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Simultaneous Enantioseparation and Rapid Determination of Atenolol and Amlodipine Besylate by Capillary Electrochromatography

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Abstract

Simultaneous enantioseparation and rapid determination method of atenolol (AN) and amlodipine besylate (AMB) was firstly established using diphenylmethane diisocyanate-β-CD-modified COF (MDI-β-CD-modified COF) as chiral solid phases (CSP) by capillary electrochromatography (CEC). The optimal separation conditions were explored and the concentration of the acetate buffer solution was 20 mmol/L, pH = 5.0, operating voltage 20 kV, column temperature 20 °C, and then the four enantiomers of AN and AMB were baseline separated less than 5 min. The method validation was assessed by applying standard addition technique. The results showed that the concentration of each enantiomer exhibited a good linear relationship with the chromatographic peak area (r2 > 0.9918); the limit of detection (LOD) was 0.55–0.98 mg/L; the limit of quantification (LQD) was 1.83–3.27 mg/L; the average recoveries were in the range of 95.4–103.0%; the relative standard deviation (RSD) was less than 3.8%. The method established is rapid, simple, sensitive, accurate and reliable, and it can be used for routine analysis and quality control of the two chiral drugs separately or in combinations.

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References

  1. Hassen HY, Ndejjo R, Musinguzi G, Van Geertruyden JP, Abrams S, Bastiaens H (2021) Effectiveness of community-based cardiovascular disease prevention interventions to improve physical activity: a systematic review and meta-regression. Prev Med. https://doi.org/10.1016/j.ypmed.2021.106797

    Article  PubMed  Google Scholar 

  2. Nesrine TL (2015) Simultaneous determination of binary mixture of amlodipine besylate and atenolol based on dual wavelengths. Spectrochim Acta Part A Mol Biomol Spectrosc 149:201–207

    Article  Google Scholar 

  3. Paradkar SG, Sinha SR (2018) Drug utilization among hypertensive patients in the outpatient department of medicine in a tertiary care hospital: a cross-sectional study. Clin Exp Hypertens 40:150–154

    Article  Google Scholar 

  4. Pandya PA, Shah PA, Shrivastav PS (2021) Application of supercritical fluid chromatography for separation and quantitation of 15 co-formulated binary anti-hypertensive medications using a single elution protocol. Biomed Chromatogr. https://doi.org/10.1002/bmc.5035

    Article  PubMed  Google Scholar 

  5. Sahoo SK, Pathni AK, Krishna A, Moran AE, Cohn J, Bhatia S, Maheshwari N, Sharma B (2021) Research letter: antihypertensive drugs market in India: an insight on size, trends, and prescribing preferences in the private health sector 2016–2018. Glob Heart. https://doi.org/10.5334/gh.999

    Article  PubMed  PubMed Central  Google Scholar 

  6. Vishnuvardhan C, Radhakrishnanand P, Navalgund SG, Atcha KR, Satheeshkumar N (2014) RP-HPLC method for the simultaneous estimation of eight cardiovascular drugs. Chromatographia 77:265–275

    Article  CAS  Google Scholar 

  7. Walid ME, Ehab FE, Asmaa AE, Ramzia IE, Gabor P (2014) Synchronized separation of seven medications representing most commonly prescribed antihypertensive classes by using reversed-phase liquid chromatography: application for analysis in their combined formulations. J Sep Sci 37:748–757

    Article  Google Scholar 

  8. Nesrine TL (2015) Spectrophotometric methods for simultaneous determination of amlodipine besylate and atenolol in their tablet dosage form. Spectrosc Spectral Anal 35:3538–3543

    Google Scholar 

  9. Spanakis M, Niopas I (2013) Determination of atenolol in human plasma by HPLC with fluorescence detection: validation and application in a pharmacokinetic study. J Chromatogr Sci 51:128–132

