Chinese Journal of Chromatography ›› 2020, Vol. 38 ›› Issue (9): 1046-1056.DOI: 10.3724/SP.J.1123.2020.03018
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Received:
2020-03-18
Online:
2020-09-08
Published:
2020-12-11
Contact:
JIA Li
Supported by:
LI Zhenqun, JIA Li. Research progress of molecularly imprinted polymers in separation of chiral drugs by capillary electrochromatography[J]. Chinese Journal of Chromatography, 2020, 38(9): 1046-1056.
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URL: https://www.chrom-china.com/EN/10.3724/SP.J.1123.2020.03018
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
Rs: resolution; MAA: methacrylic acid; 2-VP: 2-vinylpyridine; EDMA: ethylene glycol dimethacrylate; AIBN: 2, 2′-azo-bis-isobutyronitrile. | ||||||
L-Phenylalanine | MAA | EDMA | AIBN | D/L-phenylalanine | 1.35 | [ |
D/L-tyrosine | 0.75 | |||||
D/L-phenylglycine | 0.98 | |||||
D/L-Dopa | 0.68 | |||||
L-Tryptophan | MAA | EDMA | AIBN | D/L-tryptophan | 0.94 | [ |
Dansyl-L-leucine | MAA | EDMA | AIBN | dansyl-D/L-leucine | 1.04 | [ |
Dansyl-L-leucine | MAA, 2-VP | EDMA | AIBN | dansyl-D/L-leucine | 1.20 | [ |
dansyl-D/L-phenylalanine | 0.56 | |||||
dansyl-D/L-glycine | 1.04 | |||||
dansyl-D/L-isoleucine | 0.98 | |||||
L-Phenylalanine anilide | MAA | EDMA | AIBN | D/L-phenylalanine anilide | 1.68 | [ |
Table 1 Application of molecularly imprinted polymers (MIPs) as stationary phases in packed capillary columns for chiral resolution by CEC
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
Rs: resolution; MAA: methacrylic acid; 2-VP: 2-vinylpyridine; EDMA: ethylene glycol dimethacrylate; AIBN: 2, 2′-azo-bis-isobutyronitrile. | ||||||
L-Phenylalanine | MAA | EDMA | AIBN | D/L-phenylalanine | 1.35 | [ |
D/L-tyrosine | 0.75 | |||||
D/L-phenylglycine | 0.98 | |||||
D/L-Dopa | 0.68 | |||||
L-Tryptophan | MAA | EDMA | AIBN | D/L-tryptophan | 0.94 | [ |
Dansyl-L-leucine | MAA | EDMA | AIBN | dansyl-D/L-leucine | 1.04 | [ |
Dansyl-L-leucine | MAA, 2-VP | EDMA | AIBN | dansyl-D/L-leucine | 1.20 | [ |
dansyl-D/L-phenylalanine | 0.56 | |||||
dansyl-D/L-glycine | 1.04 | |||||
dansyl-D/L-isoleucine | 0.98 | |||||
L-Phenylalanine anilide | MAA | EDMA | AIBN | D/L-phenylalanine anilide | 1.68 | [ |
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
4-SSA: 4-styrenesulfonic acid; MAM: 2-methacrylamidopropylmethacrylate; POSS: polyhedral oligomeric silsesquioxanes; DVB: divinylbenzene; γ-MPS: 3-(trimethoxysilyl)propyl methacrylate; -: no data. | ||||||
S-2-Phenylpropionic acid | trans-3-(3-pyridyl)-acrylic acid | DVB | azo-bis-cyclohexanecarbonitrile | R/S-2-phenylpropionic acid | - | [ |
S-Ketoprofen | MAA, 4-SSA | EDMA | AIBN | R/S-ketoprofen | 10.5 | [ |
