Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase

Suedee, Roongnapa; Heard, Charles Martin

doi:10.1002/(sici)1520-636x(1997)9:2<139::aid-chir11>3.0.co;2-o

Cited by 28 publications

(7 citation statements)

References 15 publications

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“…Mixtures of microcrystalline cellulose and cellulose derivatives were used by Suedee and Heard (111). For the mixtures they used triphenylcarbamates and tested the separation of racpropranolol and raobupranolol.…”

Section: B Survey Of Applications Of Racemic Separationsmentioning

confidence: 99%

Enantiomer Separations

Mller¹,

G√onther²

2003

Handbook of Thin-Layer Chromatography

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Section: B Survey Of Applications Of Racemic Separationsmentioning

confidence: 99%

Enantiomer Separations

Mller¹,

G√onther²

2003

Handbook of Thin-Layer Chromatography

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“…Among the many commercially available stationary phases (CSPs) for HPLC enantioseparation, polysaccharide derivative phases are among the most widely used for practical applications. The important advantages of polysaccharides, in addition to their availability from natural sources, are the ease of substitution and functionalization of the hydroxy groups of the glucose unit and potential for application in large-scale separation ions, even by TLC (Negawa and Shoji 1992; Francotte and Wolf, 1992;Suedee and Heard, 1996).…”

Section: Resolution Of Enantiomer On Cellulose Derivativesmentioning

confidence: 99%

“…On the other hand, the introduction of either electron-donating or electron-withdrawing substituents tends to improve the optical resolution abilities of phenyl carbamate derivative CSPs 1995;Suedee and Heard, 1996;Okamoto et al, 1986). Substitution at a meta or para position on the phenyl moiety is considered to be preferable to substitution at an ortho position for benzoate and phenyl carbamate derivatives of cellulose prepared CSPs with a higher chiral recognition ability (Suedee and Heard, 1996;Okamoto et al, 1986Okamoto et al, 1987. Yuasa et al (1990) reported the use of crystalline cellulose (Avicel, E. Merck, Darmstadt, Germany) as chiral stationary phase for TLC and investigated the separation of D,L-tryptophan and other D,L-amino acids.…”

Section: Resolution Of Enantiomer On Cellulose Derivativesmentioning

confidence: 99%

“…The best chiral separations were obtained with a solvent system consisting of ethanol:pyridine:water (1:1:1, v/v/v), which enabled the resolution of D,L-tryptophan, D,L-histidine, D,L-phenylalanine, D,L-tyrosine, and D,L-B-3,4-dihydroxyphenylalanine using ascending chromatography for 6 h at 25°C. With the exception of histidine, the D-amino acids had higher R f values than the L. Suedee and Heard (1996) reported the use of cellulose phenyl carbamate derivatives as stationary phases for resolution of the enantiomers of the b-blockers propranolol and bupranolol by TLC. The derivatives examined were cellulose trisphenyl carbamate, cellulose tris (2,3di-chlorophenylcarbamate), cellulose tris (2,4-dichlorophenyl carbamate), cellulose tris (2,6-dichlorophenyl carbamate), cellulose tris (3,4-dichlorophenyl carbamate), cellulose tris (3,5-dichlorophenyl carbamate), cellulose tris (2,3-dimethylphenyl carbamate), and cellulose tris (3,5-dimethylphenyl carbamate).…”

Section: Resolution Of Enantiomer On Cellulose Derivativesmentioning

confidence: 99%

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Application of thin-layer chromatography in enantiomeric chiral analysis—an overview

Aboul‐Enein

El-Awady

Heard

et al. 1999

Biomed. Chromatogr.

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Several chiral drugs are produced and administered as pure enantiomers, whereas many others, especially of synthetic origin, are used mainly in the form of racemates. The biological and pharmacological activity of chiral compounds depends on their configuration. The racemic drugs may exhibit quite different activity from the optically pure drugs. Often only one of the enantiomers is pharmacologically active and/or even can be toxic. Since numerous enantiomers have been shown to behave differently from at least one point of view, whether pharmacokinetic, pharmacodynamic, toxicological or interaction, there seems to be hardly any exception to the general rule that a racemate cannot be considered as a single drug entity. A variety of chromatographic methods have been developed for optical resolution recently. Usually direct separation of the enantiomers is carried out on HPTLC chiral precoated plates or on plates impregnated with chiral substances. TLC techniques are a developing branch of separation and quantitation of drugs, both in pharmaceutical dosage forms and in biological material. This review presents an overview of the current successful enantioseparations of drugs by TLC and their potential in the analysis of the drug racemates. Copyright © 1999 John Wiley & Sons, Ltd.

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“…9 Indeed, this material was the CSP used for the HPLC analysis in the current work. Additional stereoselective applications have been identified for this material, including the resolution of ␤-blockers by thin-layer chromatography 10 and enantioselective release of propranolol enantiomers from tablet formulations. 11 More recently, we observed that when CDMPC was equilibrated with ± propranolol in PBS buffer an imbalance in enantiomer adsorption occurred.…”

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confidence: 99%

Differential permeation of propranolol enantiomers across human skin in vitro from formulations containing an enantioselective excipient

1999

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This work tested the hypothesis that a stereospecific topical formulation could be used to engineer differential permeation rates for each enantiomer of an applied racemate across human skin in vitro. Racemic and enantiomerically pure R or S propranolol HCI were formulated with cellulose tris(3,5‐dimethyl phenyl carbamate) (CDMPC) and applied to excised human skin using side‐by‐side Franz‐type diffusion cells. When the pure enantiomers were used, there was a marked difference between the penetration rates of R and S propranolol (flux ratio: 2.06; P = 0.04). When racemic propranolol was used, the difference was reduced, although still statistically significant (flux ratio: 1.2; P = 0.08), particularly in view of the differential activities of the two enantiomers. Control experiments, in which no CDMPC was present, produced equal permeation rates. The results can be rationalised in terms of differential adsorption onto CDMPC within the vehicle, whereby S‐propranolol is preferentially bound relative to R‐propranolol. This causes an imbalance in the apparent donor phase concentrations that (in accordance with Fickian diffusion laws and thermodynamic activity) gives rise to differences in permeation rates. The diminished differential observed when the racemate was used, rather than individual enantiomers, is less easily rationalised. In this work, it was the permeation of the eutomer (S‐propranolol) that was retarded, although the general principle of stereoselectively retarded skin permeation has been established. Chirality 11:680–683, 1999. © 1999 Wiley‐Liss, Inc.

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Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase

Cited by 28 publications

References 15 publications

Enantiomer Separations

Enantiomer Separations

Application of thin-layer chromatography in enantiomeric chiral analysis—an overview

Differential permeation of propranolol enantiomers across human skin in vitro from formulations containing an enantioselective excipient

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