Recent advances in molecular imprinting technology for the separation and analysis of proteins

doi:10.3724/SP.J.1123.2019.06017

Abstract

Abstract:

Proteins, which have complex structures and fall under diverse categories, are closely associated with different kinds of life activities. Majority of the proteins exist in low concentrations in complex biological samples, because of which their direct analysis without sample pretreatment is difficult. Thus, selective separation of the target proteins from complex biological samples is essential for efficient analysis. Molecularly imprinted polymers, containing numerous imprinted cavities that are complementary with the templates in terms of shape, size, and functional groups, have great potential for use in the selective recognition and separation of the target proteins from complex biological samples. However, the large size, structural flexibility, and complex structures of proteins hinder their efficient separation and analysis by conventional molecular imprinting technology. In this review, several novel molecular imprinting techniques, including surface imprinting, epitope imprinting, and metal chelate imprinting, are introduced. The emergence of these novel technologies has contributed to advances in protein analysis. The applications of these molecular imprinting techniques to the separation and analysis of proteins in the last three years are summarized herein. Finally, the promising future of molecular imprinting techniques in the area of proteins is prospected.

Key words: molecular imprinting, proteins, separation and determination, review

SUN Xiaoyu, MA Runtian, SHI Yanping. Recent advances in molecular imprinting technology for the separation and analysis of proteins[J]. Chinese Journal of Chromatography, 2020, 38(1): 50-59.

