Skip to main content
Erschienen in: Journal of Polymer Research 8/2021

01.08.2021 | ORIGINAL PAPER

Construction of β-cyclodextrin linked glycidyl methacrylate polymers for stereoselective separation of chiral drug

verfasst von: Apparav Wale, Khudbudin Mulani, Supriya Deshpande, C. R. Rajan, Surendra Ponrathnam

Erschienen in: Journal of Polymer Research | Ausgabe 8/2021

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

In this present study, a series of cross-linked porous polymers based on Glycidyl Methacrylate (GMA) were synthesized by suspension polymerization using cyclohexanol and hexanol as pore generating solvents. β-cyclodextrin (β-CD) was covalently bonded to the polymers by using Hexamethylene Diisocyanate (HMDI) and Sebacoyl Chloride (SC) as spacer arms. The effects of matrix properties such as pore volume, type of crosslinker, and spacer on the loading of β-cyclodextrin were investigated. The stereoselective binding of enantiomers of the anti-depressant drug citalopram was studied using β-cyclodextrin loaded polymers under batch adsorption mode. The capacity factor and selectivity of isomers were investigated also. This study reveals that these β-cyclodextrin bonded Glycidyl Methacrylate (GMA) polymers are potentially suitable for chromatographic separation of citalopram.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Ahuja S (1991) Chiral separations by chromatography, American Chemical Society, Washington D. C. Ch.1 Ahuja S (1991) Chiral separations by chromatography, American Chemical Society, Washington D. C. Ch.1
2.
Zurück zum Zitat Easson L, Stedman E (1933) Studies on the relationship between chemical constitution and physiological action. Biochem J 27(4):1257–1266CrossRef Easson L, Stedman E (1933) Studies on the relationship between chemical constitution and physiological action. Biochem J 27(4):1257–1266CrossRef
3.
Zurück zum Zitat Eliel E, Wilen S, Mander L (2003) Stereochemistry of organic compounds, Ch.7, pp 309 Eliel E, Wilen S, Mander L (2003) Stereochemistry of organic compounds, Ch.7, pp 309
4.
Zurück zum Zitat Cakmak R, Ercan S, Sunkur M, Yilmaz H (2017) Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies. Org Commun 10(3):216–227CrossRef Cakmak R, Ercan S, Sunkur M, Yilmaz H (2017) Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies. Org Commun 10(3):216–227CrossRef
5.
Zurück zum Zitat Okamoto Y, Hatada K, Kawashima M (1984) Chromatographic resolution. 7. Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel. J Am Chem Soc 106:185357–185359CrossRef Okamoto Y, Hatada K, Kawashima M (1984) Chromatographic resolution. 7. Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel. J Am Chem Soc 106:185357–185359CrossRef
6.
Zurück zum Zitat Lipkowitz KB, Green K, Yang J, Pearl G, Peterson MA (1993) Theoretical study of enantiodifferentiation in solid state cyclodextrins. Chirality 5:51CrossRef Lipkowitz KB, Green K, Yang J, Pearl G, Peterson MA (1993) Theoretical study of enantiodifferentiation in solid state cyclodextrins. Chirality 5:51CrossRef
7.
Zurück zum Zitat Rahim N, Tay K, Mohamad S (2016) β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers. J Incl Phenom Macrocycl Chem 85:303–315CrossRef Rahim N, Tay K, Mohamad S (2016) β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers. J Incl Phenom Macrocycl Chem 85:303–315CrossRef
8.
Zurück zum Zitat Xiao Y, Ng S, Tan T (2012) Recent development of cyclodextrin chiral stationary phases and their applications in chromatography. J Chromatogr A 1269 Xiao Y, Ng S, Tan T (2012) Recent development of cyclodextrin chiral stationary phases and their applications in chromatography. J Chromatogr A 1269
