화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.54, 341-349, October, 2017
Green strategy to produce large core.shell affinity beads for gravity-driven API purification processes
E-mail:
In this work, Molecular Imprinted Polymers (MIPs)-layered silica beads which have affinity for a model pharmaceutical impurity, acetamide (ACET) were developed using supercritical carbon dioxide (scCO2) technology. Silica beads were first functionalized using two different green strategies, grafting to (MPS/ EtOH in scCO2) and grafting from (plasma technology). These core beads were then used as seed particles in the synthesis, in scCO2 of a MIP layer. Dynamic binding tests were performed in order to evaluate the affinity of the resulting silica core - MIP shell beads to ACET and the efficiency of its removal from an active pharmaceutical ingredient - Beclomomethasone dipropionate (API) crude mixture. ACET was preferentially retained over analogue molecules, benzamide (BENZ) and pivalamide (PIV). The core-shell MIP beads were packed in a SPE column (396.5 mg in a 3 mL SPE tube) and evaluated as a potential gravity-driven purification device, enabling the removal of 100% of ACET whilst losing only 0.37% of API from a model mixture solution-10 mL of ACET and API (0.25 mg mL-1 + 3.5 mg mL-1).
  1. Pennington J, Cohen RD, Tian Y, Boulineau F, J. Pharm. Biomed. Anal., 114, 488 (2015)
  2. Committee for Medicinal Products for Human Use (CHMP), Questions and answers on the Guideline on the limits of genotoxic impurities. European Medicines Agency. Available at: http://www.ema.europa.eu/docs/en_GB/ document_library/Scientific_guideline/2009/09/WC500002907.pdf.
  3. Contrera JF, Regul. Toxicol. Pharmacol., 59, 133 (2011)
  4. Siew WE, Livingston AG, Ates C, Merschaert A, Sep. Purif. Technol., 102, 1 (2013)
  5. Szekely G, Gil M, Sellergren B, Heggie W, Ferreira FC, Green Chem., 15, 210 (2013)
  6. Degerman M, Jakobsson N, Nilsson B, Chem. Eng. Technol., 31(6), 875 (2008)
  7. European Medicines Agency, doc. ref. EMEA/CHMP/QWP/251334/2006.
  8. Raman NVVSS, Prasad AVSS, Reddy KR, J. Pharm. Biomed. Anal., 55, 662 (2011)
  9. Raillard SP, Org. Process Res. Dev., 14, 946 (2010)
  10. Szekely G, Bandarra J, Heggie W, Ferreira FC, Sellergren B, Sep. Purif. Technol., 86, 190 (2012)
  11. Del Blanco SG, Donato L, Drioli E, Sep. Purif. Technol., 87, 40 (2012)
  12. Shamsipur M, Fasihi J, Ashtari K, Anal. Chem., 79, 7116 (2007)
  13. Milja TE, Prathish KP, Rao TP, J. Hazard. Mater., 188(1-3), 384 (2011)
  14. He C, Long Y, Pan J, Li K, Liu F, J. Biochem. Biophys. Methods, 70, 133 (2007)
  15. Zhao WH, Sheng N, Zhu R, Wei FD, Cal Z, Zhai MJ, Du SH, Hu Q, J. Hazard. Mater., 179(1-3), 223 (2010)
  16. Yu B, Tian C, Cong HL, Xu T, J. Mater. Sci., 51(11), 5240 (2016)
  17. Lu CM, Li H, Xu MM, Wang SS, Li G, Zhong W, Qin SY, Sep. Sci. Technol., 50(14), 2124 (2015)
  18. Li J, Zhang Z, Xu S, Chen L, Zhou N, Xiong H, Peng H, J. Mater. Chem., 21, 19267 (2011)
  19. Gao DM, Zhang ZP, Wu MH, Xie CG, Guan GJ, Wang DP, J. Am. Chem. Soc., 129(25), 7859 (2007)
