Membrane-assisted chiral resolution of pharmaceuticals: Ibuprofen separation by ultrafiltration using bovine serum albumin as chiral selector

Separation Science and Technology

Volumn 37, Issue 14, 2002, Pages 3227-3244

  Bowen, W Richard ^a   Nigmatullin, Rinat R ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Bovine serum albumin; Chiral resolution; Ibuprofen; Ultrafiltration

Indexed keywords

DRUG PRODUCTS; ORGANIC SOLVENTS; PH; POLARIZATION; PROTEINS; THERMODYNAMICS;

GEL FORMATION; OPTICAL RESOLUTION;

ULTRAFILTRATION;

ACETONITRILE; BOVINE SERUM ALBUMIN; IBUPROFEN; METHANOL;

ALBUMIN; PHARMACEUTICAL INDUSTRY; ULTRAFILTRATION;

ALKALINITY; ARTICLE; BINDING AFFINITY; CHIRAL CHROMATOGRAPHY; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; GELATION; HYDRODYNAMICS; MOLECULAR INTERACTION; OPTICAL RESOLUTION; PH; POLARIZATION; SEPARATION TECHNIQUE; THERMODYNAMICS; ULTRAFILTRATION;

EID: 0036401354     PISSN: 01496395     EISSN: None     Source Type: Journal    
DOI: 10.1081/SS-120006159     Document Type: Article

References (27)

1. Crossley, R. Chirality and Biological Activity of Drugs; CRC Press: London, 1995.
2. Sasaki, M. Importance of chirality in organophosphorous agrochemicals. In Chirality in Agrochemicals; Kurihara, N.; Miyamoto, J., Eds.; Wiley: New York, 1998; 46-93.
3. Van Eikeren, P. Commercial manufacture of chiral pharmaceuticals. In Chiral Separation: Application and Technology; Ahuja, S., Ed.; ASC: Washington, 1997; 9-35.
4. Drioli, E.; Giorno, L. Biocatalytic Membrane Reactors: Applications in Biotechnology and the Pharmaceutical Industry; Taylor and Francis Ltd.: London, 1999.
5. Brice, L.J.; Pirkle, W.H. Enantioselective transport through liquid membranes. In Chiral Separation: Application and Technology; Ahuja, S., Ed.; ASC: Washington, 1997; 309-334.
6. Bryjak, M.; Kozlowski, J.; Wieczorek, P.; Kafarsky, P. Enantioselective transport of amino-acid through supported chiral liquid membranes. J. Membr. Sci. 1993, 85 (2), 221-228.
7. Pickering, P.J.; Chaudhuri, J.B. Enantioselective extraction of (D)-phenylalanine from racemic (D/L)-phenylalanine using chiral emulsion liquid membranes. J. Membr. Sci. 1997, 127 (2), 115-130.
8. Newcomb, M.; Toner, J.L.; Helgeson, R.C.; Cram, D.J. Host-guest complexation. 20. Chiral recognition in transport as a molecular basis for a catalytic resolving machine. J. Am. Chem. Soc. 1979, 101, 4941-4947.
9. Aoki, T. Macromolecular design of permselective membranes. Prog. Polym. Sci. 1999, 24 (7), 951-993.
10. Krieg, H.M.; Breytenbach, J.C.; Keizer, K. Chiral resolution by β-cyclodextrin polymer-impregnated ceramic membranes. J. Membr. Sci. 2000, 164 (1-2), 177-185.
11. Mathew-Krotz, J.; Shea, K.J. Imprinted polymer membranes for the selective transport of targeted neutral molecules. J. Am. Chem. Soc. 1996, 118 (34), 8154-8155.
12. Dzgoev, A.; Haupt, K. Enantioselective molecularly imprinted polymers membranes. Chirality 1999, 11 (5-6), 465-469.
13. Lopez, J.L.; Matson, S.L. A multiphase/extractive enzyme membrane reactor for production of diltiazem chiral intermediate. J. Membr. Sci. 1997, 125 (1), 189-211.
14. Drioli, E.; Giorno, L. Biocatalytic membrane reactor: Applications and perspectives. Trends Biotechnol. 2000, 18 (8), 339-349.
15. Xin, J.-Y.; Li, S.-B.; Xu, Y.; Wang, L.-L. Enzymatic resolution of (S)-(+)-naproxen in a trapped aqueous-organic solvent biphase continuous reactor. Biotechnol. Bioeng. 2000, 68 (1), 78-83.
16. Poncet, S.; Random, J.; Rocca, J.L. Enantiomeric separation of tryptophan by ultrafiltration using the BSA solution system. Sep. Sci. Technol. 1997, 32 (12), 2029-2038.
17. Higuchi, A.; Ishida, Y.; Nakagawa, T. Surface modified polysulfone membranes: Separation of mixed proteins and optical resolution of tryptophan. Desalination 1993, 90 (1-3), 127-136.
18. Higuchi, A.; Hara, M.; Horiuchi, T.; Nakagawa, T. Optical resolution of amino acids by ultrafiltration membranes containing serum albumin. J. Membr. Sci. 1994, 93 (2), 157-164.
19. Higuchi, A.; Hashimoto, T.; Yonehara, M.; Kubota, N.; Watanabe, K.; Uemiya, S.; Kojima, T.; Hara, M. Effect of surfactants agents and lipids on optical resolution of amino acids by ultrafiltration membranes containing serum albumin. J. Membr. Sci. 1997, 130 (1-2), 31-39.
20. Gamier, F.; Random, J.; Rocca, J.L. Enantiomeric separation by ultrafiltration: Complexation mechanism of tryptophan analogs to bovine serum albumin. Sep. Purif. Technol. 1999, 16 (3), 243-250.
21. Random, J.; Gamier, F.; Rocca, J.L.; Maisterrena, B. Optimisation of the enantiomeric separation of tryptophan analogs by membrane processes. J. Membr. Sci. 2000, 175 (1), 111-117.
22. Ahuja, S. Chiral Separations by Chromatography; ASC: Washington, 1991.
23. Haginaka, J. Enantiomer separation of drugs by capillary electrophoresis using proteins as chiral selectors. J. Chromatogr. A 2000, 875 (1-2), 235-254.
24. Yamasaki, K.; Maruyama, T.; Yoshimoto, K.; Tsutsumi, Y.; Narazaki, R.; Fukuhara, A.; Kragh-Hansen, U.; Otagiri, M. Interactive binding to the two principal ligand binding sites of human serum albumin: Effect of the neutral-to-base transition. Biochim. Biophys. Acta Protein Struct. Mol. Enzym. 1999, 1432 (2), 313-323.
25. Cheruvallath, V.K.; Riley, C.M.; Narayanan, S.R.; Lindenbaum, S.; Perrin, J.H. A quantitative circular dichroic investigation of the binding of the enantiomers of ibuprofen and naproxen to human serum albumin. J. Pharm. Biomed. Anal. 1997, 15 (11), 1719-1724.
26. Hage, D.S.; Noctor, T.A.G.; Weiner, I.W. Characterization of protein binding of chiral drugs by high-performance affinity chromatography. Interactions of R- and S-ibuprofen with human serum albumin. J. Chromatogr. A 1995, 693 (1), 23-32.
27. Hage, D.S. Chromatographic and electrophoretic studies of protein binding to chiral solutes. J. Chromatogr. A 2001, 906 (1-2), 459-481.