S-Ofloxacin | MAA, 4-SSA | EDMA | AIBN | R/S-ofloxacin | 4.4 | [ |
S-Ibuprofen | MAA, 4-SSA | EDMA | AIBN | R/S-ibuprofen | 9.0 | [ |
S-Fenoprofen | MAA, 4-SSA | EDMA | AIBN | R/S-fenoprofen | 8.4 | [ |
S-Naproxen | MAA, 4-SSA | EDMA | AIBN | R/S-naproxen | 6.3 | [ |
S-Flurbiprofen | MAA, 4-SSA | EDMA | AIBN | R/S-flurbiprofen | 2.0 | [ |
S-3-(Benzyloxycarbonyl)-4-oxazolidine carboxylic acid | MAA, 4-SSA | EDMA | AIBN | R/S-3-(benzyloxycarbonyl)-4-oxazolidine carboxylic acid | 6.0 | [ |
S-Mandelic acid | MAA, 4-SSA | EDMA | AIBN | R/S-mandelic acid | 2.6 | [ |
S-N-(1-Phenyethyl)phthalamic acid | MAA, 4-SSA | EDMA | AIBN | R/S-N-(1-phenyethyl) phthalamic acid | 3.2 | [ |
S-O-Acetylmandelic acid | MAA, 4-SSA | EDMA | AIBN | R/S-O-acetylmandelic acid | 6.0 | [ |
S-Phenylsuccinic acid | MAA, 4-SSA | EDMA | AIBN | R/S-phenylsuccinic acid | 0.9 | [ |
S-2-Phenylpropionic acid | MAA, 4-SSA | EDMA | AIBN | R/S-2-phenylpropionic acid | 0.8 | [ |
R-Atenolol | MAA, 4-SSA | EDMA | AIBN | R/S-atenolol | 3.6 | [ |
S-Sulpiride | MAA, 4-SSA | EDMA | AIBN | R/S-sulpiride | 3.0 | [ |
S-(1-Naphthyl)-ethylamine | MAA, 4-SSA | EDMA | AIBN | R/S-(1-naphthyl)-ethylamine | 1.2 | [ |
4S, 5R-4-Methyl-5-phenyl-2-oxazolidinone | MAA, 4-SSA | EDMA | AIBN | 4S, 5R/4R, 5S-4-methyl-5-phenyl-2-oxazolidinone | 5.0 | [ |
S-Naproxen | MAM | MAM | AIBN | R/S-naproxen | 2.2 | [ |
S-Amlodipine | MAM | MAM | AIBN | R/S-amlodipine | 16.1 | [ |
S-Ketoprofen | MAM | MAM | AIBN | R/S-ketoprofen | 4.6 | [ |
S-Amlodipine | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-amlodipine | 10.4 | [ |
S-Naproxen | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-naproxen | 1.41 | [ |
S-Ofloxacin | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-ofloxacin | 1.55 | [ |
S-Amlodipine | methacryllsobutyl POSS, MAA | MAM | AIBN | R/S-amlodipine | 14.8 | [ |
D-Zopiclone | methacryllsobutyl POSS, MAA | MAM | AIBN | D/L-zopiclone | 2.49 | [ |
S-Naproxen | methacryllsobutyl POSS, MAA | MAM | AIBN | R/S-naproxen | 2.68 | [ |
S-Amlodipine | octavinyl-POSS, MAA | - | AIBN | R/S-amlodipine | 14.3 | [ |
S-Propranolol | MAA | γ-MPS | AIBN | R/S-propranolol | - | [ |
Z-L-Asp-OH | MAA, 4-VP | EDMA | AIBN | Z-D/L-Asp-OH | 0 | [ |
L-Tryptophan | dopamine | - | - | D/L-tryptophan | 1.65 | [ |
L-Tyrosine | dopamine | - | - | D/L-tyrosine | 1.76 | [ |
Gly-L-Phe | dopamine | - | - | Gly-D/L-Phe | 3.15 | [ |
S-Ofloxacin | dopamine | - | - | R/S-ofloxacin | 2.16 | [ |
R-Mandelic acid | norepinephrine | - | - | R/S-mandelic acid | 1.82 | [ |
L-Histidine | norepinephrine | D/L-histidine | 1.63 | [ |
Table 2 Application of MIPs as stationary phases in open-tubular columns for chiral resolution by CEC
