Application of antibiotics as chiral selectors for capillary electrophoretic enantioseparation of pharmaceuticals: A review

Biomedical Chromatography

Volumn 28, Issue 1, 2014, Pages 10-26

  Dixit, Shuchi ^a   Park, Jung Hag ^a  

^a Yeungnam University   (South Korea)

Author keywords

Antibiotics; Capillary electrophoresis; Enantioseparation; Pharmaceuticals; Review

Indexed keywords

CAPILLARY ELECTROPHORESIS; CHIRALITY;

CAPACITIVELY COUPLED CONTACTLESS CONDUCTIVITY DETECTION; CHIRAL SELECTOR; CHIRAL SEPARATIONS; EMERGING TRENDS; ENANTIOSEPARATIONS; NON-AQUEOUS; NON-AQUEOUS CAPILLARY ELECTROPHORESIS;

ANTIBIOTICS;

AMINOGLYCOSIDE ANTIBIOTIC AGENT; ANSAMYCIN DERIVATIVE; ANTIBIOTIC AGENT; AVOPARCIN; AZITHROMYCIN; BALHIMYCIN; BOROMYCIN; CHIRAL SELECTOR; CLARITHROMYCIN; CLINDAMYCIN PHOSPHATE; CLOFIBRIC ACID; EREMOMYCIN; ERYTHROMYCIN; FENOPROFEN; FOLINIC ACID; IBUPROFEN; KANAMYCIN; KETOPROFEN; LINCOSAMIDE DERIVATIVE; MACROLIDE; NEOMYCIN; POLYPEPTIDE ANTIBIOTIC AGENT; REAGENT; RIFAMYCIN; RIFAMYCIN B; RISTOCETIN A; STREPTOMYCIN; TEICOPLANIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

CAPILLARY ELECTROPHORESIS; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHIRAL CHROMATOGRAPHY; CHIRALITY; COMPLEX FORMATION; CONCENTRATION RESPONSE; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENANTIOSEPARATION; HYDROGEN BOND; NONAQUEOUS CAPILLARY ELECTROPHORESIS; QUANTITATIVE ANALYSIS; REPRODUCIBILITY; REVIEW; STEREOSPECIFICITY;

ANTIBIOTICS; CAPILLARY ELECTROPHORESIS; ENANTIOSEPARATION; PHARMACEUTICALS; REVIEW;

ANTI-BACTERIAL AGENTS; ELECTROPHORESIS, CAPILLARY; HUMANS; STEREOISOMERISM;

EID: 84890246402     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.2950     Document Type: Review

References (100)

