Advertisement

Analytical and Bioanalytical Chemistry

, Volume 405, Issue 12, pp 4245–4252 | Cite as

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

  • Meenakshi SinghEmail author
  • Abhishek Kumar
  • Nazia Tarannum
Research Paper

Abstract

Molecularly imprinted polymers selective for aspartame have been prepared using N-[2-ammonium-ethyl-piperazinium) maleimidopropane sulfonate copolymer bearing zwitterionic centres along the backbone via a surface-confined grafting procedure. Aspartame, a dipeptide, is commonly used as an artificial sweetener. Polymerisation on the surface was propagated by means of Michael addition reaction on amino-grafted silica surface. Electrostatic interactions along with complementary H-bonding and other hydrophobic interactions inducing additional synergetic effect between the template (aspartame) and the imprinted surface led to the formation of imprinted sites. The MIP was able to selectively and specifically take up aspartame from aqueous solution and certain pharmaceutical samples quantitatively. Hence, a facile, specific and selective technique using surface-grafted specific molecular contours developed for specific and selective uptake of aspartame in the presence of various interferrants, in different kinds of matrices is presented.

Keywords

Aspartame Dipeptide Molecularly imprinted polymer Sulfobetaine polymer 

Notes

Acknowledgement

The work was supported by UGC, new Delhi [F.no.41-331/2012(SR)].