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
4-SSA: 4-styrenesulfonic acid; MAM: 2-methacrylamidopropylmethacrylate; POSS: polyhedral oligomeric silsesquioxanes; DVB: divinylbenzene; γ-MPS: 3-(trimethoxysilyl)propyl methacrylate; -: no data. | ||||||
S-2-Phenylpropionic acid | trans-3-(3-pyridyl)-acrylic acid | DVB | azo-bis-cyclohexanecarbonitrile | R/S-2-phenylpropionic acid | - | [ |
S-Ketoprofen | MAA, 4-SSA | EDMA | AIBN | R/S-ketoprofen | 10.5 | [ |
S-Ofloxacin | MAA, 4-SSA | EDMA | AIBN | R/S-ofloxacin | 4.4 | [ |
S-Ibuprofen | MAA, 4-SSA | EDMA | AIBN | R/S-ibuprofen | 9.0 | [ |
S-Fenoprofen | MAA, 4-SSA | EDMA | AIBN | R/S-fenoprofen | 8.4 | [ |
S-Naproxen | MAA, 4-SSA | EDMA | AIBN | R/S-naproxen | 6.3 | [ |
S-Flurbiprofen | MAA, 4-SSA | EDMA | AIBN | R/S-flurbiprofen | 2.0 | [ |
S-3-(Benzyloxycarbonyl)-4-oxazolidine carboxylic acid | MAA, 4-SSA | EDMA | AIBN | R/S-3-(benzyloxycarbonyl)-4-oxazolidine carboxylic acid | 6.0 | [ |
S-Mandelic acid | MAA, 4-SSA | EDMA | AIBN | R/S-mandelic acid | 2.6 | [ |
S-N-(1-Phenyethyl)phthalamic acid | MAA, 4-SSA | EDMA | AIBN | R/S-N-(1-phenyethyl) phthalamic acid | 3.2 | [ |
S-O-Acetylmandelic acid | MAA, 4-SSA | EDMA | AIBN | R/S-O-acetylmandelic acid | 6.0 | [ |
S-Phenylsuccinic acid | MAA, 4-SSA | EDMA | AIBN | R/S-phenylsuccinic acid | 0.9 | [ |
S-2-Phenylpropionic acid | MAA, 4-SSA | EDMA | AIBN | R/S-2-phenylpropionic acid | 0.8 | [ |
R-Atenolol | MAA, 4-SSA | EDMA | AIBN | R/S-atenolol | 3.6 | [ |
S-Sulpiride | MAA, 4-SSA | EDMA | AIBN | R/S-sulpiride | 3.0 | [ |
S-(1-Naphthyl)-ethylamine | MAA, 4-SSA | EDMA | AIBN | R/S-(1-naphthyl)-ethylamine | 1.2 | [ |
4S, 5R-4-Methyl-5-phenyl-2-oxazolidinone | MAA, 4-SSA | EDMA | AIBN | 4S, 5R/4R, 5S-4-methyl-5-phenyl-2-oxazolidinone | 5.0 | [ |
S-Naproxen | MAM | MAM | AIBN | R/S-naproxen | 2.2 | [ |
S-Amlodipine | MAM | MAM | AIBN | R/S-amlodipine | 16.1 | [ |
S-Ketoprofen | MAM | MAM | AIBN | R/S-ketoprofen | 4.6 | [ |
S-Amlodipine | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-amlodipine | 10.4 | [ |
S-Naproxen | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-naproxen | 1.41 | [ |
S-Ofloxacin | 4-methylphenyl dicyclohexyl propylene, MAA | EDMA | AIBN | R/S-ofloxacin | 1.55 | [ |
S-Amlodipine | methacryllsobutyl POSS, MAA | MAM | AIBN | R/S-amlodipine | 14.8 | [ |
D-Zopiclone | methacryllsobutyl POSS, MAA | MAM | AIBN | D/L-zopiclone | 2.49 | [ |
S-Naproxen | methacryllsobutyl POSS, MAA | MAM | AIBN | R/S-naproxen | 2.68 | [ |
S-Amlodipine | octavinyl-POSS, MAA | - | AIBN | R/S-amlodipine | 14.3 | [ |
S-Propranolol | MAA | γ-MPS | AIBN | R/S-propranolol | - | [ |
Z-L-Asp-OH | MAA, 4-VP | EDMA | AIBN | Z-D/L-Asp-OH | 0 | [ |
