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

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.

[1]  M. Syu,et al.  Designing a molecularly imprinted polymer as an artificial receptor for the specific recognition of creatinine in serums. , 2006, Biomaterials.

[2]  K Mosbach,et al.  Assay system for the herbicide 2,4-dichlorophenoxyacetic Acid using a molecularly imprinted polymer as an artificial recognition element. , 1998, Analytical chemistry.

[3]  Toshifumi Takeuchi,et al.  A molecularly imprinted synthetic polymer receptor selective for atrazine , 1995 .

[4]  J. Stobaugh,et al.  Target specific sample preparation from aqueous extracts with molecular imprinted polymers. , 2002, Journal of pharmaceutical and biomedical analysis.

[5]  M. Whitcombe,et al.  Synthetic strategies for the generation of molecularly imprinted organic polymers. , 2005, Advanced drug delivery reviews.

[6]  D. Richman.  Resistance, drug failure, and disease progression. , 1994, AIDS research and human retroviruses.

[7]  Feng-xia Qiao,et al.  Recognition mechanism of water-compatible molecularly imprinted solid-phase extraction and determination of nine quinolones in urine by high performance liquid chromatography. , 2008, Journal of chromatography. A.

[8]  P. Cormack,et al.  Molecularly imprinted polymers: synthesis and characterisation. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[9]  B. Gazzard,et al.  Comparison of first-line antiretroviral therapy with regimens including nevirapine, efavirenz, or both drugs, plus stavudine and lamivudine: a randomised open-label trial, the 2NN Study , 2004, The Lancet.

[10]  E. Turiel,et al.  Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: recent developments and future trends. , 2007, Journal of chromatography. A.

[11]  F. Aweeka,et al.  An LC-MS-MS method for the determination of nevirapine, a non-nucleoside reverse transcriptase inhibitor, in human plasma. , 2003, Journal of pharmaceutical and biomedical analysis.

[12]  I. Wilson,et al.  Optimisation of procedures for the extraction of structural analogues of propranolol with molecular imprinted polymers for sample preparation. , 2000, Journal of Chromatography A.

[13]  J. Andzelm,et al.  Theoretical study of chemical reactions using density functional methods with nonlocal corrections , 1993 .

[14]  F. Sánchez-Baeza,et al.  A New Methodology for the Rational Design of Molecularly Imprinted Polymers , 2007 .

[15]  R. Venn,et al.  Synthesis and properties of molecular imprints of darifenacin: The potential of molecular imprinting for bioanalysis , 1999 .

[16]  D. Hartree.  The Wave Mechanics of an Atom with a non-Coulomb Central Field. Part III. Term Values and Intensities in Series in Optical Spectra , 1928, Mathematical Proceedings of the Cambridge Philosophical Society.

[17]  L. Andersson,et al.  Towards molecular-imprint based SPE of local anaesthetics , 2002 .

[18]  Ram B. Gupta,et al.  Molecularly-imprinted polymers selective for tetracycline binding , 2004 .

[19]  J. Grassi,et al.  Sensitive Enzyme Immunoassay for Measuring Plasma and Intracellular Nevirapine Levels in Human Immunodeficiency Virus-Infected Patients , 2004, Antimicrobial Agents and Chemotherapy.

[20]  L. I. Andersson,et al.  A highly selective solid phase extraction sorbent for pre-concentration of sameridine made by molecular imprinting , 1997 .

[21]  D. Richman,et al.  Natural occurrence of drug resistance mutations in the reverse transcriptase of human immunodeficiency virus type 1 isolates. , 1994, AIDS research and human retroviruses.

[22]  Takeuchi,et al.  Atrazine-selective polymers prepared by molecular imprinting of trialkylmelamines as dummy template species of atrazine , 2000, Analytical chemistry.

[23]  O. Brüggemann.  Catalytically active polymers obtained by molecular imprinting and their application in chemical reaction engineering. , 2001, Biomolecular engineering.

[24]  I. Nicholls.  Towards the rational design of molecularly imprinted polymers , 1998, Journal of molecular recognition : JMR.

[25]  V. Pichon.  Selective sample treatment using molecularly imprinted polymers. , 2007, Journal of Chromatography A.

[26]  James J. P. Stewart,et al.  Fast semiempirical calculations , 1982 .

[27]  M. Kempe.  Antibody-mimicking polymers as chiral stationary phases in HPLC. , 1996, Analytical chemistry.

[28]  J. Song,et al.  Determination of metformin in plasma by capillary electrophoresis using field-amplified sample stacking technique. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[29]  J. Pav,et al.  HPLC-UV method for the quantitation of nevirapine in biological matrices following solid phase extraction. , 1999, Journal of pharmaceutical and biomedical analysis.

[30]  R. Tidwell,et al.  High-performance liquid chromatography assay for the quantification of HIV protease inhibitors and non-nucleoside reverse transcriptase inhibitors in human plasma. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.