1. Arai T, Nimura N and Kinoshita T. Investigation of enantioselective separation of quinolonecarboxylic acid by capillary zone electrophoresis using vancomycin as chiral selector. Journal of Chromatography. A 1996; 736: 303-311.
2. Armstrong DW and Nair UB. Capillary electrophoretic enantioseparations using macrocyclic antibiotics as chiral selectors. Electrophoresis 1997; 18: 2331-2342.
3. Armstrong DW and Rundlett KL. CE resolution of neutral and anionic racemates with glycopeptide antibiotics and micelles. Journal of Liquid Chromatography 1995; 18: 3659-3674.
4. Armstrong DW, Rundlett K and Chen J. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis. Chirality 1994a; 6: 496-509.
5. Armstrong DW, Rundlett KL and Reid GL. Use of a macrocyclic antibiotic, rifamycin B, and indirect detection for the resolution of racemic amino alcohols by CE. Analytical Chemistry 1994b; 66: 1690-1695.
6. Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C and Chen JR. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Analytical Chemistry 1994c; 66: 1473-1484.
7. Armstrong DW, Gasper MP and Rundlett KL. Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A. Journal of Chromatography. A 1995; 689: 285-304.
8. Armstrong DW, Schneiderheinze J, Nair U, Magid LJ and Butler PD. Self-association of rifamycin B: possible effects on molecular recognition. Journal of Physical Chemistry. B 1999; 103: 4338-4341.
9. Bardone MR, Paternoster M and Coronelli C. Teicomycins, new antibiotics from Actinoplanes teichomyceticus species nova. II Extraction and chemical characterization. Journal of Antibiotics 1978; 31: 170-177.
10. Barna JCJ, Williams DH, Stone DJM, Leung TWC and Dodrell DM. Structure elucidation of the teicoplanin antibiotics. Journal of the American Chemical Society 1984; 106: 4895-4902.
11. Beggs WH and Andrews FA. Nonspecific ionic inhibition of ethambutol binding by Mycobacterium smegmatis. Antimicrobial Agents and Chemotherapy 1968; 4: 115-119.
12. Berthod A, He BL and Beesley TE. Temperature and enantioseparation by macrocyclic glycopeptide chiral stationary phases. Journal of Chromatography. A 2004; 1060: 205-214.
13. Blanco M and Valverde I. Choice of chiral selector for enantioseparation by capillary electrophoresis. Trends in Analytical Chemistry 2003; 22: 428-439.
14. Caldwell J. Importance of stereospecific bioanalytical monitoring in drug development. Journal of Chromatography. A 1996; 719: 3-13.
15. Chankvetadze B. Capillary Electrophoresis in Chiral Analysis. Wiley: New York, 1997.
16. Chankvetadze B. Enantioseparations by using capillary electrophoretic techniques: the story of 20 and a few more years. Journal of Chromatography. A 2007; 1168: 45-70.
17. Chankvetadze B. Separation of enantiomers with charged chiral selectors in CE. Electrophoresis 2009; 30: S211-S221.
18. Chankvetadze B and Blaschke G. Enantioseparations using capillary electromigration techniques in non-aqueous buffers. Electrophoresis 2000; 21: 4159-4178.
19. Chen B, Du Y and Li P. Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector. Electrophoresis 2009; 30: 2747-2754.
20. Chen B, Du Y and Wang H. Study on enantiomeric separation of basic drugs by NACE in methanol-based medium using erythromycin lactobionate as a chiral selector. Electrophoresis 2010; 31: 371-377.
21. Desiderio C and Fanali S. Chiral analysis by capillary electrophoresis using antibiotics as chiral selector. Journal of Chromatography. A 1998; 807: 37-56.
22. Desiderio C, Polcaro CM, Padiglioni P and Fanali S. Enantiomeric separation of acidic herbicides by capillary electrophoresis using vancomycin as chiral selector. Journal of Chromatography. A 1997; 781: 503-513.
23. Du Y and Chen B. Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography. Journal of Chromatography. A 2010; 1217: 1806-1812.
