Advertisement

Journal of the Iranian Chemical Society

, Volume 15, Issue 7, pp 1569–1580 | Cite as

Magnetic molecularly imprinted polymer nanoparticles for dispersive micro solid-phase extraction and determination of buprenorphine in human urine samples by HPLC-FL

  • Biuck Habibi
  • Shiva Rostamkhani
  • Mehrdad Hamidi
Original Paper
  • 78 Downloads

Abstract

A simple, sensitive and accessible while reliable method was developed and validated for quantitation of buprenorphine (Bup) as a highly lipophilic drug in human urine samples. The proposed method is based on a rapid and easy dispersive micro solid-phase extraction procedure using magnetic molecularly imprinted polymer nanoparticles (MMIPNPs), magnetite (Fe3O4) cores surrounded by polyamidoamine and Bup as template, followed by high-performance liquid chromatographic analysis with fluorescence detector (HPLC-FL). The prepared MMIPNP adsorbent was characterized by different techniques. Transmission electron microscopy images show that the Fe3O4 core nanoparticles are well enwrapped by MIP layers. In determination process, Bup could be quantitatively extracted using MMIPNPs and then can be easily desorbed by mixture of sodium hydroxide (0.1 mol/L) and methanol (1:9, v/v) solution before injection to HPLC. The relative recoveries of Bup were found to be 97.4–100.3%, and the linear dynamic range was within the ranges of 1–1000 ng/mL with R2 of 0.9998. Remarkably high quality of 0.21 and 0.71 ng/mL was obtained as the limit of detection and limit of quantification, respectively. The developed method was successfully applied for determination of Bup in infected human urine samples.

Keywords

Buprenorphine Molecularly imprinted polymer Magnetic nanoparticle Dispersive micro solid-phase extraction HPLC Fluorescence Urine sample 

Notes

Acknowledgements

The authors gratefully acknowledge the research council of Azarbaijan Shahid Madani University for financial support and also appreciate the entire ZUMS employee for their friendly manner.