L-Tryptophan | dopamine | - | - | D/L-tryptophan | 1.65 | [ |
L-Tyrosine | dopamine | - | - | D/L-tyrosine | 1.76 | [ |
Gly-L-Phe | dopamine | - | - | Gly-D/L-Phe | 3.15 | [ |
S-Ofloxacin | dopamine | - | - | R/S-ofloxacin | 2.16 | [ |
R-Mandelic acid | norepinephrine | - | - | R/S-mandelic acid | 1.82 | [ |
L-Histidine | norepinephrine | D/L-histidine | 1.63 | [ |
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
TRIM: trimethylolpropane trimethacrylate; L-PheAN: L-phenylalanine anilide; DAMA: 2-(dimethylamino)ethyl methacrylate; TFMAA: trifluoromethyl acrylic acid. | ||||||
S-Propranolol | MAA | TRIM | AIBN | R/S-propranolol | 1.26 | [ |
S-Metoprolol | MAA | TRIM | AIBN | R/S-metoprolol | 1.17 | [ |
S-Ropivacaine | MAA | TRIM | AIBN | R/S-ropivacaine | 1.10 | [ |
R/S-bupivacaine | - | [ | ||||
R/S-mepivacaine | - | [ | ||||
L-PheAN | MAA, 2-VP | EDMA | AIBN | D/L-phenylalanine | 1.22 | [ |
D/L-tyrosine | 0.86 | [ | ||||
D/L-phenylglycine | 0.73 | [ | ||||
D/L-tryptophan | 0 | [ | ||||
D/L-serine | 0 | [ | ||||
R-Binaphthol | MAA | EDMA | AIBN | R/S-binaphthol | 2.20 | [ |
S-Naproxen | MAA | EDMA | AIBN | R/S-naproxen | 1.73 | [ |
S-Ibuprofen | 4-VP | EDMA | AIBN | R/S-ibuprofen | 2.20 | [ |
5S, 11S-Tröger’s base | MAA | EDMA | AIBN | 5R, 11R/5S, 11S-Tröger’s base | 1.56 | [ |
L-Tetrahydropalmatine | MAA | EDMA | AIBN | D/L-tetrahydropalmatine | 1.43 | [ |
R-Binaphthol | DAMA | EDMA | AIBN | R/S-binaphthol | - | [ |
S-Naproxen | MAA | γ-MPS | AIBN | R/S-naproxen | 8.82 | [ |
S-Zolmitriptan | MAA | γ-MPS | AIBN | R/S-zolmitriptan | 4.26 | [ |
S-Zolmitriptan | TFMAA | γ-MPS | AIBN | R/S-zolmitriptan | 0.68 | [ |
S-Zolmitriptan | cinnamic acid | γ-MPS | AIBN | R/S-zolmitriptan | 1.83 | [ |
L-Tyrosine | MAA, 4-VP | EDMA | AIBN | D/L-tyrosine | - | [ |
D/L-tryptophan | - | [ | ||||
D/L-phenylalanine | - | [ | ||||
S-Ornidazole | MAA, 4-VP | EDMA | AIBN | R/S-ornidazole | - | [ |
R/S-secnidazole | - | [ | ||||
RR/SS/RS/SR-Ractopamine | Acrylamide, γ-MPS | - | AIBN | RR/SS/RS/SR-ractopamine | - | [ |
S-Norepinephrine | Itaconic acid | EDMA | AIBN | R/S-norepinephrine | - | [ |
R/S-epinephrine | - | [ | ||||
D-Zopiclone | MAA | EDMA | AIBN | D/L-zopiclone | 2.09 | [ |
Table 3 Application of MIPs as stationary phases in monolithic columns for chiral resolution by CEC
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
TRIM: trimethylolpropane trimethacrylate; L-PheAN: L-phenylalanine anilide; DAMA: 2-(dimethylamino)ethyl methacrylate; TFMAA: trifluoromethyl acrylic acid. | ||||||
S-Propranolol | MAA | TRIM | AIBN | R/S-propranolol | 1.26 | [ |
S-Metoprolol | MAA | TRIM | AIBN | R/S-metoprolol | 1.17 | [ |
S-Ropivacaine | MAA | TRIM | AIBN | R/S-ropivacaine | 1.10 | [ |
