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 complexformation 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.

Design of Tailor-Made Biopolymer-Based Capsules for Biological Application by Combining Porous Particles and Polysaccharide Assembly

“…pH-triggered particles are designed with the aim of inducing a change in hydrophilicity/hydrophobicity upon protonation/deprotonation equilibrium in the particle. Previously reported pH–responsive systems include esters [ 113 ], acetals [ 114 ], boronic acids [ 115 ], hydrazones [ 116 ], imines [ 117 ] and functional groups. To ensure drug release, the cleavage of acid/base-sensitive bonds must induce a significant change in permeability, which is often achieved via structural fragmentation, depolymerisation or polarity change.…”

Explanation of the Formation of Complexes between Representatives of Oxazolidinones and HDAS-β-CD Using Molecular Modeling as a Complementary Technique to cEKC and NMR

“…Due to the C1-O-C4 glycosidic bridges that connect the individual glucopyranose units, the α-CD and γ-CD molecules are flexible. However, native β-CD is a fairly rigid structure due to the odd number of glucopyranose units that form the secondary belt due to the interaction of the C2 hydroxyl group of one glucopyranose unit with the C3 hydroxyl group of the adjacent glucopyranose unit, resulting in low solubility in water [26]. In this context, the chemical modification of native β-CD disrupts the hydrogen bonds belt and, thus, improves water solubility.…”

Modification of conducting arylidene copolymers by formation of inclusion complexes: synthesis, characterization, and applications as highly corrosion inhibitors for mild steel

“…The dominant driving forces for creating supramolecular structures are the hydrophobic interaction and the hydrogen bonding in the crystal structure and the hydrous solutions [ 18 , 19 ]. Cyclodextrin, the most common kind, comprises seven units of glucopyranose and two types of hydroxyl groups, secondary and primary groups, resulting in a macromolecule with twenty-one hydroxyl groups in total [ 20 ].…”