24. Eichelbaum M. Pharmacokinetic and pharmacodynamic consequences of stereoselective drug metabolism in man. Biochemical Pharmacology 1992; 37: 93-96.
25. Ekborg-Ott KH, Zientara GA, Schneiderheinze JM, Gahm K and Armstrong DW. Avoparcin, a new macrocyclic antibiotic chiral run buffer additive for capillary electrophoresis. Electrophoresis 1999; 20: 2438-2457.
26. Fanali S and Desiderio C. Use of vancomycin as chiral selector in capillary electrophoresis. Optimization and quantitation of loxiglumide enantiomers in pharmaceuticals. Journal of High Resolution Chromatography 1996; 19: 322-326.
27. Fanali S, Desiderio C and Aturki Z. Enantiomeric resolution study by capillary electrophoresis. Selection of the appropriate chiral selector. Journal of Chromatography A 1997; 772: 185-194.
28. Fanali S, Desiderio C, Schulte G, Heitmeier S, Strickmann D, Chankvetadze B and Blaschke G. Chiral capillary electrophoresis-electrospray mass spectrometry coupling using vancomycin as chiral selector. Journal of Chromatography. A 1998; 800: 69-76.
29. Fanali S, Aturki Z, Desiderio C and Righetti PG. Use of MDL 63 246 (Hepta-Tyr) antibiotic in capillary zone electrophoresis. II. Chiral resolution of α-hydroxy acids. Journal of Chromatography A 1999; 838: 223-235.
30. Fanali S, Cartoni C and Aturki Z. Enantioseparation of (S)-carboxymethylcysteine and N-acetamidocarboxymethylcysteine by capillary electrophoresis using vancomycin. Journal of Separation Science 2001a; 24: 789-794.
31. Fanali S, Cartoni C and Desiderio C. Chiral separation of newly synthesized arylpropionic acids by capillary electrophoresis using cyclodextrins or a glycopeptides antibiotic as chiral selectors. Chromatographia 2001b; 54: 87-92.
32. Fantacuzzi M, Bettoni G, D'Orazio G and Fanali S. Enantiomeric separation of some demethylated analogues of clofibric acid by capillary zone electrophoresis and nano-liquid chromatography. Electrophoresis 2006; 27: 1227-1236.
33. Ficarra R, Cutroneo P, Aturki Z, Tommasini S, Calabro ML, Phan-Tan-Luu R, Fanali S and Ficarra P. An experimental design methodology applied to the enantioseparation of a non-steroidal anti-inflammatory drug candidate. Journal of Pharmaceutical and Biomedical Analysis 2002; 29: 989-997.
34. Gao W and Kang J. Separation of atropisomers of anti-hepatitis drug dimethyl diphenyl bicarboxylate analogues by capillary electrophoresis with vancomycin as the chiral selector. Journal of Chromatography. A 2006; 1108: 145-148.
35. Gasper MP, Berthod A, Nair UB and Armstrong DW. Comparison and modeling study of vancomycin, ristocetin A and teicoplanin for CE enantioseparations. Analytical Chemistry 1996; 68: 2501-2514.
36. Gause GF, Brazhnikova MG, Lomakina NN, Berdnikova TF, Fedorova GB, Tokareva NL, Borisova VN and Batta G. Eremomycin - new glycopeptide antibiotic: chemical properties and structure. Journal of Antibiotics 1989; 42: 1790-1799.
37. Geiser L and Veuthey JL. Non-aqueous capillary electrophoresis 2005-2008. Electrophoresis 2009; 30: 36-49.
38. Gerhard U, Mackay JP, Maplestone RA and Williams DH. The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. Journal of the American Chemical Society 1993; 115: 232-237.
39. Gong XY, Dobrunz D, Kumin M, Wiesner M, Revell JD, Wennemers H and Hauser PC. Separating stereoisomers of di-, tri-, and tetrapeptides using capillary electrophoresis with contactless conductivity detection. Journal of Separation Science 2008; 31: 565-573.
40. Gübitz G and Schmid MG. Recent progress in chiral separation principles in capillary electrophoresis. Electrophoresis 2000; 21: 4112-4135.
41. Gübitz G and Schmid MG. Chiral separation by capillary electromigration techniques. Journal of Chromatography. A 2008; 1204: 140-156.
