Water-compatible 'aspartame'-imprinted polymer grafted on silica surface for selective recognition in aqueous solution

Analytical and Bioanalytical Chemistry

Volumn 405, Issue 12, 2013, Pages 4245-4252

  Singh, Meenakshi ^a   Kumar, Abhishek ^a   Tarannum, Nazia ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Aspartame; Dipeptide; Molecularly imprinted polymer; Sulfobetaine polymer

Indexed keywords

ADDITION REACTIONS; GRAFTING (CHEMICAL); HYDROPHOBICITY; SILICA; SUGAR SUBSTITUTES;

ARTIFICIAL SWEETENERS; ASPARTAME; DI-PEPTIDES; HYDROPHOBIC INTERACTIONS; MOLECULAR CONTOURS; MOLECULARLY IMPRINTED POLYMER; SELECTIVE RECOGNITION; SULFOBETAINE POLYMERS;

PEPTIDES;

ASPARTAME; POLYMER; SILICON DIOXIDE; SULFONIC ACID DERIVATIVE; SWEETENING AGENT; WATER;

ADSORPTION; ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; ISOLATION AND PURIFICATION; METHODOLOGY; MOLECULAR IMPRINTING; POLYMERIZATION; SURFACE PROPERTY;

ADSORPTION; ASPARTAME; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR IMPRINTING; POLYMERIZATION; POLYMERS; SILICON DIOXIDE; SULFONIC ACIDS; SURFACE PROPERTIES; SWEETENING AGENTS; WATER;

EID: 84886819609     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-6812-6     Document Type: Article

References (65)

