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Journal of Sol-Gel Science and Technology

, Volume 86, Issue 1, pp 226–238 | Cite as

Improving imprinted shape cavities of molecularly imprinted sol–gel host matrix with minimal relaxation for sensing of creatinine

  • Qian Yee Ang
  • Florence Chan
  • Pei Chin Tan
  • Siew Chun Low
Original Paper: Sol-gel, hybrids and solution chemistries
  • 186 Downloads

Abstract

Molecularly imprinted polymer (MIP) is of great attention in biomimetic recognition systems due to its selective molecular recognition towards any guest of interest. In this study, creatinine (Cre) was eluted from MIP via physical means to create the best molecular fitting to Cre. Among the polar eluents, methanol could overcome the intermolecular attractions between Cre and aluminium ion (Al3+) while conserving the Cre-shape memory to optimum with the minimal relaxation of the sol–gel host matrix simultaneously. With regard to the optimised shape complementarity of MIP, the solvation effect was scrutinised to reveal the interactions with Cre and MIP/NIP, respectively. Again, the Cre-adsorption in methanol compromised both the binding magnitude and imprinting factor reasonably the best at 19.48 ± 0.64 mg g−1 and 2.00 ± 0.09, respectively. Nevertheless, MIP was capable of selective uptake of Cre even in the presence of interfering analogues, i.e., creatine (Cr), N-hydroxysuccinimide (N-hyd), and 2-pyrrolidinone (2-pyr), by competitive selectivity coefficients of 3.01 ± 1.11, 3.75 ± 0.57, and 5.24 ± 4.59, respectively. In overall, MIP has proven its feasibility as a selective sorbent in capturing the molecule of interest with good recognition ability.

Relaxation of sol-gel host matrix upon effective extraction of Cre template.

Keywords

Molecularly imprinted polymer Sol–gel host matrix Creatinine Template removal Minimal relaxation Shape complementarity 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support from ScienceFund (305/PJKIMIA/6013393). QYA is financially assisted by the Ministry of Higher Education (MOHE) and Universiti Malaysia Perlis (UniMAP).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