42. Ha PTT, Schepdael AV, Roets E and Hoogmartens J. Investigating the potential of erythromycin and derivatives as chiral selector in capillary electrophoresis. Journal of Pharmaceutical and Biomedical Analysis 2004; 34: 861-870.
43. Ha PTT, Hoogmartens J and Schepdael AV. Recent advances in pharmaceutical applications of chiral capillary electrophoresis. Journal of Pharmaceutical and Biomedical Analysis 2006; 41: 1-11.
44. Hou JG, He TX, Han XQ, Du XZ, Mao XF, Deng HL and Gao JZ. Chiral separation of erythromycin as a new chiral selector on CE. Chinese Chemical Letters 2003a; 14: 280-282.
45. Hou JG, He TX, Mao XF, Du XZ, Deng HL and Gao JZ. Enantiomeric separation using erythromycin as a new capillary zone electrophoresis chiral selector. Analytical Letters 2003b; 36: 1437-1449.
46. Huang H, Wang Q and Huang B. Preparation and evaluation of stable coating for capillary electrophoresis using coupled chitosan as coated modifier. Talanta 2006; 69: 463-468.
47. International Conference on Harmonization. ICH-Topic Q2A: Validation of Analytical Procedures. International Conference on Harmonization of Technical Requirement for Registration of Pharmaceuticals for Human Use: Geneva, 1996.
48. Jiang Z, Kang J, Bischoff D, Bister B, Süssmuth RD and Schurig V. Evaluation of balhimycin as a chiral selector for enantioresolution by capillary electrophoresis. Electrophoresis 2004; 25: 2687-2692.
49. Jiang Z, Bertazzo M, Süssmuth RD, Yang J, Smith NW and Schurig V. Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis. Electrophoresis 2006; 27: 1154-1162.
50. Jordan DC. Antibiotics, Vol. 1. Springer: New York, 1967; 84.
51. Kang J, Wistuba D and Schurig V. Fast enantiomeric separation with vancomycin as chiral additive by co-electroosmotic flow capillary electrophoresis: increase of the detection sensitivity by the partial filling technique. Electrophoresis 2003; 24: 2674-2679.
52. Kang J, Bischoff D, Jiang ZJ, Bister B, Süssmuth R and Schurig V. A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis: dimerization and enantioselectivity. Analytical Chemistry 2004; 76: 2387-2392.
53. Kang JW, Yang YT, You JM and Ou QY. Fast chiral separation of amino acid derivatives and acidic drugs by co-electroosmotic flow capillary electrophoresis with vancomycin as chiral selector. Journal of Chromatography. A 1998; 825: 81-87.
54. Kumar AP and Park JH. Azithromycin as a new chiral selector in capillary electrophoresis. Journal of Chromatography. A 2011; 1218: 1314-1317.
55. Lämmerhofer M. Chiral separations by capillary electromigration techniques in nonaqueous media I. Enantioselective nonaqueous capillary electrophoresis. Journal of Chromatography A 2005; 1068: 3-30.
56. Lucy CA and McDonald ML. Separation of chloride isotopes by capillary electrophoresis based on the isotope effect on ion mobility. Analytical Chemistry 1995; 67: 1074-1078.
57. Maier V, Petr J, Knob R, Horakova J and Sevcik J. Electrokinetic partial filling technique as a powerful tool for enantiomeric separation of dl-lactic acid by CE with contactless conductivity detection. Electrophoresis 2007; 28: 1815-1822.
58. Maier V, Ranc V, Svidrnoch M, Petr J, Sevcík J, Tesarová E and Armstrong DW. Study on the use of boromycin as a chiral selector in capillary electrophoresis. Journal of Chromatography. A 2012; 1237: 128-132.
59. McFarland JW, Berger CM, Froshauer SA, Hayashi SF, Hecker SJ, Jaynes BH, Jefson MR, Kamicker BJ, Lipinski CA, Lundy KM, Reese CP and Vu CB. Quantitative structure-activity relationships among macrolide antibacterial agents: in vitro and in vivo potency against pasteurella multocida. Journal of Medicinal Chemistry 1997; 40: 1340-1346.
