Enantioselective Study on the Biodegradation of Verapamil and Cytalopram by Chiral Capillary Electrophoresis

Abstract

Many of the currently available drugs are chiral compounds that are marketed as racemates or, to a lesser extent, in the form of one of the enantiomers since a pair of enantiomers may have different toxicological and ecotoxicological properties compared to each other. The evaluation of enantioselectivity in biodegradation processes is essential for environmental risk assessment. The objective of this research is to study the enantioselectivity in the biodegradation of two common chiral drugs, citalopram and verapamil, using highly sulphated-γ-cyclodextrin (HS-γ-CD) as chiral selector in Capillary Electrophoresis. Biodegradation experiments were performed in batch mode using a minimal salt medium inoculated with an activated sludge and supplemented with the corresponding enantiomeric mixture. The cultures were incubated at 20 °C for 28 days. Abiotic degradation of verapamil and citalopram enantiomers was also assessed. The concentration of the enantiomers of verapamil and citalopram were monitored using 0.7% and 0.1% m/v HS-γ-CD solutions as chiral selector, respectively. Separations were carried out using the complete filling technique. The results of biodegradability tests indicate that citalopram could be considered potentially persistent while verapamil is presumed to be a non-persistent compound. No evidence of enantioselectivity was observed in any of the biodegradation processes.

Recent Advances in Separation and Analysis of Chiral Compounds

“…Sulfated-β-CD (S-β-CD) and sulfobuthylether-β-CD sodium (SBE-β-CD) were used in chiral CE separation of racemic bioactive ferrocene-modified azoles and chiral fluoroquinolones, respectively. , Ionic liquid modified SBE-β-CD was also prepared to give a superior CE enantio-separation for racemic drugs to original SBE-β-CD . Sulfated-γ-CD (HS-γ-CD) was employed as CE chiral selector to investigate the enantioselective biodegradation of citalopram and verapamil . A series of positively charged N -heterocyclic CD derivatives were prepared for enantio-separation of 22 ionic model analytes.…”

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

“…2.4 | Immobilization of propargylated reduced N-nornoscapine on azidefunctionalized silica via Huisgen reaction (9) Azide-functionalized silica (3.3 g) was dissolved in methanol (45 ml). Then sodium ascorbate (0.66 g) and CuSO 4 .5H 2 O (0.33 g) were dissolved in water (6 ml) and added to the reaction mixture.…”

“…2,3 However, it is noteworthy that the development of a chiral pharmaceutical ingredient in a racemic form can be more affordable for the pharmaceutical industry. 4 Resolution of enantiomers is achievable using different techniques such as crystallization, [5][6][7] capillary electrophoresis (CE), [8][9][10] and chromatography. 11,12 Although some may prefer non-chromatographic techniques in chiral separation, sometimes using chromatographic methods is inevitable in large-scale purification.…”

Development of a Chiral Capillary Electrophoresis Method for the Enantioseparation of Verapamil Using Cyclodextrins as Chiral Selectors and Experimental Design Optimization

“…The stereoselective biodegradation of VER and citalopram (a chiral selective serotonin reuptake inhibitor) was studied by Martin-Biosca et al using CE and highly sulphatedγ-cyclodextrin (HS-γ-CD) as CS. The biodegradability results showed that VER is not considered to be a persistent compound in the environment; in the biodegradation process, there was no evidence of enantioselectivity [17]. VER was used as a model chiral substance in testing amino acid chiral ionic liquids as dual CS systems with hydroxypropyl-β-CD (HPβ-CD) [18], stereoselectivity interactions between human serum albumin (HAS) [19], or a new on-capillary sample enrichment technique which leads to a sensitivity improvement in CE [20].…”