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

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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.

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References

  1. S. Rossi, Australian Medicines Handbook (The Australian Medicines Handbook Unit Trust, Adelaide, 2013)

    Google Scholar 

  2. B.L. Leighton, L.W. Crock, Anesth. Analg. 125, 1779 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  3. A. Elkader, B. Sproule, Clin. Pharmacokinet. 44, 661 (2005)

    Article  CAS  PubMed  Google Scholar 

  4. P. Marquet, Buprenorphine Therapy of Opiate Addiction (Humana, Totowa, 2002)

    Google Scholar 

  5. J.M. Just, K.S. Just, K. Weckbecker, Sucht 18, 20 (2017)

    Google Scholar 

  6. M. Huestis, E. Cone, S. Pirnay, A. Umbricht, K. Preston, Drug Alcohol Depend. 131, 258 (2013)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  8. A. Pan, M. Zakowski, Clin. Obstet. Gynecol. 60, 447 (2017)

    Article  PubMed  Google Scholar 

  9. R. Kronstrand, T.G. Seldén, M. Josefsson, J. Anal. Toxicol. 27, 464 (2003)

    Article  CAS  PubMed  Google Scholar 

  10. A. Joshi, B. Parris, Y. Liu, C. Heidbreder, P.M. Gerk, M. Halquist, Biomed. Chromatogr. 31 (2017) art. no. e3785

  11. D.J. Christoffersen, C. Brasch-Andersen, J.L. Thomsen, M. Worm-Leonhard, P. Damkier, K. Brøsen, Forensic Sci. Med. Pathol. 11, 193 (2015)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  13. S. Hegstad, H. Khiabani, E. Øiestad, T. Berg, A. Christophersen, J. Anal. Toxicol. 31, 214 (2007)

    Article  CAS  PubMed  Google Scholar 

  14. F. Musshoff, J. Trafkowski, U. Kuepper, B. Madea, J. Mass Spectrom. 41, 633 (2006)

    Article  CAS  PubMed  Google Scholar 

  15. K.-W. Chan, H. Harun, Aust. J. Forensic Sci. 49, 186 (2017)

    Article  Google Scholar 

  16. Y. Liu, X. Li, A. Xu, A.F. Nasser, C. Heidbreder, J. Pharm. Biomed. Anal. 120, 142 (2016)

    Article  CAS  PubMed  Google Scholar 

  17. M.J. Swortwood, K.B. Scheidweiler, A.J. Barnes, L.M. Jansson, M.A. Huestis, J. Chromatogr. A 1446, 70 (2016)

    Article  CAS  PubMed  Google Scholar 

  18. W. Sun, S. Qu, Z. Du, J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 951, 57 (2014)

    Google Scholar 

  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)

    Article  CAS  Google Scholar 

  20. T.Y. Chiang, L.H. Pao, C.H. Hsiong, P.W. Huang, K.W. Lin, O.Y.P. Hu, Chromatographia 74, 575 (2011)

    Article  CAS  Google Scholar 

  21. D.C. Fuller, J. Anal. Toxicol. 32, 626 (2008)

    Article  CAS  PubMed  Google Scholar 

  22. A. Lisi, R. Kazlauskas, G. Trout, J. Chromatogr. B Biomed. Sci. Appl. 692, 67 (1997)

    Article  CAS  PubMed  Google Scholar 

  23. L.K. Nahar, R. Andrews, S. Paterson, J. Anal. Toxicol. 39, 519 (2015)

    Article  CAS  PubMed  Google Scholar 

  24. J.R. Gervais, G.A. Hobbs, J. Anal. Toxicol. 40, 208 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. F. Chiadmi, J. Schlatter, Anal. Chem. Insights 9, 9 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  26. L. Mercolini, R. Mandrioli, M. Conti, C. Leonardi, G. Gerra, M.A. Raggi, J. Chromatogr. B 847, 95 (2007)