60. Nadkarni SR, Patel MV, Chatterjee S, Vijayakumar EKS, Desikan KR, Blumbach J and Ganguli BN. Balhimycin, a new glycopeptide antibiotic produced by amycolatopsis sp. Y-86, 21022: taxonomy, production, isolation and biological activity. Journal of Antibiotics 1994; 47: 334-341.
61. Nair JB and Izzo CG. Anion screening for drugs and intermediates by capillary ion electrophoresis. Journal of Chromatography. A 1993; 640: 445-461.
62. Nation RL. Chirality in new drug development: clinical pharmacokinetic considerations. Clinical Pharmacokinetics 1994; 27: 249-255.
63. Nishi H, Nakamura K, Nakai H and Sato T. Enantiomer separation by capillary electrophoresis using DEAE-Dextran and aminoglycosidic antibiotics. Chromatographia 1996; 43: 426-430.
64. Oswald TM and Ward TJ. Enantioseparations with the macrocyclic antibiotic ristocetin A using a countercurrent process in CE. Chirality 1999; 11: 663-668.
65. Pollock JRA and Stevens R (eds). Dictionary of Organic Compounds, 4th edn. Oxford University Press: New York, 1965.
66. Pormsila W, Gong XY and Hauser PC. Determination of the enantiomers of α-hydroxy- and α-amino acids in capillary electrophoresis with contactless conductivity detection. Electrophoresis 2010; 31: 2044-2048.
67. Preinerstorfer B, Laemmerhofer M and Lindner W. Advances in enantioselective separations using electromigration capillary techniques. Electrophoresis 2009; 30: 100-132.
68. Prokhorova AF, Shapovalova EN, Shpak AV, Staroverov SM and Shpigun OA. Enantiorecognition of profens by capillary electrophoresis using a novel chiral selector eremomycin. Journal of Chromatography. A 2009; 1216: 3674-3677.
69. Prokhorova AF, Kuznetsov MA, Shapovalova EN, Staroverov SM and Shpigun OA. Enantioseparations of aromatic carboxylic acid by capillary electrophoresis using eremomycin as a chiral selector in a chitosan-modified capillary. Procedia Chemistry 2010a; 2: 8-13.
70. Prokhorova AF, Shapovalova EN and Shpigun OA. Chiral analysis of pharmaceuticals by capillary electrophoresis using antibiotics as chiral selectors. Journal of Pharmaceutical and Biomedical Analysis 2010b; 53: 1170-1179.
71. Rentsch KM. The importance of stereoselective determination of drugs in the clinical laboratory. Journal of Biochemical and Biophysical Methods 2002; 54: 1-9.
72. Reilly J, Sanchez-felix M and Smith NW. Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics. Chirality 2003; 15: 731-742.
73. Rundlett KL and Armstrong DW. Effect of micelles and mixed micelles on efficiency and selectivity of antibiotic-based capillary electrophoretic enantioseparations. Analytical Chemistry 1995; 67: 2088-2095.
74. Rundlett KL, Gasper MP, Zhou EY and Armstrong DW. Capillary electrophoretic enantiomeric separations using the glycopeptide antibiotic, teicoplanin. Chirality 1996; 8: 88-107.
75. Sánchez-Hernández L, Crego AL, Marina ML and García-Ruiz C. Sensitive chiral analysis by CE: an update. Electrophoresis 2008; 29: 237-251.
76. Sánchez-Marroquin A and Teran J. Chemical changes during production of erythromycin. Revista de la Sociedad Quimica de Mexico 1996; 4: 101-104.
77. Shiozawa H, Zerella R, Bardsley B, Tuck KL and Williams DH. Noncovalent bond lengths and their cooperative shortening: dimers of vancomycin group antibiotics in crystals and in solution. Helvetica Chimica Acta 2003; 86: 1359-1370.
78. Slama I, Dufresne C, Jourdan E, Fahrat F, Villet A, Ravel A, Grosset C and Peyrin E. Vancomycin dimerization and chiral recognition studied by high-performance liquid chromatography. Analytical Chemistry 2002; 74: 5205-5211
79. Strege MA, Huff BE and Risley RS. Evaluation of macrocyclic antibiotic A82846B as a chiral selector for capillary electrophoresis separations. LC-GC 1996; 14: 144-150.
