caa a22 4500 605510970 CHVBK 20210128100648.0 cr unu---uuuuu 210128e20150601xx s 000 0 eng 10.1007/s00894-015-2689-y doi (NATIONALLICENCE)springer-10.1007/s00894-015-2689-y Benchmark studies of UV-vis spectra simulation for cinnamates with UV filter profile [Elektronische Daten] [Ricardo Garcia, Vinícius Maltarollo, Káthia Honório, Gustavo Trossini] Skin cancer is a serious public health problem worldwide, being incident over all five continents and affecting an increasing number of people. As sunscreens are considered an important preventive measure, studies to develop better and safer sunscreens are crucial. Cinnamates are UVB filters with good efficiency and cost-benefit, therefore, their study could lead to the development of new UV filters. A benchmark to define the most suitable density functional theory (DFT) functional to predict UV-vis spectra for ethylhexyl methoxycinnamate was performed. Time-dependent DFT (TD-DFT) calculations were then carried out [B3LYP/6-311 + G(d,p) and B3P86/6-311 + G(d,p) in methanol environment] for seven cinammete derivatives implemented in the Gaussian 03 package. All DFT/TD-DFT simulations were performed after a conformational search with the Monte-Carlo method and MMFF94 force field. B3LYP and B3P86 functionals were better at reproducing closely the experimental spectra of ethylhexyl methoxycinnamate. Calculations of seven cinnamates showed a λmax of around 310nm, corroborating literature reports. It was observed that the energy for the main electronic transition was around 3.95eV and could be explained by electron delocalization on the aromatic ring and ester group, which is important to UV absorption. The methodology employed proved to be suitable for determination of the UV spectra of cinnamates and could be used as a tool for the development of novel UV filters. Springer-Verlag Berlin Heidelberg, 2015 Cinnamates nationallicence TD-DFT nationallicence Molecular modeling nationallicence UV filters nationallicence UV spectra simulation nationallicence Garcia Ricardo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut Maltarollo Vinícius Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut Honório Káthia School of Arts, Sciences and Humanities, University of São Paulo, São Paulo, SP, Brazil aut Trossini Gustavo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/6(2015-06-01), 1-13 1610-2940 21:6<1 2015 21 894 https://doi.org/10.1007/s00894-015-2689-y text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2689-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Garcia Ricardo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Maltarollo Vinícius Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Honório Káthia School of Arts, Sciences and Humanities, University of São Paulo, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Trossini Gustavo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Lineu Prestes, 580 - Bloco 13 Superior, CEP: 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/6(2015-06-01), 1-13 1610-2940 21:6<1 2015 21 894