Composite membrane of bacterially-derived cellulose and molecularly imprinted polymer for use as a transdermal enantioselective controlled-release system of racemic propranolol.
A composite membrane for transdermal delivery of S-propranolol enantiomer was developed based on the controlled pore functionalization of bacterial cellulose membranes using a molecularly imprinted polymer (MIP) layer synthesis. The reactive pore-filling of an asymmetric porous cellulose membrane with a MIP thin-layer was effected using a silanized coupler as an additional anchor for the MIP. MIP thin-layers with specific binding sites for S-propranolol were synthesized by copolymerization of methacrylic acid with a cross-linker, ethylene glycol dimethacrylate in the presence of S-propranolol as the template molecule and the latter was subsequently extracted. Selective transport of S-propranolol through the MIP composite membrane was obtained, although this was determined mostly by the parent cellulose membrane with some ancillary contributory effect from the MIP layer. In addition, an enantioselectivity in the transport of propranolol prodrug enantiomers was found, suggesting that the shape and functional groups orientation, which are similar to that of the print molecule were essential for enantiomeric recognition of the MIP composite membrane. The enantioselectivity of S-MIP membranes was also shown when the release of propranolol enantiomers was studied in vitro using rat skin, with racemic propranolol contained in the donor compartment. The composite membrane of bacterially-derived cellulose and molecularly imprinted polymer may have great potential for use as a transdermal enantioselective controlled-release system for racemic propranolol.
Bodhibukkana
Chatchada
C
Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hatyai, Songkla 90112, Thailand.
Srichana
Teerapol
T
Kaewnopparat
Sanae
S
Tangthong
Naruedom
N
Bouking
Pisit
P
Martin
Gary P
GP
Suedee
Roongnapa
R
D000279:Administration, Cutaneous; D000818:Animals; D001696:Biomechanical Phenomena; D002482:Cellulose / Q000737:chemistry* / Q000493:pharmacokinetics* / Q000648:ultrastructure; D003692:Delayed-Action Preparations / Q000008:administration & dosage / Q000493:pharmacokinetics*; D017097:Electric Impedance; D041822:Gluconacetobacter xylinus / Q000737:chemistry; D006898:Hydroxylamines / Q000737:chemistry; D008297:Male; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry / Q000493:pharmacokinetics; D016062:Porosity; D011433:Propranolol / Q000737:chemistry* / Q000493:pharmacokinetics*; D051381:Rats; D017208:Rats, Wistar; D012821:Silanes / Q000737:chemistry; D012995:Solubility; D013237:Stereoisomerism
D003692:Delayed-Action Preparations; D006898:Hydroxylamines; D008689:Methacrylates; C494687:N,O-dimethacryloylhydroxylamine; D011108:Polymers; D012821:Silanes; C008384:methacrylic acid; C017492:methacryloxypropyltrimethoxysilane; D002482:Cellulose; D011433:Propranolol