Monosubstituted hydrazone β-cyclodextrin derivatives for pH-sensitive complex formation with aromatic drugs

Maciej Majdecki; Agata Krzak; Kamila Sadowska; Olga Swiech

doi:10.1007/s10847-018-0841-x

Monosubstituted hydrazone β-cyclodextrin derivatives for pH-sensitive complex formation with aromatic drugs

Abstract

A new and convenient synthetic pathway was developed to produce monosubstituted cyclodextrins with high yields. Each of the β-cyclodextrin derivatives described in this work has an aromatic substituent connected with cyclodextrin core by a pH-sensitive hydrazone linker and a carbon chain. Carbon chains differ in lengths having one or three carbon atoms. The correlation between water solubility and linker length was determined using UV–Vis spectroscopy, while the dependence of hydrazone bond hydrolysis on the electrolyte pH was confirmed by cyclic voltammetry. The pH-dependent complex-formation ability between the hydrazone derivative of cyclodextrin and anthracycline drug was examined by square wave voltammetry. The significantly big solubility and the appropriate pH, at which the hydrolysis of the hydrazone bond occurs, make the newly synthesized derivatives attractive for pharmaceutical and medical applications.

Citations

5

CrossRef
0

Web of Science
5

Scopus

Authors (4)

Cite as

Full text

download paper

downloaded 66 times

Publication version: Accepted or Published Version
License: open in new tab

Keywords

Details

Category:: Articles
Type:: artykuł w czasopiśmie wyróżnionym w JCR
Published in:: Journal of Inclusion Phenomena and Macrocyclic Chemistry no. 93, pages 77 - 83,
ISSN: 1388-3127
Language:: English
Publication year:: 2019
Bibliographic description:: Majdecki M., Krzak A., Sadowska K., Swiech O.: Monosubstituted hydrazone β-cyclodextrin derivatives for pH-sensitive complex formation with aromatic drugs// JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY. -Vol. 93, iss. 1-2 (2019), s.77-83
DOI:: Digital Object Identifier (open in new tab) 10.1007/s10847-018-0841-x
Verified by:: Gdańsk University of Technology