References

  1. 1.
    Lemieux RU (1996) How water provides the impetus for molecular recognition in aqueous solution. Acc Chem Res 29:373–380CrossRefGoogle Scholar
  2. 2.
    Haupt K, Mosbach K (2000) Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev 100:2495–2504CrossRefGoogle Scholar
  3. 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 34:1812–1832CrossRefGoogle Scholar
  4. 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 5:124–133CrossRefGoogle Scholar
  5. 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 137:4469–4474CrossRefGoogle Scholar
  6. 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 146:381–387CrossRefGoogle Scholar
  7. 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 99:270–276CrossRefGoogle Scholar
  8. 8.
    Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRefGoogle Scholar
  9. 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 125:15101–15109CrossRefGoogle Scholar
  10. 10.
    Cobb Z, Sellergren B, Andersson LI (2007) Water-compatible molecularly imprinted polymers for efficient direct injection on-line solid-phase extraction of ropivacaine and bupivacaine from human plasma. Analyst 132:1262–1271CrossRefGoogle Scholar
  11. 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 50:11731–11734CrossRefGoogle Scholar
  12. 12.
    Yan H, Rowa KH, Yang G (2008) Water-compatible molecularly imprinted polymers for selective extraction of ciprofloxacin from human urine. Talanta 75:227–232Google Scholar
  13. 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 853:346–353CrossRefGoogle Scholar
  14. 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 16:7114–7120Google Scholar
  15. 15.
    Frasconi M, Tel-Vered R, Riskin M, Willner I (2010) Surface plasmon resonance analysis of antibiotics using imprinted boronic acid-functionalized Au-nanoparticle composites. Anal Chem 82:2512–2519CrossRefGoogle Scholar
  16. 16.
    Riskin M, Tel-Vered R, Lioubashevski WI (2009) Ultrasensitive surface plasmon resonance detection of trinitroanaline by a bis-aniline-cross-linked Au-nanoparticle composites. J Am Chem Soc 131:7368–7378CrossRefGoogle Scholar
  17. 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 4:3019–3026CrossRefGoogle Scholar
  18. 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 810:1–17CrossRefGoogle Scholar
  19. 19.
    Shea KJ, Sasaki DY (1991) An analysis of small-molecule binding to functionalized synthetic polymers by 13CP/MAS NMR and FT-IR spectroscopy. J Am Chem Soc 113:4109–4120CrossRefGoogle Scholar
  20. 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 122:6217–6225CrossRefGoogle Scholar
  21. 21.
    Yang H, Zhang S, Tan F, Zhuang Z, Wang X (2005) Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc 127:1378–1379CrossRefGoogle Scholar
  22. 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 1216:807–814CrossRefGoogle Scholar
  23. 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 30:3205–3211CrossRefGoogle Scholar
  24. 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 74:1126–1131CrossRefGoogle Scholar
  25. 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 81:967–976CrossRefGoogle Scholar
  26. 26.
    Wang H, He Y, He X, Li W, Chen L, Zhang Y (2009) BSA-imprinted synthetic receptor for reversible template recognition. J Sep Sci 32:1981–1986CrossRefGoogle Scholar
  27. 27.
    Diltemiz SE, Say R, Buyuktiryaki S, Hur D, Denizli EA (2008) Quantum dot nanocrystals having guanosine imprinted nanoshell for DNA recognition. Talanta 75:890–896CrossRefGoogle Scholar
  28. 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 81:1615–1621CrossRefGoogle Scholar
  29. 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 39:4497–4499CrossRefGoogle Scholar
  30. 30.
    Li Y, Yang HH, You QH, Zhuang ZX, Wang XR (2006) Protein recognition via surface molecularly imprinted polymer nanowires. Anal Chem 78:317–320CrossRefGoogle Scholar
  31. 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 19:215–222CrossRefGoogle Scholar
  32. 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 124:14838–14839CrossRefGoogle Scholar
  33. 33.
    Carte SR, Rimmer S (2004) Surface molecularly imprinted polymer core-shell particles. Adv Funct Mater 14:553–561CrossRefGoogle Scholar
  34. 34.
    Nicholls IA, Rosengren JP (2002) Molecular imprinting of surfaces. Bioseparation 10:301–305CrossRefGoogle Scholar
  35. 35.
    Fatibello-Filho O, Marcolino-Junior HL, Pereira AV (1999) Solid-phase reactor with copper (II) phosphate for flow-injection spectrophotometric determination of aspartame in tabletop sweeteners. Anal Chim Acta 384:167–174CrossRefGoogle Scholar
  36. 36.
    Ranney RE, Oppermann JA, Muldoon E, McMahon FG (1976) Comparative metabolism of aspartame in experimental animals and humans. J Toxicol Environ Health 2:441–451CrossRefGoogle Scholar
  37. 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 2:979–985Google Scholar
  38. 38.
    Odaci D, Timur S, Telefoncu A (2004) Carboxyl esterase-alcohol oxidase based biosensor for the aspartame determination. Food Chem 84:493–496CrossRefGoogle Scholar
  39. 39.
    Rencuzogullari E, Tuylu BA, Topaktas M, Ila HB, Kayraldiz A, Arsla M, Diler SB (2004) Genotoxicity of aspartame. Drug Chem Toxicol 27:257–268CrossRefGoogle Scholar
  40. 40.
    Newman LC, Lipton RB (2001) Migraine MLT-Down: an unusual presentation of migraine in patients with aspartame-triggered headaches. Headache 41:899–901Google Scholar
  41. 41.
    Lau OW, Luk SF, Chan NW (1988) Spectrophotometric determination of aspartame in soft drinks with ninhydrin as reagent. Analyst 113:765–768CrossRefGoogle Scholar
  42. 42.
    Nobrega JA, Fatibello-Filho O, Vieira IC (1994) Flow injection spectrophotometric determination of aspartame in dietary products. Analyst 119:2101–2104CrossRefGoogle Scholar
  43. 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 23:340–343CrossRefGoogle Scholar
  44. 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 33:734–738CrossRefGoogle Scholar
  45. 45.
    Motellier S, Wainer IW (1990) Direct stereochemical resolution of aspartame stereoisomers and their degradation products by high-performance liquid chromatography on a chiral crown ether based stationary phase. J Chromatogr 516:365–373CrossRefGoogle Scholar
  46. 46.
    Lawrence JF, Iyenger JR (1987) Liquid chromatographic determination of beta-aspartame in diet soft drinks, beverage powders and pudding mixes. J Chromatogr 404:261–266CrossRefGoogle Scholar
  47. 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 166:431–434CrossRefGoogle Scholar
  48. 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 540:85–101CrossRefGoogle Scholar
  49. 49.
    Verzella G, Mangia A (1985) High performance liquid chromatographic analysis of aspartame. J Chromatogr 346:417–422CrossRefGoogle Scholar
  50. 50.
    Argoudelis CJ (1984) Isocratic liquid chromatography method for the simultaneous determination of aspartame and other additives in soft drinks. J Chromatogr 303:256–262CrossRefGoogle Scholar
  51. 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 20:1437–1444CrossRefGoogle Scholar
  52. 52.
    Di Pietra AM, Cavrini V, Bonazzi D, Benfenati L (1990) HPLC analysis of aspartame and saccharin in pharmaceutical and dietary formulations. Chromatographia 30:215–219CrossRefGoogle Scholar
  53. 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 270:45–53CrossRefGoogle Scholar
  54. 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 773:163–168CrossRefGoogle Scholar
  55. 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 850:277–281CrossRefGoogle Scholar
  56. 56.
    Mulchandani A, Male KB, Luong JHT, Gibbe BF (1990) Enzymatic assay technique for the determination of aspartame. Anal Chim Acta 234:465–469CrossRefGoogle Scholar
  57. 57.
    Hamano T, Mitsuhashi Y, Aoki N, Yamamoto S (1990) Enzymic method for the spectrophometric determination of aspartame in beverages. Analyst 115:435–438CrossRefGoogle Scholar
  58. 58.
    L. Campanella, Z. Aturki, M.P. Sammartino, J. Pharm. Corporation, Sunnyvale, CA, 1989Google Scholar
  59. 59.
    Kim SK, Jung MY, Kim SY (1997) Photodecomposition of aspartame in aqueous solutions. Food Chem 59:273–278CrossRefGoogle Scholar
  60. 60.
    Mather BD, Viswanathan K, Miller KM, Long TE (2006) Michael addition reactions in macromolecular design for emerging technologies. Prog Polym Sci 31:487–531CrossRefGoogle Scholar
  61. 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 3:467–477Google Scholar
  62. 62.
    Olsztynska S, Komorowska M, Vrielynck L, Dupuy N (2001) Vibrational spectroscopic study of L-phenylalanine: Effect of pH. Appl Spectrosc 55:901–907Google Scholar
  63. 63.
    Tarbin JA, Sharman M (2001) Development of molecularly imprinted phase for the selective retention of stilbene-type estrogenic compounds. Anal Chim Acta 433:71–79CrossRefGoogle Scholar
  64. 64.
    Wulff G, Knorr K (2002) Stoichiometric noncovalent interaction in molecular imprinting. Bioseparation 10:257–276CrossRefGoogle Scholar
  65. 65.
    Willard HH, Merritt LL Jr, Dean JA Jr, Settle FA (1986) Instrumental methods of analysis, 7th edn. Wordsworth Publishing Company, USA, pp 600–603Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Meenakshi Singh
    • 1
    Email author
  • Abhishek Kumar
    • 1
  • Nazia Tarannum
    • 1
  1. 1.Department of Chemistry, MMVBanaras Hindu UniversityVaranasiIndia

Personalised recommendations