Figures/Tables 7

References

1	Dinc M , Esen C , Mizaikoff B . TrAC-Trends Anal Chem, 2019, 114: 202
2	Huang S , Xu J , Zheng J , et al. Anal Bioanal Chem, 2018, 410 (17): 3991
3	Ben Aissa A , Herrera-Chacon A , Pupin R R , et al. Biosens Bioelectron, 2017, 88: 101
4	Shi W , Zhang S-Q , Li K-B , et al. Sep Purif Technol, 2018, 202: 165
5	Pan J , Chen W , Ma Y , et al. Chem Soc Rev, 2018, 47 (15): 5574
6	Xu J , Prost E , Haupt K , et al. Sensor Actuat B-Chem, 2018, 258: 10
7	Wang X , Yu J , Li J , et al. Sensor Actuat B-Chem, 2018, 255: 268
8	Zhang X , Yang S , Jiang R , et al. Sensor Actuat B-Chem, 2018, 254: 1078
9	Zhang Z , Li Y , Zhang X , et al. Nanoscale, 2019, 11 (11): 4854
10	Ma R T , Shi Y P . Chinese Journal of Chromatography, 2016, 34 (3): 223
10	马润恬, 师彦平. 色谱, 2016, 34 (3): 223
11	Peng S , Li H , Shi S Y . Chinese Journal of Chromatography, 2019, 37 (3): 293
11	彭胜, 李奂, 施树云. 色谱, 2019, 37 (3): 293
12	Ansari S , Masoum S . TrAC-Trends Anal Chem, 2019, 114: 29
13	Wang X , Yu S , Liu W , et al. ACS Sensors, 2018, 3 (2): 378
14	Hou H Q , Su L M , Huang Y Y , et al. Chinese Journal of Chromatography, 2016, 34 (12): 1206
14	侯会卿, 苏黎明, 黄嫣嫣, et al. 色谱, 2016, 34 (12): 1206
15	Chrzanowska A M , Poliwoda A , Wieczorek P P . J Chromatogr A, 2015, 1392: 1
16	Peng M , Xiang H , Hu X , et al. J Chromatogr A, 2016, 1474: 8
17	Sun Z A , Qi Y X , Wang X , et al. Chinese Journal of Chromatography, 2018, 36 (8): 176
17	孙治安, 祁玉霞, 王霞, et al. 色谱, 2018, 36 (8): 176
18	Zhang W , Han Y , Chen X , et al. Food Chem, 2017, 232: 145
19	Sonawane S L , Asha S K . J Polym Sci Pol Chem, 2017, 55 (9): 1558
20	Wang H , Liu Y , Yao S , et al. Food Chem, 2018, 240: 1262
21	Ning F , Qiu T , Wang Q , et al. Food Chem, 2017, 221: 1797
22	Qiu H T , Zheng N N , Fang Q H , et al. Chinese Journal of Chromatography, 2019, 37 (7): 692
22	邱昊田, 郑宁宁, 方权辉, et al. 色谱, 2019, 37 (7): 692
23	Wang S , Ye J , Bie Z , et al. Chem Sci, 2014, 5 (3): 1135
24	Fan H , Wang J , Meng Q , et al. Food Chem, 2019, 281: 1
25	Hua S , Zhao L , Cao L , et al. Chem Eng J, 2018, 345: 414
26	Huang W , Hou X , Tong Y , et al. RSC Adv, 2019, 9 (10): 5394
27	Bie Z , Chen Y , Ye J , et al. Angew Chem Int Edit, 2015, 54 (35): 10211
28	Zhao X-L , Li D-Y , He X-W , et al. J Mater Chem B, 2014, 2 (43): 7575
29	Li W , Sun Y , Yang C , et al. ACS Appl Mater Inter, 2015, 7 (49): 27188
30	Demirci B , Bereli N , Asliyuce S , et al. J Sep Sci, 2017, 40 (7): 1610
31	Xu W , Wang Y , Wei X , et al. Anal Chim Acta, 2019, 1048: 1
32	Zhang Z , Zhang X , Niu D , et al. J Mate Chem B, 2017, 5 (22): 4214
33	Zhou J , Wang Y , Ma Y , et al. Appl Surf Sci, 2019, 486: 265
34	Fan J-P , Yu J-X , Yang X-M , et al. Chem Eng J, 2018, 337: 722
35	Qin Y P , Wang H Y , He X W , et al. Talanta, 2018, 185: 620
36	Bakhshpour M , Tamahkar E , Andac M , et al. Colloid Surface B, 2017, 158: 453
37	Dolak I , Canpolat G , Ers?z A , et al. Sep Sci Technol, 2019 1
38	Li Y Y , Zhang X , Chen W J , et al. Chinese Journal of Chromatography, 2019, 37 (4): 392
38	李园园, 张鑫, 陈炜杰, et al. 色谱, 2019, 37 (4): 392
39	Lan F , Ma S , Ma J , et al. Mat Sci Eng C Mater, 2017, 70: 1076
40	Zhang Z , Wang H , Wang H , et al. Analyst, 2018, 143 (23): 5849
41	Xu K , Wang Y , Wei X , et al. Microchim Acta, 2018, 185 (2): 146
42	Xu X , Guo P , Luo Z , et al. RSC Adv, 2017, 7 (30): 18765
43	Xie X , Hu Q , Ke R , et al. Chem Eng J, 2019, 371: 130
44	Zhang Z , Li L . J Sep Sci, 2018, 41 (11): 2479
45	Wang Y , Yang C , Sun Y , et al. J Sep Sci, 2018, 41 (3): 765
46	Su Y , Qiu B , Chang C , et al. RSC Adv, 2018, 8 (11): 6192
47	Li Y , Chen Y , Huang L , et al. Analyst, 2017, 142 (2): 302
48	Wang H , Ying X , Liu J , et al. J Polym Res, 2017, 24 (6): 93
49	Boitard C , Rollet A L , Menager C , et al. Chem Commun, 2017, 53 (63): 8846
50	Shoghi E , Mirahmadi-Zare S Z , Ghasemi R , et al. Microchim Acta, 2018, 185 (4): 241
51	Qian L , Sun J , Hou C , et al. Talanta, 2017, 168: 174
52	Xu X , Liu R , Guo P , et al. Food Chem, 2018, 256: 91
53	Li Z , Guan P , Hu X , et al. Polymers, 2018, 10 (3): 298
54	Zhang X , Zhang N , Du C , et al. Chem Eng J, 2017, 317: 988
55	Bagán H , Zhou T , Eriksson N L , et al. RSC Adv, 2017, 7 (66): 41705
56	?imen D , Bereli N , Anda? M , et al. Sep Sci Plus, 2018, 1 (6): 454
57	Gong X , Tang B , Liu J J , et al. Biosens Bioelectron, 2017, 87: 858
58	Yang F , Deng D , Dong X , et al. J Chromatogr A, 2017, 1494: 18
59	Qin Y P , Jia C , He X W , et al. ACS Appl Mater Inter, 2018, 10 (10): 9060
60	Luo J , Huang J , Cong J , et al. ACS Appl Mater Inter, 2017, 9 (8): 7735
61	Bie Z , Xing R , He X , et al. Anal Chem, 2018, 90 (16): 9845
62	Xie J , Zhong G , Cai C , et al. Talanta, 2017, 169: 98
63	Zhu H , Yao H , Xia K , et al. Chem Eng J, 2018, 346: 317
64	Ma R-T , Ha W , Chen J , et al. J Mater Chem B, 2016, 4 (15): 2620
65	Sun X Y , Ma R T , Chen J , et al. Microchim Acta, 2018, 185 (12): 565
66	Li D , Tu T , Yang M , et al. Talanta, 2018, 184: 316
67	Wang P , Zhu H , Liu J , et al. Chem Eng J, 2019, 358: 143
68	Sun X-Y , Ma R-T , Chen J , et al. J Mater Chem B, 2018, 6 (4): 688
69	He P , Zhu H , Ma Y , et al. Chem Eng J, 2019, 367: 55
70	Sun X-Y , Ma R-T , Chen J , et al. Microchim Acta, 2017, 184 (10): 3729
71	Ma R-T , Sun X-Y , Ha W , et al. J Mater Chem B, 2017, 5 (36): 7512