10971_2018_4608_MOESM1_ESM.docx (854 kb)
Supplementary information

References

  1. 1.
    Ye L, Mosbach K (2008) Molecular imprinting: synthetic materials as substitutes for biological antibodies and receptors. Chem Mater 20(3):859–868CrossRefGoogle Scholar
  2. 2.
    Pandey S, Mishra SB (2011) Sol–gel derived organic–inorganic hybrid materials: synthesis, characterizations and applications. J Sol Gel Sci Technol 59(1):73–94CrossRefGoogle Scholar
  3. 3.
    Lofgreen JE, Ozin GA (2014) Controlling morphology and porosity to improve performance of molecularly imprinted sol-gel silica. Chem Soc Rev 43(3):911–933CrossRefGoogle Scholar
  4. 4.
    Haupt K, Mosbach K (2000) Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev 100(7):2495–2504CrossRefGoogle Scholar
  5. 5.
    Ng S-M, Narayanaswamy R (2010) Demonstration of a simple, economical and practical technique utilising an imprinted polymer for metal ion sensing. Microchim Acta 169(3):303–311CrossRefGoogle Scholar
  6. 6.
    Florea AM, Sarbu A, Donescu D, Radu A-L, Zaharia A, Iordache T-V (2015) The structure effect upon gallic acid re-binding in molecularly imprinted organosilica. J Sol Gel Sci Technol 76(3):529–541CrossRefGoogle Scholar
  7. 7.
    Chen L, Wang X, Lu W, Wu X, Li J (2016) Molecular imprinting: perspectives and applications. Chem Soc Rev 45(8):2137–2211CrossRefGoogle 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(5):2922–2942CrossRefGoogle Scholar
  9. 9.
    Azodi-Deilami S, Abdouss M, Asadi E, Hassani Najafabadi A, Sadeghi S, Farzaneh S, Asadi S (2014) Magnetic molecularly imprinted polymer nanoparticles coupled with high performance liquid chromatography for solid-phase extraction of carvedilol in serum samples. J Appl Polym Sci 131(23):41209CrossRefGoogle Scholar
  10. 10.
    Morais EC, Brambilla R, Correa GG, Dalmoro V, Dos Santos JHZ (2017) Imprinted silicas for paracetamol preconcentration prepared by the sol–gel process. J Sol Gel Sci Technol 83(1):90–99CrossRefGoogle Scholar
  11. 11.
    Cieplak M, Szwabinska K, Sosnowska M, Chandra BKC, Borowicz P, Noworyta K, D’Souza F, Kutner W (2015) Selective electrochemical sensing of human serum albumin by semi-covalent molecular imprinting. Biosens Bioelectron 74:960–966CrossRefGoogle Scholar
  12. 12.
    Smolinska-Kempisty K, Ahmad OS, Guerreiro A, Karim K, Piletska E, Piletsky S (2017) New potentiometric sensor based on molecularly imprinted nanoparticles for cocaine detection. Biosens Bioelectron 96:49–54CrossRefGoogle Scholar
  13. 13.
    Bedwell TS, Whitcombe MJ (2015) Analytical applications of MIPs in diagnostic assays: future perspectives. Anal Bioanal Chem 408(7):1735–1751CrossRefGoogle Scholar
  14. 14.
    Guardia L, Badía R, Granda-Valdés M, Díaz-García ME (2012) Screening of a molecularly imprinted sol–gel library for nafcillin recognition. J Sol Gel Sci Technol 63(3):537–545CrossRefGoogle Scholar
  15. 15.
    Reddy KK, Gobi KV (2013) Artificial molecular recognition material based biosensor for creatinine by electrochemical impedance analysis. Sens Actuators B 183:356–363CrossRefGoogle Scholar
  16. 16.
    Zhou L, Kong Y, Zhong S, Zhou X (2013) Preparation and characterization of molecularly imprinted organic–inorganic hybrid materials by sol–gel processing for selective recognition of ibuprofen. J Sol Gel Sci Technol 66(1):59–67CrossRefGoogle Scholar
  17. 17.
    Soleimani E, Bahrami A, Afkhami A, Shahna FG (2017) Determination of urinary trans,trans-muconic acid using molecularly imprinted polymer in microextraction by packed sorbent followed by liquid chromatography with ultraviolet detection. J Chromatogr B 1061:65–71CrossRefGoogle Scholar
  18. 18.
    El Nashar RM, Abdel Ghani NT, El Gohary NA, Barhoum A, Madbouly A (2017) Molecularly imprinted polymers based biomimetic sensors for mosapride citrate detection in biological fluids. Mater Sci Eng C 76:123–129CrossRefGoogle Scholar
  19. 19.
    Du C, Hu X, Guan P, Gao X, Song R, Li J, Qian L, Zhang N, Guo L (2016) Preparation of surface-imprinted microspheres effectively controlled by orientated template immobilization using highly cross-linked raspberry-like microspheres for the selective recognition of an immunostimulating peptide. J Mat Chem B 4(8):1510–1519CrossRefGoogle Scholar
  20. 20.
    Yungerman I, Srebnik S (2006) Factors contributing to binding-site imperfections in imprinted polymers. Chem Mater 18(3):657–663CrossRefGoogle Scholar
  21. 21.
    Polyakov M (1931) Adsorption properties and structure of silica gel. Zhur Fiz Khim 2:799–805Google Scholar
  22. 22.
    Piletska EV, Guerreiro AR, Whitcombe MJ, Piletsky SA (2009) Influence of the polymerization conditions on the performance of molecularly imprinted polymers. Macromolecules 42(14):4921–4928CrossRefGoogle Scholar
  23. 23.
    Ang QY, Low SC (2015) Morphology and kinetic modeling of molecularly imprinted organosilanol polymer matrix for specific uptake of creatinine. Anal Bioanal Chem 407(22):6747–6758CrossRefGoogle Scholar
  24. 24.
