Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation

Roldo, Marta; Hornof, M.; Caliceti, Paolo; Bernkop‐Schnürch, Andreas

doi:10.1016/s0939-6411(03)00157-7

Cited by 258 publications

(108 citation statements)

References 17 publications

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“…The results of the mucoadhesion studies (Table III) indicate that the increase in the mucoadhesive strength for TH2 was only 1.75 fold. This is occurs due to less immobilization of thiol group on to xyloglucan polymeric structure (Roldo et al, 2004). Mucoadhesion strength was found to increase as pH was increased and reaches maximum at pH 5.0, but further increase in the pH of reaction conditions did not result into increase in mucoadhesion.…”

Section: In Vitro Mucoadhesion Studiesmentioning

confidence: 93%

Synthesis and characterization of a cysteine xyloglucan conjugate as mucoadhesive polymer

Bhalekar¹,

Sonawane

Shimpi³

2013

Braz. J. Pharm. Sci.

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The aim of this study was to improve the mucoadhesive potential of xyloglucan polymer by the covalent attachment of cysteine as thiol moiety. The parent polymer xyloglucan was chemically modified by introducing sulphydryl bearing compound L-cysteine HCl. Different batches of xyloglucan-cysteine conjugates were prepared at varying reaction pH (2-6) and evaluated for optimum thiol incorporation, disulphide group content, swelling behavior, rheological properties and mucoadhesive properties. The obtained conjugates characterized in vitro by quantification of immobilized thiol groups; showed maximum thiol incorporation on xyloglucan (7.67 ± 0.14 %) at pH 5. The disulphide group content was found maximum (2.83 ± 0.12) at pH 6. The water uptake at end of 4 h was 5.0 for xyloglucan and was found to decrease in thiolated derivatives with increase in thiolation. Mucoadhesion studies revealed that mucoadhesion of xyloglucan-cysteine conjugate increased more than twice compared to the unmodified polymer. The viscosity of thiomer was more than that of xyloglucan because of formation of disulphide bonds.Uniterms: Mucoadhesion. Thiomer. Xyloglucan. L-cysteine HCl.O objetivo deste estudo foi melhorar o potencial mucoadesivo do polímero xiloglicano pela ligação covalente de cisteína como unidade de tiol. O polímero xiloglicano foi quimicamente modificado pela introdução de cloridrato de cisteína como grupo contendo sulfidrila. Prepararam-se diferentes lotes de conjugados cisteína-xiloglicano em pH variando de 2 a 6, avaliando-se a incorporação ótima de tiol, o conteúdo de dissulfeto, o comportamento de inchamento, as propriedades reológicas e mucoadesivas. Os conjugados obtidos foram caracterizados in vitro pela quantificação de grupos tiol, mostrando máxima incorporação na xiloglicana (7.67 ± 0.14 %) em pH 5. O conteúdo de grupos dissulfeto foi máximo (2.83 ± 0.12) em pH 6. O índice de inchamento em % no fim de 4 h foi 83.87 para o xiloglicano e diminuiu para os derivados tiolados. O conteúdo foi mínimo para TH2 (78.26), aumentou pouco até TH5 (83.33) e diminuiu, posteriormente, para TH6 (80.13). Os estudos de mucoadesão revelaram que o conjugado xiloglicano-cisteína aumentou mais que duas vezes comparativamente ao polímero não modificado. A viscosidade do tiômero foi maior do que a do xiloglicano devido à formação das ligações dissulfeto.

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Section: In Vitro Mucoadhesion Studiesmentioning

confidence: 93%

Synthesis and characterization of a cysteine xyloglucan conjugate as mucoadhesive polymer

Bhalekar¹,

Sonawane

Shimpi³

2013

Braz. J. Pharm. Sci.