9.
Zurück zum Zitat Nawrocki J (1997) The silanol group and its role in liquid chromatography. J Chromatogr A 779:1–2CrossRef Nawrocki J (1997) The silanol group and its role in liquid chromatography. J Chromatogr A 779:1–2CrossRef
10.
Zurück zum Zitat Svec F, Hradil J, Coupek J, Kalal J (1975) Reactive polymers I. Macroporous methacrylate Copolymer containing epoxy groups. Die Angewante macromolecular Chemie 48:135 Svec F, Hradil J, Coupek J, Kalal J (1975) Reactive polymers I. Macroporous methacrylate Copolymer containing epoxy groups. Die Angewante macromolecular Chemie 48:135
11.
Zurück zum Zitat Liu D, Zhang T, Cheng Y, Jia Q (2014) Poly(glycidyl methacrylate-co-N-methylolacrylamide-co-ethylene dimethacrylate) monolith coupled to high-performance liquid chromatography for the determination of adenosine phosphates in royal jelly. J Sep Sci 37(14):1826CrossRef Liu D, Zhang T, Cheng Y, Jia Q (2014) Poly(glycidyl methacrylate-co-N-methylolacrylamide-co-ethylene dimethacrylate) monolith coupled to high-performance liquid chromatography for the determination of adenosine phosphates in royal jelly. J Sep Sci 37(14):1826CrossRef
12.
Zurück zum Zitat Tasfiyati A, Iftitah E, Sakti S, Sabarudin A (2016) Evaluation of glycidyl methacrylate-based monolith functionalized with weak anion exchange moiety inside 0.5 mm i.d. column for liquid chromatographic separation of DNA. Anal Chem Res 7:9–16CrossRef Tasfiyati A, Iftitah E, Sakti S, Sabarudin A (2016) Evaluation of glycidyl methacrylate-based monolith functionalized with weak anion exchange moiety inside 0.5 mm i.d. column for liquid chromatographic separation of DNA. Anal Chem Res 7:9–16CrossRef
13.
Zurück zum Zitat Aversa T, Silva C, Rocha P, Lucas E (2016) Influence of exchange group of modified glycidyl methacrylate polymer on phenol removal: A study by batch and continuous flow processes. J Environ Manage 182(1):301CrossRef Aversa T, Silva C, Rocha P, Lucas E (2016) Influence of exchange group of modified glycidyl methacrylate polymer on phenol removal: A study by batch and continuous flow processes. J Environ Manage 182(1):301CrossRef
14.
Zurück zum Zitat Muzammil E, Khan A, Stuparu M (2017) Post-polymerization modification reactions of poly(glycidyl methacrylate)s. RSC Adv 7:55874CrossRef Muzammil E, Khan A, Stuparu M (2017) Post-polymerization modification reactions of poly(glycidyl methacrylate)s. RSC Adv 7:55874CrossRef
15.
Zurück zum Zitat Rolland A, Hérault D, Touchard F, Saluzzo C, Duval R, Lemaire M (2001) Enantiopure poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate): a new material for supported catalytic asymmetric hydrogen transfer reduction. Tetrahedron: Asymmetry 12:811 Rolland A, Hérault D, Touchard F, Saluzzo C, Duval R, Lemaire M (2001) Enantiopure poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate): a new material for supported catalytic asymmetric hydrogen transfer reduction. Tetrahedron: Asymmetry 12:811
16.
Zurück zum Zitat Kimmins S, Wyman P, Cameron N (2014) Amine-functionalization of glycidyl methacrylate-containing emulsion-templated porous polymers and immobilization of proteinase K for biocatalysis. Polymer 55(1):416–425CrossRef Kimmins S, Wyman P, Cameron N (2014) Amine-functionalization of glycidyl methacrylate-containing emulsion-templated porous polymers and immobilization of proteinase K for biocatalysis. Polymer 55(1):416–425CrossRef
17.
