, 70:1531 | Cite as

Synthesis of Molecularly Imprinted Polymers for Nevirapine by Dummy Template Imprinting Approach

  • Weeranuch Kareuhanon
  • Vannajan Sanghiran Lee
  • Piyarat Nimmanpipug
  • Chatchai Tayapiwatana
  • Mookda Pattarawarapan


Nevirapine (NVP) and its structurally related analogs including nicotinamide (NAM), benzamide (BZM) and benzophenone (BZP) were used as templates in the synthesis of molecularly imprinted polymers for NVP. Molecular modeling was used to estimate binding energy of the complex formation between methacrylic acid (MAA) monomer and the selected templates, while equilibrium binding studies were applied to evaluate the polymer binding efficiency. The data indicated that NAM is the best candidate to prepare MIPs for retaining NVP due to a relatively similar binding energy between the NVP–MAA and NAM–MAA complex. The NAM-imprinted polymer showed a high binding affinity and selectivity toward NVP. When the polymer was applied as a sorbent in solid-phase extraction of NVP from human plasma, high recovery and reproducibility were obtained.


Column liquid chromatography Molecular imprinting and modeling Dummy template Nevirapine and nicotinamide 



The authors gratefully acknowledge the Government Pharmaceutical Organization (GPO), Thailand for providing NVP for this study, the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Thailand Research Fund (TRF) and Commission on Higher Education, Ministry of Education for financial support to this research.


