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Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for sunscreen

  • Original Paper: Sol-gel and hybrid materials with surface modification for applications
  • Published:
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Abstract

To allay concerns that sunscreen ingredients are harmful to skin health, we have developed phenylalanine (Phe) and leucine (Leu) dipeptide functionalized silica-based nanoporous material (Phe-Leu-OMe-Meso) as a safe ultraviolet filter for skin protection from UVA/UVB sun irradiation. The selected peptide-based functional molecules are composed of natural amino acids, which have obvious advantages compared with other biological molecules and organic molecules, such as low toxicity and high stability. Octyl salicylate (OS) is adopted as the drug molecule to observe the adsorption behavior of the nanoporous materials. The results confirm that Phe groups effectively improve the OS loaded capacity of Phe-Leu-OMe-Meso by aromatic π–π stacking interaction, and the experimental data obey the pseudo-second-order kinetic model and the Langmuir, Freundlich, Temkin isotherm model. Moreover, in vitro evaluation of the spectrophotometric sun protection factor indicates that Leu groups make Phe-Leu-OMe-Meso possess an excellent sunscreen efficacy close to that of mesoporous TiO2 and exhibit a synergistic effect with OS on sun protection. In summary, the dipeptide functionalization of silica-based nanoporous material has an excellent prospect in the application of sunscreen.

Highlights

  • Phenylalanyl-leucine organic silicon precursor (Phe-Leu-OMe-Si) was prepared by choosing leucine of the aliphatic family and phenylalanine of the aromatic family as initial reactants.

  • Dipeptide functionalization of silica-based nanoporous material was used for sun protection for the first time, which has a positive significance.

  • The dipeptide-based functional molecules provide two functions: Leu groups make Phe-Leu-OMe-Meso possess excellent sunscreen efficacy close to that of mesoporous TiO2 and exhibit a synergistic effect with octyl salicylate on sun protection; Phe groups effectively improved octyl salicylate (OS) loaded capacity of Phe-Leu-OMe-Meso by aromatic π–π stacking interaction.

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Acknowledgements

The authors would like to thank Nanjing Tech University for its support throughout the course of this research. This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

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Authors and Affiliations

  1. School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 Pu Zhu South Road, Nanjing, 211816, Jiangsu, People’s Republic of China

    Haohua Ma, Jianqiang Wang, Wenpei Zhang & Cheng Guo

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  1. Haohua Ma
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  2. Jianqiang Wang
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  3. Wenpei Zhang
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  4. Cheng Guo
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Correspondence to Haohua Ma.

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Ma, H., Wang, J., Zhang, W. et al. Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for sunscreen. J Sol-Gel Sci Technol 97, 466–478 (2021). https://doi.org/10.1007/s10971-020-05417-6

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  • DOI: https://doi.org/10.1007/s10971-020-05417-6

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