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“…Thiolation reaction with Traut's reagent (2-iminothiolane) has the advantages of being a one-step reaction and protecting the thiolating agent from oxidation. The degree of thiol substitution in thiolated chitosan can be obtained based on Ellman's method for assaying thiols [33][34][35][36][37][38][39][40][41][42][43]. Thiolated chitosan possesses better mucoadhesiveness and permeation properties as compared to unmodified chitosan [33][34][35][36][37][38][39][40][41][42][43].…”

Section: Thiolationmentioning

confidence: 99%

“…Nanoparticles of thiolated chitosan may be obtained as a result of an ionic cross-linking reaction of thiolated chitosan with TPP [100]. Thiolated chitosan nanoparticles have been studied for applications in drug delivery as well as for permeation enhancement [33][34][35][36][37][38][39][40][41][42][43].…”

Section: Thiolationmentioning

confidence: 99%

“…Thus, in the current chapter, an overview on the drug delivery applications of cross-linked [23] and chemically modified chitosan is given. Important modified and cross-linked derivatives include carboxymethyl-chitosan (CMC), O-carboxymethyl-chitosan (O-CMC), N,O-carboxymethyl-chitosan (N,O-CMC) and N-carboxymethyl-chitosan (N-CMC) [14][15][16][17][18][19], succinylchitosan [24][25][26][27][28][29][30][31][32], thiolated chitosan [33][34][35][36][37][38][39][40][41][42][43], and chitosan grafted with PNIPAAm and PNVCL (chitosang-PNIPAAm and chitosan-g-PNVCL) [44][45][46][47].…”

Section: Introductionmentioning

confidence: 99%

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Approaches for Functional Modification or Cross‐Linking of Chitosan

Anitha

Rejinold

Bumgardner

et al. 2012

Chitosan‐Based Systems for Biopharmaceuticals

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“…Chitosan was cross-linked with 2-iminothiolane and reported as having increased mucoadhesive properties [11]. Carboxymethyl dextran was modified by the covalent attachment of cysteine which improved the mucoadhesive properties [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a Novel Mucoadhesive Derivative of Psyllium Seed Polysaccharide

Rao¹,

Gaikwad²,

Shevate³

2017

Int J Pharm Pharm Sci

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Objective: In the present study, thiol-functionalization of psyllium seed polysaccharide (PSY) was cross-linked with thioglycolic acid by esterification in an attempt to reveal the mucoadhesive properties of thiolated psyllium seed polysaccharide (TPSY). Methods:The crosslinking was carried out by the microwave-assisted method. A simplex centroid design was employed to systematically study the mucoadhesive strength, mucoadhesive retention time and drug release profile. Comparative evaluation of carbopol-based ciprofloxacin hydrochloride (HCl) tablets containing PSY and TPSY was carried out. Acute oral toxicity studies and repeated oral toxicity for TPSY were also conducted.Results: Thiol-functionalization was confirmed by-SH stretch in Fourier Transform infra-red spectra at 2353 cm -1 . Thiolation was observed in thiolated PSY (TPSY) by a change in the surface morphology of psyllium from fibrous to granular and resulted in 82 %swelling in deionized water. TPSY was found to contain 102.35 mmol of thiol groups/g as determined by the Ellman's method. The percent increase in mucoadhesive strength of TPSY was found to be 50.31 % as compared to PSY and 128.30 % as compared to carbopol. The percent increase in mucoadhesive retention time of TPSY was found to be 110 % as compared to PSY and 50 % as compared to carbopol. Conclusion:Mucoadhesion strength and mucoadhesive retention time were greater of tablets containing a higher amount of TPSY. Further, the acute oral toxicity studies and repeated oral toxicity for TPSY proved it as non-toxic and hence safe for human use.

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Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation

Cited by 258 publications

References 17 publications

Synthesis and characterization of a cysteine xyloglucan conjugate as mucoadhesive polymer

Synthesis and characterization of a cysteine xyloglucan conjugate as mucoadhesive polymer

Approaches for Functional Modification or Cross‐Linking of Chitosan

Synthesis and Characterization of a Novel Mucoadhesive Derivative of Psyllium Seed Polysaccharide

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