Abstract
A novel imidazolium-embedded N,N-dimethylaminopropyl-functionalized silica-based stationary phase (Sil-ImCl) was prepared and further used for hydrophilic interaction/reversed-phase mixed-mode chromatography. The Sil-ImCl stationary phase was respectively characterized by Fourier transform infrared spectrometry, thermogravimetric analysis, and element analysis. A variety of hydrophilic or hydrophobic compounds were used to evaluate the retention mechanisms of the developed stationary phase, and the effects of buffer salt concentration and pH of mobile phase on the retention of these compounds were also investigated. The developed stationary phase was successfully applied for separation of nucleosides and nucleic acid bases, water-soluble vitamins, phenols, and positional isomers. Moreover, simultaneous separation of polar and nonpolar compounds was also achieved with high resolution, outperforming the commercially available C8 column and amino column. Furthermore, the Sil-ImCl stationary phase has been successfully applied for separation of secondary metabolites of Hansfordia sinuosae. All these results demonstrate that the Sil-ImCl stationary phase might be promising for separation of complex polar and nonpolar compounds with high efficiency, especially in biological industry.
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Wang S, Guo Q, Wang L, Lin L, Shi H, Cao H, Cao B (2015) Detection of honey adulteration with starch syrup by high performance liquid chromatography. Food Chem 172:669–674
Ilisz I, Grecsó N, Fülöp F, Lindner W, Péter A (2015) High-performance liquid chromatographic enantioseparation of cationic 1,2,3,4-tetrahydroisoquinoline analogs on Cinchona alkaloid-based zwitterionic chiral stationary phases. Anal Bioanal Chem 407(3):961–972
Shaaban H, Górecki T (2015) Current trends in green liquid chromatography for the analysis of pharmaceutically active compounds in the environmental water compartments. Talanta 132:739–752
Yin W, Cheng L, Chai H, Guo R, Liu R, Chu C, Palasota JA, Cai X (2015) Silica-based 2-(N, N-dimethylamino)-1,3-propanediol hydrophilic interaction liquid chromatography stationary phase for separating cephalosporins and carbapenems. Anal Bioanal Chem 407(20):6217–6220
Grimm SH, Höfner G, Wanner KT (2015) Development and validation of an LC-ESI-MS/MS method for the triple reuptake inhibitor indatraline enabling its quantification in MS binding assays. Anal Bioanal Chem 407(2):471–485
Wu L, Takatsu A, Park SR, Yang B, Yang H, Kinumi T, Wang J, Bi J, Wang Y (2015) Development and co-validation of porcine insulin certified reference material by high-performance liquid chromatography-isotope dilution mass spectrometry. Anal Bioanal Chem 407(11):3125–3135
Ji S, Zhang F, Wu S, Yang B, Liang X (2014) Facile preparation of polyvinyl alcohol coated SiO2 stationary phases for high performance liquid chromatography. Analyst 139(21):5594–5599
Yang Y, Geng X (2011) Mixed-mode chromatography and its applications to biopolymers. J Chromatogr A 1218(49):8813–8825
Gargano AF, Leek T, Lindner W, Lämmerhofer M (2013) Mixed-mode chromatography with zwitterionic phosphopeptidomimetic selectors from Ugi multicomponent reaction. J Chromatogr A 1317:12–21
Hu K, Feng S, Wu M, Wang S, Zhao W, Jiang Q, Yu A, Zhang S (2014) Development of a V-shape bis(tetraoxacalix[2]arene[2]triazine) stationary phase for high performance liquid chromatography. Talanta 130:63–70
Sun M, Qiu H, Wang L, Liu X, Jiang S (2009) Poly(1-allylimidazole)-grafted silica, a new specific stationary phase for reversed-phase and anion-exchange liquid chromatography. J Chromatogr A 1216(18):3904–3909
