Moghadam, Ali; Ijaz, Muhammad; Asim, Mulazim Hussain; Mahmood, Arshad; Jelkmann, Max; Matuszczak, Barbara; Bernkop-Schnürch, Andreas (2018): Supplementary data to: Non-ionic thiolated cyclodextrins - The next generation [dataset]. PANGAEA, https://doi.org/10.1594/PANGAEA.891616,

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Supplement to: Moghadam, A et al. (2018): Non-ionic thiolated cyclodextrins - the next generation. International Journal of Nanomedicine, 13, 4003-4013, https://doi.org/10.2147/IJN.S153226

Current study was aimed to develop a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Thiolated β-CD was prepared through bromine substitution of its hydroxyl groups followed by replacement to thiol groups using thiourea. The thiolated β-CD was characterized in vitro via dissolution studies, cytotoxicity studies, mucoadhesion studies on freshly excised porcine intestinal mucosa, and inclusion complex formation with miconazole nitrate. Thiolated β-CDs namely β-CD-SH600 and β-CD-SH1200 displayed 558.66 ± 78 and 1163.45 ± 96 µmol thiol groups per gram of polymer, respectively. Stability constant (Kc) of 190 M-1 confirmed the inclusion complex formation of miconazole nitrate with β-CD-SH. Inclusion complexes of β-CD-SH600 and β-CD-SH1200 resulted in 157 and 257-fold increased solubility of miconazole nitrate, respectively. In addition, more than 80 % of thiol groups were stable even after 6 hours at pH 5. Both β-CD-SH showed on at least 1.3-folds improved solubility in water. In contrast to cationic thiolated cyclodextrins of the first generation, both thiomers showed no significant cytotoxicity. The mucoadhesive properties of the new thiolated CDs were 39.73- and 46.37-fold improved, respectively. These results indicate that β-CD-SH might provide a new favorable tool for delivery of poorly soluble drugs providing a prolonged residence time on mucosal surfaces.