References

  1. 1.
    S. Rossi, Australian Medicines Handbook (The Australian Medicines Handbook Unit Trust, Adelaide, 2013)Google Scholar
  2. 2.
    B.L. Leighton, L.W. Crock, Anesth. Analg. 125, 1779 (2017)CrossRefGoogle Scholar
  3. 3.
    A. Elkader, B. Sproule, Clin. Pharmacokinet. 44, 661 (2005)CrossRefGoogle Scholar
  4. 4.
    P. Marquet, Buprenorphine Therapy of Opiate Addiction (Humana, Totowa, 2002)Google Scholar
  5. 5.
    J.M. Just, K.S. Just, K. Weckbecker, Sucht 18, 20 (2017)Google Scholar
  6. 6.
    M. Huestis, E. Cone, S. Pirnay, A. Umbricht, K. Preston, Drug Alcohol Depend. 131, 258 (2013)CrossRefGoogle Scholar
  7. 7.
    J.R. Bastian, H. Chen, H. Zhang, S. Rothenberger, R. Tarter, D. English, R. Venkataramanan, S.N. Caritis, Am. J. Obstet. Gynecol. 216, 64 (2017)CrossRefGoogle Scholar
  8. 8.
    A. Pan, M. Zakowski, Clin. Obstet. Gynecol. 60, 447 (2017)CrossRefGoogle Scholar
  9. 9.
    R. Kronstrand, T.G. Seldén, M. Josefsson, J. Anal. Toxicol. 27, 464 (2003)CrossRefGoogle Scholar
  10. 10.
    A. Joshi, B. Parris, Y. Liu, C. Heidbreder, P.M. Gerk, M. Halquist, Biomed. Chromatogr. 31 (2017) art. no. e3785Google Scholar
  11. 11.
    D.J. Christoffersen, C. Brasch-Andersen, J.L. Thomsen, M. Worm-Leonhard, P. Damkier, K. Brøsen, Forensic Sci. Med. Pathol. 11, 193 (2015)CrossRefGoogle Scholar
  12. 12.
    I.K. Zhurkovich, A.O. Rudenko, V.V. Chelovechkova, I.A. Merkusheva, N.V. Lugovkina, N.G. Kovrov, M.V. Pchelintsev, E.V. Verbitskaya, É.É. Zvartau, Pharm. Chem. J. 48, 690 (2015)CrossRefGoogle Scholar
  13. 13.
    S. Hegstad, H. Khiabani, E. Øiestad, T. Berg, A. Christophersen, J. Anal. Toxicol. 31, 214 (2007)CrossRefGoogle Scholar
  14. 14.
    F. Musshoff, J. Trafkowski, U. Kuepper, B. Madea, J. Mass Spectrom. 41, 633 (2006)CrossRefGoogle Scholar
  15. 15.
    K.-W. Chan, H. Harun, Aust. J. Forensic Sci. 49, 186 (2017)CrossRefGoogle Scholar
  16. 16.
    Y. Liu, X. Li, A. Xu, A.F. Nasser, C. Heidbreder, J. Pharm. Biomed. Anal. 120, 142 (2016)CrossRefGoogle Scholar
  17. 17.
    M.J. Swortwood, K.B. Scheidweiler, A.J. Barnes, L.M. Jansson, M.A. Huestis, J. Chromatogr. A 1446, 70 (2016)CrossRefGoogle Scholar
  18. 18.
    W. Sun, S. Qu, Z. Du, J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 951, 57 (2014)Google Scholar
  19. 19.
    H.R. Lin, C.L. Chen, C.L. Huang, S.T. Chen, A.C. Lua, J. Chromatogr. B J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 925, 10 (2013)CrossRefGoogle Scholar
  20. 20.
    T.Y. Chiang, L.H. Pao, C.H. Hsiong, P.W. Huang, K.W. Lin, O.Y.P. Hu, Chromatographia 74, 575 (2011)CrossRefGoogle Scholar
  21. 21.
    D.C. Fuller, J. Anal. Toxicol. 32, 626 (2008)CrossRefGoogle Scholar
  22. 22.
    A. Lisi, R. Kazlauskas, G. Trout, J. Chromatogr. B Biomed. Sci. Appl. 692, 67 (1997)CrossRefGoogle Scholar
  23. 23.
    L.K. Nahar, R. Andrews, S. Paterson, J. Anal. Toxicol. 39, 519 (2015)CrossRefGoogle Scholar
  24. 24.
    J.R. Gervais, G.A. Hobbs, J. Anal. Toxicol. 40, 208 (2016)CrossRefGoogle Scholar
  25. 25.
    F. Chiadmi, J. Schlatter, Anal. Chem. Insights 9, 9 (2014)Google Scholar
  26. 26.
    L. Mercolini, R. Mandrioli, M. Conti, C. Leonardi, G. Gerra, M.A. Raggi, J. Chromatogr. B 847, 95 (2007)CrossRefGoogle Scholar
  27. 27.
    C.L. Liao, C.Y. Lee, T.H. Chiu, G.L. Chen, S.C. Kuo, J. Food Drug Anal. 16, 1 (2008)Google Scholar
  28. 28.
    S.-T. Ho, J.-J. Wang, W. Ho, O.Y.-P. Hu, J. Chromatogr. B Biomed. Sci. Appl. 570, 339 (1991)CrossRefGoogle Scholar
  29. 29.
    S.-Y. Liu, K.-S. Liu, C.-H. Kuei, J.-I. Tzeng, S.-T. Ho, J.-J. Wang, J. Chromatogr. B 818, 233 (2005)CrossRefGoogle Scholar
  30. 30.
