Skip to main content
SpringerLink
Log in

Solar filters as feasible acceptors of atomic oxygen

  • Communication
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

The triazine derivative Tinosorb S has been shown to accept atomic oxygen generated by N-oxide photodeoxygenation. This is a unique example of a solar filter and mechanism-directed antioxidant. The concept has been proved by a combination of steady-state and laser-flash photolysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Notes and references

  1. J. Cadet, S. Mouret, J.-L. Ravanat, T. Douki, Photoinduced damage to cellular DNA: direct and photosensitized reactions, Photochem. Photobiol., 2012, 88, 1048–1065.

    Article  CAS  Google Scholar 

  2. G. P. Pfeifer, A. Besaratinia, UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer, Photochem. Photobiol. Sci., 2012, 11, 90–97.

    Article  CAS  Google Scholar 

  3. J. Cadet, E. Sage, T. Douki, Ultraviolet radiation-mediated damage to cellular DNA, Mutat. Res., 2005, 571, 3–17.

    Article  CAS  Google Scholar 

  4. E. Sage, P.-M. Girard, S. Francesconi, Unravelling UVA-induced mutagenesis, Photochem. Photobiol. Sci., 2012, 11, 74–80.

    Article  CAS  Google Scholar 

  5. A. Banyasz, I. Vayá, P. Changenet-Barret, T. Gustavsson, T. Douki, D. Markovitsi, Base pairing enhances fluorescence and favors cyclobutane dimer formation induced upon absorption of UVA radiation by DNA, J. Am. Chem. Soc., 2011, 133, 5163–5165.

    Article  CAS  Google Scholar 

  6. S. Mouret, C. Baudouin, M. Charveron, A. Favier, J. Cadet, T. Douki, Cyclobutane pyrimidine dimers are predominant DNA lesions in whole human skin exposed to UVA radiation, Proc. Natl. Acad. Sci. U. S. A., 2006, 103, 13765–13770.

    Article  CAS  Google Scholar 

  7. E. Venditti, F. Brugè, P. Astolfi, I. Kochevar, E. Damiani, Nitroxides and a nitroxide-based UV filter have the potential to photoprotect UVA-irradiated human skin fibroblasts against oxidative damage, J. Dermatol. Sci., 2011, 63, 55–61.

    Article  CAS  Google Scholar 

  8. N. Bastien, J.-F. Millau, M. Rouabhia, R. J. H. Davies, R. Drouin, The sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid photosensitizes the formation of oxidized guanines in cellulo after UV-A or UV-B exposure, J. Invest. Dermatol., 2010, 130, 2463–2471.

    Article  CAS  Google Scholar 

  9. O. R. Wauchope, S. Shakya, N. Sawwan, J. F. Liebman, A. Greer, Photocleavage of plasmid DNA by dibenzothiophene S-oxide under anaerobic conditions, J. Sulfur Chem., 2007, 28, 11–16.

    Article  CAS  Google Scholar 

  10. J. F. Orrego, T. N. Truong, F. Mondragon, A linear energy relationship between activation energy and absolute hardness: a case study with the O(3P) atom-addition reactions to polyaromatic hydrocarbons, J. Phys. Chem. A, 2008, 112, 8205–8207.

    Article  CAS  Google Scholar 

  11. M. Zhang, G. E. Ravilious, L. M. Hicks, J. M. Jez, R. D. McCulla, Redox switching of adenosine-5′-phosphosulfate kinase with photoactivatable atomic oxygen precursors, J. Am. Chem. Soc., 2012, 134, 16979–16982.

    Article  CAS  Google Scholar 

  12. B. Herzog, M. Wehrle, K. Quass, Photostability of UV absorber systems in sunscreens, Photochem. Photobiol., 2009, 85, 869–878.

    Article  CAS  Google Scholar 

  13. P. F. McGarry, S. Jockusch, Y. Fujiwara, N. A. Kaprinidis, N. J. Turro, DMSO solvent induced photochemistry in highly photostable compounds. The role of intermolecular hydrogen bonding, J. Phys. Chem. A, 1997, 101, 764–767.

    Article  CAS  Google Scholar 

  14. J. Zou, Q. Chen, S. Tang, X. Jin, K. Chen, T. Zhang, X. Xiao, Olaquindox-induced genotoxicity and oxidative DNA damage in human hepatoma G2 (HepG2) cells, Mutat. Res., 2009, 676, 27–33.

    Article  CAS  Google Scholar 

  15. V. Junnotula, U. Sarkar, S. Sinha, K. S. Gates, Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxide antitumor agents: mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide, J. Am. Chem. Soc., 2009, 131, 1015–1024.

    Article  CAS  Google Scholar 

  16. A. Albini, M. Alpegiani, The photochemistry of the N-oxide function, Chem. Rev., 1984, 84, 43–71.

    Article  CAS  Google Scholar 

  17. G. Bucher, J. C. Scaiano, Laser flash photolysis of pyridine N-oxide: kinetic studies of atomic oxygen [O(3P)] in solution, J. Phys. Chem., 1994, 98, 12471–12473.

    Article  CAS  Google Scholar 

  18. Z. Wan, W. S. Jenks, Oxenoid reactivity observed on the photolysis of certain aromatic sulfoxides, J. Am. Chem. Soc., 1995, 117, 2667–2668.

    Article  CAS  Google Scholar 

  19. Y. Ogawa, S. Iwasaki, S. Okuda, A study on the transition state in the photooxygenations by aromatic amine N-oxides, Tetrahedron Lett., 1981, 22, 2277–2280.

    Article  CAS  Google Scholar 

  20. E. Damiani, P. Astolfi, L. Greci, Nitroxide-based UV-filters: a new strategy against UV-damage?, Household Pers. Care Today, 2008, 2, 20–23.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universitat Politècnica de València, Camino de Vera s/n, 46022, Valencia, Spain

    Neus Durán-Giner, Susana Encinas & Miguel A. Miranda

Authors
  1. Neus Durán-Giner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Susana Encinas
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Miguel A. Miranda
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Susana Encinas or Miguel A. Miranda.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Durán-Giner, N., Encinas, S. & Miranda, M.A. Solar filters as feasible acceptors of atomic oxygen. Photochem Photobiol Sci 12, 725–728 (2013). https://doi.org/10.1039/c3pp25407k

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c3pp25407k

Search

Navigation