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The Enantioselective-Controlled Delivery of Propranolol by Cellulose

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The Enantioselective-Controlled Delivery of Propranolol by Cellulose The Enantioselective-Controlled Delivery of Propranolol by Cellulose Membrane Grafted with Molecularly Imprinted Polymer Chatchada Bodhibukkana A Thesis Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Pharmaceutical Sciences Prince of Songkla University 2008 i Copyright of Prince of Songkla University Thesis Title The Enantioselective-Controlled Delivery of Propranolol by Cellulose Membrane Grafted with Molecularly Imprinted Polymer Author Miss Chatchada Bodhibukkana Major program Pharmaceutical Sciences Major Advisor Examining Committee ………………………………………… ………………………………Chairperson (Assoc. Prof. Dr. Roongnapa Srichana) (Assoc. Prof. Dr. Ruedeekorn Wiwattanapatapee) ………………………………Committee Co-advisor (Assoc. Prof. Dr. Varaporn Junyaprasert ) ………………………………………… ………………………………Committee (Assoc. Prof. Dr. Teerapol Srichana) (Assoc. Prof. Dr. Roongnapa Srichana) ………………………………………… ………………………………Committee (Prof. Gary P. Martin) (Assoc. Prof. Dr. Teerapol Srichana) The Graduate School, Prince of Songkla University, has approved this thesis as partial fulfillment of the requirements for the Doctor of Philosophy Degree in Pharmaceutical Sciences …………………………………………… (Assoc. Prof. Dr. Krerkchai Thongnoo) Dean of Graduate School ii propranolol !" #$ %& '(")* %&% **+, - )!,!. */*- 0 1,!2 ( 2550 ! 26 7 %8%),(9-+:%&;*,< + (composite membrane) #$ ; :%%* %&% **+, (Molecularly imprinted polymer, MIP) *& !" L* %&L* ; ; S-enantiomer ; racemic propranolol + ,: N68 +%& +N$'O !,& %&$*- #$ ") ,: N!,8 * %&% **+, - +. silanisation %&$ *- ( #$ %&;,: N!,8 * %:) ; +P ( (% *& N" 9 +. * Q#!,& Q" #6&!,8 MIP %&%:) ; * ( S-propranolol ;9$ ,: N68 :* Q#!,& N) methacrylic acid ethylene glycol dimethacrylate #6&+P cross-linker % S- propranolol +P (,)** ,8 ( -" -(,)**;9$ , Q+N Q)"*% **+,%&L* ; ; ,8 #6&; 26 7 9 * %&L* S-propranolol + ") %& L* ; ; S-MIP membrane ,8 ) NV+P W ; #$ X ( %&!,8 * %&% **+,;+P (,)!) N" +- %+/1 * &68 N ; %8 L* 9*Q"! %) , & 26 7 ") propranolol prodrug #6& N"NX ) iii $+ ;,%(,) N$'O !,& prodrugs %:) :,V( ;; S-MIP membrane %& ; ;; ( -Q" %%&-& - ,8 %:) :" :6(,)**(" %&- ; %8 26 7 in vitro study ,8 S-MIP membrane 9 ++ L* S-propranolol ; racemic propranolol 26 7 W W)N ,N $ #6&W N"NX 962, 1 * +- #$ ; :%%* %&% **+, - N, !"+P W)N ,L* N, racemic propranolol ; %8W ,!%8 N"NX ) ++ S-MIP membrane +P ++ facilitate transport W Q [fixed carrier] & 26 7 ,'' #6&+O;;,( ^ (! pH ) %&%W( +` N) S-propranolol [fixed carrier] ; 9W ( ++ L* :) 9 S- MIP composite membraneQ" #6& ;; - (,)** ,8 ;$- ,'' pH 7.4 %&L* S-enantiomer ; racemic propranolol ;$ ) 0% racemic propranolol prodrugs %& propranolol prodrug Q 9*& *W " $W)N ,N $ Q" & 26 7 W poloxamer chitosan gel ( L* *) chitosan gel :) 9%&% +P (,) %& L* ; ; S-propranolol 0%& poloxamer gel #6&%:) N ) Q :) ( ( chitosan gel N" W %&$ (high flux) *" ,8%:) 9 L* S-propranolol W W)N ,N $ , ,8 chitosan gel ;69$ *& Q+ !"+P reservoir N, $W)N ,( Q+ enantiomer-controlled delivery patch ! reservoir (%68 chitosan gel %&% racemic propranolol HCl " Q+ N) S-MIP composite membrane laminated backing #6& transdermal patch %& (%68 ,8 9:) 9 S-propranolol % , :,V iv & +%&W)N ,N $ 26 7 (in vivo ) #6&: 1,!; 2 ( (Cmax , T max AUC 0-24 ) %&Q"; W + ,8 9%:%Q" , N" S- propranolol gel topical application ; W !%8 N"NX ) S-MIP composite membrane %2, 1 * N, Q+ !"+P %& L* ; ; W)N , racemic propranolol v Thesis Title The Enantioselective-Controlled Delivery of Propranolol by Cellulose Membrane Grafted with Molecularly Imprinted Polymer Author Miss Chatchada Bodhibukkana Major program Pharmaceutical Sciences Academic year 2007 ABSTRACT The aim of this thesis was to develop a composite membrane of bacterially- derived cellulose and molecularly imprinted polymer (MIP) for use as a transdermal enantioselective controlled-release system of racemic propranolol. The composite membranes were produced by the controlled pore functionalization of bacterial cellulose membranes using a molecularly imprinted polymer layer synthesis. The reactive pore-filling of an asymmetric porous cellulose membrane with a MIP thin- layer was modified using a silanised 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 