R/S-bupivacaine | - | [ | ||||
R/S-mepivacaine | - | [ | ||||
L-PheAN | MAA, 2-VP | EDMA | AIBN | D/L-phenylalanine | 1.22 | [ |
D/L-tyrosine | 0.86 | [ | ||||
D/L-phenylglycine | 0.73 | [ | ||||
D/L-tryptophan | 0 | [ | ||||
D/L-serine | 0 | [ | ||||
R-Binaphthol | MAA | EDMA | AIBN | R/S-binaphthol | 2.20 | [ |
S-Naproxen | MAA | EDMA | AIBN | R/S-naproxen | 1.73 | [ |
S-Ibuprofen | 4-VP | EDMA | AIBN | R/S-ibuprofen | 2.20 | [ |
5S, 11S-Tröger’s base | MAA | EDMA | AIBN | 5R, 11R/5S, 11S-Tröger’s base | 1.56 | [ |
L-Tetrahydropalmatine | MAA | EDMA | AIBN | D/L-tetrahydropalmatine | 1.43 | [ |
R-Binaphthol | DAMA | EDMA | AIBN | R/S-binaphthol | - | [ |
S-Naproxen | MAA | γ-MPS | AIBN | R/S-naproxen | 8.82 | [ |
S-Zolmitriptan | MAA | γ-MPS | AIBN | R/S-zolmitriptan | 4.26 | [ |
S-Zolmitriptan | TFMAA | γ-MPS | AIBN | R/S-zolmitriptan | 0.68 | [ |
S-Zolmitriptan | cinnamic acid | γ-MPS | AIBN | R/S-zolmitriptan | 1.83 | [ |
L-Tyrosine | MAA, 4-VP | EDMA | AIBN | D/L-tyrosine | - | [ |
D/L-tryptophan | - | [ | ||||
D/L-phenylalanine | - | [ | ||||
S-Ornidazole | MAA, 4-VP | EDMA | AIBN | R/S-ornidazole | - | [ |
R/S-secnidazole | - | [ | ||||
RR/SS/RS/SR-Ractopamine | Acrylamide, γ-MPS | - | AIBN | RR/SS/RS/SR-ractopamine | - | [ |
S-Norepinephrine | Itaconic acid | EDMA | AIBN | R/S-norepinephrine | - | [ |
R/S-epinephrine | - | [ | ||||
D-Zopiclone | MAA | EDMA | AIBN | D/L-zopiclone | 2.09 | [ |
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
BMA: butyl methacrylate; MPDE: 4-methyl phenyl dicyclohexyl ethylene; MBAA: N, N′-methylenebiacrylamide; APS: ammonium persulfate. | ||||||
S-Propranolol | N-acryloyl-alanine | EDMA | AIBN | R/S-propranolol | 1.48 | [ |
S-Propranolol | MAA | TRIM | AIBN | R/S-propranolol | - | [ |
S-Ofloxacin | MAA, BMA | EDMA | AIBN | R/S-ofloxacin | 1.53 | [ |
D-Zopiclone | MAA, MPDE | EDMA | AIBN | D/L-zopiclone | 3.29 | [ |
L-Tryptophan | acrylamide | MBAA | APS | D/L-tryptophan | 2.73 | [ |
Table 4 Application of MIPs as pseudo stationary phases for chiral resolution by CEC
Print molecule | Monomer | Crosslinker | Initiator | Analyte | Rs | Ref. |
BMA: butyl methacrylate; MPDE: 4-methyl phenyl dicyclohexyl ethylene; MBAA: N, N′-methylenebiacrylamide; APS: ammonium persulfate. | ||||||
S-Propranolol | N-acryloyl-alanine | EDMA | AIBN | R/S-propranolol | 1.48 | [ |
S-Propranolol | MAA | TRIM | AIBN | R/S-propranolol | - | [ |
S-Ofloxacin | MAA, BMA | EDMA | AIBN | R/S-ofloxacin | 1.53 | [ |
D-Zopiclone | MAA, MPDE | EDMA | AIBN | D/L-zopiclone | 3.29 | [ |
L-Tryptophan | acrylamide | MBAA | APS | D/L-tryptophan | 2.73 | [ |
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