80. Valko IE, Siren H and Riekkola ML. Determination of association constants of dansylamino acids and β-cyclodextrin in N-methylformamide by capillary electrophoresis. Electrophoresis 1997; 18: 919-923.
81. Valtcheva L, Mohammed J, Pettersson G and Hjerten S. Chiral separation of β-blockers by high-performance capillary electrophoresis based on non-immobilized cellulase as enantioselective protein. Journal of Chromatography 1993; 638: 263-267.
82. Vespalec R, Billiet HAH, Frank J and Bocek P. Vancomycin as a chiral selector in capillary electrophoresis: an appraisal of advantages and limitations. Electrophoresis 1996; 17: 1214-1221.
83. Waksman SA and Woodruff HB. Actinomyces antibioticus, a new soil organism antagonistic to pathogenic and nonpathogenic bacteria. Journal of Bacteriology 1941; 42: 231-249.
84. Wan H and Blomberg LG. Enantioseparation of amino acids and dipeptides using vancomycin as chiral selector in capillary electrophoresis. Electrophoresis 1996; 17: 1938-1944.
85. Wang F and Khaledi MG. Chiral separations by nonaqueous capillary electrophoresis. Analytical Chemistry 1996; 68: 3460-3467.
86. Wang C, Armstrong DW and Risley DS. Empirical observations and mechanistic insights on the first boron-containing chiral selector for LC and supercritical fluid chromatography. Analytical Chemistry 2007a; 79: 8125-8135.
87. Wang Z, Wang J, Hu Z and Kang J. Enantioseparation by CE with vancomycin as chiral selector: improving the separation performance by dynamic coating of the capillary with poly(dimethylacrylamide). Electrophoresis 2007b; 28: 938-943.
88. Wang Z, Ouyang J and Baeyens WRG. Recent developments of enantioseparation techniques for adrenergic drugs using liquid chromatography and capillary electrophoresis: a review. Journal of Chromatography B 2008; 862: 1-14.
89. Wang Z, Mu C, Kang J and Hu Z. Separation and determination of stereoisomeric impurity of folinic acid diastereomers by CE with vancomycin as a selector. Chromatographia 2012; 75: 1211-1215.
90. Ward TJ. Chiral separations. Analytical Chemistry 2006; 78: 3947-3956.
91. Ward TJ and Farris AB. Chiral separations using the macrocyclic antibiotics: a review. Journal of Chromatography. A 2001; 906: 73-89.
92. Ward TJ and Oswald TM. Enantioselectivity in capillary electrophoresis using the macrocyclic antibiotics. Journal of Chromatography. A 1997; 792: 309-325.
93. Ward TJ, Dann C and Blaylock A. Enantiomeric resolution using the macrocyclic antibiotics rifamycin B and rifamycin SV as chiral selectors in capillary electrophoresis. Journal of Chromatography. A 1995; 715: 337-344.
94. Ward TJ, Dann C and Brown AP. Separation of enantiomers using vancomycin in a countercurrent process by suppression of electroosmosis. Chirality 1996; 8: 77-83.
95. Ward TJ, Farris AB and Woodling K. Synergistic chiral separations using the glycopeptides ristocetin A and vancomycin. Journal of Biochemical and Biophysical Methods 2001; 48: 163-174.
96. Xu G, Du Y, Chen B and Chen J. Investigation of the enantioseparation of basic drugs with erythromycin lactobionate as a chiral selector in CE. Chromatographia 2010; 72: 289-295.
97. Xu J, Pan T, Wang W and Tang X. Isolation and structural assignment of the antibiotic produced by a streptomyces fusant. Zhongguo Kangshengsu Zazhi 1996; 21: 1-4.
98. Ye B and Khaledi MG. Abstract no. 133. Presented at the 6th International Symposium on High Performance Capillary Electrophoresis, San Diego, CA, 1994.
99. Yu T, Du Y and Chen B. Evaluation of clarithromycin lactobionate as a novel chiral selector for enantiomeric separation of basic drugs in capillary electrophoresis. Electrophoresis 2011; 32: 1898-1905.
100. Zhang Y, Jin Z and Jiao R. Breeding of glutamylhydrazine-resistant strains of Nocardia mediterranei with increased yield of rifamycin SV. Kangshengsu 1984; 9: 365-369.