1. Lemieux RU (1996) How water provides the impetus for molecular recognition in aqueous solution. Acc Chem Res 29:373-380
2. Haupt K, Mosbach K (2000) Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev 100:2495-2504
3. Wulff G (1995) Molecular imprinting in cross-linked materials with the aid of molecular templates-a way towards artificial antibodies. Angew Chem Int Ed 34:1812-1832
4. Xu SF, Li JH, Song XL, Liu JS, Lu HZ, Chen LX (2013) Photonic and magnetic dual responsive molecularly imprinted polymers: preparation, recognition characteristics and properties as a novel sorbent for caffeine in complicated samples. Anal Methods 5:124-133
5. Zhou CH, Wang TT, Liu JQ, Guo C, Peng Y, Bai JL, Liu M, Dong JW, Gao N, Ning BA, Gao ZX (2012) Molecularly imprinted photonic polymer as an optical sensor to detect chloramphenicol. Analyst 137:4469-4474
6. Wang YT, Zhang ZQ, Jain V, Yi JJ, Mueller S, Sokolov J, Liu ZX, Levon K, Rigas B, Rafailovich MH (2010) Potentiometric sensors based on surface molecular imprinting: detection of cancer biomarkers and viruses. Sensors Actuators B Chem 146:381-387
7. Zhang XF, Xu SX, Lim JM, Lee YI (2012) Molecularly imprinted solid phase microextraction fiber for trace analysis of catecholamines in urine and serum samples by capillary electrophoresis. Talanta 99:270-276
8. Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922-2942
9. Dirion B, Cobb Z, Schillinger E, Andersson LI, Sellergren B (2003) Water-compatible molecularly imprinted polymers obtained via high-throughput synthesis and experimental design. J Am Chem Soc 125:15101-15109
10. Cobb Z, Sellergren B, Andersson LI (2007) Water-compatible molecularly imprinted polymers for efficient direct injection online solid-phase extraction of ropivacaine and bupivacaine from human plasma. Analyst 132:1262-1271
11. Pan G, Zhang Y, Ma Y, Li C, Zhang H (2011) Efficient one-pot synthesis of water-compatible molecularly imprinted polymer microspheres by facile RAFT precipitation polymerization. Angew Chem Int Ed 50:11731-11734
12. Yan H, Rowa KH, Yang G (2008) Water-compatible molecularly imprinted polymers for selective extraction of ciprofloxacin from human urine. Talanta 75:227-232
13. Zygiel PD, O'Donnell E, Fraier D, Chassaing C, Cormack PAG (2007) Evaluation of water-compatible molecularly imprinted polymers as solid-phase extraction sorbents for the selective extraction of sildenafil and its desmethyl metabolite from plasma samples, J. Chrom B 853:346-353
14. Riskin M, Tel-Vered R, Frasconi M,Willner I (2010) Stereoselective and chiroselective surface plasmon resonance (SPR) analysis of amino acids by molecularly imprinted Au-nanoparticle composites. Chem Eur J 16:7114-7120
15. Frasconi M, Tel-Vered R, Riskin M, Willner I (2010) Surface plasmon resonance analysis of antibiotics using imprinted boronic acidfunctionalized Au-nanoparticle composites. Anal Chem 82:2512-2519
16. Riskin M, Tel-Vered R, Lioubashevski WI (2009) Ultrasensitive surface plasmon resonance detection of trinitroanaline by a bisaniline-cross-linked Au-nanoparticle composites. J Am Chem Soc 131:7368-7378
17. Tarannum N, Singh M (2012)Water-compatible surface imprinting of 'baclofen' on silica surface for selective recognition and detection in aqueous solution. Anal Methods 4:3019-3026
18. Sajonz P, Kele M, Zhong G, Sellergren B, Guiochon G (1998) Study of the thermodynamics and mass transfer kinetics of two enantiomers on a polymeric imprinted stationary phase. J Chromatogr A 810:1-17
19. Shea KJ, Sasaki DY (1991) An analysis of small-molecule binding to functionalized synthetic polymers by 13CP/MAS NMR and FTIR spectroscopy. J Am Chem Soc 113:4109-4120
20. Brunkan NM, Gagne MR (2000) Effect of chiral cavities associated with molecularly imprinted platinum centers on the selectivity of ligand-exchange reactions at platinum. J Am Chem Soc 122:6217-6225
21. Yang H, Zhang S, Tan F, Zhuang Z, Wang X (2005) Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc 127:1378-1379
22. Qin L, He X, Zhang W, Li W, Zhang Y (2009) Surface-modified polystyrene beads as photografting imprinted polymer matrix for chromatographic separation of proteins. J Chromatogr A 1216:807-814
23. Li Y, Li X, Li Y, Dong C, Jin P, Qi J (2009) Selective recognition of veterinary drugs residues by artificial antibodies designed using a computational approach. Biomaterials 30:3205-3211
24. He C, Long Y, Pan J, Li K, Liu F (2008) Molecularly imprinted silica prepared with immiscible ionic liquid as solvent and porogen for selective recognition of testosterone. Talanta 74:1126-1131
25. Zhang Y, Liu R, Hu Y, Li G (2009) Microwave heating in preparation of magnetic molecularly imprinted polymer beads for trace analysis in complicated samples. Anal Chem 81:967-976
26. Wang H, He Y, He X, Li W, Chen L, Zhang Y (2009) BSAimprinted synthetic receptor for reversible template recognition. J Sep Sci 32:1981-1986
27. Diltemiz SE, Say R, Buyuktiryaki S, Hur D, Denizli EA (2008) Quantum dot nanocrystals having guanosine imprinted nanoshell for DNA recognition. Talanta 75:890-896
28. Wang H, He Y, Ji T, Yuan X (2009) Surface molecular imprinting on Mn-doped ZnS quantum dots for room temperature phosphorescence optosensing of pentachlorophenol in water. Anal Chem 81:1615-1621
29. Li Y, Yin XF, Chen FR, Yang HH, Zhuang ZX, Wang XR (2006) Synthesis of magnetic molecularly imprinted polymer nanowires using a nanoporous alumina template. Macromolecules 39:4497-4499
30. Li Y, Yang HH, You QH, Zhuang ZX, Wang XR (2006) Protein recognition via surface molecularly imprinted polymer nanowires. Anal Chem 78:317-320
31. Yao Q, Zhou Y (2009) Surface functional imprinting of bensulfuron-methyl at surface of silica nanoparticles linked by silane coupling agent. J Inorg Organomet Polym 19:215-222
