Improved Enantioselectivity for Atenolol Employing Pivot Based Molecular Imprinting

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Aug 1

PMID 30060464

Citations 10

Authors

Andreea Elena Bodoki

Bogdan-Cezar Iacob

Laura Elena Gliga

Simona Luminita Oprean

David A Spivak

Nicholas A Gariano

Ede Bodoki

Affiliations

Soon will be listed here.

Abstract

In the last few decades, molecular imprinting technology went through a spectacular evolution becoming a well-established tool for the synthesis of highly selective biomimetic molecular recognition platforms. Nevertheless, there is still room for advancement in the molecular imprinting of highly polar chiral compounds. The aim of the present work was to investigate the favorable kosmotropic effect of a ternary complex involving a polar chiral template (eutomer of atenolol) and a functional monomer, bridged by a central metal ion through well-defined, spatially directional coordinate bonds. The efficiency of the chiral molecular recognition was systematically assessed on polymers obtained both by non-covalent and metal-mediated molecular imprinting. The influence on the chromatographic retention and enantioselectivity of different experimental variables (functional monomers, cross-linkers, chaotropic agents, metal ions, porogenic systems, etc.) were studied on both slurry packed and monolithic HPLC columns. Deliberate changes in the imprinting and rebinding (chromatographic) processes, along with additional thermodynamic studies shed light on the particularities of the molecular recognition mechanism. The best performing polymer in terms of enantioselectivity (α = 1.60) was achieved using 4-vinyl pyridine as functional monomer and secondary ligand for the Co(II)-mediated imprinting of S-atenolol in the presence of EDMA as cross-linker in a porogenic mixture of [BMIM][BF₄]:DMF:DMSO = 10:1:5, //.

Citing Articles

Unlocking New Avenues: Solid-State Synthesis of Molecularly Imprinted Polymers.

Iacob B, Bodoki A, Da Costa Carvalho D, Serpa Paulino A, Barbu-Tudoran L, Bodoki E Int J Mol Sci. 2024; 25(10).

PMID: 38791542 PMC: 11122393. DOI: 10.3390/ijms25105504.

Advances in Molecular Imprinting Technology for the Extraction and Detection of Quercetin in Plants.

Ye K, Xu S, Zhou Q, Wang S, Xu Z, Liu Z Polymers (Basel). 2023; 15(9).

PMID: 37177253 PMC: 10180927. DOI: 10.3390/polym15092107.

Ruxolitinib-Loaded Imprinted Polymeric Drug Reservoir for the Local Management of Post-Surgical Residual Glioblastoma Cells.

Baraian A, Iacob B, Soritau O, Tomuta I, Tefas L, Barbu-Tudoran L Polymers (Basel). 2023; 15(4).

PMID: 36850247 PMC: 9962605. DOI: 10.3390/polym15040965.

Highly selective electrochemical sensing based on electropolymerized ion imprinted polyaniline (IIPANI) on a bismuth modified carbon paste electrode (CPE-Bi) for monitoring Nickel(ii) in river water.

Setiyanto H, Purwaningsih D, Saraswaty V, Mufti N, Zulfikar M RSC Adv. 2022; 12(45):29554-29561.

PMID: 36320738 PMC: 9574646. DOI: 10.1039/d2ra05196f.

Recent molecularly imprinted polymers applications in bioanalysis.

Suzaei F, Daryanavard S, Abdel-Rehim A, Bassyouni F, Abdel-Rehim M Chem Zvesti. 2022; 77(2):619-655.

PMID: 36213319 PMC: 9524737. DOI: 10.1007/s11696-022-02488-3.

References

Lee W, Cheng C, Pan H, Chung T, Hwang C . Chromatographic characterization of molecularly imprinted polymers. Anal Bioanal Chem. 2008; 390(4):1101-9. DOI: 10.1007/s00216-007-1765-2. View

Weng X, Bao Z, Xing H, Zhang Z, Yang Q, Su B . Synthesis and characterization of cellulose 3,5-dimethylphenylcarbamate silica hybrid spheres for enantioseparation of chiral β-blockers. J Chromatogr A. 2013; 1321:38-47. DOI: 10.1016/j.chroma.2013.10.048. View

Denderz N, Lehotay J . Application of the van't Hoff dependences in the characterization of molecularly imprinted polymers for some phenolic acids. J Chromatogr A. 2012; 1268:44-52. DOI: 10.1016/j.chroma.2012.10.025. View

