Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for
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ORIGINAL PAPER: SOL-GEL AND HYBRID MATERIALS WITH SURFACE MODIFICATION FOR APPLICATIONS
Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for sunscreen Haohua Ma
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Jianqiang Wang1 Wenpei Zhang1 Cheng Guo1 ●
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Received: 12 July 2020 / Accepted: 17 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
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-OMeMeso 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. Graphical Abstract
Supplementary information The online version of this article (https:// doi.org/10.1007/s10971-020-05417-6) contains supplementary material, which is available to authorized users. * Haohua Ma [email protected] 1
School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 Pu Zhu South Road, Nanjing 211816 Jiangsu, People’s Republic of China
Journal of Sol-Gel Science and Technology
Keywords
Functionalized mesoporous silica Phenylalanyl-leucine UV filter ●
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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. ●
1 Introduction Long-term ultraviolet (UV) radiation can cause photodamage to the skin [1, 2]. UV filters are widely used in su
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