Ital. 126, 599-603.
14. Monti, S., F. Manoli, S. Sortino, R. Morrone and G. Nicolosi (2005) Binding of a chiral drug to a protein: an investigation of the 2-(3-benzoyl-phenyl)propionic acid/bovine serum albumin system by circular dichroism and fluorescence. Phys. Chem. Chem. Phys., 7, 4002-4008.
15. Monti, S., N. Camaioni and P. Bortolus (1991) Photochemistry in a cyclodextrin cavity. Primary processes in the photoreduction of 3-and 4-benzoylpyridine studied by laser flash-photolysis. Photochem. Photobiol. 54, 577-584.
16. Zandomeneghi, M. (1995) Circular dichroism of ketoprofen complexed to serum albumins: conformational selection by the protein: a novel optical purity determination technique. Chirality 7, 446-451.
17. For a review on serum albumins see T. Peters Jr. (1985) Serum albumin. Adv. Protein Chem. 37, 161-245.
18. Dubois, N., F. Lapicque, M. Abiteboul and P. Netter (1993) Stereoselective protein binding of ketoprofen: effect of albumin concentration and of the biological system. Chirality 5, 126-134.
19. Cosa, G., L. J. Martinez and J. C. Scaiano (1999) Influence of solvent polarity and base concentration on the photochemistry of ketoprofen: independent singlet and triplet pathways. Phys. Chem. Chem. Phys. 1, 3533-3537.
20. Sudlow, G., D. J. Birkett and D. N. Wade (1976) Further characterization of specific drug binding sites on human serum albumin. Mol. Pharmacol. 12, 1052-1061.
21. He, X. M. and D. C. Carter (1992) Atomic structure and chemistry of human serum albumin. Nature 358, 209-215.
22. Carter, D. C. and J. X. Ho (1994) Structure of serum albumin. Adv. Prot. Chem. 45, 153-203.
23. Prieto, J. P., A. Lahoz, F. Bosca, R. Martinez-Manez and M. A. Miranda (2004) Stereodifferentiation in the decay of triplets and biradicals involved in intramolecular hydrogen transfer from phenols or indoles to π, π* aromatic ketones. J. Org. Chem. 69, 374-381.
24. Prieto, J. P., F. Bosca, R. E. Galian, A. Lahoz, L. R. Domingo and M. A. Miranda (2003) Photoreaction between 2-benzoylthiophene and phenol or indole J. Org. Chem. 68, 5104-5113.
25. Miranda, M. A., L. A. Martinez, A. Samadi, F. Bosca, and I. M. Morera (2002) Stereoselective intramolecular hydrogen abstraction by a chiral benzophenone derivative. Chem. Commun. 280-281.
26. Jovanovic, S. V. and S. Steenken (1992) Substituent effects on the spectral, acid-base, and redox properties of indolyl radicals: a pulse radiolysis study. J. Phys. Chem. 96, 6674-6679.
27. Scaiano, J. C., E. B. Abuin and L. C. Stewart (1982) Photochemistry of benzophenone in micelles. Formation and decays of radical pairs. J. Am. Chem. Soc. 104, 5673-5679.
28. Land, E. J. (1968) Extinction coefficients of triplet-triplet transitions. Proc. R. Soc. A 305, 457-471.
29. Bent, D. V. and E. Hayon (1975) Excited state chemistry of aromatic aminoacids and related peptides. III. Tryptophan. J. Am. Chem. Soc. 97, 2612-2619.
30. Bent, D. V. and E. Hayon (1975) Excited state chemistry of aromatic aminoacids and related peptides. I. Tyrosine. J. Am. Chem. Soc. 97, 2599-2606.
31. Mohat, N., F. L. Cozens, T. Hancock-Chen, J. C. Scaiano, J. McLean and J. Kim (1998) Magnetic field effects on the behavior of radicals in protein and DNA environments. Photochem. Photobiol. 67, 111-118.