    K.S. Hasheminasab, A.R. Fakhari, Anal. Chim. Acta 767, 75 (2013)CrossRefGoogle Scholar
  31. 31.
    E. Souri, F.S. Ahmadi, M.B. Tehrani, M.M. Hosseini, S.F. Vatan, Iran. J. Pharm. Res. 16, 112 (2017)Google Scholar
  32. 32.
    M. García-Fernández, M.T. Fernández-Abedul, A. Costa-García, Electroanalysis 12, 483 (2000)CrossRefGoogle Scholar
  33. 33.
    A.R. Fakhari, A. Sahragard, H. Ahmar, Electroanalysis 26, 2474 (2014)CrossRefGoogle Scholar
  34. 34.
    M. Behpour, A. Valipour, M. Keshavarz, Mater. Sci. Eng., C 42, 500 (2014)CrossRefGoogle Scholar
  35. 35.
    A.A. Ensafi, E. Khoddami, B. Rezaei, Talanta 116, 1113 (2013)CrossRefGoogle Scholar
  36. 36.
    A. Farmany, M. Shamsara, H. Mahdavi, Sens. Actuators B Chem. 239, 279 (2017)CrossRefGoogle Scholar
  37. 37.
    E. Guihen, Trends Anal. Chem. 46, 1 (2013)CrossRefGoogle Scholar
  38. 38.
    C. Bendicho, C. Bendicho-Lavilla, I. Lavilla, Trends Anal. Chem. 77, 109 (2016)CrossRefGoogle Scholar
  39. 39.
    J. González-Sálamo, B. Socas-Rodríguez, J. Hernández-Borges, M.Á. Rodríguez-Delgado, Trends Anal. Chem. 85, 203 (2016)CrossRefGoogle Scholar
  40. 40.
    M. Faraji, Nanochem. Res. 1, 264 (2016)Google Scholar
  41. 41.
    J.G.S.A.V. Herrera, H.C.F.J. Hernández-Borges, LC GC Eur. 29, 180 (2016)Google Scholar
  42. 42.
    L.Y. Ma, Q. Li, J. Li, L. Xu, J. Sep. Sci. 41, 678 (2018)CrossRefGoogle Scholar
  43. 43.
    E.M. Reyes-Gallardo, R. Lucena, S. Cárdenas, RSC Adv. 7, 2308 (2017)CrossRefGoogle Scholar
  44. 44.
    M. Tankiewicz, J. Fenik, M. Biziuk, Talanta 86, 8 (2011)CrossRefGoogle Scholar
  45. 45.
    G. Lasarte-Aragonés, R. Lucena, S. Cárdenas, M. Valcárcel, Bioanalysis 3, 2533 (2011)CrossRefGoogle Scholar
  46. 46.
    X. Ding, Y. Wang, Y. Wang, Q. Pan, J. Chen, Y. Huang, K. Xu, Anal. Chim. Acta 861, 36 (2015)CrossRefGoogle Scholar
  47. 47.
    M. Faraji, Y. Yamini, M. Rezaee, J. Iran. Chem. Soc. 7, 1 (2010)CrossRefGoogle Scholar
  48. 48.
    S. Laurent, A.A. Saei, S. Behzadi, A. Panahifar, M. Mahmoudi, Expert Opin. Drug Deliv. 11, 1449 (2014)CrossRefGoogle Scholar
  49. 49.
    X. Li, J. Wei, K.E. Aifantis, Y. Fan, Q. Feng, F.Z. Cui, F. Watari, J. Biomed. Mater. Res. A 104, 1285 (2016)CrossRefGoogle Scholar
  50. 50.
    X. Mou, Z. Ali, S. Li, N. He, J. Nanosci. Nanotechnol. 15, 54 (2015)CrossRefGoogle Scholar
  51. 51.
    C. Pascal, J. Pascal, F. Favier, M. Elidrissi Moubtassim, C. Payen, Chem. Mater. 11, 141 (1999)CrossRefGoogle Scholar
  52. 52.
    G. Giakisikli, A.N. Anthemidis, Anal. Chim. Acta 789, 1 (2013)CrossRefGoogle Scholar
  53. 53.
    J. He, M. Huang, D. Wang, Z. Zhang, G. Li, J. Pharm. Biomed. Anal. 101, 84 (2014)CrossRefGoogle Scholar
  54. 54.
    A. Bazmandegan-Shamili, S. Dadfarnia, A.M. Haji Shabani, M. Saeidi, M. Rohani Moghadam. Food Anal. Methods 9, 2621 (2016)CrossRefGoogle Scholar
  55. 55.
    J. Xie, J. Xie, J. Deng, X. Fang, H. Zhao, D. Qian, H. Wang, J. Sep. Sci. 39, 2422 (2016)CrossRefGoogle Scholar
  56. 56.
    G. Sheykhaghaei, M. Hossainisadr, S. Khanahmadzadeh, M. Seyedsajadi, A. Alipouramjad, J. Chromatogr. B 1011, 1 (2016)CrossRefGoogle Scholar
  57. 57.
    S. Azodi-Deilami, A. Hassani Najafabadi, E. Asadi, M. Abdouss, D. Kordestani, Microchim. Acta 181, 1823 (2014)CrossRefGoogle Scholar
  58. 58.
    T. Madrakian, R. Haryani, M. Ahmadi, A. Afkhami, Anal. Methods 7, 428 (2015)CrossRefGoogle Scholar
  59. 59.
    B. Pan, D. Cui, Y. Sheng, C. Ozkan, F. Gao, R. He, Q. Li, P. Xu, T. Huang, Cancer Res. 67, 8156 (2007)CrossRefGoogle Scholar
  60. 60.
    O. Veiseh, J.W. Gunn, M. Zhang, Adv. Drug Deliv. Rev. 62, 284 (2010)CrossRefGoogle Scholar
  61. 61.
