Literature DB >> 31773345

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

João Victor Teixeira Gomes1, Anne Cherem Peixoto da Silva1, Murilo Lamim Bello1, Carlos Rangel Rodrigues2, Bianca Aloise Maneira Corrêa Santos3.   

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. Graphical abstractA 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.

Entities:  

Keywords:  Bemotrizinol; Molecular modeling; Sunscreen; TD-DFT; Triazine

Mesh:

Substances:

Year:  2019        PMID: 31773345     DOI: 10.1007/s00894-019-4237-7

Source DB:  PubMed          Journal:  J Mol Model        ISSN: 0948-5023            Impact factor:   1.810


  27 in total

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Review 4.  Photoprotection: a review of the current and future technologies.

Authors:  Steven Q Wang; Yevgeniy Balagula; Uli Osterwalder
Journal:  Dermatol Ther       Date:  2010 Jan-Feb       Impact factor: 2.851

5.  Tris-biphenyl triazine, a new ultraviolet filter studied in terms of photoprotective efficacy.

Authors:  C Couteau; E Paparis; C Chauvet; L Coiffard
Journal:  Int J Pharm       Date:  2015-04-02       Impact factor: 5.875

6.  Substituent effects on the ultraviolet absorption properties of stilbene compounds-Models for molecular cores of absorbents.

Authors:  Zhengjun Fang; Feng Wu; Qiang Tao; Qiwen Qin; Chaktong Au; Yajun Li; Houpeng Zhang; Nanfang Wang; Bing Yi
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2019-02-20       Impact factor: 4.098

Review 7.  Photoprotection: extending lessons learned from studying natural sunscreens to the design of artificial sunscreen constituents.

Authors:  Lewis A Baker; Barbara Marchetti; Tolga N V Karsili; Vasilios G Stavros; Michael N R Ashfold
Journal:  Chem Soc Rev       Date:  2017-06-19       Impact factor: 54.564

8.  Theoretical insights into the photo-protective mechanisms of natural biological sunscreens: building blocks of eumelanin and pheomelanin.

Authors:  Barbara Marchetti; Tolga N V Karsili
Journal:  Phys Chem Chem Phys       Date:  2016-02-07       Impact factor: 3.676

9.  Hydrogen bond dynamics governs the effective photoprotection mechanism of plant phenolic sunscreens.

Authors:  Fang Liu; Likai Du; Zhenggang Lan; Jun Gao
Journal:  Photochem Photobiol Sci       Date:  2017-02-15       Impact factor: 3.982

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Authors:  D M Parkin; D Mesher; P Sasieni
Journal:  Br J Cancer       Date:  2011-12-06       Impact factor: 7.640

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  1 in total

1.  Theragra chalcogramma Hydrolysates, Rich in Gly-Leu-Pro-Ser-Tyr-Thr, Exerts Anti-Photoaging Potential via Targeting MAPK and NF-κB Pathways in SD Rats.

Authors:  Defeng Xu; Mouming Zhao; Haisheng Lin; Caihong Li
Journal:  Mar Drugs       Date:  2022-04-24       Impact factor: 6.085

  1 in total

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