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. vi 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 results obtained, demonstrated the potential use of the composite membrane of bacterially-derived cellulose and molecularly imprinted polymer as a transdermal enantioselective controlled-release system of racemic propranolol. The result obtained from the in vitro release study showed that the selective release characteristic of the S-MIP membrane is the facilitated permeation via the ‘fixed-carrier’ mechanism such that the interaction between ‘fixed-carrier’ sites and S-propranolol can occur in aqueous buffers, and factors such as pH have been shown to have an influence. The template recognition of the S-MIP composite membrane was found to be highest in pH 7.4 buffer and the selective controlled delivery of the active S-enantiomer from racemic propranolol was greater than that from racemic propranolol prodrugs. In addition, the propranolol prodrug did not show the ability in increasing the penetration of the drug across the excised rat skin. Subsequently, the MIP thin-layer composited cellulose membrane with selectivity for S-propranolol was employed as the enantioselective-controlled release system. The effect of gel reservoir (poloxamer and chitosan) on enantioselective delivery was investigated. The chitosan gel allowed excellent selectivity for delivery of the S-propranolol enantiomer, whilst the more rheologically vii structured poloxamer gel formulation provided no selective release of S-propranolol. The chitosan gel exhibited high flux and had the ability to enantioselective deliver S- propranolol across excised rat skin. The reservoir patch for enantiomer-controlled delivery of propranolol was therefore fabricated by incorporating the chitosan gel formulation containing racemic propranolol hydrochloride into the MIP composite membrane laminated backing. These patch devices were shown to exhibit the significant stereoselectivity uptake of propranolol when attached to the skin, using pharmacokinetic studies in Wistar rats. S -Propranolol enantiomer plasma concentration profiles for the transdermal patch in the in vivo study were comparable to data for the gel formulations that were applied directly to skin, and containing a single S-enantiomer of propranolol. The results demonstrate that the transdermal patch based on the MIP composite membrane-controlled release system may have potential in the enantioselective-controlled delivery of the S-isomer of racemic propranolol. viii ACKNOWLEDGEMENTS I am especially grateful to my advisors Associate Professor Dr. Roongnapa Srichana and Associate Professor Dr. Teerapol Srichana for their advice and guidance throughout the course of this study. I express my sincere thanks to supervisors Professor Gary P. Martin, Professor Marc Brown and Dr. Stuart Jones for their suggestions and especially for their supports during my study in London. I would also like to thank Dr. Sanae Kaewnopparat and Miss Kiammarat Bauking for their assistance in cellulose membrane production, and Dr. Thanaporn Amnuaikit, Mr. Pisit Bauking and Mrs. Rachawan Limviwatkul for their assistance in technical work with animal experimentation. Financial support from the Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program (Grant No. PHD/0160/2545) is acknowledged Special thanks must go to my mother for her love and understanding, encouragement and supports and particularly for everything that she has done for me all of my life. Chatchada Bodhibukkana ix CONTENTS Page Contents x List of Tables xix List of Figures xxiii Chapters 1. Introduction 1.1. Literature reviews 1 1.1.1. Chirality 1 1.1.1.1. History of optical isomerism 1 1.1.1.2. Stereochemistry and biological activities 2 1.1.1.3. Classification of drug activity 5 1.1.1.3. Chiral separations 9 1.1.2. Transdermal drug delivery 13 1.1.2.1. Basic structure of the skin 13 1.1.2.2. Basic skin functions 21 1.1.2.3. Routes of absorption across the skin 22 1.1.2.4. Transdermal drug delivery system 25 1.1.3. Molecularly imprinted polymer 29 1.1.3.1. The concept of molecular imprinting 29 1.1.3.2. Configurations and applications of molecular imprinted 33 polymers 1.1.3.3. Molecularly imprinted membrane 34 x CONTENTS (continued) Page 1.2. Objectives of the thesis 40 1.2.1. Propranolol: the drug of
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