Prolonged exposure to sun radiation may lead to early onset of skin aging and development of skin cancer. Skin possesses inherent antioxidant protection, but, when these defenses are not properly balanced, reactive oxygen species have the potential to harm cellular structures. Therefore, it is essential to produce novel vanillin derivatives as promising lead candidates in the field of pharmaceutical research. This study aimed to synthesize vanillin derivatives, preparation of nanoemulsions and evaluate their Sun protection factor (SPF) response.
Vanillin derivatives (V-1 to V-5) were synthesized by condensing 4-(benzyloxy)-3-methoxybenzaldehyde (I) with substituted anilines in ethanol, using glacial acetic acid as a catalyst. The key intermediate, 4-(benzyloxy)-3-methoxybenzaldehyde (I), was obtained through the reaction of vanillin with benzyl bromide in the presence of anhydrous potassium carbonate in dimethylformamide (DMF). The structures of the newly synthesized derivatives were characterized using IR, ¹H NMR and ¹³C NMR spectroscopy. Various physicochemical and pharmacokinetic properties of the synthesized derivatives were computed to evaluate their potential as drug candidates. All synthesized compounds were docked with MMP1 and MMP2. Subsequently, nanoemulsion formulations NEV-1 to NEV-5 were prepared and characterized, followed by in vitro and in vivo SPF evaluations.
All the compounds satisfied the Lipinski's rule and might be candidates for biological study. All the-synthesized derivatives showed toxicity class classification 4. Toxicological prediction results showed that all the synthesized compounds were predicted to be nonhepatotoxic, nonmutagenic and noncytotoxic. The synthesized compounds V-5, V-4 and V-3 shown the strongest binding affinity with Matrix metalloproteinase-1 (MMP1) but V-3 and V-4 showed the strong binding affinities with Matrix metalloproteinase-2 (MMP2). Nanoemulsion prepared successfully and the maximum particle size 902 was obtained for NEV-2 but minimum 66.30 obtained for NEV-4. NEV-5 showed the highest PDI value 0.511. NEV-2 showed the highest zeta potential value 5.92. In vitro SPF study, it was found that NEV-4 and NEV-3 showed the highest SPF values 8.641 and 6.876 respectively. The in vivo SPF determination was done and it was found that NEV-4 and NEV-3 showed the highest SPF values 8.73 and 6.860 respectively. Based upon present findings, it was concluded that synthesized derivatives are new and significantly potent to have beneficial impact on skin to protect from sunburn and same may be used for cosmetic purpose.
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