Aqueous biphasic systems composed of ionic liquids and sodium carbonate as enhanced routes for the extraction of tetracycline

Biotechnology Progress

Volumn 29, Issue 3, 2013, Pages 645-654

  Marques, Carlos F C ^a   Mourão, Teresa ^a   Neves, Catarina M S S ^a   Lima, Álvaro S ^b   Boal Palheiros, Isabel ^a   Coutinho, João A P ^a   Freire, Mara G ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b TIRADENTES UNIVERSITY   (Brazil)

Author keywords

Aqueous two phase system; Extraction; Ionic liquid; Sodium carbonate; Tetracycline

Indexed keywords

ALKYL SIDE-CHAIN LENGTHS; ALTERNATIVE APPROACH; AQUEOUS BIPHASIC SYSTEM; AQUEOUS TWO PHASE SYSTEM; DOWNSTREAM-PROCESSING; SINGLE-STEP EXTRACTIONS; SODIUM CARBONATE; TETRACYCLINE;

ANTIBIOTICS; CHAIN LENGTH; CHLORINE COMPOUNDS; EXTRACTION; ISOMERS; PHASE DIAGRAMS; POSITIVE IONS; SODIUM BICARBONATE; SOLVENT EXTRACTION; STEREOCHEMISTRY;

IONIC LIQUIDS;

CARBONIC ACID DERIVATIVE; CATION; IMIDAZOLE DERIVATIVE; IONIC LIQUID; SODIUM CARBONATE; TETRACYCLINE;

ARTICLE; BIOTECHNOLOGY; CHEMICAL MODEL; CHEMISTRY; FRACTIONATION; ISOLATION AND PURIFICATION; ISOMERISM; METHODOLOGY; PH; REGRESSION ANALYSIS;

BIOTECHNOLOGY; CARBONATES; CATIONS; CHEMICAL FRACTIONATION; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; IONIC LIQUIDS; ISOMERISM; LEAST-SQUARES ANALYSIS; MODELS, CHEMICAL; TETRACYCLINE;

BACTERIA (MICROORGANISMS);

EID: 84879263798     PISSN: 87567938     EISSN: 15206033     Source Type: Journal    
DOI: 10.1002/btpr.1708     Document Type: Article

References (64)

