Effect of an ionic liquid on vancomycin crystallization

Geon Soo Ha; Jin-Hyun Kim

Korean Journal of Chemical Engineering, Vol.32, No.4, 576-582, April, 2015

DOI10.1007/s11814-015-0014-1 Export Citation

Effect of an ionic liquid on vancomycin crystallization

Geon Soo Ha, and Jin-Hyun Kim^†

Department of Chemical Engineering, Kongju National University, Cheonan 330-717, Korea

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We first developed a vancomycin crystallization process using an ionic liquid (IL) and improved the crystallization efficiency by optimization of crystallization conditions (pH, conductivity, solution of distilled water and IL/acetone ratio, crystallization temperature, IL concentration). We also investigated the effect of major process parameters on crystallization, using an electron microscope, and identified morphology by XRD analysis. Using ILs (1-butyl-3- methylimidazolium tetrafluoroborate ([BMIm][BF4]), 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIm] [PF6])), vancomycin crystals were successfully formed under the optimal crystallization conditions: pH 4.5; conductivity, 10 mS/cm; solution of distilled water and IL/acetone ratio, 1 : 3.5 (v/v); crystallization temperature, 10 oC; IL concentration, 20% (v/v). When using an IL ([BMIm][BF4]), the time required for crystallization in the existing crystallization methods (~24 hr) was dramatically decreased (~9 hr) and high-quality vancomycin crystals were successfully formed.

Keywords:Vancomycin;Crystallization;Ionic Liquid;Process Parameter;Investigation

[References]

Yan H, Qi D, Cheng X, Song Z, Li W, He B, J. Antibiot., 51, 750 (1998)
Griffith RS, J. Antimicrob. Chemoter., 14, 1 (1984)
Kim SI, Han CY, Jung HS, Lee JS, Ok SY, Kim SC, Korean J. Anesthesiol., 51, 727 (2006)
United States Pharmacopoeia (USP 29), Vancomycin hydrochloride, United State Pharmacopeial Convention, Inc. (2006). (2006)
Javadzadeh Y, Mohammadi A, Khoei N, Nokhodchi A, Acta Pharmacol. Sin., 59, 187 (2009)
Kim SI, Jeong KE, Jeong SY, Kim CU, J. Korean Oil Chem. Soc., 25, 232 (2008)
Kim WS, Lee EK, Korean J. Biotechnol. Bioeng., 20, 164 (2005)
Kim KJ, Prospect. Ind. Chem., 4(4), 1 (2001)
Lee JY, Lee KH, Chae HJ, Kim JH, Korean J. Chem. Eng., 27(5), 1538 (2010)
Kim YN, Lee JY, Kim JH, Process Biochem., 46, 2068 (2011)
Kwak EA, Kim SJ, Kim JH, Korean J. Chem. Eng., 29(11), 1487 (2012)
Kroon MC, Toussaint VA, Shariati A, Florusse LJ, Spronsen JV, Witkamp GJ, Peters CJ, Green Chem., 10, 333 (2008)
Tang B, Bi W, Tian M, Row KH, J. Chromatogr. B, 904, 1 (2012)
Li XX, Xu XD, Dan YY, Zhang ML, Crystallogr. Rep., 54, 1285 (2009)
Judge RA, Takahashi S, Longenecker KL, Fry EH, Zapatero CA, Chi ML, Cryst. Growth Des., 9, 3463 (2009)
Wang Z, Fang W, Li Y, Zhang J, Gu Q, Korean J. Chem. Eng., 31(6), 919 (2014)
Hebel D, Urdingen M, Hekmat D, Botz DW, Cryst. Growth Des., 13, 2499 (2013)
Pusey ML, Paley MS, Turner MB, Rogers RD, Cryst. Growth Des., 7, 787 (2007)
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Claudius JS, Neau SH, Int. J. Pharm., 168, 41 (1998)
Kim SJ, Kim JH, Korean J. Chem. Eng., 10.1007/s11814-014-0222-0. (2014)
Freire MG, Santos LMNBF, Fernandes AM, Coutinho JAP, Marrucho IM, Fluid Phase Equilib., 261(1-2), 449 (2007)
Garcia-Ruiz JM, Gonzalez-Ramirez LA, Gavira JA, Otalora F, Acta Crystallogr. Sect. D-Biol. Crystallogr., 58, 1638 (2002)

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[1] Yan H, Qi D, Cheng X, Song Z, Li W, He B, J. Antibiot., 51, 750 (1998)

[2] Griffith RS, J. Antimicrob. Chemoter., 14, 1 (1984)

[3] Kim SI, Han CY, Jung HS, Lee JS, Ok SY, Kim SC, Korean J. Anesthesiol., 51, 727 (2006)

[4] United States Pharmacopoeia (USP 29), Vancomycin hydrochloride, United State Pharmacopeial Convention, Inc. (2006). (2006)

[5] Javadzadeh Y, Mohammadi A, Khoei N, Nokhodchi A, Acta Pharmacol. Sin., 59, 187 (2009)

[6] Kim SI, Jeong KE, Jeong SY, Kim CU, J. Korean Oil Chem. Soc., 25, 232 (2008)

[7] Kim WS, Lee EK, Korean J. Biotechnol. Bioeng., 20, 164 (2005)

[8] Kim KJ, Prospect. Ind. Chem., 4(4), 1 (2001)

[9] Lee JY, Lee KH, Chae HJ, Kim JH, Korean J. Chem. Eng., 27(5), 1538 (2010)

[10] Kim YN, Lee JY, Kim JH, Process Biochem., 46, 2068 (2011)

[11] Kwak EA, Kim SJ, Kim JH, Korean J. Chem. Eng., 29(11), 1487 (2012)

[12] Kroon MC, Toussaint VA, Shariati A, Florusse LJ, Spronsen JV, Witkamp GJ, Peters CJ, Green Chem., 10, 333 (2008)

[13] Tang B, Bi W, Tian M, Row KH, J. Chromatogr. B, 904, 1 (2012)

[14] Li XX, Xu XD, Dan YY, Zhang ML, Crystallogr. Rep., 54, 1285 (2009)

[15] Judge RA, Takahashi S, Longenecker KL, Fry EH, Zapatero CA, Chi ML, Cryst. Growth Des., 9, 3463 (2009)

[16] Wang Z, Fang W, Li Y, Zhang J, Gu Q, Korean J. Chem. Eng., 31(6), 919 (2014)

[17] Hebel D, Urdingen M, Hekmat D, Botz DW, Cryst. Growth Des., 13, 2499 (2013)

[18] Pusey ML, Paley MS, Turner MB, Rogers RD, Cryst. Growth Des., 7, 787 (2007)

[19] Lee JW, Jung YT, Suh JW, Lee KS, US Patent, 7,018,814 (2006). (2006)

[20] Food US, Drug Administration, Vancomycin solubility study, Report to office of generic drugs; http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/ucm082291.pdf (2008). (2008)

[21] Claudius JS, Neau SH, Int. J. Pharm., 168, 41 (1998)

[22] Kim SJ, Kim JH, Korean J. Chem. Eng., 10.1007/s11814-014-0222-0. (2014)

[23] Freire MG, Santos LMNBF, Fernandes AM, Coutinho JAP, Marrucho IM, Fluid Phase Equilib., 261(1-2), 449 (2007)

[24] Garcia-Ruiz JM, Gonzalez-Ramirez LA, Gavira JA, Otalora F, Acta Crystallogr. Sect. D-Biol. Crystallogr., 58, 1638 (2002)