  20. Liu R, Guan G, Wang S, Zhang Z, Analyst, 136, 184 (2011)
  21. Ngo VG, Bressy C, Leroux C, Margaillan A, Polymer, 50(14), 3095 (2009)
  22. Hair ML, Guzonas D, Boils D, Macromolecules, 3, 341 (1991)
  23. Han L, Mao Z, Wu J, Guo Y, Ren T, Gao C, Biomaterials, 34, 975 (2013)
  24. Hansson S, Trouillet V, Tischer T, Goldmann AS, Carlmark A, Barner-Kowollik C, Malmstrom E, Biomacromolecules, 14(1), 64 (2013)
  25. Basuki JS, Esser L, Zetterlund PB, Whittaker MR, Boyer C, Davis TP, Macromolecules, 46(15), 6038 (2013)
  26. Barroso T, Viveiros R, Temtem M, Casimiro T, Rego AMBD, Aguiar-Ricardo A, ACS Macro Lett., 1, 356 (2012)
  27. da Silva MS, Nobrega FL, Aguiar-Ricardo A, Cabrita EJ, Casimiro T, J. Supercrit. Fluids, 58(1), 150 (2011)
  28. da Silva MS, Viveiros R, Coelho MB, Aguiar-Ricardo A, Casimiro T, Chem. Eng. Sci., 68(1), 94 (2012)
  29. Martins ANC, Simeonov SP, Frija LMT, Viveiros R, Lourenco A, da Silva MS, Casimiro T, Afonso CAM, Ind. Crop. Prod., 60, 226 (2014)
  30. Park EJ, Kim WS, Hwang HS, Park C, Lim KT, Macromol. Symp., 249-250, 196 (2007)
  31. Stojanovic D, Orlovic A, Markovic S, Radmilovic V, Uskokovic PS, Aleksic R, J. Mater. Sci., 44(23), 6223 (2009)
  32. Prasad BB, Banerjee S, React. Funct. Polym., 55(2), 159 (2003)
  33. Prasad BB, Banerjee S, Chromatographia, 55, 171 (2002)
  34. Reddy U, Hussain MK, Bobbarala V, Penumajji S, Int. J. Pharm., 2, 453 (2011)
  35. Huchon G, Magnussen H, Chuchalin A, Dymek L, Gonod FB, Bousquet J, Respir. Med., 103, 41 (2009)
  36. Meltzer EO, Jacobs RL, LaForce CF, Kelley CL, Dunbar SA, Tantry SK, Allergy Asthma Proc., 33, 249 (2012)
  37. Moisan M, Zakrzewski Z, J. Phys. D-Appl. Phys., 24, 1025 (1991)
  38. Tatarova E, Dias A, Henriques J, do Rego AMB, Ferraria AM, Abrashev MV, Luhrs CC, Phillips J, Dias FM, Ferreira CM, J. Phys. D Appl. Phys. 385501 (2014).
  39. Casimiro T, Banet-Osuna AM, Ramos AM, da Ponte MN, Aguiar-Ricardo A, Eur. Polym. J., 41, 1947 (2005)
  40. Freris I, Cristofori D, Riello P, Benedetti A, J. Colloid Interface Sci., 331(2), 351 (2009)
  41. Bourgeatlami E, Espiard P, Guyot A, Polymer, 36(23), 4385 (1995)
  42. Pardal F, Lapinte V, Robin JJ, J. Polym. Sci. A: Polym. Chem., 47(18), 4617 (2009)
  43. Gupta S, Ramamurthy PC, Madras G, Polym. Chem., 2, 221 (2011)
  44. Stojanovic D, Orlovic A, Glisic SB, Markovic S, Radmilovic V, Uskokovic PS, Aleksic R, J. Supercrit. Fluids, 52(3), 276 (2010)
  45. Andreozzi L, Castelvetro V, Ciardelli G, Corsi L, Faetti M, Fatarella E, Zulli F, J. Colloid Interface Sci., 289(2), 455 (2005)
  46. Syu M, Deng J, Nian Y, Anal. Chim. Acta, 504, 167 (2004)
  47. Wang HY, Xia SL, Sun H, Li YK, Cao SK, Kobayashi T, J. Chromatogr. B, 804, 127 (2004)
  48. Chapuis F, Pichon V, Lanza F, Sellergren B, Hennion MC, J. Chromatogr. B, 804, 93 (2004)
  49. Jodlbauer J, Maier NM, Lindner W, J. Chromatogr. A, 945, 45 (2002)
  50. Vallano PT, Remcho VT, J. Chromatogr. A, 888, 87 (2000)
  51. Zhu R, Zhao W, Zhai M, Wei F, Cai Z, Sheng N, Hu Q, Anal. Chim. Acta, 658, 209 (2010)
  52. Szekely G, Fritz E, Bandarra J, Heggie W, Sellergren B, J. Chromatogr. A, 1240, 52 (2012)