    Y.w. Jun, J.H. Lee, J. Cheon, Angew. Chem. Int. Ed. 47, 5122 (2008)Google Scholar
  62. 62.
    L. Wang, K. Neoh, E. Kang, B. Shuter, S.C. Wang, Adv. Funct. Mater. 19, 2615 (2009)CrossRefGoogle Scholar
  63. 63.
    E. Tombácz, R. Turcu, V. Socoliuc, L. Vékás, Biochem. Biophys. Res. Commun. 468, 442 (2015)CrossRefGoogle Scholar
  64. 64.
    H. Shen, B. Liu, Q. Xiang, C. Wang, S.Q. Mao, RSC Adv. 6, 81330 (2016)CrossRefGoogle Scholar
  65. 65.
    P. Yáñez-Sedeño, S. Campuzano, J.M. Pingarrón, Anal. Chim. Acta 1, 1 (2017)CrossRefGoogle Scholar
  66. 66.
    A. Zamora-Gálvez, A. Ait-Lahcen, L.A. Mercante, E. Morales-Narváez, A. Amine, A. Merkoçi, Anal. Chem. 88, 3578 (2016)CrossRefGoogle Scholar
  67. 67.
    R. Ahmad, N.B.W. Griffete, A. Lamouri, N. Felidj, M.M. Chehimi, C. Mangeney, Chem. Mater. 27, 5464 (2015)CrossRefGoogle Scholar
  68. 68.
    S. Ansari, M. Karimi, Talanta 164, 612 (2017)CrossRefGoogle Scholar
  69. 69.
    T. Kubo, K. Otsuka, TrAC Trend. Anal. Chem. 81, 102 (2016)CrossRefGoogle Scholar
  70. 70.
    N. Griffete, J. Fresnais, A. Espinosa, C. Wilhelm, A. Bée, C. Ménager, Nanoscale 7, 18891 (2015)CrossRefGoogle Scholar
  71. 71.
    J. Wackerlig, R. Schirhagl, Anal. Chem. 88, 250 (2015)CrossRefGoogle Scholar
  72. 72.
    H. Jiang, D. Jiang, J. Shao, X. Sun, Biosens. Bioelectron. 75, 411 (2016)CrossRefGoogle Scholar
  73. 73.
    E. Abdollahi, M. Abdouss, A. Mohammadi, RSC Adv. 6, 39095 (2016)CrossRefGoogle Scholar
  74. 74.
    T. Madrakian, A. Afkhami, H. Mahmood-Kashani, M. Ahmadi, Talanta 105, 255 (2013)CrossRefGoogle Scholar
  75. 75.
    T. Madrakian, M. Ahmadi, A. Afkhami, M. Soleimani, Analyst 138, 4542 (2013)CrossRefGoogle Scholar
  76. 76.
    R. Sedghi, M. Yassari, B. Heidari, Colloids Surf B Biointerfaces 162, 154 (2018)CrossRefGoogle Scholar
  77. 77.
    L.L. Wu, R.P. Liang, J. Chen, J.D. Qiu, Electrophoresis 39, 356 (2018)CrossRefGoogle Scholar
  78. 78.
    M. Hassanzadeh, M. Ghaemy, New J. Chem. 41, 2277 (2017)CrossRefGoogle Scholar
  79. 79.
    A.H. Lu, E.E.L. Salabas, F. Schüth, Angew. Chem. Int. Ed. 46, 1222 (2007)CrossRefGoogle Scholar
  80. 80.
    N.M. Mahmoodi, F. Najafi, A. Neshat, Ind. Crops Prod. 42, 119 (2013)CrossRefGoogle Scholar
  81. 81.
    H.M. Fatatry, W.M. Osman, Int. J. Adv. Res. Chem. Sci. 1, 47 (2014)Google Scholar
  82. 82.
    T. Madrakian, A. Afkhami, M.A. Zolfigol, M. Ahmadi, N. Koukabi, Nano-Micro Lett. 4, 57 (2012)CrossRefGoogle Scholar
  83. 83.
    C. Gonzato, M. Courty, P. Pasetto, K. Haupt, Adv. Funct. Mater. 21, 3947 (2011)CrossRefGoogle Scholar
  84. 84.
    S.-Y. Zhao, D.K. Lee, C.W. Kim, H.G. Cha, Y.H. Kim, Y.S. Kang, Bull. Korean Chem. Soc. 27, 237 (2006)CrossRefGoogle Scholar
  85. 85.
    A. Patterson, Phys. Rev. 56, 978 (1939)CrossRefGoogle Scholar
  86. 86.
    H. Feng, N. Wang, L. Yuan, J. Li, Q. Cai, Sens. Actuators B Chem. 195, 266 (2014)CrossRefGoogle Scholar
  87. 87.
    T.P. Lee, B. Saad, W.S. Khayoon, B. Salleh, Talanta 88, 129 (2012)CrossRefGoogle Scholar
  88. 88.
    C. Basheer, G.C. Han, M.H. Toh, K.L. Hian, Anal. Chem. 79, 6845 (2007)CrossRefGoogle Scholar
  89. 89.
    K.Y. Foo, B.H. Hameed, Chem. Eng. J. 156, 2 (2010)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Biuck Habibi
    • 1
  • Shiva Rostamkhani
    • 1
  • Mehrdad Hamidi
    • 2
  1. 1.Electroanalytical Chemistry Laboratory, Department of Chemistry, Faculty of SciencesAzarbaijan Shahid Madani UniversityTabrizIran
  2. 2.Department of Pharmaceutical Nanotechnology, Zanjan Pharmaceutical Nanotechnology Research Center (ZPNRC), School of PharmacyZanjan University of Medical SciencesZanjanIran

Personalised recommendations