    Article  CAS  Google Scholar 

  27. C.L. Liao, C.Y. Lee, T.H. Chiu, G.L. Chen, S.C. Kuo, J. Food Drug Anal. 16, 1 (2008)

    CAS  Google Scholar 

  28. S.-T. Ho, J.-J. Wang, W. Ho, O.Y.-P. Hu, J. Chromatogr. B Biomed. Sci. Appl. 570, 339 (1991)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  30. K.S. Hasheminasab, A.R. Fakhari, Anal. Chim. Acta 767, 75 (2013)

    Article  CAS  PubMed  Google Scholar 

  31. E. Souri, F.S. Ahmadi, M.B. Tehrani, M.M. Hosseini, S.F. Vatan, Iran. J. Pharm. Res. 16, 112 (2017)

    PubMed  PubMed Central  Google Scholar 

  32. M. García-Fernández, M.T. Fernández-Abedul, A. Costa-García, Electroanalysis 12, 483 (2000)

    Article  Google Scholar 

  33. A.R. Fakhari, A. Sahragard, H. Ahmar, Electroanalysis 26, 2474 (2014)

    Article  CAS  Google Scholar 

  34. M. Behpour, A. Valipour, M. Keshavarz, Mater. Sci. Eng., C 42, 500 (2014)

    Article  CAS  Google Scholar 

  35. A.A. Ensafi, E. Khoddami, B. Rezaei, Talanta 116, 1113 (2013)

    Article  CAS  PubMed  Google Scholar 

  36. A. Farmany, M. Shamsara, H. Mahdavi, Sens. Actuators B Chem. 239, 279 (2017)

    Article  CAS  Google Scholar 

  37. E. Guihen, Trends Anal. Chem. 46, 1 (2013)

    Article  CAS  Google Scholar 

  38. C. Bendicho, C. Bendicho-Lavilla, I. Lavilla, Trends Anal. Chem. 77, 109 (2016)

    Article  CAS  Google Scholar 

  39. J. González-Sálamo, B. Socas-Rodríguez, J. Hernández-Borges, M.Á. Rodríguez-Delgado, Trends Anal. Chem. 85, 203 (2016)