Analyte	Supports	Preparation method	Q/(mg/g)	IF	Reference
Q: adsorption capacity; IF: imprinting factor; Cyt C: cytochrome C; Con A: concanavalin A; HSA: human serum albumin; PMMA: poly(methyl methacrylate); -: no supports was used; /: the information was missing from the original reference.
Lys	glass substrate	surface imprinting	30.00	3.00	[38]
	Fe₃O₄/PMMA	surface imprinting	120.50	4.11	[39]
	Fe₃O₄@SiO₂	surface imprinting	124.30	3.20	[40]
	Fe₃O₄@SiO₂	surface imprinting	108.00	2.56	[41]
	MWCNTs	surface imprinting	418.00	4.10	[42]
BHb	Fe₃O₄@VTEO	surface imprinting	164.20	4.93	[31]
	Fe₃O₄@SiO₂	surface imprinting	84.50	3.95	[43]
	SiO₂	surface imprinting	90.30	3.10	[44]
	SiO₂	surface imprinting	67.70	5.00	[45]
	Fe₃O₄@SiO₂	surface imprinting	169.29	/	[46]
	Fe₃O₄@Au	surface imprinting	89.12	3.42	[47]
BSA	calcium alginate	surface imprinting	5.50	3.60	[48]
	SiO₂ particles	surface imprinting	162.82	3.03	[32]
	γ-Fe₂O₃	surface imprinting	300.00	4.00	[49]
	Fe₃O₄@void	surface imprinting	130.19	2.79	[34]
	Fe₃O₄@SiO₂	surface imprinting	147.00	2.90	[50]
	Fe₃O₄@IL	surface imprinting	50.60	3.33	[51]
Bromelain	mesoporous carbon	surface imprinting	135.96	2.16	[52]
Cyt C	-	metal chelate imprinting	86.47	3.48	[53]
	Fe₃O₄@SiO₂	epitope imprinting and surface imprinting	67.60	4.54	[54]
	cellulose nanofibers	metal chelate imprinting	208.40	8.20	[36]
Hb	SiO₂	epitope imprinting	/	/	[55]
	-	metal chelate imprinting	4.91	1.57	[56]
Con A	MCNTs	metal chelate imprinting	45.05	4.50	[35]
PSA	polystyrene core particles	epitope imprinting and surface imprinting	0.18	2.01	[57]
ADP-ribosylated proteins	silica gels	epitope imprinting	1917.50	2.60	[58]
HSA	MNCTs	surface imprinting, epitope imprinting and metal chelate imprinting	103.67	2.57	[59]

Analyte	Supports	Preparation method	Q/(mg/g)	IF	Reference
Q: adsorption capacity; IF: imprinting factor; Cyt C: cytochrome C; Con A: concanavalin A; HSA: human serum albumin; PMMA: poly(methyl methacrylate); -: no supports was used; /: the information was missing from the original reference.
Lys	glass substrate	surface imprinting	30.00	3.00	[38]
	Fe₃O₄/PMMA	surface imprinting	120.50	4.11	[39]
	Fe₃O₄@SiO₂	surface imprinting	124.30	3.20	[40]
	Fe₃O₄@SiO₂	surface imprinting	108.00	2.56	[41]
	MWCNTs	surface imprinting	418.00	4.10	[42]
BHb	Fe₃O₄@VTEO	surface imprinting	164.20	4.93	[31]
	Fe₃O₄@SiO₂	surface imprinting	84.50	3.95	[43]
	SiO₂	surface imprinting	90.30	3.10	[44]
	SiO₂	surface imprinting	67.70	5.00	[45]
	Fe₃O₄@SiO₂	surface imprinting	169.29	/	[46]
	Fe₃O₄@Au	surface imprinting	89.12	3.42	[47]
BSA	calcium alginate	surface imprinting	5.50	3.60	[48]
	SiO₂ particles	surface imprinting	162.82	3.03	[32]
	γ-Fe₂O₃	surface imprinting	300.00	4.00	[49]
	Fe₃O₄@void	surface imprinting	130.19	2.79	[34]
	Fe₃O₄@SiO₂	surface imprinting	147.00	2.90	[50]
	Fe₃O₄@IL	surface imprinting	50.60	3.33	[51]
Bromelain	mesoporous carbon	surface imprinting	135.96	2.16	[52]
Cyt C	-	metal chelate imprinting	86.47	3.48	[53]
	Fe₃O₄@SiO₂	epitope imprinting and surface imprinting	67.60	4.54	[54]
	cellulose nanofibers	metal chelate imprinting	208.40	8.20	[36]
Hb	SiO₂	epitope imprinting	/	/	[55]
	-	metal chelate imprinting	4.91	1.57	[56]
Con A	MCNTs	metal chelate imprinting	45.05	4.50	[35]
PSA	polystyrene core particles	epitope imprinting and surface imprinting	0.18	2.01	[57]
ADP-ribosylated proteins	silica gels	epitope imprinting	1917.50	2.60	[58]
HSA	MNCTs	surface imprinting, epitope imprinting and metal chelate imprinting	103.67	2.57	[59]

