Analytical and semipreparative high performance liquid chromatography enantioseparation of bicalutamide and its chiral impurities on an immobilized polysaccharide-based chiral stationary phase

Journal of Chromatography A

Volumn 1445, Issue , 2016, Pages 166-171

  Sadutto, Daniele ^a   Ferretti, Rosella ^a   Zanitti, Leo ^a   Casulli, Adriano ^a   Cirilli, Roberto ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Bicalutamide; Chiralpak IA; Enantiomers; Impurities; Semipreparative resolution; Temperature variable HPLC

Indexed keywords

DICHROISM; DISEASES; ENANTIOMERS; ETHANOL; HEXANE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMPURITIES; LIQUID CHROMATOGRAPHY; MIXTURES;

ABSOLUTE CONFIGURATION; BICALUTAMIDE; CHIRAL STATIONARY PHASE; CHIRALPAK IA; OPERATIONAL CONDITIONS; POLYSACCHARIDE-BASED CHIRAL STATIONARY PHASE; SEMI-PREPARATIVE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIES; TEMPERATURE VARIABLES;

CHROMATOGRAPHY;

2 PROPANOL; ACETIC ACID ETHYL ESTER; ALCOHOL; AMYLOSE; BICALUTAMIDE; HEXANE; ANILIDE; N-HEXANE; NITRILE; POLYSACCHARIDE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHIRAL STATIONARY PHASE; CHIRALITY; CIRCULAR DICHROISM; DRUG IMPURITY; ELUTION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; TEMPERATURE; CHEMICAL ANALYSIS; CHEMISTRY; PROCEDURES; STEREOISOMERISM;

2-PROPANOL; AMYLOSE; ANILIDES; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; ETHANOL; HEXANES; NITRILES; POLYSACCHARIDES; STEREOISOMERISM; TOSYL COMPOUNDS;

EID: 84962877571     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2016.04.011     Document Type: Article

References (23)

