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
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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).
Keywords:Supercritical carbon dioxide;3-(Trimethoxysilyl) propyl methacrylate;Plasma technology functionalization;Genotoxin removal;Surface imprinting technique
- Pennington J, Cohen RD, Tian Y, Boulineau F, J. Pharm. Biomed. Anal., 114, 488 (2015)
- 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.
- Contrera JF, Regul. Toxicol. Pharmacol., 59, 133 (2011)
- Siew WE, Livingston AG, Ates C, Merschaert A, Sep. Purif. Technol., 102, 1 (2013)
- Szekely G, Gil M, Sellergren B, Heggie W, Ferreira FC, Green Chem., 15, 210 (2013)
- Degerman M, Jakobsson N, Nilsson B, Chem. Eng. Technol., 31(6), 875 (2008)
- European Medicines Agency, doc. ref. EMEA/CHMP/QWP/251334/2006.
- Raman NVVSS, Prasad AVSS, Reddy KR, J. Pharm. Biomed. Anal., 55, 662 (2011)
- Raillard SP, Org. Process Res. Dev., 14, 946 (2010)
- Szekely G, Bandarra J, Heggie W, Ferreira FC, Sellergren B, Sep. Purif. Technol., 86, 190 (2012)
- Del Blanco SG, Donato L, Drioli E, Sep. Purif. Technol., 87, 40 (2012)
- Shamsipur M, Fasihi J, Ashtari K, Anal. Chem., 79, 7116 (2007)
- Milja TE, Prathish KP, Rao TP, J. Hazard. Mater., 188(1-3), 384 (2011)
- He C, Long Y, Pan J, Li K, Liu F, J. Biochem. Biophys. Methods, 70, 133 (2007)
- Zhao WH, Sheng N, Zhu R, Wei FD, Cal Z, Zhai MJ, Du SH, Hu Q, J. Hazard. Mater., 179(1-3), 223 (2010)
- Yu B, Tian C, Cong HL, Xu T, J. Mater. Sci., 51(11), 5240 (2016)
- Lu CM, Li H, Xu MM, Wang SS, Li G, Zhong W, Qin SY, Sep. Sci. Technol., 50(14), 2124 (2015)
- Li J, Zhang Z, Xu S, Chen L, Zhou N, Xiong H, Peng H, J. Mater. Chem., 21, 19267 (2011)
- Gao DM, Zhang ZP, Wu MH, Xie CG, Guan GJ, Wang DP, J. Am. Chem. Soc., 129(25), 7859 (2007)
- Liu R, Guan G, Wang S, Zhang Z, Analyst, 136, 184 (2011)
- Ngo VG, Bressy C, Leroux C, Margaillan A, Polymer, 50(14), 3095 (2009)
- Hair ML, Guzonas D, Boils D, Macromolecules, 3, 341 (1991)
- Han L, Mao Z, Wu J, Guo Y, Ren T, Gao C, Biomaterials, 34, 975 (2013)
- Hansson S, Trouillet V, Tischer T, Goldmann AS, Carlmark A, Barner-Kowollik C, Malmstrom E, Biomacromolecules, 14(1), 64 (2013)
- Basuki JS, Esser L, Zetterlund PB, Whittaker MR, Boyer C, Davis TP, Macromolecules, 46(15), 6038 (2013)
- Barroso T, Viveiros R, Temtem M, Casimiro T, Rego AMBD, Aguiar-Ricardo A, ACS Macro Lett., 1, 356 (2012)
- da Silva MS, Nobrega FL, Aguiar-Ricardo A, Cabrita EJ, Casimiro T, J. Supercrit. Fluids, 58(1), 150 (2011)
- da Silva MS, Viveiros R, Coelho MB, Aguiar-Ricardo A, Casimiro T, Chem. Eng. Sci., 68(1), 94 (2012)
- Martins ANC, Simeonov SP, Frija LMT, Viveiros R, Lourenco A, da Silva MS, Casimiro T, Afonso CAM, Ind. Crop. Prod., 60, 226 (2014)
- Park EJ, Kim WS, Hwang HS, Park C, Lim KT, Macromol. Symp., 249-250, 196 (2007)
- Stojanovic D, Orlovic A, Markovic S, Radmilovic V, Uskokovic PS, Aleksic R, J. Mater. Sci., 44(23), 6223 (2009)
- Prasad BB, Banerjee S, React. Funct. Polym., 55(2), 159 (2003)
- Prasad BB, Banerjee S, Chromatographia, 55, 171 (2002)
- Reddy U, Hussain MK, Bobbarala V, Penumajji S, Int. J. Pharm., 2, 453 (2011)
- Huchon G, Magnussen H, Chuchalin A, Dymek L, Gonod FB, Bousquet J, Respir. Med., 103, 41 (2009)
- Meltzer EO, Jacobs RL, LaForce CF, Kelley CL, Dunbar SA, Tantry SK, Allergy Asthma Proc., 33, 249 (2012)
- Moisan M, Zakrzewski Z, J. Phys. D-Appl. Phys., 24, 1025 (1991)
- 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).
- Casimiro T, Banet-Osuna AM, Ramos AM, da Ponte MN, Aguiar-Ricardo A, Eur. Polym. J., 41, 1947 (2005)
- Freris I, Cristofori D, Riello P, Benedetti A, J. Colloid Interface Sci., 331(2), 351 (2009)
- Bourgeatlami E, Espiard P, Guyot A, Polymer, 36(23), 4385 (1995)
- Pardal F, Lapinte V, Robin JJ, J. Polym. Sci. A: Polym. Chem., 47(18), 4617 (2009)
- Gupta S, Ramamurthy PC, Madras G, Polym. Chem., 2, 221 (2011)
- Stojanovic D, Orlovic A, Glisic SB, Markovic S, Radmilovic V, Uskokovic PS, Aleksic R, J. Supercrit. Fluids, 52(3), 276 (2010)
- Andreozzi L, Castelvetro V, Ciardelli G, Corsi L, Faetti M, Fatarella E, Zulli F, J. Colloid Interface Sci., 289(2), 455 (2005)
- Syu M, Deng J, Nian Y, Anal. Chim. Acta, 504, 167 (2004)
- Wang HY, Xia SL, Sun H, Li YK, Cao SK, Kobayashi T, J. Chromatogr. B, 804, 127 (2004)
- Chapuis F, Pichon V, Lanza F, Sellergren B, Hennion MC, J. Chromatogr. B, 804, 93 (2004)
- Jodlbauer J, Maier NM, Lindner W, J. Chromatogr. A, 945, 45 (2002)
- Vallano PT, Remcho VT, J. Chromatogr. A, 888, 87 (2000)
- Zhu R, Zhao W, Zhai M, Wei F, Cai Z, Sheng N, Hu Q, Anal. Chim. Acta, 658, 209 (2010)
- Szekely G, Fritz E, Bandarra J, Heggie W, Sellergren B, J. Chromatogr. A, 1240, 52 (2012)