Mechanism of the photosensitizing action of a mixture humic acid-riboflavin in the degradation of water-contaminants

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 219, Issue 1, 2011, Pages 84-89

  Pajares, Adriana ^a   Bregliani, Mabel ^a   Natera, José ^b   Criado, Susana ^b   Miskoski, Sandra ^b   Escalada, Juan P ^a   García, Norman A ^b  

^a UNIVERSIDAD NACIONAL DE LA PATAGONIA AUSTRAL   (Argentina)

^b DEPARTAMENTO DE QUÍMICA   (Argentina)

Author keywords

Humic acid; Hydroxyaromatics; Photooxidation; Photosensitization; Riboflavin

Indexed keywords

EID: 79952988882     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2011.01.021     Document Type: Article

References (39)

1. J.I. Edges, and J.M. Oades Comparative organic geochemistrys of soils and marine sediments Org. Geochem. 27 1997 319 361 (Pubitemid 28065623)
2. M.C. Scapini, V.H. Conzonno, V.T. Balzaretti, and A. Fernández Cirelli Comparison of marine and river water humic substances in a Patagonian environment (Argentina) Aquat. Sci. 72 2010 1 12
3. A. Momzikoff, R. Santus, and M. Giraud A study of the photosensitizing properties of seawater Mar. Chem. 12 1983 1 14
4. J.N. Chacón, J. McLearie, and R.S. Sinclair Singlet oxygen yields and radical contributions in the dye-sensitized photo-oxidation in methanol of esters of polyunsatured fatty acids (oleic, linoleic, linolenic and arachidonic) Photochem. Photobiol. 47 1998 647 656
5. A. Paul, S. Hackbarth, E. Zwirnmann, B. Roeder, and C.E.W. Steimberg Photosensitized generation of singlet oxygen and its quenching by humic substances E.A. Ghabbour, G. Davies, Humic Substances. Molecular Details and Applications in Land and Water Conservation 2005 Taylor and Francis Oxon 99 116
6. M. Neamtu, and N.H. Frimmel Degradation of endocrine disrupting bisphenol A by 254 nm irradiation in different water matrices and effect on yeast cells Water Res. 40 2006 3745 3750 (Pubitemid 44750060)
7. Y. Barbieri, W.A. Massad, D.J. Díaz, J. Sanz, F. Amat-Guerri, and N.A. García Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin. Kinetics, mechanism and photoproducts Chemosphere 73 2008 564 571
8. H.D. Burrows, L.M. Canle, J.A. Santaballa, and S. Steenken Reaction pathways and mechanisms of photodegradation of pesticides J. Photochem. Photobiol. B: Biol. 67 2002 71 108 (Pubitemid 34746524)
9. F. Amat-Guerri, and N.A. García Photodegradation of hydroxylated N-heteroaromatic derivatives in natural-like aquatic environments. A review of kinetic data of pesticide model compounds Chemosphere 59 2005 1067 1082
10. N.A. García Singlet molecular oxygen-mediated photodegradation of aquatic phenolic pollutants J. Photochem. Photobiol. B: Biol. 22 1994 185 196 (Pubitemid 24082917)
11. D.M. Leech, T. Matthew, R.G. Snyder, and Wetzel Natural organic matter and sunlight accelerate the degradation of 17β-estradiol in water Sci. Total Environ. 407 2009 2087 2092
12. J.P. Aguer, and C. Richard Reactive species produced on irradiation at 365 nm of aqueous solutions of humic acids J. Photochem. Photobiol. A: Chem. 93 1991 193 198 (Pubitemid 126164956)
13. Z. Peng, F. Wu, and N. Deng Photodegradation of bisphenol A in simulated lake water containing algae, humics acid and ferric ions Environ. Pollut. 144 2006 840 846 (Pubitemid 44344891)
14. E. Haggi, S. Bertolotti, and N.A. García Modeling the environmental degradation of water contaminants. Kinetics and mechanism of the riboflavin-sensitised-photooxidation of phenolic compounds Chemosphere 55 2004 1501 1507 (Pubitemid 38507398)
15. M. Kepczynski, A. Czosnyka, and M. Nowakowska Photooxidation of phenol in aqueous nanodispersion of humic acid J. Photochem. Photobiol. A: Chem. 185 2007 198 205
16. A.L. Boreen, B.L. Edhlund, J.B. Cotner, and K. McNeil Indirect photodegradation of dissolved free amino acids: the contribution of singlet oxygen and the differential reactivity of DOM from various sources Environ. Sci. Technol. 42 2008 5492 5498