1. Albertsson PA. Partitioning of proteins in liquid polymer-polymer two-phase systems. Nature. 1958;182:709-711.
2. Hatti-Kaul R. Aqueous two-phase systems. A general overview. Mol Biotechnol. 2001;19:269-277.
3. Freire MG, Cláudio AFM, Araújo JMM, Coutinho JAP, Marrucho IM, Canongia Lopes JN, Rebelo LPN. Aqueous biphasic systems: a boost brought about by using ionic liquids. Chem Soc Rev. 2012;41:4966-4995.
4. Gutowski KE, Broker GA, Willauer HD, Huddleston JG, Swatloski RP, Holbrey JD, Rogers RD. Controlling the aqueous miscibility of ionic liquids: aqueous biphasic systems of water-miscible ionic liquids and water-structuring salts for recycle, metathesis, and separations. J Am Chem Soc. 2003;125:6632-6633.
5. Bridges NJ, Gutowski KE, Rogers RD. Investigation of aqueous biphasic systems formed from solutions of chaotropic salts with kosmotropic salts (salt-salt ABS). Green Chem. 2007;9:177-183.
6. Sadeghi R, Golabiazar R, Shekaari H. The salting-out effect and phase separation in aqueous solutions of tri-sodium citrate and 1-butyl-3-methylimidazolium bromide. J Chem Thermodyn. 2010;42:441-453.
7. Mourão T, Cláudio AFM, Boal-Palheiros I, Freire MG, Coutinho JAP. Evaluation of the impact of phosphate salts on the formation of ionic-liquid-based aqueous biphasic systems. J Chem Thermodyn. 2012;54:398-405.
8. Freire MG, Neves CMSS, Canongia Lopes JN, Marrucho IM, Coutinho JAP, Rebelo LPN. Impact of self-aggregation on the formation of ionic-liquid-based aqueous biphasic systems. J Phys Chem B. 2012;116:7660-7668.
9. Passos H, Ferreira AR, Cláudio AFM, Coutinho JAP, Freire MG. Characterization of aqueous biphasic systems composed of ionic liquids and a citrate-based biodegradable salt. Biochem Eng J. 2012;67:68-72.
10. Freire MG, Pereira, JFB, Francisco M, Rodríguez H, Rebelo LPN, Rogers RD, Coutinho JAP. Insight into the interactions that control the phase behaviour of new aqueous biphasic systems composed of polyethylene glycol polymers and ionic liquids. Chem Eur J. 2012;18:1831-1839.
11. Zafarani-Moattar MT, Hamzehzadeh S, Nasiri S. A new aqueous biphasic system containing polypropylene glycol and a water-miscible ionic liquid. Biotechnol Prog. 2012;28:146-156.
12. Domínguez-Pérez M, Tomé LIN, Freire MG, Marrucho IM, Cabeza O, Coutinho JAP. Extraction of biomolecules using aqueous biphasic systems formed by ionic liquids and aminoacids. Sep Purif Technol. 2010;72:85-91.
13. Freire MG, Louros CLS, Rebelo LPN, Coutinho JAP. Aqueous biphasic systems composed of a water-stable ionic liquid+carbohydrates and their applications. Green Chem. 2011;13:1536-1545.
14. Abraham MH, Zissimos AM, Huddleston JG, Willauer HD, Rogers RD, Acree WE Jr. Some novel liquid partitioning systems: water-ionic liquids and aqueous biphasic systems. Ind Eng Chem Res. 2003;42:413-418.
15. Oliveira FS, Freire MG, Pratas MJ, Pauly J, Daridon JL, Marrucho IM, Coutinho JAP. Solubility of adamantane in phosphonium-based ionic liquids. J Chem Eng Data. 2010;55:662-665.
16. Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R. Solubility of carbohydrates in ionic liquids. Energy Fuel. 2010;24:737-745.
17. Seddon KR. Ionic liquids: a taste of the future. Nat Mater. 2003;2:363-365.
18. Huddleston JG, Rogers RD. Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction. Chem Commun. 1998;1765-1766.
19. Zhao H, Xia S, Ma P. Use of ionic liquids as 'green' solvents for extractions. J Chem Technol Biotechnol. 2005;80:1089-1096.
20. Freire MG, Teles ARR, Canongia Lopes JN, Rebelo LPN, Marrucho IM, Coutinho JAP, Partition coefficients of alkaloids in biphasic ionic-liquid-aqueous systems and their dependence on the Hofmeister series. Sep Sci Technol. 2012;47:284-291.
21. Freire MG, Neves CMSS, Marrucho IM, Canongia Lopes JN, Rebelo LPN, Coutinho JAP. High-performance extraction of alkaloids using aqueous two-phase systems with ionic liquids. Green Chem. 2010;2:1715-1718.
22. Tomé LIN, Catambas VR, Teles RR, Freire MG, Marrucho IM, Coutinho JAP. Tryptophan extraction using hydrophobic ionic liquids. Sep Purif Technol. 2010;72:167-173.
