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Spectroscopic and chromatographic investigation of chiral interactions between tiaprofenic acid and alginate-metal-complexes.

ABSTRACT: Alginate-metal-complexes of Ca, Ba, Zn, Fe and Al were prepared in the form of beads. The preparation was based on the ionotropic method to obtain blank beads (unloaded) and beads loaded with tiaprofenic acid. IR spectra of blank beads, drug loaded beads and physical mixtures of the drug with the blank beads were recorded. The comparison of these spectra, especially in the region of hydroxyl group, implied chiral interactions between the drug and the complexes. Additionally, the drug was released from the loaded beads in aqueous phosphate buffer solutions (PBS) at pH = 7.4. Chiral HPLC was used to determine the enantiomeric excess, % ee, of the released drug. The determined % ee values indicated chiral interactions between tiaprofenic acid and alginate-metal-complexes. However, various mathematical models were used to simulate the release kinetics for each enantiomer. The metal content of Na, Ca, Ba, Zn, Fe and Al in the studied materials was measured using atomic absorption spectroscopy.

SUBMITTER: Alkhayer G

PROVIDER: S-EPMC9056893 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Spectroscopic and chromatographic investigation of chiral interactions between tiaprofenic acid and alginate-metal-complexes.

Alkhayer Ghaidaa G Khudr Hussein H Koudsi Yahia Y

RSC advances 20200923 58

Alginate-metal-complexes of Ca, Ba, Zn, Fe and Al were prepared in the form of beads. The preparation was based on the ionotropic method to obtain blank beads (unloaded) and beads loaded with tiaprofenic acid. IR spectra of blank beads, drug loaded beads and physical mixtures of the drug with the blank beads were recorded. The comparison of these spectra, especially in the region of hydroxyl group, implied chiral interactions between the drug and the complexes. Additionally, the drug was release ...[more]

PMID: 35515692

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Project description:Six-coordinate MnIII complexes are typically high-spin (S = 2), however, the scorpionate ligand, both in its traditional, hydridotris(pyrazolyl)borate form, Tp- and Tp*- (the latter with 3,5-dimethylpyrazole substituents) and in an aryltris(carbene)borate (i.e., N-heterocyclic carbene, NHC) form, [Ph(MeIm)3B]-, (MeIm = 3-methylimidazole) lead to formation of bis(scorpionate) complexes of MnIII with spin triplet ground states; three of which were investigated herein: [Tp2Mn]SbF6 (1SBF6), [Tp*2Mn]SbF6 (2SBF6), and [{Ph(MeIm)3B}2Mn]CF3SO3 (3CF3SO3). These trigonally symmetric complexes were studied experimentally by magnetic circular dichroism (MCD) spectroscopy (the propensity of 3 to oxidize to MnIV precluded collection of useful MCD data) including variable temperatures and fields (VTVH-MCD) and computationally by ab initio CASSCF/NEVPT2 methods. These combined experimental and theoretical techniques establish the 3A2g electronic ground state for the three complexes, and provide information on the energy of the "conventional" high-spin excited state (5Eg) and other, triplet excited states. These results show the electronic effect of pyrazole ring substituents in comparing 1 and 2. The tunability of the scorpionate ligand, even by perhaps the simplest change (from pyrazole in 1 to 3,5-dimethylpyrazole in 2) is quantitatively manifested through perturbations in ligand-field excited-state energies that impact ground-state zero-field splittings. The comparison with the NHC donor is much more dramatic. In 3, the stronger σ-donor properties of the NHC lead to a quantitatively different electronic structure, so that the lowest lying spin triplet excited state, 3Eg, is much closer in energy to the ground state than in 1 or 2. The zero-field splitting (zfs) parameters of the three complexes were calculated and in the case of 1 and 2 compare closely to experiment (lower by < 10%, < 2 cm-1 in absolute terms); for 3 the large magnitude zfs is reproduced, although there is ambiguity about its sign. The comprehensive picture obtained for these bis(scorpionate) MnIII complexes provides quantitative insight into the role played by the scorpionate ligand in stabilizing unusual electronic structures.

Dataset Information

Spectroscopic and chromatographic investigation of chiral interactions between tiaprofenic acid and alginate-metal-complexes.

Publications

Spectroscopic and chromatographic investigation of chiral interactions between tiaprofenic acid and alginate-metal-complexes.

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