| Full text | |
| Author(s): |
Total Authors: 3
|
| Affiliation: | [1] Sao Paulo State Univ, Sch Sci, Dept Chem, BR-17033360 Sao Paulo - Brazil
[2] Univ Estadual Campinas, Inst Chem, Dept Phys Chem, Campinas, SP - Brazil
Total Affiliations: 2
|
| Document type: | Journal article |
| Source: | CHIRALITY; v. 30, n. 9, p. 1049-1053, SEP 2018. |
| Web of Science Citations: | 0 |
| Abstract | |
The electronic circular dichroism (ECD) spectra of naproxen enantiomers were studied as a function of solvents using experimental (circular dichroism) and theoretical (time-dependent density functional theory) approaches. The (R)- and (S)-naproxen enantiomers presented an unusual inversion in their ECD signals in the presence of ethanol and water when compared with polar aprotic solvents such as acetonitrile. From a practical point of view, these findings deserve great attention because these solvents are widely used for high-performance liquid chromatography analysis in quality control of chiral pharmaceutical drugs. This is particularly relevant to naproxen because the (S)-naproxen has anti-inflammatory properties, whereas (R)-naproxen is hepatotoxic. A time-dependent density functional theory computer simulation was conducted to investigate the signal inversion using the solvation model based on density, a reparameterization of polarized continuum model. Electronic circular dichroism signals of conformers were calculated by computer simulation and their contribution to the combined spectra obtained according to Boltzmann weighting. It was found that the experimentally observed ECD signal inversion can be associated with the minor or major contribution of different conformers of naproxen. (AU) | |
| FAPESP's process: | 14/50926-0 - INCT 2014: biodiversity and natural products |
| Grantee: | Vanderlan da Silva Bolzani |
| Support Opportunities: | BIOTA-FAPESP Program - Thematic Grants |
| FAPESP's process: | 15/22338-9 - Study of the interaction between drugs and human serum albumin (HSA) based on computer simulation, DFT and TDDFT, experiments of electronic circular dichroism, ECD, and determination of the bond formation constant |
| Grantee: | Aguinaldo Robinson de Souza |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 16/20549-5 - Development and application of fluorescent probes and probes based on circular dichroism for the interaction studies of ligands with protein, characterization of amyloid proteins and determination of enzymatic activity |
| Grantee: | Valdecir Farias Ximenes |
| Support Opportunities: | Regular Research Grants |