Bakkour R, Bolotin J, Sellergren B, Hofstetter T . Molecularly Imprinted Polymers for Compound-Specific Isotope Analysis of Polar Organic Micropollutants in Aquatic Environments. Anal Chem. 2018; 90(12):7292-7301. DOI: 10.1021/acs.analchem.8b00493. View

Zhao L, Ban L, Zhang Q, Huang Y, Liu Z . Preparation and characterization of imprinted monolith with metal ion as pivot. J Chromatogr A. 2011; 1218(50):9071-9. DOI: 10.1016/j.chroma.2011.10.027. View

Younes A, Ates H, Mangelings D, Vander Heyden Y . A separation strategy combining three HPLC modes and polysaccharide-based chiral stationary phases. J Pharm Biomed Anal. 2013; 75:74-85. DOI: 10.1016/j.jpba.2012.11.019. View

Greaves T, Drummond C . Solvent nanostructure, the solvophobic effect and amphiphile self-assembly in ionic liquids. Chem Soc Rev. 2012; 42(3):1096-120. DOI: 10.1039/c2cs35339c. View

Cheong W, Ali F, Choi J, Lee J, Yune Sung K . Recent applications of molecular imprinted polymers for enantio-selective recognition. Talanta. 2013; 106:45-59. DOI: 10.1016/j.talanta.2012.11.049. View

Wang C, Li X, Yang J, Zhao Y, Liu Z, Aisa H . Preparation of ionic liquid-mediated imprinted monolith for selective capture and purification of corilagin. J Chromatogr B Analyt Technol Biomed Life Sci. 2016; 1041-1042:98-103. DOI: 10.1016/j.jchromb.2016.12.023. View

10.

Yang S, Wang Y, Jiang Y, Li S, Liu W . Molecularly Imprinted Polymers for the Identification and Separation of Chiral Drugs and Biomolecules. Polymers (Basel). 2019; 8(6). PMC: 6432457. DOI: 10.3390/polym8060216. View

11.

Meng A, Lejeune J, Spivak D . Multi-analyte imprinting capability of OMNiMIPs versus traditional molecularly imprinted polymers. J Mol Recognit. 2009; 22(2):121-8. DOI: 10.1002/jmr.901. View

12.

Iacob B, Bodoki E, Florea A, Bodoki A, Oprean R . Simultaneous enantiospecific recognition of several β-blocker enantiomers using molecularly imprinted polymer-based electrochemical sensor. Anal Chem. 2015; 87(5):2755-63. DOI: 10.1021/ac504036m. View

13.

Wang Q, Hosoya K, Svec F, Frechet J . Polymeric porogens used in the preparation of novel monodispersed macroporous polymeric separation media for high-performance liquid chromatography. Anal Chem. 1992; 64(11):1232-8. DOI: 10.1021/ac00035a008. View

14.

Pan J, Chen W, Ma Y, Pan G . Molecularly imprinted polymers as receptor mimics for selective cell recognition. Chem Soc Rev. 2018; 47(15):5574-5587. DOI: 10.1039/c7cs00854f. View

15.

Iacob B, Bodoki E, Oprean R . Recent advances in capillary electrochromatography using molecularly imprinted polymers. Electrophoresis. 2014; 35(19):2722-32. DOI: 10.1002/elps.201400253. View

16.

Zhao Q, Zhou J, Zhang L, Huang Y, Liu Z . Coatings of molecularly imprinted polymers based on polyhedral oligomeric silsesquioxane for open tubular capillary electrochromatography. Talanta. 2016; 152:277-82. DOI: 10.1016/j.talanta.2016.02.019. View

17.

Ali M, Dutta P, Pandey S . Effect of ionic liquid on prototropic and solvatochromic behavior of fluorescein. J Phys Chem B. 2010; 114(46):15042-51. DOI: 10.1021/jp106601a. View

18.

Bai L, Chen X, Huang Y, Zhang Q, Liu Z . Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot. Anal Bioanal Chem. 2013; 405(27):8935-43. DOI: 10.1007/s00216-013-7304-4. View

19.

Zhong D, Huang Y, Xin X, Liu Z, Aisa H . Preparation of metallic pivot-based imprinted monolith for polar template. J Chromatogr B Analyt Technol Biomed Life Sci. 2013; 934:109-16. DOI: 10.1016/j.jchromb.2013.07.006. View

20.

Denderz N, Lehotay J, cizmarik J, Cibulkova Z, Simon P . Thermodynamic study of molecularly imprinted polymer used as the stationary phase in high performance liquid chromatography. J Chromatogr A. 2012; 1235:77-83. DOI: 10.1016/j.chroma.2012.02.051. View