Naphthoxazole-based singlet oxygen fluorescent probes

Photochemistry and Photobiology

Volumn 89, Issue 6, 2013, Pages 1427-1432

  Ruiz González, Rubén ^a   Zanocco, Renzo ^b   Gidi, Yasser ^b   Zanocco, Antonio L ^b   Nonell, Santi ^a   Lemp, Else ^b  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; OXAZOLE DERIVATIVE; SINGLET OXYGEN;

CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

FLUORESCENT DYES; OXAZOLES; OXIDATION-REDUCTION; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SINGLET OXYGEN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84887406337     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/php.12106     Document Type: Article

References (31)

1. Redmond, R. W., and, I. E. Kochevar, (2006) Spatially resolved cellular responses to singlet oxygen. Photochem. Photobiol. 82, 1178-1186.
2. Agostinis, P., K. Berg, K. A. Cengel, T. H. Foster, A. W. Girotti, S. O. Gollnick, S. M. Hahn, M. R. Hamblin, A. Juzeniene, D. Kessel, M. Korbelik, J. Moan, P. Mroz, D. Nowis, J. Piette, B. C. Wilson, and, J. Golab, (2011) Photodynamic therapy of cancer: An update. CA Cancer J. Clin. 61, 250-281.
3. Soh, N., (2006) Recent advances in fluorescent probes for the detection of reactive oxygen species. Anal. Bioanal. Chem. 386, 532-543.
4. Wu, H., Q. Song, G. Ran, X. Lu, and, B. Xu, (2011) Recent developments in the detection of singlet oxygen with molecular spectroscopic methods. Trends Anal. Chem. 30, 133-141.
5. Nonell, S., and, S. E. Braslavsky, (2000) Time-resolved singlet oxygen detection. In Singlet Oxygen, UV-A and Ozone. (Edited by, L. Packer, and, H. Sies,), Methods Enzymol. 319, 37-49. Academic Press, San Diego.
6. Ogilby, P. R., (2010) Singlet oxygen: There is indeed something new under the sun. Chem. Soc. Rev. 39, 3181-3209.
7. Schweitzer, C., and, R. Schmidt, (2003) Physical mechanisms of generation and deactivation of singlet oxygen. Chem. Rev. 103, 1685-1758.
8. Gandin, E., Y. Lion, and, A. Van de Vorst, (1983) Quantum yield of singlet oxygen production by xanthene derivatives. Photochem. Photobiol. 37, 271-278.
9. Rabello, B. R., A. P. Gerola, D. S. Pellosi, A. L. Tessaro, J. L. Aparício, W. Caetano, and, N. Hioka, (2012) Singlet oxygen dosimetry using uric acid as a chemical probe: Systematic evaluation. J. Photochem. Photobiol. A 238, 53-62.
10. Kalai, T., E. Hideg, I. Vass, and, K. Hideg, (1998) Double (fluorescent and spin) sensors for detection of reactive oxygen species in the thylakoid membrane. Free Radic. Biol. Med. 24, 649-652.
11. Hideg, E., (2004) Detection of free radicals and reactive oxygen species. Methods Mol. Biol. 274, 249-260.
12. Umezawa, N., K. Tanaka, Y. Urano, K. Kikuchi, T. Higuchi, and, T. Nagano, (1999) Novel fluorescent probes for singlet oxygen. Angew. Chem. Int. Ed. Eng. 38, 2899-2901.
13. Tanaka, K., T. Miura, N. Umezawa, Y. Urano, K. Kikuchi, T. Higuchi, and, T. Nagano, (2001) Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen. J. Am. Chem. Soc. 123, 2530-2536.
14. Song, B., G. Wang, M. Tan, and, J. Yuan, (2006) A europium(III) complex as an efficient singlet oxygen luminescence probe. J. Am. Chem. Soc. 128, 13442-13450.
15. Invitrogen-Molecular Probes (2005) Singlet Oxygen Sensor Green Reagent. Available at: http://probes.invitrogen.com/media/pis/mp36002.pdf. Accessed on 18 March 2013.
16. ®: Photochemical behavior in solution and in a mammalian cell. Photochem. Photobiol. 87, 671-679.
17. Lin, H., Y. Shen, D. Chen, L. Lin, B. C. Wilson, B. Li, and, S. Xie, (2013) Feasibility study on quantitative measurements of singlet oxygen generation using singlet oxygen sensor green. J. Fluoresc. 23, 41-47.
18. Xu, K., L. Wang, M. Qiang, L. Wang, P. Li, and, B. Tang, (2011) A selective near-infrared fluorescent probe for singlet oxygen in living cells. Chem. Commun. 47, 7386-7388.
19. ®. Chem. Commun. 20, 2920-2922.
20. Demas, J. N., and, G. A. Crosby, (1971) Measurement of photoluminescence quantum yields-Review. J. Phys. Chem. 75, 991-1024.
21. Eaton, D. F., (1988) Reference materials for fluorescence measurement. Pure Appl. Chem. 60, 1107-1114.
22. Montalti, M., A. Credi, L. Prodi, and, G. M.T, (2006) Handbook of Photochemistry, 3rd edn. CRC Press, Boca Raton, FL.
23. Jiménez-Banzo, A., X. Ragàs, P. Kapusta, and, S. Nonell, (2008) Time-resolved methods in biophysics. 7. Photon counting vs. analog time-resolved singlet oxygen phosphorescence detection. Photochem. Photobiol. Sci. 7, 1003-1010.
24. g) sensitization. J. Photochem. Photobiol. A 79, 11-17.
25. Mac, M., B. Tokarczyk, T. Uchacz, and, A. Danel, (2007) Charge transfer fluorescence of benzoxazol derivatives investigation of solvent effect on fluorescence of these dyes. J. Photochem. Photobiol. A 191, 32-41.
26. Machado, A. E., J. de Miranda, S. Guilardi, D. Nicodem, and, D. Severino, (2003) Photophysics and spectroscopic properties of 3-benzoxazol-2-yl-chromen- 2-one. Spectrochim. Acta A Mol. Biomol. Spectrosc. 59, 345-355.
27. Fayed, T., (2004) Probing of micellar and biological systems using 2-(p-dimethylaminostyryl)benzoxazole-An intramolecular charge transfer fluorescent probe. Colloids Surf. A 236, 171-177.
28. Gollnick, K., and, A. Griesbeck, (1985) Singlet oxygen photooxygenation of furans-isolation and reactions of (4 2)-cycloaddition products (unsaturated sec-ozonides). Tetrahedron 41, 2057-2068.
29. Lemp, E., A. Zanocco, and, E. Lissi, (2003) Linear free energy relationship analysis of solvent effects on singlet oxygen reactions. Curr. Org. Chem. 7, 799-819.
30. Clennan, E. L., and, A. Pace, (2005) Advances in singlet oxygen chemistry. Tetrahedron 61, 6665-6691.
31. Wilkinson, F., W. P. Helman, and, A. B. Ross, (1995) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663-677.