Separation of drug stereoisomers by the formation of. beta. -cyclodextrin inclusion complexes

Journal Article · Fri May 30 00:00:00 EDT 1986 · Science (Washington, D.C.); (United States)

DOI:https://doi.org/10.1126/science.3704640· OSTI ID:5334127

Armstrong, D W; Ward, T J; Armstrong, R D; Beesley, T E

For many drugs, only racemic mixtures are available for clinical use. Because different stereoisomers of drugs often cause different physiological responses, the use of pure isomers could elicit more exact therapeutic effects. Differential complexation of a variety of drug stereoisomers by immobilized ..beta..-cyclodextrin was investigated. Chiral recognition and racemic resolution were observed with a number of compounds from such clinically useful classes as ..beta..-blockers, calcium-channel blockers, sedative hypnotics, antihistamines, anticonvulsants, diuretics, and synthetic opiates. Separation of the diastereomers of the cardioactive and antimalarial cinchona alkaloids and of two antiestrogens was demonstrated as well. Three dimensional projections of ..beta..-cyclodextrin complexes of propanol, which is resolved by this technique, and warfarin, which is not, are compared. These studies have improved the understanding and application of the chiral interactions of ..beta..-cyclodextrin, and they have demonstrated a means to measure optical purity and to isolate or produce pure enantiomers of drugs. In addition, this highly specific technique could also be used in the pharmacological evaluation of enantiometric drugs. 27 references, 3 figures, 2 tables.

• Research Organization: Texas Tech Univ., Lubbock
• DOE Contract Number: AS05-84ER13159
• OSTI ID: 5334127
• Journal Information: Science (Washington, D.C.); (United States), Journal Name: Science (Washington, D.C.); (United States) Vol. 232; ISSN SCIEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
CARBOHYDRATES
CHROMATOGRAPHY
COMPLEXES
DATA
DEXTRIN
DRUGS
EXPERIMENTAL DATA
INFORMATION
ISOMERS
LIQUID COLUMN CHROMATOGRAPHY
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYSACCHARIDES
RACEMATES
SACCHARIDES
SEPARATION PROCESSES
STEREOCHEMISTRY