23. Ventura SPM, Neves CMSS, Freire MG, Marrucho IM, Oliveira J, Coutinho JAP. Evaluation of anion influence on the formation and extraction capacity of ionic-liquid-based aqueous biphasic systems. J Phys Chem B. 2009;113:9304-9310.
24. Li S, He C, Liu H, Li K, Liu F. Ionic liquid-based aqueous two-phase system, a sample pretreatment procedure prior to high-performance liquid chromatography of opium alkaloids. J Chromatogr B. 2005;826:58-62.
25. Cláudio AFM, Freire MG, Freire CSR, Silvestre AJD, Coutinho JAP. Extraction of vanillin using ionic-liquid-based aqueous two-phase systems. Sep Purif Technol. 2010;75:39-47.
26. Cláudio AFM, Ferreira AM, Freire CSR, Silvestre AJD, Freire MG, Coutinho JAP. Optimization of the gallic acid extraction using ionic-liquid-based aqueous two-phase systems. Sep Purif Technol. 2012;97:142-149.
27. Zafarani-Moattar MT, Hamzehzadeh S. Partitioning of amino acids in the aqueous biphasic system containing the water-miscible ionic liquid 1-butyl-3-methylimidazolium bromide and the water-structuring salt potassium citrate. Biotechnol Prog. 2011;27:986-997.
28. Du Z, Yu YL, Wang JH. Extraction of proteins from biological fluids by use of an ionic liquid/aqueous two-phase system. Chem Eur J. 2007;13:2130-2137.
29. Tzeng YP, Shen CW, Yu T. Liquid-liquid extraction of lysozyme using a dye-modified ionic liquid. J Chromatogr A. 2008;1193:1-6.
30. Ventura SPM, Barros RLF, Barbosa JMP, Soares CMF, Lima AS, Coutinho JAP. Production and purification of an extracellular lipolytic enzyme using ionic liquid-based aqueous two-phase systems. Green Chem. 2012;14:734-740.
31. Passos H, Sousa ACA, Ramiro Pastorinho M, Nogueira AJA, Rebelo LPN, Coutinho JAP, Freire MG. Ionic-liquid-based aqueous biphasic systems for improved detection of bisphenol A in human fluids. Anal Methods. 2012;4:2664-2667.
32. Li C-X, Han J, Wang Y, Yan Y-S, Xu X-H, Pan J-M. Extraction and mechanism investigation of trace roxithromycin in real water samples by use of ionic liquid-salt aqueous two-phase system. Anal Chim Acta. 2009;653:178-183.
33. Jiang Y, Xia H, Guo C, Mahmood I, Liu H. Phenomena and mechanism for separation and recovery of penicillin in ionic liquids aqueous solution. Ind Eng Chem Res. 2007;46:6303-6312.
34. Han J, Wang Y, Kang W, Li C, Yan Y, Pan J, Xie X. Phase equilibrium and macrolide antibiotics partitioning in real water samples using a two-phase system composed of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate and an aqueous solution of an inorganic salt. Microchim Acta. 2010;169:15-22.
35. Bienkowski PR, Lee DD, Byers CH. Evaluation of separation and purification processes in the antibiotic industry. Appl Biochem Biotechnol. 1988;18:261-273.
36. Mahajan GB, Balachandran L. Antibacterial agents from actinomycetes-a review. Front Biosci. 2012;4:240-253.
37. Duggar BM, Aureomycin: a product of the continuing search for new antibiotics. Ann NY Acad Sci. 1948;51:177-181.
38. Neidleman SL. Tetracylines in antibiotics, isolation, separation, and purification. J Chromatogr Library. 1978;15:715-759.
39. Darken MA, Berenson H, Shirk RJ, Sjolander NO. Production of tetracycline by Streptomyces aureofaciens in synthetic media. Appl Microbiol. 1960;8:46-51.
40. Merchuk JC, Andrews BA, Asenjo JA. Aqueous two-phase systems for protein separation. Studies on phase inversion. J Chromatogr B. 1998;711:1-2.
41. Deive FJ, Rodriguez A, Marrucho IM, Rebelo LPN. Aqueous biphasic systems involving alkylsulfate-based ionic liquids. J Chem Thermodyn. 2011;43:1565-1572.
42. Neves CMSS, Freire MG, Coutinho JAP. Improved recovery of ionic liquids from contaminated aqueous streams using aluminium-based salts. RSC Adv. 2012;2:10882-10890.
43. Li Z, Pei Y, Liu L, Wan J. (Liquid+liquid) equilibria for (acetate-based ionic liquids+inorganic salts) aqueous two-phase systems. J Chem Thermodyn. 2010;42:932-937.
44. Louros CLS, Cláudio AFM, Neves CMSS, Freire MG, Marrucho IM, Pauly J, Coutinho JAP. Extraction of biomolecules using phosphonium-based ionic liquids+K3PO4 aqueous biphasic systems. Int J Mol Sci. 2010;11:1777-1791.
