Nonaqueous Capillary Electrophoretic Separation of Analogs of (24R)-1,24-Dihydroxyvitamin D3 Derivative as Predicted by Quantum Chemical Calculations

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 13; p. 5055
• Main Authors: Grodner, Błażej, Żołek, Teresa, Kutner, Andrzej
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 28.06.2023; MDPI
• Subjects: Analogs; Blood vessels; Cancer; Capillary electrophoresis; Cytokines; Density functional theory; Dipoles; Electric fields; Electrophoresis; Electrostatic properties; Impurities; Laboratory animals; Methods; Molecular orbitals; nonaqueous capillary electrophoresis; Polarizability; PRI-2201; PRI-2203; PRI-2204; Prostate; Separation; Solvents; Steroids; Vitamin D; Vitamin D3; vitamin D3 derivatives of calcipotriol
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28135055

Nonaqueous capillary electrophoretic (NACE) separation was obtained of analogs of (24R)-1,24-dihydroxyvitamin D3 derivative (calcipotriol) as predicted by quantum chemical calculations supported by the density functional theory (DFT). Among the key electronic properties investigated, absolute values of the dipole polarizability and energy gap between HOMO and LUMO molecular orbitals of the analog molecules differ significantly for particular analogs, and there is a direct relationship with their electrophoretic migration time. These differences and relationships suggest that the structurally related analogs should be separable in the electrostatic field. Indeed, the robust, sensitive, and rapid NACE method was first developed for the identification and determination of the anticancer analog of calcipotriol (coded PRI-2205) and its process-related impurities (coded PRI-2201, PRI-2203, and PRI-2204) in organic and aqueous biological solutions. The direct relation between the calculated electronic properties of the analogs and the experimental electrophoretic migration time could be a promising prospect for theoretically predicting the electrophoretic separations.