Zurück zum Zitat Thudi L, Jasti L, Swarnalatha Y, Fadnavis N, Mulani K, Deokar S, Ponrathnam S (2012) Enzyme immobilization on epoxy supports in reverse micellar media: Prevention of enzyme denaturation. J Mol Catal B Enzym 74(1–2):54 Thudi L, Jasti L, Swarnalatha Y, Fadnavis N, Mulani K, Deokar S, Ponrathnam S (2012) Enzyme immobilization on epoxy supports in reverse micellar media: Prevention of enzyme denaturation. J Mol Catal B Enzym 74(1–2):54
18.
Zurück zum Zitat Radivoje P, Slobodan J, Zoran V (2001) Immobilization of invertase on a new type of macroporous glycidyl methacrylate. Biotechnol Lett 23:1171CrossRef Radivoje P, Slobodan J, Zoran V (2001) Immobilization of invertase on a new type of macroporous glycidyl methacrylate. Biotechnol Lett 23:1171CrossRef
19.
Zurück zum Zitat Alharthi S, Rassi Z (2020) Various Strategies in Post-Polymerization Functionalization of Organic Polymer-Based Monoliths Used in Liquid Phase Separation Techniques. Molecules 25(6):1323CrossRef Alharthi S, Rassi Z (2020) Various Strategies in Post-Polymerization Functionalization of Organic Polymer-Based Monoliths Used in Liquid Phase Separation Techniques. Molecules 25(6):1323CrossRef
20.
Zurück zum Zitat Jialiang G, Yuan X, Yuanjinh L, Jacques C, Zhengjin J (2016) Effect of the crosslinker type on the enantioseparation performance of β-cyclodextrin functionalized monoliths prepared by the one-pot approach. J Chromatgr A 1467:288–296CrossRef Jialiang G, Yuan X, Yuanjinh L, Jacques C, Zhengjin J (2016) Effect of the crosslinker type on the enantioseparation performance of β-cyclodextrin functionalized monoliths prepared by the one-pot approach. J Chromatgr A 1467:288–296CrossRef
21.
Zurück zum Zitat Wei Z, Bofeng W, Shoujiang L, Yueming W, Shaoyan W (2017) Preparation and Chromatographic Application of β-Cyclodextrin Molecularly Imprinted Microspheres for Paeoniflorin. Polymers 9(6):214CrossRef Wei Z, Bofeng W, Shoujiang L, Yueming W, Shaoyan W (2017) Preparation and Chromatographic Application of β-Cyclodextrin Molecularly Imprinted Microspheres for Paeoniflorin. Polymers 9(6):214CrossRef
22.
Zurück zum Zitat Montgomery SA, Loft H, Sanchez C, Reines EH, Papp M (2001) Escitalopram (S-Enantiomer of Citalopram): Clinical Efficacy and Onset of Action Predicted from a Rat Model. Pharmacol Toxicol 88:282–286CrossRef Montgomery SA, Loft H, Sanchez C, Reines EH, Papp M (2001) Escitalopram (S-Enantiomer of Citalopram): Clinical Efficacy and Onset of Action Predicted from a Rat Model. Pharmacol Toxicol 88:282–286CrossRef
23.
Zurück zum Zitat Dubois M, Gilles KA, Hamilton JK (1956) Colorimetric Method for Determination of Sugars and Related Substances. Anal Chem 28:350CrossRef Dubois M, Gilles KA, Hamilton JK (1956) Colorimetric Method for Determination of Sugars and Related Substances. Anal Chem 28:350CrossRef
24.
Zurück zum Zitat Okay O (2000) Macroporous copolymer networks. Prog Polym Sci 25:711–779CrossRef Okay O (2000) Macroporous copolymer networks. Prog Polym Sci 25:711–779CrossRef
25.
Zurück zum Zitat Qi T, Sonoda A, Makita Y, Kanoh H, Ooi K, Hirotsu T (2002) Porous properties of poly(glycidyl methacrylate-co-trimethylolpropane trimethacrylate) resins synthesized by suspension polymerization. J Appl Polym Sci 83:2374–2381CrossRef Qi T, Sonoda A, Makita Y, Kanoh H, Ooi K, Hirotsu T (2002) Porous properties of poly(glycidyl methacrylate-co-trimethylolpropane trimethacrylate) resins synthesized by suspension polymerization. J Appl Polym Sci 83:2374–2381CrossRef
26.
