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. 2025 Apr 8;10(15):14884-14907.
doi: 10.1021/acsomega.4c10102. eCollection 2025 Apr 22.

Quantum Chemical Calculations, Topological Properties, ADME/Molecular Docking Studies, and Hirshfeld Surface Analysis on Some Organic UV-Filters

Feride Akman  1   2 , Buşra Kutlu  1
Affiliations

Quantum Chemical Calculations, Topological Properties, ADME/Molecular Docking Studies, and Hirshfeld Surface Analysis on Some Organic UV-Filters

Feride Akman et al. ACS Omega. .

Abstract

This study aimed to find a theoretical solution to the problem of photochemical instability of organic UV filters by changing the solvent environments. For this purpose, the four most important organic filters containing UV-sensitive groups, such as oxybenzone, avobenzone, octinoxate, and padimate O, were first selected, and the theoretically optimized geometries were determined by the density functional theory (DFT) method using the B3LYP/6-31G(d,p) basis set. Frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) analyses were conducted to reveal differences in the reactivities of the molecules. The oscillator strengths, absorption wavelengths, and excitation energies in gas, water, ethanol, and n-hexane phases were determined with the help of the conductor-like polarizable continuum model (CPCM) and time-dependent density functional theory (TD-DFT) to study the effect of solvents on chemical parameters. In light of the obtained data, Natural localized molecular orbital (NLMO), atoms in molecules (AIM), and natural bond orbital (NBO) analyses were done to determine the stability and UV filtering capacity of the molecules. Additionally, topological and Fukui investigations were included. Molecular docking, ADME (absorption, delivery, metabolism, and excretion) properties, and Hirshfeld surface analysis were conducted. Finally, with the help of the theoretical data obtained, the results in different solvent environments are interpreted and compared with each other.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Optimized molecular structure of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 2
Figure 2
FMO diagram of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 3
Figure 3
Theoretical UV–vis spectra of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d) in gas and water, ethanol, and n-hexane as solvents.
Figure 4
Figure 4
AIM analysis of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 5
Figure 5
MEP surfaces of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 6
Figure 6
RDG (right)-NCI(left) analysis of avobenzone in various solvents: gas (a), water (b), ethanol (c), and n-hexane (d).
Figure 7
Figure 7
ELF projection maps filled with color for oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 8
Figure 8
Molecular docking (best docked post) of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate (d) with the retinoic acid-related orphan receptor γ(t) (RORγ(t)).
Figure 9
Figure 9
H-bond interaction surfaces (left) and 2D receptor–ligand interaction diagram (right) of oxybenzone (a), avobenzone (b), octinoxate (c), and padimate (d) with the retinoic acid-related orphan receptor γ(t) (RORγ(t)).
Figure 10
Figure 10
Bioavailability radar (left) and BOILED-Egg (right) for oxybenzone (a), avobenzone (b), octinoxate (c), and padimate O (d).
Figure 11
Figure 11
Crystal packing diagram of oxybenzone (a) and avobenzone (b).
Figure 12
Figure 12
3D Hirsfeld surface of oxybenzone (a) and avobenzone (b) as the dnorm, di, de, shape index, and curvedness index, respectively.
Figure 13
Figure 13
Fingerprint plots (hirshfeld surface plotted on the shape index and quantitative noncovalent interactions) for oxybenzone (a) and avobenzone (b).
See this image and copyright information in PMC

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