45. Pereira JFB, Vicente F, Santos-Ebinuma VC, Araújo JM, Pessoa A, Freire MG, Coutinho JAP. Extraction of tetracycline from fermentation broth using aqueous two-phase systems composed of polyethylene glycol and cholinium-based salts. Proc Biochem. 2013; DOI:10.1016/j.procbio.2013.02.025.
46. Ventura SPM, Sousa SG, Serafim LS, Lima AS, Freire MG, Coutinho JAP. Ionic liquid based aqueous biphasic systems with controlled pH: the ionic liquid cation effect. J Chem Eng Data. 2011;56:4253-4260.
47. Pei Y, Wang J, Liu L, Wu K, Zhao Y. Liquid-liquid equilibria of aqueous biphasic systems containing selected imidazolium ionic liquids and salts. J Chem Eng Data. 2007;52:2026-2031.
48. Shill K, Padmanabhan S, Xin Q, Prausnitz JM, Clark DS, Blanch HW. Ionic liquid pretreatment of cellulosic biomass: enzymatic hydrolysis and ionic liquid recycle. Biotechnol Bioeng. 2011;108:511-520.
49. Yu C, Han J, Hu S, Yan Y, Li Y. Phase diagrams for aqueous two-phase systems containing the 1-ethyl-3-methylimidazolium tetrafluoroborate/1-propyl-3-methylimidazolium tetrafluoroborate and trisodium phosphate/sodium sulfite/sodium dihydrogen phosphate at 298.15 K: experiment and correlation. J Chem Eng Data. 2011;56:3577-3584.
50. Freire MG, Carvalho PJ, Gardas RL, Marrucho IM, Santos LMNBF, Coutinho JAP. Mutual solubilities of water and the [Cnmim][Tf2N] hydrophobic ionic liquids. J Phys Chem B. 2008;112:1604-1610.
51. Online database of chemicals from around the world. Available at: http://www.chemblink.com/. Accessed on July 20, 2012.
52. Neves CMSS, Ventura SPM, Freire MG, Marrucho IM, Coutinho JAP. Evaluation of cation influence on the formation and extraction capability of ionic-liquid-based aqueous biphasic systems. J Phys Chem B. 2009;113:5194-5199.
53. Freire MG, Neves CMSS, Shimizu K, Bernardes CES, Marrucho IM, Coutinho JAP, Canongia Lopes JN, Rebelo LPN. J Phys Chem B. 2010;114:15925-15934.
54. Qiang Z, Adams C. Potentiometric determination of acid dissociation constants (pKa) for human and veterinary antibiotics. Water Res. 2004;38:2874-2890.
55. Liu Q, Yu J, Li W, Hu X, Xia H, Liu H, Yang P. Partitioning behavior of penicillin G in aqueous two phase system formed by ionic liquids and phosphate. Sep Purif Technol. 2006;41:2849-2858.
56. Han J, Wang Y, Yu C-L, Yan Y-S, Xie X-Q. Extraction and determination of chloramphenicol in feed water, milk, and honey samples using an ionic liquid/sodium citrate aqueous two-phase system coupled with high-performance liquid chromatography. Anal Bioanal Chem. 2011;399:1295-1304.
57. Wang Y, Han J, Xie X-Q, Li C-X. Extraction of trace acetylspiramycin in real aqueous environments using aqueous two-phase system of ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate and phosphate. Cent Eur J Chem. 2010;8:1185-1191.
58. Freire MG, Neves CMSS, Marrucho IM, Coutinho JAP, Fernandes AM. Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium-based ionic liquids. J Phys Chem A. 2010;114:3744-3749.
59. Mokhtarani B, Karimzadeh R, Amini MH. Partitioning of ciprofloxacin in aqueous two-phase system of poly(ethylene glycol) and sodium sulphate. Biochem Eng J. 2008;38:241-247.
60. Stolls J. Sorption of veterinary pharmaceuticals in soils: a review. Environ Sci Technol. 2001;35:3397-3406.
61. Bora MM, Borthakur S, Rao PC, Dutta NN. Aqueous two-phase partitioning of cephalosporin antibiotics: effect of solute chemical nature. Sep Purif Technol. 2005;45:153-156.
62. Viana Marques DA, Pessoa-Junior A, Lima-Filho JL, Converti A, Perego P, Porto ALF. Extractive fermentation of clavulanic acid by Streptomyces DAUFPE 3060 using aqueous two-phase system. Biotechnol Prog. 2011;27:95-103.
63. Fadnavis NW, Satyavathi B, Deshpande AA. Reverse micellar extraction of antibiotics from aqueous solutions. Biotechnol Prog. 1997;13:503-505.
64. Ren Z, Zhang W, Lv Y, Li J. Simultaneous extraction and concentration of penicillin G by hollow fiber renewal liquid membrane. Biotechnol Prog. 2009;25:468-475.