  1. 1.
    Van Leth F, Phanuphak P, Ruxrungtham K, Baraldi E, Miller S, Gazzard B et al (2004) Lancet 363:1253–1263. doi: 10.1016/S0140-6736(04)15997-7 CrossRefGoogle Scholar
  2. 2.
    Najera I, Richman DD, Olivares I, Rojas JM, Peinado MA, Perucho M et al (1994) AIDS Res Hum Retroviruses 10:1479–1488. doi: 10.1089/aid.1994.10.1479 CrossRefGoogle Scholar
  3. 3.
    Richman DD (1994) AIDS Res Hum Retroviruses 10:901–905. doi: 10.1089/aid.1994.10.901 CrossRefGoogle Scholar
  4. 4.
    Pav JW, Rowland LS, Korpalski DJ (1999) J Pharm Biomed Anal 20:91–98. doi: 10.1016/S0731-7085(98)00312-4 CrossRefGoogle Scholar
  5. 5.
    Rezk NL, Tidwell RR, Kashuba ADM (2004) J Chromatogr B Analyt Technol Biomed Life Sci 805:241–247. doi: 10.1016/j.jchromb.2004.03.002 CrossRefGoogle Scholar
  6. 6.
    Chi J, Jayewardene AL, Stone JA, Aweeka FT (2003) J Pharm Biomed Anal 31:953–959. doi: 10.1016/S0731-7085(02)00708-2 CrossRefGoogle Scholar
  7. 7.
    Azoulay S, Nevers MC, Creminon C, Heripret L, Durant J, Dellamonica P et al (2004) Antimicrob Agents Chemother 48:104–109. doi: 10.1128/AAC.48.1.104-109.2004 CrossRefGoogle Scholar
  8. 8.
  9. 9.
    Mayes AG, Whitcombe MJ (2005) Adv Drug Delivery Rev 57:1742–1778. doi: 10.1016/j.addr.2005.07.011 CrossRefGoogle Scholar
  10. 10.
    Tamayo FG, Turiel E, Martin-Esteban A (2007) J Chromatogr A 1152:32–40. doi: 10.1016/j.chroma.2007.02.109 CrossRefGoogle Scholar
  11. 11.
    Pichon V (2007) J Chromatogr A 1152:41–53. doi: 10.1016/j.chroma.2007.02.109 CrossRefGoogle Scholar
  12. 12.
    Andersson LI, Paprica A, Arvidsson T (1997) Chromatographia 46:57–62. doi: 10.1007/BF02490930 CrossRefGoogle Scholar
  13. 13.
    Venn RF, Goody RJ (1999) Chromatographia 50:407–414. doi: 10.1007/BF02490734 CrossRefGoogle Scholar
  14. 14.
    Martin P, Wilson ID, Jones GR (2000) J Chromatogr A 889:143–147. doi: 10.1016/S0021-9673(00)00570-7 CrossRefGoogle Scholar
  15. 15.
    Matsui J, Fujiwara K, Takeuchi T (2000) Anal Chem 72:1810–1813. doi: 10.1021/ac9911950 CrossRefGoogle Scholar
  16. 16.
    Stewart JJP, Csaszar P, Pulay P (1982) J Comput Chem 3:227–228. doi: 10.1002/jcc.540030214 CrossRefGoogle Scholar
  17. 17.
    Hartree DR (1928) Proc Camb Philol Soc 24:426–437. doi: 10.1017/S0305004100015954 CrossRefGoogle Scholar
  18. 18.
    Andzelm J, Sosa C, Eades RA (1993) J Phys Chem 97:4664–4669. doi: 10.1021/j100120a018 CrossRefGoogle Scholar
  19. 19.
    Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA et al (1995) Gaussian 94, Revision B.3ÈE.2. Gaussian, Inc., PittsburghGoogle Scholar
  20. 20.
    Song JZ, Chen HF, Tian SJ, Sun ZP (1998) J Chromatogr B Biomed Sci Appl 708:277–283. doi: 10.1016/S0378-4347(97)00635-X CrossRefGoogle Scholar
  21. 21.
    Salvador JP, Estevez MC, Marco MP, Sanchez-Baeza F (2007) Anal Lett 40:1294–1306. doi: 10.1080/00032710701326668 CrossRefGoogle Scholar
  22. 22.
    Cormack Peter AG, Elorza Amaia Z (2004) J Chromatogr B Analyt Technol Biomed Life Sci 804:173–182. doi: 10.1016/j.jchromb.2004.02.013 CrossRefGoogle Scholar
  23. 23.
    Kempe M (1996) Anal Chem 68:1948–1953. doi: 10.1021/ac9512160 CrossRefGoogle Scholar
  24. 24.
    Haupt K, Dzgoev A, Mosbach K (1998) Anal Chem 70:628–631. doi: 10.1021/ac9711549 CrossRefGoogle Scholar
  25. 25.
    Sun HW, Qiao FX (2008) J Chromatogr A 1212:1–9. doi: 10.1016/j.chroma.2008.09.107 CrossRefGoogle Scholar
  26. 26.
    Moring SE, Wong OS, Stobaugh JF (2002) J Pharm Biomed Anal 27:719–728. doi: 10.1016/S0731-7085(01)00495-2 CrossRefGoogle Scholar
  27. 27.
    Hsieha RY, Tsaib HA, Syu MJ (2006) Biomaterials 27:2083–2089. doi: 10.1016/j.biomaterials.2005.09.024 CrossRefGoogle Scholar
  28. 28.
    Andersson LI, Abdel-Rehim M, Nicklasson L, Schweitz L, Nilsson S (2002) Chromatographia 55:S65–S69. doi: 10.1007/BF02493355 CrossRefGoogle Scholar
  29. 29.
    Cai W, Gupta RB (2004) Sep Purif Technol 35:215–221. doi: 10.1016/S1383-5866(03)00143-6 CrossRefGoogle Scholar
  30. 30.
    Gregg SJ, Sing KSW (1982) In: Adsorption, Surface Area and Porosity, 2nd edn. Academic Press, LondonGoogle Scholar
  31. 31.
    Bruggemann O (2001) Biomol Eng 18:1–7. doi: 10.1016/S1389-0344(01)00076-4 CrossRefGoogle Scholar
  32. 32.
    Matsui J, Miyoshi Y, Doblhoff-Dier O, Takeuchi T (1995) Anal Chem 67:4404–4408. doi: 10.1021/ac00119a032 CrossRefGoogle Scholar

Copyright information

© Vieweg+Teubner | GWV Fachverlage GmbH 2009

Authors and Affiliations

  • Weeranuch Kareuhanon
    • 1
  • Vannajan Sanghiran Lee
    • 1
  • Piyarat Nimmanpipug
    • 1
  • Chatchai Tayapiwatana
    • 2
  • Mookda Pattarawarapan
    • 1
  1. 1.Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of ScienceChiang Mai UniversityChiang MaiThailand
  2. 2.Division of Clinical Immunology, Faculty of Associated Medical SciencesChiang Mai UniversityChiang MaiThailand

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