Analyte	Supports	Preparation method	Q/(mg/g)	IF	Reference
AHSG: alpha-2-Heremans-Schmid glycoprotein; IgG: immunoglobulin G; PGMA: poly(glycidyl methacrylate); PSG: poly(styrene-glycidyl methacrylate).
Trf	Fe₃O₄-NH₂	surface imprinting	2.62	17.47	[66]
	MCNTs	surface imprinting, epitope imprinting and metal chelate imprinting	68.48	2.17	[59]
OVA	Fe₃O₄@PGMA	surface imprinting	190.70	7.51	[63]
	GO	surface imprinting	278.00	9.5	[60]
	Fe₃O₄@VTEO	surface imprinting	81.20	2.28	[62]
	PSG NPs	metal chelate imprinting	138.92	4.44	[67]
	Fe₃O₄-NH₂	surface imprinting	/	3.86	[68]
	SiO₂	surface imprinting and metal chelate imprinting	243.40	4.82	[69]
Protein C	-	metal chelate imprinting	30.40	1.72	[30]
AHSG	Fe₃O₄@SiO₂	epitope imprinting	/	10.7	[61]
HRP	Fe₃O₄@SiO₂	epitope imprinting	/	10.7	[61]
	Fe₃O₄@SiO₂	surface imprinting	62.00	3.78	[70]
	Fe₃O₄@Au	surface imprinting	/	/	[64]
	Fe₃O₄-NH₂	surface imprinting	34.09	2.74	[68]
	Fe₃O₄@pTiO₂	surface imprinting	67.70	3.51	[65]
IgG	Fe₃O₄@Au	surface imprinting	33.2	/	[71]

Analyte	Supports	Preparation method	Q/(mg/g)	IF	Reference
AHSG: alpha-2-Heremans-Schmid glycoprotein; IgG: immunoglobulin G; PGMA: poly(glycidyl methacrylate); PSG: poly(styrene-glycidyl methacrylate).
Trf	Fe₃O₄-NH₂	surface imprinting	2.62	17.47	[66]
	MCNTs	surface imprinting, epitope imprinting and metal chelate imprinting	68.48	2.17	[59]
OVA	Fe₃O₄@PGMA	surface imprinting	190.70	7.51	[63]
	GO	surface imprinting	278.00	9.5	[60]
	Fe₃O₄@VTEO	surface imprinting	81.20	2.28	[62]
	PSG NPs	metal chelate imprinting	138.92	4.44	[67]
	Fe₃O₄-NH₂	surface imprinting	/	3.86	[68]
	SiO₂	surface imprinting and metal chelate imprinting	243.40	4.82	[69]
Protein C	-	metal chelate imprinting	30.40	1.72	[30]
AHSG	Fe₃O₄@SiO₂	epitope imprinting	/	10.7	[61]
HRP	Fe₃O₄@SiO₂	epitope imprinting	/	10.7	[61]
	Fe₃O₄@SiO₂	surface imprinting	62.00	3.78	[70]
	Fe₃O₄@Au	surface imprinting	/	/	[64]
	Fe₃O₄-NH₂	surface imprinting	34.09	2.74	[68]
	Fe₃O₄@pTiO₂	surface imprinting	67.70	3.51	[65]
IgG	Fe₃O₄@Au	surface imprinting	33.2	/	[71]

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