Design and Synthesis of Novel Peptides to Protect Ferulic Acid against Ultraviolet Radiation Based on Domain Site IIA of Bovine Serum Albumin.

Yinghan Wu,Hisham N Farrag,Tamaki Kato,Hua Li,Shinya Ikeno

doi:10.3390/biom11091285

Abstract

Ferulic acid (FA) is known for its excellent antioxidant properties, which can provide many health benefits. One of its drawbacks is its instability under UVA light, which limits its potency. In this study, the new peptides LW2 (QNKRFYFRKNQ) and CW2 (a cyclic form of LW2) were designed based on bovine serum albumin site IIA conformation. A UVA irradiation experiment was performed to investigate the protective ability of these peptides towards FA against UVA damage. The percentages of FA remaining under UV irradiation due to the protection of CW2 and LW2 were 83% and 76%, respectively. The results showed the importance of the cationic residues and hydrophobic residues included in the peptide sequences. Moreover, the cyclic rigid structure showed greater protective ability as compared to its linear counterpart.

Highlights

In this study, the new peptides LW2 (QNKRFYFRKNQ) and CW2 were designed based on bovine serum albumin site IIA conformation
It was shown that almost half of the Ferulic acid (FA) was destroyed in this period
On maintaining the UVA irradiation up to 12 h later, the solution became stable and its RR value held at 29.6%

Summary

Methods

The calculated masses of CW2, protected LW2, deprotected LW2, and CEG were computationally determined as 1509.795, 3256.576, 1528.743, and 615.229, respectively, using ChemDraw 20.0 software. The preparation of linear peptide followed the standard solid-phase peptide synthesis method (SPPS) using 9-fluorenylmethoxycarbonyl (Fmoc) chemistry and 2-chlorotrityl resin as the solid support [19]. All Fmoc-protected amino acids, resin, piperidine, O-benzotriazole-N,N,N 0 ,N 0 -tetramethyluronium hexafluorophosphate (HBTU), 1-hydroxybenzotriazole hydrate (HOBt·H2 O), N,N-diisopropylethylamine (DIEA), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl), and. 2,2,2-trifluoroacetic acid (TFA) were purchased from Watanabe Chemical Industries, Ltd. Ferulic acid and other reagents were purchased from Wako Pure.

Results

Discussion

Conclusion