Hydrophobic thiolation of pectin with 4-aminothiophenol: synthesis and in vitro characterization.

AAPS PharmSciTech
Glen PereraAndreas Bernkop-Schnürch

Abstract

The aim of this study was to modify pectin by covalent attachment of the water-insoluble ligand 4-aminothiophenol to its polymeric backbone. 4-Aminothiophenol is a ligand which is highly prone to oxidation. Therefore, this ligand allows oxidative cross-linking of pectin under mild oxidative conditions. Additionally, hydrophobization of pectin can be achieved by the mentioned modification which offers certain advantages over highly hydrophilic native pectins. 4-Aminothiophenol was covalently attached to pectin via amide bond formation between carboxylic moieties of pectin and the amino-group of 4-aminothiophenol. Two different pectin-4-aminothiophenol conjugates were synthesized and investigated regarding the amount of coupled ligand, rheological behavior under oxidative conditions, swelling behavior, and cytotoxic effects. Within this study, 557.3 +/- 49.0 and 158.8 +/- 23.1 micromol 4-aminothiophenol have been coupled per gram pectin. Within both conjugates, around 75% of the bound ligand appeared in its reduced form. Within rheological studies, a 500-fold increase in viscosity was achieved by addition of hydrogen peroxide as an oxidizing agent. Investigations on the swelling behavior revealed that this hydrophobic modificatio...Continue Reading

References

Jul 9, 1999·Pharmaceutical Research·A Bernkop-SchnürchS Steininger
Oct 12, 2000·Carbohydrate Research·A OosterveldA G Voragen
Apr 11, 2001·Journal of Controlled Release : Official Journal of the Controlled Release Society·A Bernkop-SchnürchM F Richter
May 4, 2002·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Michaela K Marschütz, Andreas Bernkop-Schnürch
Mar 19, 2003·Chemical Research in Toxicology·Rajeshwar P VermaCynthia D Selassie
Mar 22, 2003·Drug Development and Industrial Pharmacy·Rasmané SemdéKarim Amighi
Jul 5, 2003·International Journal of Pharmaceutics·Andreas Bernkop-SchnürchTheresa Zoidl
Mar 17, 2004·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Alexander H Krauland, Andreas Bernkop-Schnürch
Mar 3, 2007·The Journal of Pharmacy and Pharmacology·Sayeh MajzoobAndreas Bernkop-Schnürch
Apr 22, 2008·International Journal of Pharmaceutics·Pornsak Sriamornsak, Ross A Kennedy
Aug 25, 2009·Biomaterials·Duangkamon SakloetsakunAndreas Bernkop-Schnürch

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Citations

Sep 4, 2013·International Journal of Pharmaceutics·Sabine HauptsteinAndreas Bernkop-Schnürch
Jun 25, 2014·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Sonja BonengelAndreas Bernkop-Schnürch
Sep 13, 2013·Drug Development and Industrial Pharmacy·Sabine HauptsteinAndreas Bernkop-Schnürch
Jun 19, 2012·Expert Opinion on Drug Delivery·Sabine Hauptstein, Andreas Bernkop-Schnürch
May 5, 2010·Journal of Controlled Release : Official Journal of the Controlled Release Society·Glen PereraAndreas Bernkop-Schnürch
Dec 3, 2014·Carbohydrate Polymers·Elizângela A M S AlmeidaEdvani C Muniz
May 7, 2014·Critical Reviews in Food Science and Nutrition·Jun ChenShun-Jing Luo
Apr 11, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Sonja BonengelAndreas Bernkop-Schnürch

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