Novel esters derived from 4-hydroxychalcones as potential sunscreens with antimicrobial action

Abstract

Ten novel 4-esterchalcones, licochalcone analogues, were strategically synthesized to study the effect of electro-donating or electro-withdrawing substituents in the aryl enone moiety on their pharmacological and photoprotective properties. 4-Esterchalcones had their drug-like character evaluated, which demonstrated positive characteristics for the development of novel drug candidates. In the in vitro antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of Staphylococcus aureus, Candida albicans and C. tropicalis with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL⁻¹, and the isobutyryl 4-esterchalcone 5d (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL⁻¹. In the UV-Vis study, λ_max were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high ε_max values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on Artemia salina.

Graphical Abstract

Keywords:

• Chalcones
• drug research
• UV/Vis spectroscopy
• photochemistry
• Artemia salina

Additional information

Funding

This work was supported by the [Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)] under Grant [number 403134/2021-8]; and [Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)]. Fellowships from CNPq (M.F.R.S., L.V.C., E.O.L. and P.F.A.F.) and CAPES (A.P.S. and H.D.S.S.) are also acknowledged.