Insights on Potential Photoprotective Activity of Two Butylchalcone Derivatives: Synthesis, Spectroscopic Characterization and Molecular Modeling

The development of photoprotective agents presents a growing interest due to skin disorders, e.g., cancer. In order to obtain natural-based compounds with potential photoprotective activity, we promote the synthesis and extensive characterization of a butylchalcone derivative (E)-3-(4-butylphenyl)-1...

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Published inPhotonics Vol. 10; no. 3; p. 228
Main Authors Aguiar, Antônio S. N., Dias, Pablo G. M., Queiroz, Jaqueline E., Firmino, Pollyana P., Custódio, Jean M. F., Dias, Lucas D., Aquino, Gilberto L. B., Camargo, Ademir J., Napolitano, Hamilton B.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.03.2023
Subjects
Absorption spectra
Antioxidants
butylchalcone
Chemical properties
Chemical synthesis
Comparative analysis
Crystals
Density functional theory
Density functionals
DFT
Electron transfer
Electron transitions
Electron transport
Free radicals
Molecular modelling
NMR
Nuclear magnetic resonance
Scavenging
Skin diseases
Software
Solvents
Sunscreen
supramolecular arrangement
X-ray diffraction
Germany
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Summary:The development of photoprotective agents presents a growing interest due to skin disorders, e.g., cancer. In order to obtain natural-based compounds with potential photoprotective activity, we promote the synthesis and extensive characterization of a butylchalcone derivative (E)-3-(4-butylphenyl)-1-(4-methylphenyl)-prop-2-en-1-one (BMP). Moreover, we carried out a comparative analysis of two chalcones bearing a methyl (BMP) and bromo (BBP) substituent groups (at para position), on respective electronic structures and supramolecular arrangement, using density functional theory (DFT). Through theoretical calculations carried out by DFT, it was possible to verify its antioxidant property by the mechanisms of free radical scavenging, H-atom transfer (HAT), and one-electron transfer (ET), and their stabilities. Finally, from the analysis of chalcone’s electronic transitions in the excited state calculated by the time-dependent (TD)-DFT method as well as UV-vis absorption spectra of the BMP and BBP (200–390 nm), it is possible to highlight their potential use as organic photoprotective agents.
ISSN:2304-6732
2304-6732
DOI:10.3390/photonics10030228