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Molecular modeling as a design tool for sunscreen candidates: a case study of bemotrizinol

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A Correction to this article was published on 06 January 2020

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Abstract

Sunscreen-based photoprotection is an important strategy to prevent photoaging and skin cancer. Among the effective and modern sunscreens, triazine compounds are known as an important class based on their physical-chemical properties, such as photostability and UV broad-spectrum absorption (UVA and UVB). Molecular modeling and quantum mechanical calculations approaches can be helpful to orientate the design of sunscreens. Herein, a case study is presented to demonstrate the importance of the molecular modeling as a design tool for promising sunscreen candidates based on the synthesis research previously described of bemotrizinol, a broad-spectrum photostable organic UV filter present in many sunscreens products. Time-dependent density functional theory (TD-DFT) calculations performed in gas phase on the isolated organic UV filters proved to reproduce the experimental UV absorption, guiding the choice of the most efficient candidate as sunscreen. The present work highlights the importance of molecular modeling as an effective tool to support synthesis research, increasing the possibility of obtaining promising compounds with reduced costs and effluent production.

A case study to demonstrate the importance of the molecular modeling as a design tool for promising sunscreen candidates is presented. The method proved to be a valuable tool to reproduce the experimental UV absorption and to determinate the most efficient molecule as sunscreen among the candidates.

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Change history

  • 06 January 2020

    The original version of this article unfortunately contained mistakes. Table 1 was missing and the presentation of Table 2 was incorrect. In Table 2, the second [λexp (nm)] and last [MADa] columns, many values are wrongly in the same cell/line. For example, in column 2, line 2, the first number (342) should be above the other (318).

Abbreviations

UVR, UV:

ultraviolet radiation

ROS:

reactive oxygen species

TD-DFT:

time-dependent density functional theory

PM6:

parametric method 6

BEMT:

bemotrizinol

MAD:

mean absolute deviation

B3LYP:

Becke 3-parameter Lee-Yang-Parr

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Acknowledgments

The authors would like to acknowledge the contribution to this paper from the undergraduate students Lucas Pereira Marques and Carolina Jardim Martins for helping with the data collection.

Funding

This study was supported by grants and fellowships from CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico), FAPERJ (Fundação de Amparo à Pesquisa do Estado do Rio de Janeiro), and UFRJ (Universidade Federal do Rio de Janeiro), Brazil.

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Authors and Affiliations

  1. Laboratório de Planejamento Farmacêutico e Simulação Computacional (LaPFarSC), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-902, Brazil

    João Victor Teixeira Gomes, Anne Cherem Peixoto da Silva, Murilo Lamim Bello & Bianca Aloise Maneira Corrêa Santos

  2. Laboratório de Modelagem Molecular & QSAR (ModMolQSAR), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-902, Brazil

    Carlos Rangel Rodrigues

Authors
  1. João Victor Teixeira Gomes
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  2. Anne Cherem Peixoto da Silva
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  3. Murilo Lamim Bello
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  4. Carlos Rangel Rodrigues
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  5. Bianca Aloise Maneira Corrêa Santos
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The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Corresponding author

Correspondence to Bianca Aloise Maneira Corrêa Santos.

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The original version of this article was revised: Table 1 was missing and the presentation of Table 2 was incorrect. In Table 2, second [λexp (nm)] and last [MADa] columns, many values are wrongly in the same cell/line.

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Teixeira Gomes, J.V., Cherem Peixoto da Silva, A., Lamim Bello, M. et al. Molecular modeling as a design tool for sunscreen candidates: a case study of bemotrizinol. J Mol Model 25, 362 (2019). https://doi.org/10.1007/s00894-019-4237-7

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