Sun M, Feng J, Luo C, Liu X, Jiang S (2013) Benzimidazole modified silica as a novel reversed-phase and anion-exchange mixed-mode stationary phase for HPLC. Talanta 105:135–141
Sun M, Feng J, Liu S, Xiong C, Liu X, Jiang S (2011) Dipyridine modified silica--a novel multi-interaction stationary phase for high performance liquid chromatography. J Chromatogr A 1218(24):3743–3749
Zimmermann A, Greco R, Walker I, Horak J, Cavazzini A, Lämmerhofer M (2014) Synthetic oligonucleotide separations by mixed-mode reversed-phase/weak anion-exchange liquid chromatography. J Chromatogr A 1354:43–55
Yang F, Bai Q, Zhao K, Gao D, Tian L (2015) Preparation of a novel weak cation exchange/hydrophobic interaction chromatography dual-function polymer-based stationary phase for protein separation using “thiol-ene click chemistry”. Anal Bioanal Chem 407(6):1721–1734
Shen G, Zhang F, Yang B, Chu C, Liang X (2013) A novel amide stationary phase for hydrophilic interaction liquid chromatography and ion chromatography. Talanta 115:129–132
Qiao L, Wang S, Li H, Shan Y, Dou A, Shi X, Xu G (2014) A novel surface-confined glucaminium-based ionic liquid stationary phase for hydrophilic interaction/anion-exchange mixed-mode chromatography. J Chromatogr A 1360:240–247
Liu Y, Du Q, Yang B, Zhang F, Chu C, Liang X (2012) Silica based click amino stationary phase for ion chromatography and hydrophilic interaction liquid chromatography. Analyst 137(7):1624–1628
Shen A, Li X, Dong X, Wei J, Guo Z, Liang X (2013) Glutathione-based zwitterionic stationary phase for hydrophilic interaction/cation-exchange mixed-mode chromatography. J Chromatogr A 1314:63–69
Sun M, Feng J, Luo C, Liu X, Jiang S (2014) Quinolinium ionic liquid-modified silica as a novel stationary phase for high-performance liquid chromatography. Anal Bioanal Chem 406(11):2651–2658
Qiu H, Mallik AK, Takafuji M, Jiang S, Ihara H (2012) New poly(ionic liquid)-grafted silica multi-mode stationary phase for anion-exchange/reversed-phase/hydrophilic interaction liquid chromatography. Analyst 137(11):2553–2555
Li Y, Yang J, Jin J, Sun X, Wang L, Chen J (2014) New reversed-phase/anion-exchange/hydrophilic interaction mixed-mode stationary phase based on dendritic polymer-modified porous silica. J Chromatogr A 1337:133–139
Lu J, Zhang W, Zhang Y, Zhao W, Hu K, Yu A, Liu P, Wu Y, Zhang S (2014) A new stationary phase for high performance liquid chromatography: calix[4]arene derivatized chitosan bonded silica gel. J Chromatogr A 1350:61–67
Qiu H, Zhang M, Gu T, Takafuji M, Ihara H (2013) A sulfonic-azobenzene-grafted silica amphiphilic material: a versatile stationary phase for mixed-mode chromatography. Chem Eur J 19(52):18004–18010
Iverson CD, Lucy CA (2014) Aniline-modified porous graphitic carbon for hydrophilic interaction and attenuated reverse phase liquid chromatography. J Chromatogr A 1373:17–24
Aral T, Aral H, Ziyadanoğulları B, Ziyadanoğulları R (2015) Synthesis of a mixed-model stationary phase derived from glutamine for HPLC separation of structurally different biologically active compounds: HILIC and reversed-phase applications. Talanta 131:64–73
Cheng XD, Peng XT, Yu QW, Yuan BF, Feng YQ (2013) Preparation and chromatographic evaluation of a novel phosphate ester-bonded stationary phase with complexation and hydrophobic interactions retention mechanism. J Chromatogr A 1302:81–87
Ohyama K, Inoue Y, Kishikawa N, Kuroda N (2014) Preparation and characterization of surfactin-modified silica stationary phase for reversed-phase and hydrophilic interaction liquid chromatography. J Chromatogr A 1371:257–260
Voicu V, Sârbu C, Tache F, Micăle F, Rădulescu ŞF, Sakurada K, Ohta H, Medvedovici A (2014) Lipophilicity indices derived from the liquid chromatographic behavior observed under bimodal retention conditions (reversed phase/hydrophilic interaction): application to a representative set of pyridinium oximes. Talanta 122:172–179
