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Liquid Chromatographic Enantioseparation of (RS) - Baclofen by Indirect Methods - A Review

Affiliations

  • Department of Basic and Applied Sciences, GD Goenka University, Gurgaon –122103, Haryana, India

Abstract


Objective: This article surveys high-performance liquid chromatographic methods of Enantioseparation of (RS)- Baclofenstereiosomers. Methods: The methods adopted for enantioseparation of Baclofen was derivatizing Baclofen with a suitable Chiral Derivatizing Reagent (CDR) and then the resulting diasteroemrs were subjected on C 18 column. The diastereomers get separated due to different physical and chemical properties of diastereomers. Findings: Among several CDRs tested for enantiosepration of (RS) baclofen, Marfey’s reagent based CDR, FDNP-L-Leu-amide was found to have highest resolution of the Baclofen enantiomers. Applications: The chiral separation of pharmaceuticals is one of the major research topics in the pharmaceutical industry since it became evident that the potential biological or pharmacological applications are mostly restricted to one of the enantiomers, just like the (R)-enantiomer of Baclofen is about 100 times morepotent than the (S)-isomer, still it is sold as racemic drug. Therefore it was worthwhile to study the enantiosepration of (RS) Baclofen.

Keywords

Baclofen, Chiral Derivatizing Agent, Enantioseparation, Racemic, RP-High-Performance Liquid Chromatography, Thin Layer Chromatography