17. P.M. David Gara, G.N. Bosio, V.B. Arce, L. Poulsen, P.R. Ogilby, R. Guidici, M.C. González, and D. Mártire Photoinduced degradation of the herbicide clomazone. model reactions for natural and technical systems Photochem. Photobiol. 85 2009 686 692
18. I. Gutiérrez, S. Criado, S. Bertolotti, and N.A. García Dark and photoinduced interactions between trolox, a polar-solvent-soluble model for vitamin E, and riboflavin J. Photochem. Photobiol. B: Biol. 62 2001 133 139 (Pubitemid 32898833)
19. K. Zeng, H. Hwang, Y. Zhang, and H. Yu Identification of 6-aminochriysene photoproducts and study of the effect of a humic acid and riboflavin on its photolysis J. Photochem. Photobiol. B: Biol. 72 2003 95 100 (Pubitemid 37509040)
20. C. Tomlin The Pesticide Manual 1994 British Crop Protection Council and The Royal Society of Chemistry London, UK
21. C.M. Krishna, S. Uppuluri, P. Riesz, J.S. Zigler, and D. Balasubramanian A study of the photodynamic efficiencies of some eye lens constituents Photochem. Photobiol. 54 1991 51 58
22. 2-sensitised-photooxidation of isoproterenol Photochem. Photobiol. 79 2004 428 433
23. A. Pajares, J. Gianotti, E. Haggi, G. Stettler, F. Amat-Guerri, S. Bertolotti, S. Criado, and N.A. García Visible light-promoted interactions between riboflavin and 3-hydroxypyridine in aqueous solution Dyes Pigments 41 1999 233 239
24. R.L. Malcom Limitations in the use of commercial humic acids in water and soil research Environ. Sci. Technol. 20 1986 904 911
25. P.M. David Gara, G. Bosio, M.C. González, and D. Mártire Reaction of humic acid with sulfate radicals Int. J. Chem. Kinet. 40 2008 19 24
26. J.V. Goldstone Chemistry of superoxide radical in seawater: CDOM associated sink of superoxide in coastal waters Environ. Sci. Technol. 34 2000 1043 1048 (Pubitemid 30155208)
27. 2-sensitised-photooxidation of isoproterenol Photochem. Photobiol. 79 2004 428 433
28. D.O. Mártire, S.E. Braslavsky, and N.A. García Senstized photo-oxidation of dihydroxybencenes and chlorinated derivatives J. Photochem. Photobiol. A: Chem. 61 1991 113 124
29. G. Cohen, and R.E. Heikkila The generation of hydrogen peroxide, superoxide radical and hydroxyl radical by 6-hydroxydopamine, dialuric acid and related cytotoxic agents J. Biol. Chem. 249 1974 2447 2453
30. E. Silva, L. Herrera, A.M. Edwards, J. De La Fuente, and E. Lissi Enhancement of Riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by uronic acid Photochem. Photobiol. 81 2005 206 211 (Pubitemid 40327581)
31. J.P. Escalada, A. Pajares, J. Gianotti, W.A. Massad, S. Bertolotti, F. Amat-Guerri, and N.A. García Dye-sensitized photodegradation of the fungicide carbendazim and related benzimidazoles Chemosphere 65 2006 237 244 (Pubitemid 44177654)
32. F. Wilkinson, W.P. Helman, and A. Ross Rate constants for the decay of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation J. Phys. Chem. Ref. Data 24 1995 663 1021
33. V.T. Grachev, B.E. Saltzev, K.M. Dyumaev, L.D. Smirnov, and M.R. Avezov Structure of 2,3 and 2,5 dihydroxypyridines Khim. Getoer. Soedl. 1 1973 60 63
34. P.F. Heelis The photophysical and photochemical properties of flavins (isoalloxazines) Chem. Soc. Rev. 11 1982 15 39
35. F. Amat-Guerri, M.C. López-González, R. Martínez-Utrilla, and R. Sastre Singlet oxygen photogeneration by ionized and un-ionized derivatives of Rose Bengal and Eosin Y in diluted solutions J. Photochem. Photobiol. A: Chem. 53 1990 199 210
36. R.C. Weast, and M.J. Astle CRC Handbook of Chemistry and Physics 1981 CRC Press Boca Ratón, FL
37. F.E. Scully, and J. Hoingé Rate constants for reactions of singlet oxygen with phenols and other compounds in water Chemosphere 16 1987 681 694
38. M. Koizumi, S. Kato, N. Mataga, T. Matsuura, and I. Isui Photosensitized Reactions 1978 Kagakudogin Kyoto
39. S.L. Murov, I. Carmichael, and G.L. Hug Handbook of Photochemistry 2nd ed. 1993 Dekker M New York