Zurück zum Zitat Brunauer S, Deming LS, Deming WS, Teller E (1940) Theory of the van der Waals Adsorption of Gases. J Am Chem Soc 62:1723–1732CrossRef Brunauer S, Deming LS, Deming WS, Teller E (1940) Theory of the van der Waals Adsorption of Gases. J Am Chem Soc 62:1723–1732CrossRef
27.
Zurück zum Zitat Hirotsu T (2006) Plasma graft polymerization of glycidyl methacrylate and cyclodextrin immobilization. Thin Solid Films 506:173CrossRef Hirotsu T (2006) Plasma graft polymerization of glycidyl methacrylate and cyclodextrin immobilization. Thin Solid Films 506:173CrossRef
28.
Zurück zum Zitat Kim M, Way JD, Baldwin M (2004) Effects of cross-linking and spacer groups on beta-cyclodextrin bonded liquid chromatographic separation. Korean J Chem Eng 21:465CrossRef Kim M, Way JD, Baldwin M (2004) Effects of cross-linking and spacer groups on beta-cyclodextrin bonded liquid chromatographic separation. Korean J Chem Eng 21:465CrossRef
29.
Zurück zum Zitat Muderawan WI, Ong T (2006) Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. J Sep Sci 29:1849CrossRef Muderawan WI, Ong T (2006) Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. J Sep Sci 29:1849CrossRef
30.
Zurück zum Zitat Lui Y, Fan X, Gao L (2003) Synthesis and Characterization of β-Cyclodextrin Based Functional Monomers and its Copolymers with N-isopropylacrylamide. Macromol Biosci 3:715CrossRef Lui Y, Fan X, Gao L (2003) Synthesis and Characterization of β-Cyclodextrin Based Functional Monomers and its Copolymers with N-isopropylacrylamide. Macromol Biosci 3:715CrossRef
31.
Zurück zum Zitat Ali SM, Maheshwari A, Fozdar BI (2007) 1H NMR spectroscopic study of complexation of citalopram with β-cyclodextrin in aqueous solution. Magn Reson Chem 45:253–256CrossRef Ali SM, Maheshwari A, Fozdar BI (2007) 1H NMR spectroscopic study of complexation of citalopram with β-cyclodextrin in aqueous solution. Magn Reson Chem 45:253–256CrossRef
32.
Zurück zum Zitat Kosel M, Eap CB, Amey M, Baumann P (1998) Analysis of the enantiomers of citalopram and its demethylated metabolites using chiral liquid chromatography. J Chromatogr B 719:234–238CrossRef Kosel M, Eap CB, Amey M, Baumann P (1998) Analysis of the enantiomers of citalopram and its demethylated metabolites using chiral liquid chromatography. J Chromatogr B 719:234–238CrossRef
33.
Zurück zum Zitat Lomberg LG, Wan H (2000) Determination of enantiomeric excess by capillary electrophoresis. Electrophoresis 21:1940–1962CrossRef Lomberg LG, Wan H (2000) Determination of enantiomeric excess by capillary electrophoresis. Electrophoresis 21:1940–1962CrossRef
34.
Zurück zum Zitat Liu M, Da S, Feng Y, Li L (2005) Study on the preparation method and performance of a new β-cyclodextrin bonded silica stationary phase for liquid chromatography. Anal Chim Acta 533:89CrossRef Liu M, Da S, Feng Y, Li L (2005) Study on the preparation method and performance of a new β-cyclodextrin bonded silica stationary phase for liquid chromatography. Anal Chim Acta 533:89CrossRef
Metadaten
Titel
Construction of β-cyclodextrin linked glycidyl methacrylate polymers for stereoselective separation of chiral drug
verfasst von
Apparav Wale
Khudbudin Mulani
Supriya Deshpande
C. R. Rajan
Surendra Ponrathnam
Publikationsdatum
01.08.2021
Verlag
Springer Netherlands
Erschienen in
Journal of Polymer Research / Ausgabe 8/2021
Print ISSN: 1022-9760
Elektronische ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-021-02634-7

Weitere Artikel der Ausgabe 8/2021

Journal of Polymer Research 8/2021 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.