    Article  CAS  Google Scholar 

  40. M. Faraji, Nanochem. Res. 1, 264 (2016)

    Google Scholar 

  41. J.G.S.A.V. Herrera, H.C.F.J. Hernández-Borges, LC GC Eur. 29, 180 (2016)

    Google Scholar 

  42. L.Y. Ma, Q. Li, J. Li, L. Xu, J. Sep. Sci. 41, 678 (2018)

    Article  CAS  PubMed  Google Scholar 

  43. E.M. Reyes-Gallardo, R. Lucena, S. Cárdenas, RSC Adv. 7, 2308 (2017)

    Article  CAS  Google Scholar 

  44. M. Tankiewicz, J. Fenik, M. Biziuk, Talanta 86, 8 (2011)

    Article  CAS  PubMed  Google Scholar 

  45. G. Lasarte-Aragonés, R. Lucena, S. Cárdenas, M. Valcárcel, Bioanalysis 3, 2533 (2011)

    Article  CAS  PubMed  Google Scholar 

  46. X. Ding, Y. Wang, Y. Wang, Q. Pan, J. Chen, Y. Huang, K. Xu, Anal. Chim. Acta 861, 36 (2015)

    Article  CAS  PubMed  Google Scholar 

  47. M. Faraji, Y. Yamini, M. Rezaee, J. Iran. Chem. Soc. 7, 1 (2010)

    Article  CAS  Google Scholar 

  48. S. Laurent, A.A. Saei, S. Behzadi, A. Panahifar, M. Mahmoudi, Expert Opin. Drug Deliv. 11, 1449 (2014)

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  PubMed  Google Scholar 

  50. X. Mou, Z. Ali, S. Li, N. He, J. Nanosci. Nanotechnol. 15, 54 (2015)

    Article  CAS  PubMed  Google Scholar 

  51. C. Pascal, J. Pascal, F. Favier, M. Elidrissi Moubtassim, C. Payen, Chem. Mater. 11, 141 (1999)

    Article  CAS  Google Scholar 

  52. G. Giakisikli, A.N. Anthemidis, Anal. Chim. Acta 789, 1 (2013)

    Article  CAS  PubMed  Google Scholar 

  53. J. He, M. Huang, D. Wang, Z. Zhang, G. Li, J. Pharm. Biomed. Anal. 101, 84 (2014)

    Article  CAS  PubMed  Google Scholar 

  54. A. Bazmandegan-Shamili, S. Dadfarnia, A.M. Haji Shabani, M. Saeidi, M. Rohani Moghadam. Food Anal. Methods 9, 2621 (2016)

    Article  Google Scholar 

  55. J. Xie, J. Xie, J. Deng, X. Fang, H. Zhao, D. Qian, H. Wang, J. Sep. Sci. 39, 2422 (2016)

    Article  CAS  PubMed  Google Scholar 

  56. G. Sheykhaghaei, M. Hossainisadr, S. Khanahmadzadeh, M. Seyedsajadi, A. Alipouramjad, J. Chromatogr. B 1011, 1 (2016)

    Article  CAS  Google Scholar 

  57. S. Azodi-Deilami, A. Hassani Najafabadi, E. Asadi, M. Abdouss, D. Kordestani, Microchim. Acta 181, 1823 (2014)

    Article  CAS  Google Scholar 

  58. T. Madrakian, R. Haryani, M. Ahmadi, A. Afkhami, Anal. Methods 7, 428 (2015)

    Article  CAS  Google Scholar 

  59. B. Pan, D. Cui, Y. Sheng, C. Ozkan, F. Gao, R. He, Q. Li, P. Xu, T. Huang, Cancer Res. 67, 8156 (2007)

    Article  CAS  PubMed  Google Scholar 

  60. O. Veiseh, J.W. Gunn, M. Zhang, Adv. Drug Deliv. Rev. 62, 284 (2010)

    Article  CAS  PubMed  Google Scholar 

  61. Y.w. Jun, J.H. Lee, J. Cheon, Angew. Chem. Int. Ed. 47, 5122 (2008)

  62. L. Wang, K. Neoh, E. Kang, B. Shuter, S.C. Wang, Adv. Funct. Mater. 19, 2615 (2009)

    Article  CAS  Google Scholar 

  63. E. Tombácz, R. Turcu, V. Socoliuc, L. Vékás, Biochem. Biophys. Res. Commun. 468, 442 (2015)

    Article  CAS  PubMed  Google Scholar 

  64. H. Shen, B. Liu, Q. Xiang, C. Wang, S.Q. Mao, RSC Adv. 6, 81330 (2016)

    Article  CAS  Google Scholar 

  65. P. Yáñez-Sedeño, S. Campuzano, J.M. Pingarrón, Anal. Chim. Acta 1, 1 (2017)

    Article  CAS  Google Scholar 

  66. A. Zamora-Gálvez, A. Ait-Lahcen, L.A. Mercante, E. Morales-Narváez, A. Amine, A. Merkoçi, Anal. Chem. 88, 3578 (2016)