    Ang QY, Zolkeflay MH, Low SC (2016) Configuration control on the shape memory stiffness of molecularly imprinted polymer for specific uptake of creatinine. Appl Surf Sci 369:326–333CrossRefGoogle Scholar
  25. 25.
    Bossi A, Bonini F, Turner APF, Piletsky SA (2007) Molecularly imprinted polymers for the recognition of proteins: the state of the art. Biosens Bioelectron 22(6):1131–1137CrossRefGoogle Scholar
  26. 26.
    Rujuan W, Yingxia M, Cuiping L, Tao L, Xueyan D (2014) Preparation and adsorption property of glutathione magnetic molecularly imprinted polymers. Acta Chim Sin 72(5):577–582CrossRefGoogle Scholar
  27. 27.
    Lee HM, Lee SG, Park HR, Chough SH (2017) Sorption behaviors and relation between selectivity and possible cavity shapes of the molecularly imprinted materials. Microporous Mesoporous Mater 251:42–50CrossRefGoogle Scholar
  28. 28.
    Jia M, Yang J, Zhao Y-X, Liu Z-S, Aisa HA (2017) A strategy of improving the imprinting effect of molecularly imprinted polymer: effect of heterogeneous macromolecule crowding. Talanta 175:488–494CrossRefGoogle Scholar
  29. 29.
    Liu X, Chen Z, Long J, Yu H, Du X, Zhao Y, Liu J (2014) Preparation and selectivity evaluation of glutathione molecularly imprinted polymers from aqueous media. Ind Eng Chem Res 53(41):16082–16090CrossRefGoogle Scholar
  30. 30.
    Hu Y, Liu R, Zhang Y, Li G (2009) Improvement of extraction capability of magnetic molecularly imprinted polymer beads in aqueous media via dual-phase solvent system. Talanta 79(3):576–582CrossRefGoogle Scholar
  31. 31.
    Lowell S, Shields JE, Thomas MA, Thommes M (2012) Characterization of porous solids and powders: surface area, pore size and density. Springer, DordrechtGoogle Scholar
  32. 32.
    Keshk SMAS, Ramadan AM, Bondock S (2015) Physicochemical characterization of novel Schiff bases derived from developed bacterial cellulose 2,3-dialdehyde. Carbohydr Polym 127(Supplement C):246–251CrossRefGoogle Scholar
  33. 33.
    Huheey JE (1965) The electronegativity of groups. J Phys Chem 69(10):3284–3291CrossRefGoogle Scholar
  34. 34.
    Innocenzi P (2016) The sol to gel transition. Springer International Publishing, ChamGoogle Scholar
  35. 35.
    Piletsky SA, Piletskaya EV, Yano K, Kugimiya A, Elgersma AV, Levi R, Kahlow U, Takeuchi T, Karube I, Panasyuk TI, El’skaya AV (1996) A biomimetic receptor system for sialic acid based on molecular imprinting. Anal Lett 29(2):157–170CrossRefGoogle Scholar
  36. 36.
    Storck S, Bretinger H, Maier WF (1998) Characterization of micro- and mesoporous solids by physisorption methods and pore-size analysis. Appl Catal A Gen 174(1):137–146CrossRefGoogle Scholar
  37. 37.
    Galarneau A, Villemot F, Rodriguez J, Fajula F, Coasne B (2014) Validity of the t-plot method to assess microporosity in hierarchical micro/mesoporous materials. Langmuir 30(44):13266–13274CrossRefGoogle Scholar
  38. 38.
    Bhadra BN, Cho KH, Khan NA, Hong D-Y, Jhung SH (2015) Liquid-phase adsorption of aromatics over a metal–organic framework and activated carbon: effects of hydrophobicity/hydrophilicity of adsorbents and solvent polarity. J Phys Chem C 119(47):26620–26627CrossRefGoogle Scholar
  39. 39.
    Haque E, Jun JW, Jhung SH (2011) Adsorptive removal of methyl orange and methylene blue from aqueous solution with a metal-organic framework material, iron terephthalate (MOF-235). J Hazard Mater 185(1):507–511CrossRefGoogle Scholar
  40. 40.
    Torresan MF, Baruzzi AM, Iglesias RA (2017) Enhancing the adsorption of CdSe quantum dots on TiO2 nanotubes by tuning the solvent polarity. Sol Energy Mater Sol Cells 164:107–113CrossRefGoogle Scholar
  41. 41.
    Low SC, Shaimi R, Thandaithabany Y, Lim JK, Ahmad AL, Ismail A (2013) Electrophoretic interactions between nitrocellulose membranes and proteins: Biointerface analysis and protein adhesion properties. Colloids Surf B Biointerfaces 110:248–253CrossRefGoogle Scholar
  42. 42.
    Turner NW, Piletska EV, Karim K, Whitcombe M, Malecha M, Magan N, Baggiani C, Piletsky SA (2004) Effect of the solvent on recognition properties of molecularly imprinted polymer specific for ochratoxin A. Biosens Bioelectron 20(6):1060–1067CrossRefGoogle Scholar
  43. 43.
    Tsai H-A, Syu M-J (2005) Synthesis and characterization of creatinine imprinted poly(4-vinylpyridine-co-divinylbenzene) as a specific recognition receptor. Anal Chim Acta 539(1–2):107–116CrossRefGoogle Scholar
  44. 44.
    Gao B, Li Y, Zhang Z (2010) Preparation and recognition performance of creatinine-imprinted material prepared with novel surface-imprinting technique. J Chromatogr B 878(23):2077–2086CrossRefGoogle Scholar
  45. 45.
    Makote R, Collinson MM (1998) Dopamine recognition in templated silicate films Chem Commun 3:425–426.  https://doi.org/10.1039/A705536F CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Chemical EngineeringUniversiti Sains MalaysiaNibong TebalMalaysia
  2. 2.Faculty of Engineering TechnologyUniversiti Malaysia PerlisPadang BesarMalaysia

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