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Trossini GH, Maltarollo VG, Garcia RD, et al. Theoretical study of tautomers and photoisomers of avobenzone by DFT methods. J Mol Model. 2015;21(12):319doi: 10.1007/s00894-015-2863-2.
Trossini, G. H., Maltarollo, V. G., Garcia, R. D., Pinto, C. A., Velasco, M. V., Honorio, K. M., & Baby, A. R. (2015). Theoretical study of tautomers and photoisomers of avobenzone by DFT methods. Journal of molecular modeling, 21(12), 319. https://doi.org/10.1007/s00894-015-2863-2
Trossini, Gustavo H G, et al. "Theoretical study of tautomers and photoisomers of avobenzone by DFT methods." Journal of molecular modeling vol. 21,12 (2015): 319. doi: https://doi.org/10.1007/s00894-015-2863-2
Trossini GH, Maltarollo VG, Garcia RD, Pinto CA, Velasco MV, Honorio KM, Baby AR. Theoretical study of tautomers and photoisomers of avobenzone by DFT methods. J Mol Model. 2015 Dec;21(12):319. doi: 10.1007/s00894-015-2863-2. Epub 2015 Dec 02. PMID: 26631072.
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J Mol Model. 2015 Dec;21(12):319. doi: 10.1007/s00894-015-2863-2. Epub 2015 Dec 02.

Theoretical study of tautomers and photoisomers of avobenzone by DFT methods.

Journal of molecular modeling

Gustavo H G Trossini, Vinicius G Maltarollo, Ricardo D'A Garcia, Claudinéia A S O Pinto, Maria V R Velasco, Kathia M Honorio, André R Baby

Affiliations

  1. Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, São Paulo, SP, 05508-000, Brazil. [email protected].
  2. Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, São Paulo, SP, 05508-000, Brazil.
  3. School of Arts, Sciences and Humanities, University of São Paulo, São Paulo, São Paulo, Brazil.
  4. Center of Natural Sciences and Humanities, Federal University of ABC, Santo André, São Paulo, Brazil.

PMID: 26631072 DOI: 10.1007/s00894-015-2863-2

Abstract

Organic ultraviolet (UV) filters such as cinnamates, benzophenones, p-aminobenzoic derivatives, and avobenzone (which have well-established and recognized UV-filtering efficacies) are employed in cosmetic/pharmaceutical products to minimize the harm caused by exposure of the skin to sunlight. In this study, a detailed investigation of the photostability and tautomerism mechanisms of avobenzone was performed utilizing DFT methods. The UV spectral profile of avobenzone was also simulated, and the results showed good agreement with experimental data. Furthermore, the calculations were able to distinguish tautomers and photoisomers of the studied organic filter based on their properties, thus showing the potential to develop new organic UV filters. Graphical Abstract Theoretical studies of avobenzone and its tautomers by TD-DFT.

Keywords: Avobenzone; DFT methods; Molecular modeling; Photostability; Tautomerism

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