Li Y, Feng Y, Chen T, Zhang H (2011) Imidazoline type stationary phase for hydrophilic interaction chromatography and reversed-phase liquid chromatography. J Chromatogr A 1218(35):5987–5994
Qiao X, Zhang L, Zhang N, Wang X, Qin X, Yan H, Liu H (2015) Imidazolium embedded C8 based stationary phase for simultaneous reversed-phase/hydrophilic interaction mixed-mode chromatography. J Chromatogr A 1400:107–116
Qiao L, Dou A, Shi X, Li H, Shan Y, Lu X, Xu G (2013) Development and evaluation of new imidazolium-based zwitterionic stationary phases for hydrophilic interaction chromatography. J Chromatogr A 1286:137–145
Jovanović M, Stojanović BJ (2013) Thorough investigation of the retention mechanisms and retention behavior of amides and sulfonamides on amino column in hydrophilic interaction liquid chromatography. J Chromatogr A 1301:27–37
Shen A, Guo Z, Yu L, Cao L, Liang X (2011) A novel zwitterionic HILIC stationary phase based on “thiol-ene” click chemistry between cysteine and vinyl silica. Chem Commun 47(15):4550–4552
Buszewski B, Noga S (2012) Hydrophilic interaction liquid chromatography (HILIC)--a powerful separation technique. Anal Bioanal Chem 402(1):231–247
Liang T, Fu Q, Shen A, Wang H, Jin Y, Xin H, Ke Y, Guo Z, Liang X (2015) Preparation and chromatographic evaluation of a newly designed steviol glycoside modified-silica stationary phase in hydrophilic interaction liquid chromatography and reversed phase liquid chromatography. J Chromatogr A 1388:110–118
Qiu H, Wanigasekara E, Zhang Y, Tran T, Armstrong DW (2011) Development and evaluation of new zwitterionic hydrophilic interaction liquid chromatography stationary phases based on 3-P, P-diphenylphosphonium-propylsulfonate. J Chromatogr A 1218(44):8075–8082
Shen A, Guo Z, Cai X, Xue X, Liang X (2012) Preparation and chromatographic evaluation of a cysteine-bonded zwitterionic hydrophilic interaction liquid chromatography stationary phase. J Chromatogr A 1228:175–182
Sheng Q, Su X, Li X, Ke Y, Liang X (2014) A dextran-bonded stationary phase for saccharide separation. J Chromatogr A 1345:57–67
Qiao X, Wang R, Li G, Yan H, Zhou Y, Zhang L, Zhang Y (2014) Imidazolium-based iodoacetamide functional tags: design, synthesis, and property study for cysteinyl-peptide analysis by mass spectrometry. Analyst 139(4):705–708
Liu S, Qiao X, Yang Y, Yan H (2014) Novel imidazolium-embedded amine stationary phase: preparation and its performance for hydrophilic interaction chromatography. Chin J Chromatogr 32(10):1079–1083
Wu Z, Liu D, Proksch P, Guo P, Lin W (2014) Punctaporonins H-M: caryophyllene-type sesquiterpenoids from the sponge-associated fungus Hansfordia sinuosae. Mar Drugs 12(7):3904–3916
Acknowledgments
We are grateful for the financial support from National Natural Science Foundation of China (21205027), Natural Science Foundation of Hebei Province (B2015201016), the Young Talent Program in College and University of Hebei Province (BJ2014005), and Natural Science Foundation of Hebei University (2011–225).
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The authors have declared that no conflict of interest exists.
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Liu, S., Xu, H., Yu, J. et al. Novel imidazolium-embedded N,N-dimethylaminopropyl-functionalized silica-based stationary phase for hydrophilic interaction/reversed-phase mixed-mode chromatography. Anal Bioanal Chem 407, 8989–8997 (2015). https://doi.org/10.1007/s00216-015-9064-9
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DOI: https://doi.org/10.1007/s00216-015-9064-9