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. 2020 Sep 23;10(58):35121-35130.
doi: 10.1039/d0ra07665a. eCollection 2020 Sep 21.

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

Ghaidaa Alkhayer  1 , Hussein Khudr  2 , Yahia Koudsi  1
Affiliations

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

Ghaidaa Alkhayer et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Chemical structure of Tia, asymmetric carbon labeled with *.
Fig. 2
Fig. 2. The ionotropic congealing method of sodium alginate used to prepare drug-loaded and unloaded metal complexes beads. G: is the α-l-guluronic acid blocks, M: is the multivalent ion metal which binds to G chains by a cross-linked network form with a proposed structure of “egg-box” model.
Fig. 3
Fig. 3. Metal content (mol/100 g) for blank beads (blue column), and metal content for loaded beads (red column).
Fig. 4
Fig. 4. IR spectra of ANa and Tia.
Fig. 5
Fig. 5. IR spectra of blank and loaded alginate divalent metal complexes.
Fig. 6
Fig. 6. IR spectra of blank and loaded alginate trivalent metal complexes.
Fig. 7
Fig. 7. IR spectra of physical mix of tiaprofenic acid with blank beads.
Fig. 8
Fig. 8. Typical chromatograms for the released enantiomers R and S of Tia from DivB and TrivB are obtained using chiral HPLC. From the top; AFeT, AAlT, AZnT and ACaT: the chromatograms relevant to loaded beads. Tia: a reference chromatogram of Tia. ACa, AZn, AAl and AFe are the chromatograms corresponding to blank beads.
Fig. 9
Fig. 9. ESR for DivB and TrivB monitored by chiral HPLC as R/S ratio.
Fig. 10
Fig. 10. ESR for simultaneously (A1T) and consecutively (A2T and A3T) congealed beads.
Fig. 11
Fig. 11. Release behavior of Tia enantiomers, (A) ACaT, (B) AZnT, (C) AAlT, (D) AFeT monitored by chiral HPLC.
See this image and copyright information in PMC

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