    Article  CAS  Google Scholar 

  10. Arrowsmith JE, Campbell SF, Cross PE, Stubbs JK, Burges RA, Gardiner DG, Blackburn KG (1986) Long-acting dihydropyridine calcium antagonists. 1. 2-alkoxymethyl derivatives incorporating basic substituents. J Med Chem 29:1696–1702

    Article  CAS  Google Scholar 

  11. Zhang XP, Loke KE, Mital S, Chahwala S, Hintze TH (2002) Paradoxical release of nitric oxide by an L-type calcium channel antagonist, the R(+) enantiomer of amlodipine. J Cardiovasc Pharmacol 39:208–214

    Article  CAS  Google Scholar 

  12. U.S. Food and drug administration; Guidance document: development of new stereoisomeric drugs; (1992); https://www.fda.gov/regulatory-information/search-fda-guidance-documents/development-new-stereoisomeric-drugs

  13. Chen JQ, Du YX, Zhu FX, Chen B, Zhang Q, Du SJ, Li P (2015) Study of the enantioseparation capability of chiral dual system based on chondroitin sulfate C in CE. Electrophoresis 36:607–614

    Article  CAS  Google Scholar 

  14. Deeb ES (2010) Evaluation of a vancomycin-based LC column in enantiomeric separation of atenolol: method development, repeatability study and enantiomeric impurity determination. Chromatographia 71:783–787

    Article  Google Scholar 

  15. Li JX, Liu RX, Wang LY, Liu XL, Gao HJ (2019) Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism. Chirality 31:236–247

    Article  CAS  Google Scholar 

  16. George N, Herz M, Aboul-Enein HY, Shihata L, Hanafi R (2019) Surface design of enantiomeric HPLC separation on vancomycin and teicoplanin based stationary phases, a tool for chiral recognition of model β-blockers. J Chromatogr Sci 57:485–494

    Article  CAS  Google Scholar 

  17. Deng SY, Pan JM, Wang M, Huang YK, Xia ZN (2020) Study on improvement of chiral separation of capillary electrophoresis based on cyclodextrin by deep eutectic solvents. Talanta. https://doi.org/10.1016/j.talanta.2020.121419

    Article  PubMed  PubMed Central  Google Scholar 

  18. Xu H, Feng ZJ, Du YX (2020) Synthesis, application and molecular modeling study of ionic liquid functionalized lactobionic acid, 3-methyl-1-(3-sulfopropyl)-1H-imidazol-3-ium lactobionate, as a chiral selector in capillary electrophoresis. Analyst 145:1025–1032

    Article  CAS  Google Scholar 

  19. Ren SR, Zhang Q, Xue S, Liu SY, Rui MJ (2020) Use of gamithromycin as a chiral selector in capillary electrophoresis. J Chromatogr A. https://doi.org/10.1016/j.chroma.2020

    Article  PubMed  Google Scholar 

  20. Wei ZH, Wu X, Zhang B, Li R, Huang YP, Liu ZS (2011) Coatings of one monomer molecularly imprinted polymers for open tubular capillary electrochromatography. J Chromatogr A 1218:6498–6504

    Article  CAS  Google Scholar 

  21. Auditore R, Santagati NA, Aturki Z, Fanali S (2013) Enantiomeric separation of amlodipine and its two chiral impurities by nano-liquid chromatography and capillary electrochromatography using a chiral stationary phase based on cellulose tris(4-chloro-3-methylphenylcarbamate). Electrophoresis 34:2593–2600

    Article  CAS  Google Scholar 

  22. Dalgliesh CE (1952) The optical resolution of aromatic amino-acids on paper chromatogrums. J Chem Soc 137:3940–3942

    Article  Google Scholar 

  23. Rezanka P, Navratilova K, Rezanka M, Kral V, Sykora D (2014) Application of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 35:2701–2721

