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Resolution of Racemic Propranolol in Liquid Membranes Containing TA‐β‐cyclodextrin

Ferreira, Q. ; Coelhoso, I. M. Coelhoso ; Ramalhete, N. Ramalhete ; Marques, H. M. C. Marques

Separation Science and Technology Vol. 41, Nº 16, pp. 3553 - 3568, February, 2007.

ISSN (print): 1520-5754
ISSN (online): 0149-6395

Scimago Journal Ranking: 0,46 (in 2007)

Digital Object Identifier: 10.1080/01496390600997799

The pharmacological properties of propranolol enantiomers are quite different, the β‐adrenergic blocking activity resides in the (S)‐(−) isomer, while the (R)‐(+)‐enantiomer has only a membrane stabilizing effect. The inherent chirality of cyclodextrins (CDs) allows them to form diastereomeric complexes. In this work, a peracetylated β‐CD (TA‐β‐CD) that preferentially interacts with the (S)‐(−) isomer of propranolol was used. Two liquid membranes, bulk liquid membrane (BLM) and supported liquid membrane (SLM) were tested. A recovery of 30% and a enantiomeric excess of 12% were obtained, using a SLM with 10 mM of propranolol and a pH gradient between feed and stripping phases.