    Article  CAS  PubMed  Google Scholar 

  67. R. Ahmad, N.B.W. Griffete, A. Lamouri, N. Felidj, M.M. Chehimi, C. Mangeney, Chem. Mater. 27, 5464 (2015)

    Article  CAS  Google Scholar 

  68. S. Ansari, M. Karimi, Talanta 164, 612 (2017)

    Article  CAS  PubMed  Google Scholar 

  69. T. Kubo, K. Otsuka, TrAC Trend. Anal. Chem. 81, 102 (2016)

    Article  CAS  Google Scholar 

  70. N. Griffete, J. Fresnais, A. Espinosa, C. Wilhelm, A. Bée, C. Ménager, Nanoscale 7, 18891 (2015)

    Article  CAS  PubMed  Google Scholar 

  71. J. Wackerlig, R. Schirhagl, Anal. Chem. 88, 250 (2015)

    Article  CAS  PubMed  Google Scholar 

  72. H. Jiang, D. Jiang, J. Shao, X. Sun, Biosens. Bioelectron. 75, 411 (2016)

    Article  CAS  PubMed  Google Scholar 

  73. E. Abdollahi, M. Abdouss, A. Mohammadi, RSC Adv. 6, 39095 (2016)

    Article  CAS  Google Scholar 

  74. T. Madrakian, A. Afkhami, H. Mahmood-Kashani, M. Ahmadi, Talanta 105, 255 (2013)

    Article  CAS  PubMed  Google Scholar 

  75. T. Madrakian, M. Ahmadi, A. Afkhami, M. Soleimani, Analyst 138, 4542 (2013)

    Article  CAS  PubMed  Google Scholar 

  76. R. Sedghi, M. Yassari, B. Heidari, Colloids Surf B Biointerfaces 162, 154 (2018)

    Article  CAS  PubMed  Google Scholar 

  77. L.L. Wu, R.P. Liang, J. Chen, J.D. Qiu, Electrophoresis 39, 356 (2018)

    Article  CAS  PubMed  Google Scholar 

  78. M. Hassanzadeh, M. Ghaemy, New J. Chem. 41, 2277 (2017)

    Article  CAS  Google Scholar 

  79. A.H. Lu, E.E.L. Salabas, F. Schüth, Angew. Chem. Int. Ed. 46, 1222 (2007)

    Article  CAS  Google Scholar 

  80. N.M. Mahmoodi, F. Najafi, A. Neshat, Ind. Crops Prod. 42, 119 (2013)

    Article  CAS  Google Scholar 

  81. H.M. Fatatry, W.M. Osman, Int. J. Adv. Res. Chem. Sci. 1, 47 (2014)

    Google Scholar 

  82. T. Madrakian, A. Afkhami, M.A. Zolfigol, M. Ahmadi, N. Koukabi, Nano-Micro Lett. 4, 57 (2012)

    Article  CAS  Google Scholar 

  83. C. Gonzato, M. Courty, P. Pasetto, K. Haupt, Adv. Funct. Mater. 21, 3947 (2011)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  85. A. Patterson, Phys. Rev. 56, 978 (1939)

    Article  CAS  Google Scholar 

  86. H. Feng, N. Wang, L. Yuan, J. Li, Q. Cai, Sens. Actuators B Chem. 195, 266 (2014)

    Article  CAS  Google Scholar 

  87. T.P. Lee, B. Saad, W.S. Khayoon, B. Salleh, Talanta 88, 129 (2012)

    Article  CAS  PubMed  Google Scholar 

  88. C. Basheer, G.C. Han, M.H. Toh, K.L. Hian, Anal. Chem. 79, 6845 (2007)

    Article  CAS  PubMed  Google Scholar 

  89. K.Y. Foo, B.H. Hameed, Chem. Eng. J. 156, 2 (2010)

    Article  CAS  Google Scholar 

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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.

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Authors and Affiliations

  1. Electroanalytical Chemistry Laboratory, Department of Chemistry, Faculty of Sciences, Azarbaijan Shahid Madani University, Tabriz, 53714-161, Iran

    Biuck Habibi & Shiva Rostamkhani

  2. Department of Pharmaceutical Nanotechnology, Zanjan Pharmaceutical Nanotechnology Research Center (ZPNRC), School of Pharmacy, Zanjan University of Medical Sciences, Zanjan, 45139-56184, Iran

    Mehrdad Hamidi

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Habibi, B., Rostamkhani, S. & Hamidi, M. Magnetic molecularly imprinted polymer nanoparticles for dispersive micro solid-phase extraction and determination of buprenorphine in human urine samples by HPLC-FL. J IRAN CHEM SOC 15, 1569–1580 (2018). https://doi.org/10.1007/s13738-018-1355-6

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