    Article  CAS  Google Scholar 

  24. Jin X, Kang Q, Wang Y (2017) Enantioseparation of flavanoids, isoxazolines, dansyl amino acids and beta-blockers on native and phenylcarbamoylated alpha, beta and gamma-cyclodextrin chiral stationary phases. ChemistrySelect 2:9992–9998

    Article  CAS  Google Scholar 

  25. Li YJ, Tang YM, Qin SL, Li X, Dai Q, Gao LD (2019) Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography. Chirality 31:283–292

    Article  CAS  Google Scholar 

  26. Kapnissi-Christodoulou CP, Nicolaou AG, Stavrou IJ (2016) Enantioseparations in open-tubular capillary electrochromatography: recent advances and applications. J Chromatogr A 1467:145–154

    Article  CAS  Google Scholar 

  27. Fang LL, Wang P, Wen XL, Guo X, Luo LD, Yu J, Guo XJ (2017) Layer-by-layer self-assembly of gold nanoparticles/thiols β-cyclodextrin coating as the stationary phase for enhanced chiral differentiation in open tubular capillary electrochromatography. Talanta 167:158–165

    Article  CAS  Google Scholar 

  28. Li YJ, Lin XT, Qin SL, Gao LD, Tang YM, Liu SR, Wang YY (2020) β-Cyclodextrin-modified covalent organic framework as chiral stationary phase for the separation of amino acids and β-blockers by capillary electrochromatography. Chirality 32:1008–1019

    Article  CAS  Google Scholar 

  29. Bhattacharjee S, Khan MI, Li XF, Zhu QL, Wu XT (2018) Recent progress in asymmetric catalysis and chromatographic separation by chiral metal-organic frameworks. Catalysis. https://doi.org/10.3390/catal8030120

    Article  Google Scholar 

  30. Zhang Y, Jin XN, Ma XF, Wang Y (2021) Chiral porous organic frameworks and their application in enantioseparation. Anal Methods 13:8–33

    Article  CAS  Google Scholar 

  31. Yuan C, Wu XW, Gao R, Han X, Liu Y, Long YT, Cui Y (2019) Nanochannels of covalent organic frameworks for chiral selective transmembrane transport of amino acids. J Am Chem Soc 141:20187–20197

    Article  CAS  Google Scholar 

  32. Kandambeth S, Mallick A, Lukose B, Mane MV, Heine T, Banerjee R (2012) Construction of crystalline 2D covalent organic frameworks with remarkable chemical (acid/base) stability via a combined reversible and irreversible route. J Am Chem Soc 134:19524–19527

    Article  CAS  Google Scholar 

  33. Qian HL, Yang CX, Yan XP (2016) Bottom-up synthesis of chiral covalent organic frameworks and their bound capillaries for chiral separation. Nat Commun 7:12104–12110

    Article  CAS  Google Scholar 

  34. Diyymann MM, Rozing GP (1997) Capillary electrochromatography: investigation of the influence of mobile phase and stationary phase properties on electroosmotic velocity, retention, and selectivity. J Microcolumn Sep 9:399–408

    Article  Google Scholar 

  35. International Conference Harmonisation Q2(R1) Validation of Analytical Procedures: Text and Methodology, 62, US FDA Federal Register, Geneva, Switzerland (2005)

  36. Kannappan V, Mannemala SS (2016) Simultaneous enantioseparation and purity determination of chiral switches of amlodipine and atenolol by liquid chromatography. J Pharm Biomed Anal 120:221–227

    Article  CAS  Google Scholar 

Download references

Funding

The present work was partially supported by Young Creative Program of the Fundamental Research Funds in Heilongjiang Provincial Universities (2020), Grant/Award Number: No. 135509206.

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Correspondence to Shili Qin.

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Gao, L., Xing, Z., Zhang, S. et al. Simultaneous Enantioseparation and Rapid Determination of Atenolol and Amlodipine Besylate by Capillary Electrochromatography. Chromatographia 85, 373–382 (2022). https://doi.org/10.1007/s10337-022-04141-3

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