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References


  • Bowery NG. GABAB receptor pharmacology. Annual Review of Pharmacology and Toxicology. 1993 Apr; 33: 109–47. Crossref PMid:8388192
  • Birkmayer W, Danielczyk W, Weiler G. The relaxing effect on skeletal muscle of beta 4 chlorophenyl gam-ma amino butyric acid relaxant. Wiener Medizinische Wochenschrift, 1967Sep; 117(79):7–9.
  • Olpe HR, Demieville H, Baltzer V, Bencze WL, Koella WP, Wolf P, Haas HL. The biological activity of d- and l-baclofen (Lioresal). European Journal of Pharmacology. 1978 Apr; 52(1):133–6.
  • Hill DR, Bowery NG. 3H-baclofen and 3H-GABA bind to bicuculline-insensitive GABAB sites in rat brain. Nature.1981 Mar; 290:149–52. Crossref PMid:6259535
  • Terrence CF, Sax M, Fromm GH, Chang CH, Yoo CS.Effect of baclofen enantiomorphs on the spinal trigeminal nucleus and steric similarities of carbamazepine. Pharmacology. 1983 Feb; 27(2):85–94.
  • Stinson SC. Chiral Drugs. Chemical & Engineering News. 1992 Sep; 70:46–79 Crossref
  • ToshimasaToyo’oka. Resolution of chiral drugs by liquid chromatography based upon diastereomer formation with chiral derivatization reagents. Journal of Biochemical and Bio-physical Methods. 2002 Mar; 54(1):25–56. PMid:12543490
  • KochakG,Hunc F. Improved gas-liquid chromatographic method for the determination of baclofen in plasma and urine. Journal of Chromatography. 1984 May; 310(20):319– 26.
  • Fraser AD, MacNeil W, Isner AF. Toxicological analysis of a fetal baclofen (Lioresal) ingestion. Journal of Forensic Sciences. 1991; 36:1596–602. Crossref PMid:1955846
  • Giovanni ND, d’Aloja E. Death due to baclofen and dipyrone ingestion. Forensic Science International. 2001Dec; 123:26–32.
  • Ban E, Park JS, Kim CK. Semi-microbore HPLC for the determination of baclofen in human plasma using column switching. Journal of Liquid Chromatography and Related Technologies. 2004 Jan; 27(19):3051–64 Crossref
  • Tosunoglu S, Ersoy L. Determination of baclofen in human plasma and urine by high-performance liquid chromatography with fluorescence detection. Analyst. 1995 Feb; 120(2):373–5. Crossref
  • Dukova OA, Kotlovsky MY, Pokrovsky AA, Suvorova EV, Shivrina TG, KrasnovEA,Efremov AA. Identification and quantitative determination of baclofen in human blood by HPLC with mass spectrometry detection. Biochemistry Supplement Series B: Biomedical Chemistry; Moscow. 2015 April; 9(2):137–42.
  • Sørensen LK, Hasselstrøm JB. Determination of therapeutic c-aminobutyric acid analogs in forensic whole blood by hydrophilic interaction liquid chromatographyelectrospray tandem mass spectrometry. Journal of Analytical Toxicology. 2014 Feb; 38(4):177–83. Crossref PMid:24523295
  • Lanoux T, Lebrun D, Andreu P, Just B, Mateu P. Baclofen poisoning. Toxicologie Analytiqueet Clinique. 2014 Feb; 26:206–7 Crossref
  • Di Rago M, Saar E, Rodda LN, Turfus S, Kotsos A, Gerostamoulos D, Drummer OH. Fast targeted analysis of 132 acidic and neutral drugs and poisons in whole blood using LC– MS/MS. Forensic Science International. 2014; 243:35–43. Crossref PMid:24794019
  • Flardh M, Jacobson BM. Sensitive method for the determination of baclofen in plasma by means of solid-phase extraction and liquid chromatography-tandem mass spectrometry. Journal of Chromatography A. 1999; 846:169–73. Crossref
  • Cao LW, Li C. Rapid and Sensitive Analysis of Baclofen by High-Performance Liquid Chromatography with UV– Vis and FD Detection. Acta Chromatographica. 2012 Jul; 24:383–97. Crossref
  • Harrison PM, Tonkin AM, Mclean AJ. Determination of 4-amino-3-(p-chlorophenyl) butyric acid (baclofen) in plasma by high-performance liquid chromatography. Journal of Chromatography B: Biomedical Sciences and Applications. 1985 Apr; 40:424–8. Crossref
  • Wuis EW, Dirks RJM, Vree TB, Kleyn EV. High-performance liquid chromatographic analysis of bac-lofen in plasma and urine of man after precolumn extraction and derivatization with o-phthaldialdehyde. Journal of Chromatography B:Biomedical Sciences and Applications. 1985; 337(2):341– 50. Crossref
  • Chang S, Yang H. Determination of baclofen by derivatization with anthracene-2,3-dicarboxaldehyde followed by capillary electrophoresis with laser-induced fluorescence detection. Chromatographia. 2003; 57:825–30. Crossref
  • Chang SY, Zheng NY, Chen CS. Development and validation of a capillary electrophoresis method for the determination of baclofen in human plasma. International Journal of Applied Science and Engineering Research. 2004; 3:277–85.
  • Chiang MT, Chang SY, Whang CW. Analysis of baclofen by capillary electrophoresis with laser-induced fluorescence detection. Journal of Chromatography A. 2000; 877(12):233–7. Crossref
  • Sioufi A, Kaiser G, Leroux F, Dubois JP. Determination of the S(+)- and R(-)-enantiomers of baclofen in plasma and urine by gas chromatography using a chiral fused-silica capillary column and an electron-capture detector. Journal of Chromatography. 1988 Apr; 450:221–32. Crossref
  • Stefan-van SRI, Rat’ko AA. Enantioselective, potentiometric membrane electrodes based on cyclodextrins: application for the determination of R-baclofen in its pharmaceutical formulation. Talanta. 2006 Dec; 69:1049–53. Crossref PMid:18970679
  • Rat’ko A, Stefan-van SRI. Determination of baclofen enantiomers in pharmaceutical formulations using maltodextrin based enantioselective, potentiometric membrane electrodes. Farmaco. 2004 May; 59:993–7. Crossref PMid:15598435
  • Wuis EW, Beneken KEWJ, Van BLEC, Burgers RCM, Vree TB, Vander KE. Enantioselective high-performance liquid chromatographic determination of baclofen after derivatization with a chiral adduct of o-phthaldialdehyde. Journal of Chromatography B: Biomedical Sciences and Applications. 1987 Apr; 415:419–22. Crossref
  • Blotny G. Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic syn-thesis. Tetrahedron. 2006 Aug; 62:9507–22. Crossref
  • Vashistha VK, Bhushan R. Preparative enantioseparation of (RS)-Baclofen: Determination of molecular dissymmetry. Chirality. 2015 Apr; 27(4):299–305. Crossref PMid:25683386
  • Bhushan R, Kumar V. Indirect enantioseparation of a-amino acids by reversed-phase liquid chroma-tography using new chiral derivatizing reagents synthesized from s-triazine chloride. Journal of Chromatography A. 2008 Jun; 1201(1):35–42. Crossref PMid:18556008
  • Bhushan R, Dixit S. Amino acids as chiral selectors in enantioresolution by liquid chromatog-raphy.
  • Biomedical Chromatography. 2012 Feb; 26:962–71. PMid:22729784
  • Bhushan R, Dixit S. Microwave-assisted synthesis and reversed-phase high-performance liquid chromatographic separation of diastereomers of (R,S)-baclofen using ten chiral derivatizing reagents designed from trichloro-s-triazine. Journal of Chromatography A. 2010 Mar; 1217(41):6382–7. Crossref PMid:20817188
  • Marfey P. Determination of D-amino acids II Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Research Communications. 1984; 49:591–6. Crossref
  • Bhushan R, Kumar V. Indirect resolution of baclofen enantiomers from pharmaceutical dosage form by reversed-phase liquid chromatography after derivatization with Marfey’s reagent and its structural variants.
  • Biomedical Chromatography. 2008 May; 22:906–11. Crossref PMid:18512855
  • Batra S, Bhushan R. Synthesis of three strong uv-absorbing naproxen-based chiral derivatizing agents and their application for enantioseparation of baclofen by RP-HPLC. Acta Chromatographica. 2015 Nov; 272(17):267–80. Crossref
  • Bhushan R, Tanwar S. Synthesis of succinimidyl(S)-naproxen ester and its application for indirect enantioresolution of penicillamine by reversed-phase high-performance liquid chromatography. Journal of Chromatography A. 2008 Mar; 1209(1-2):174–8. Crossref PMid:18817917
  • Bhushan R, Nagar H. Indirect enantioseparation of selenomethionine by reversed-phase high-performance liquid chromatography using a newly synthesized chiral derivatizing reagent based on (S)-naproxen moiety. Biomedical Chromatography. 2014 Mar; 28(1):106–11. Crossref PMid:23519770

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