1. Cockshott I.D. Bicalutamide: clinical pharmacokinetics and metabolism. Clin. Pharmacokinet. 2004, 43:855-878.
2. WO Patent 2003032950 A1 (April 24, 2003) to AstraZeneca UK Ltd., Sweden, 41 pp.
3. Török R., Bor A., Orosz G., Lukács F., Armstrong D.W., Péter A. High-performance liquid chromatographic enantioseparation of bicalutamide and its related compounds. J. Chromatogr. A 2005, 1098:75-81.
4. Nageswara Rao R., Narasa Raju A., Nagaraju D. An improved and validated LC method for resolution of bicalutamide enantiomers using amylose tris-(3,5-dimethylphenylcarbamate) as a chiral stationary phase. J. Pharm. Biomed. Anal. 2006, 42:347-353.
5. Soma Raju I.V., Raghuram P., Sriramulu J. Novel chiral LC methods for the enantiomeric separation of bicalutamide and thalidomide on amylose based immobilized CSP. Curr. Pharm. Anal. 2011, 7:47-53.
6. James K.D., Ekwuribe N.N. Syntheses of enantiomerically pure (R)- and (S)-bicalutamide. Tetrahedron 2002, 58:5905-5908.
7. Zhang T., Kientzy C., Franco P., Ohnishi A., Kagamihara Y., Kurosawa H. Solvent versatility of immobilized 3,5-dimethylphenylcarbamate of amylose in enantiomeric separations by HPLC. J. Chromatogr. A 2005, 1075:65-75.
8. Zhang T., Schaeffer M., Franco P. Optimization of the chiral separation of a Ca-sensitizing drug on an immobilized polysaccharide-based chiral stationary phase: case study with a preparative perspective. J. Chromatogr. A 2005, 1083:96-101.
9. Sanna M.L., Maccioni E., Vigo S., Faggi C., Cirilli R. Application of an immobilised amylose-based chiral stationary phase to the development of new monoamine oxidase B inhibitors. Talanta 2010, 82:426-431.
10. Cirilli R., Simonelli A., Ferretti R., Bolasco A., Chimenti P., Secci D., Maccioni E., La Torre F. Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions. J. Chromatogr. A 2006, 1101:198-2203.
11. Cirilli R., Ferretti R., Gallinella B., La Torre F., Mai A., Rotili D. Analytical and semipreparative high performance liquid chromatography separation of stereoisomers of novel 3,4-dihydropyrimidin-4(3H)-one derivatives on the immobilised amylose-based Chiralpak IA chiral stationary phase. J. Sep. Sci. 2006, 29:1399-1406.
12. Rapposelli S., Calderone V., Cirilli R., Digiacomo M., Faggi C., La Torre F., Manganaro M., Martelli A., Testai L. Enantioselectivity in cardioprotection induced by (S)-(-)-2,2-dimethyl-N-(4'-acetamido-benzyl)-4-spiromorpholone-chromane. J. Med. Chem. 2009, 52:1477-1480.
13. Ghanem A., Hoenen H., Aboul-Enein H.Y. Application and comparison of immobilized and coated amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases for the enantioselective separation of β-blockers enantiomers by liquid chromatography. Talanta 2006, 68:602-609.
14. Zhang T., Franco P., Nguyen D., Hamasaki R., Miyamoto S., Ohnishi A., Murakami T. Complementary enantiorecognition patterns and specific method optimization aspects on immobilized polysaccharide-derived chiral stationary phases. J. Chromatogr. A 2012, 1269:178-188.
15. Ikai T., Yamamoto C., Kamigaito M., Okamoto Y. Immobilized-type chiral packing materials for HPLC based on polysaccharide derivatives. J. Chromatogr. B 2008, 875(1):2-11.
16. Ghanem A., Aboul-Enein M.N., El-Azzouny A., El-Behairy M.F. Solvent versatility of immobilized amylose and cellulose-based chiral stationary phases in enantioselective LC separation and monitoring of bio-catalyzed resolutions of acidic drugs in non-standard organic solvents. Chromatographia 2009, 70:349-363.
17. Rizzo S., Menta S., Faggi C., Pierini M., Cirilli R. Influence of the nature of alkyl substituents on the high-performanceliquid chromatography enantioseparation and retention of newatropisomeric 1,1'-bibenzimidazole derivatives on amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. J. Chromatogr. A 2014, 1363:128-136.
18. Cirilli R., Ferretti R., Gallinella B., Zanitti L., La Torre F. A new application of stopped-flow chiral HPLC: inversion of enantiomer elution order. J. Chromatogr. A 2004, 1061:27-34.
19. Cirilli R., Del Giudice M.R., Ferretti R., La Torre F. Conformational and temperature effects on separation of stereoisomers of a C3,C4-substituted β-lactamic cholesterol absorption inhibitor on amylose-based chiral stationary phases. J. Chromatogr. A 2001, 923:27-36.
20. Kazusaki M., Ohgami Y. Enantioseparation in the vicinity of compensation temperature. Chromatographia 2007, 28:125-130.
21. Ferretti R., Mai A., Gallinella B., Zanitti L., Valente S., Cirilli R. Application of 3 μm particle-based amylose-derived chiral stationary phases for the enantioseparation of potential histone deacetylase inhibitors. J. Chromatogr. A 2011, 1218:8394-8398.
22. Wang F., Dowling T., Ellison D., Wyvratt J. Comparison study of Chiralpak AD-H with AD columns in chromatographic enantioseparation of dihydropyrimidinone acid and its methyl ester. J. Chromatogr. A 2004, 1034:117-123.
23. Wang F., Wenslow R.M., Dowling T.M., Mueller K.T., Santos I., Wyvratt J.M. Characterization of a thermally induced irreversible conformational transition of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase in enantioseparation of dihydropyrimidinone acid by quasi-equilibrated liquid chromatography and solid-state NMR. Anal. Chem. 2003, 75:5877-5885.