32. Ki CD, Oh C, Chang JY (2002) The use of a thermally reversible bond for molecular imprinting of silica spheres. J Am Chem Soc 124:14838-14839
33. Carte SR, Rimmer S (2004) Surface molecularly imprinted polymer core-shell particles. Adv Funct Mater 14:553-561
34. Nicholls IA, Rosengren JP (2002) Molecular imprinting of surfaces. Bioseparation 10:301-305
35. Fatibello-Filho O, Marcolino-Junior HL, Pereira AV (1999) Solidphase reactor with copper (II) phosphate for flow-injection spectrophotometric determination of aspartame in tabletop sweeteners. Anal Chim Acta 384:167-174
36. Ranney RE, Oppermann JA, Muldoon E, McMahon FG (1976) Comparative metabolism of aspartame in experimental animals and humans. J Toxicol Environ Health 2:441-451
37. Ranney RE, Oppermann JA (1979) A review of the metabolism of the aspartyl moiety of aspartame in experimental animals and man. J Environ Pathol Toxicol 2:979-985
38. Odaci D, Timur S, Telefoncu A (2004) Carboxyl esterase-alcohol oxidase based biosensor for the aspartame determination. Food Chem 84:493-496
39. Rencuzogullari E, Tuylu BA, Topaktas M, Ila HB, Kayraldiz A, Arsla M, Diler SB (2004) Genotoxicity of aspartame. Drug Chem Toxicol 27:257-268
40. Newman LC, Lipton RB (2001) Migraine MLT-Down: an unusual presentation of migraine in patients with aspartame-triggered headaches. Headache 41:899-901
41. Lau OW, Luk SF, Chan NW (1988) Spectrophotometric determination of aspartame in soft drinks with ninhydrin as reagent. Analyst 113:765-768
42. Nobrega JA, Fatibello-Filho O, Vieira IC (1994) Flow injection spectrophotometric determination of aspartame in dietary products. Analyst 119:2101-2104
43. Furda I, Malizia PD, Kolor MG, Vemieri PJ (1975) Decomposition products of L-aspartyl-L-phenylalanine methyl ester and their identification by gas-liquid chromatography. J Agric Food Chem 23:340-343
44. Tsang W, Clarke MA, Parrish FW (1985) Determination of aspartame and its breakdown products in soft drinks by reverse-phase chromatography with UV detection. J Agric Food Chem 33:734-738
45. Motellier S, Wainer IW (1990) Direct stereochemical resolution of aspartame stereoisomers and their degradation products by highperformance liquid chromatography on a chiral crown ether based stationary phase. J Chromatogr 516:365-373
46. Lawrence JF, Iyenger JR (1987) Liquid chromatographic determination of beta-aspartame in diet soft drinks, beverage powders and pudding mixes. J Chromatogr 404:261-266
47. Keller HJ, Do KQ, Zollinger M, Winterhalter KM, Cuenod M (1987) 9-Ffluorenylmethoxycarbonylpyrogltamate, a side-product of derivatization of glutamate with 9-fluorenylmethyl chloroformate: a warning. Anal Biochem 166:431-434
48. Ladisch MR, Hendrickson RL, Firouztale E (1991) Analytical-and preparative-scale chromatographic separation of phenylalanine from aspartame using a new polymeric sorbent. J Chromatogr 540:85-101
49. Verzella G, Mangia A (1985) High performance liquid chromatographic analysis of aspartame. J Chromatogr 346:417-422
50. Argoudelis CJ (1984) Isocratic liquid chromatography method for the simultaneous determination of aspartame and other additives in soft drinks. J Chromatogr 303:256-262
51. Aboul-Enein HY, Bakr SA (1997) Comparative study of separation and determination of aspartame and its decomposition products in bulk material and diet soft drinks by HPLC and CE. J Liq Chromatogr Catogr Rel Technol 20:1437-1444
52. Di Pietra AM, Cavrini V, Bonazzi D, Benfenati L (1990) HPLC analysis of aspartame and saccharin in pharmaceutical and dietary formulations. Chromatographia 30:215-219
53. Garcia Sanchez F, Aguilar Gallardo A (1992) Liquid chromatographic and spectrofluorimetric determination of aspartame and glutamate in foodstuffs following fluorescamine fluorigenic labelling. Anal Chim Acta 270:45-53
54. Kazimierz W, Wrobel K (1997) Determination of aspartame and phenylalanine in diet soft drinks by high-performance liquid chromatography with direct spectrofluorometric detection. J Chromtogr A 773:163-168
55. Feng Q, Qi Z-H, Liu K-N, Mou S-F (1999) (1999) Determination of aspartame by ion chromatography with electrochemical integrated amperometric detection. J Chrom A 850:277-281
56. Mulchandani A, Male KB, Luong JHT, Gibbe BF (1990) Enzymatic assay technique for the determination of aspartame. Anal Chim Acta 234:465-469
57. Hamano T, Mitsuhashi Y, Aoki N, Yamamoto S (1990) Enzymic method for the spectrophometric determination of aspartame in beverages. Analyst 115:435-438
58. L. Campanella, Z. Aturki, M.P. Sammartino, J. Pharm. Corporation, Sunnyvale, CA, 1989
59. Kim SK, Jung MY, Kim SY (1997) Photodecomposition of aspartame in aqueous solutions. Food Chem 59:273-278
60. Mather BD, Viswanathan K, Miller KM, Long TE (2006) Michael addition reactions in macromolecular design for emerging technologies. Prog Polym Sci 31:487-531
61. Kumar A, Tarannum N, Singh M (2012) Surface photografting of novel zwitterionic copolymers of maleimide and diamines via Michael-type addition on silica. Mater Sci Appl 3:467-477
62. Olsztynska S, Komorowska M, Vrielynck L, Dupuy N (2001) Vibrational spectroscopic study of L-phenylalanine: Effect of pH. Appl Spectrosc 55:901-907
63. Tarbin JA, Sharman M (2001) Development of molecularly imprinted phase for the selective retention of stilbene-type estrogenic compounds. Anal Chim Acta 433:71-79
64. Wulff G, Knorr K (2002) Stoichiometric noncovalent interaction in molecular imprinting. Bioseparation 10:257-276
65. Willard HH,Merritt LL Jr, Dean JA Jr, Settle FA (1986) Instrumental methods of analysis, 7th edn. Wordsworth Publishing Company, USA, pp 600-603