Non-ionic thiolated cyclodextrins — the next generation

Non-ionic thiolated cyclodextrins — the next generation

Ali Moghadam,1,2 Muhammad Ijaz,2,3 Mulazim Hussain Asim,2,4 Arshad Mahmood,2,5 Max Jelkmann,2 Barbara Matuszczak,6 Andreas Bernkop-Schnürch2 1Institute of Biotechnology, College of Agriculture, Shiraz University, Shiraz, Iran; 2Center for Chemistry and Biomedicine, Department of Pharmaceut...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Moghadam A, Ijaz M, Asim MH, Mahmood A, Jelkmann M, Matuszczak B, Bernkop-Schnürch A
Formato: article
Lenguaje:EN
Publicado: Dove Medical Press 2018
Materias:
Thiolated cyclodextrin
mucosal delivery
inclusion complex.
Medicine (General)
R5-920
Acceso en línea:https://doaj.org/article/6c59986368e347e0bfbe06a742506ad7
Etiquetas: Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
id oai:doaj.org-article:6c59986368e347e0bfbe06a742506ad7
record_format dspace
spelling oai:doaj.org-article:6c59986368e347e0bfbe06a742506ad72021-12-02T01:38:16ZNon-ionic thiolated cyclodextrins — the next generation1178-2013https://doaj.org/article/6c59986368e347e0bfbe06a742506ad72018-07-01T00:00:00Zhttps://www.dovepress.com/non-ionic-thiolated-cyclodextrins-the-next-generation-peer-reviewed-article-IJNhttps://doaj.org/toc/1178-2013Ali Moghadam,1,2 Muhammad Ijaz,2,3 Mulazim Hussain Asim,2,4 Arshad Mahmood,2,5 Max Jelkmann,2 Barbara Matuszczak,6 Andreas Bernkop-Schnürch2 1Institute of Biotechnology, College of Agriculture, Shiraz University, Shiraz, Iran; 2Center for Chemistry and Biomedicine, Department of Pharmaceutical Technology, Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria; 3Department of Pharmacy, COMSATS Institute of Information and Technology, Lahore, Pakistan; 4Department of Pharmaceutics, Faculty of Pharmacy, University of Sargodha, Sargodha, Pakistan; 5Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad, Pakistan; 6Center for Chemistry and Biomedicine, Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria Introduction: The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Materials and methods: Thiolated beta CD (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. Results: Thiolated β-CDs namely β-CD-SH600 and β-CD-SH1200 displayed 558.66 ± 78 and 1,163.45 ± 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 compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs 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. Conclusion: 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. Keywords: thiolated cyclodextrin, mucosal delivery, inclusion complexMoghadam AIjaz MAsim MHMahmood AJelkmann MMatuszczak BBernkop-Schnürch ADove Medical PressarticleThiolated cyclodextrinmucosal deliveryinclusion complex.Medicine (General)R5-920ENInternational Journal of Nanomedicine, Vol Volume 13, Pp 4003-4013 (2018)
institution DOAJ
collection DOAJ
language EN
topic Thiolated cyclodextrin
mucosal delivery
inclusion complex.
Medicine (General)
R5-920
spellingShingle Thiolated cyclodextrin
mucosal delivery
inclusion complex.
Medicine (General)
R5-920
Moghadam A
Ijaz M
Asim MH
Mahmood A
Jelkmann M
Matuszczak B
Bernkop-Schnürch A
Non-ionic thiolated cyclodextrins — the next generation
description Ali Moghadam,1,2 Muhammad Ijaz,2,3 Mulazim Hussain Asim,2,4 Arshad Mahmood,2,5 Max Jelkmann,2 Barbara Matuszczak,6 Andreas Bernkop-Schnürch2 1Institute of Biotechnology, College of Agriculture, Shiraz University, Shiraz, Iran; 2Center for Chemistry and Biomedicine, Department of Pharmaceutical Technology, Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria; 3Department of Pharmacy, COMSATS Institute of Information and Technology, Lahore, Pakistan; 4Department of Pharmaceutics, Faculty of Pharmacy, University of Sargodha, Sargodha, Pakistan; 5Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad, Pakistan; 6Center for Chemistry and Biomedicine, Department of Pharmaceutical Chemistry, Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria Introduction: The current study was aimed at developing a novel mucoadhesive thiolated cyclodextrin (CD) without ionizable groups and an intact ring backbone for drug delivery. Materials and methods: Thiolated beta CD (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. Results: Thiolated β-CDs namely β-CD-SH600 and β-CD-SH1200 displayed 558.66 ± 78 and 1,163.45 ± 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 compounds showed at least 1.3-fold improved solubility in water. In contrast to cationic thiolated CDs 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. Conclusion: 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. Keywords: thiolated cyclodextrin, mucosal delivery, inclusion complex
format article
author Moghadam A
Ijaz M
Asim MH
Mahmood A
Jelkmann M
Matuszczak B
Bernkop-Schnürch A
author_facet Moghadam A
Ijaz M
Asim MH
Mahmood A
Jelkmann M
Matuszczak B
Bernkop-Schnürch A
author_sort Moghadam A
title Non-ionic thiolated cyclodextrins — the next generation
title_short Non-ionic thiolated cyclodextrins — the next generation
title_full Non-ionic thiolated cyclodextrins — the next generation
title_fullStr Non-ionic thiolated cyclodextrins — the next generation
title_full_unstemmed Non-ionic thiolated cyclodextrins — the next generation
title_sort non-ionic thiolated cyclodextrins — the next generation
publisher Dove Medical Press
publishDate 2018
url https://doaj.org/article/6c59986368e347e0bfbe06a742506ad7
work_keys_str_mv AT moghadama nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT ijazm nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT asimmh nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT mahmooda nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT jelkmannm nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT matuszczakb nonionicthiolatedcyclodextrinsmdashthenextgeneration
AT bernkopschnurcha nonionicthiolatedcyclodextrinsmdashthenextgeneration
_version_ 1718402963455606784

Ejemplares similares