Nanoaggregation of inclusion complexes of glibenclamide with cyclodextrins

Lucio, David; Irache, Juan Manuel; Font, Marı́a; Martínez-Ohárriz, María Cristina

doi:10.1016/j.ijpharm.2017.01.028

Cited by 24 publications

(12 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is not surprising as the capacity of cyclodextrins to increase the solubility of hydrophobic DX molecules has been reported in the past (38,39). The reason for this solubility increase is the formation of inclusion complexes between the drugs and cyclodextrin molecules (21,40,41). It has been reported previously that DX forms a 1:1 inclusion complex with HPBCD and its binding constant has been determined by several authors ranging between 2000 and 2500 M −1 (42,43).…”

Section: Loading and Releasementioning

confidence: 64%

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

et al. 2019

View full text Add to dashboard Cite

Hydrogels have been extensively investigated as a platform for drug delivery. However, their use for the delivery of hydrophobic drugs has been limited by their incompatibility with hydrophobic drug molecules. The chemical modification of the structure of the hydrogels to include hydrophobic moieties has been proven to be a good alternative to increase the stability and solubility of hydrophobic drugs in the polymer matrix of the hydrogel. The inclusion of hydroxypropyl-β-cyclodextrins (HPBCD) and Tween ® 85 (T85) within hydrogel matrices has the potential to improve hydrophobic drug loading and release. HPBCD have the ability to host hydrophobic drug molecules in their cone-like structure, forming inclusion complexes through host-guest interactions. On the other hand, T85 is an amphiphilic molecule and, consequently, has the potential to increase hydrophilic drug loading within the hydrogels. In the present work, a new type of hydrogel made from poly(methyl vinyl ether-co-maleic acid) (GAN) and poly(ethylene glycol) (PEG) containing T85 and HPBCD was synthesized for hydrophobic drug release. Hydrogels were based on GAN crosslinked (PEG) and HPBCD and/or T85 via an esterification reaction in the solid state (solvent free). The synthesised hydrogels were characterised using Fourier transform infrared (FTIR) spectroscopy, swelling studies and contact angle measurements. The hydrogels showed swellings ranging from 140 to 180%. The inclusion of T85 in the hydrogels improved the wettability of the materials. On the other hand, the inclusion of HPBCD within the hydrogels decreased the wettability as the contact angle between the hydrogels and water increased with the HPBCD content. Finally, the materials were loaded with an ophthalmic drug, dexamethasone (DX). HPBC-containing hydrogels showed a higher DX uptake and, consequently, they showed a higher capacity of DX release. On the other hand, T85 containing hydrogels did not show any improvement over the hydrogels containing only GAN and PEG. The hydrogels were able to provide sustained DX release over periods of 6 hours.

show abstract

Section: Loading and Releasementioning

confidence: 64%

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Interestingly, the inclusion complexes aggregations in aqueous solutions typically result in large micelle-like structures [ 22 ], micrometer-sized rods [ 20 , 38 , 39 ], or spherical shape nanoaggregates [ 15 ], while the formation of wires is more distinctive to unmodified cyclodextrins [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

“…CD inclusion complexes, CD pseudo rotaxanes, or rotaxanes have already found their applications in the fields including food and pharmaceutical sciences [ 7 , 8 , 9 , 10 ], fluorophores properties improvement [ 11 , 12 ], and catalysis [ 13 , 14 ]. Besides the inclusion complex formation, both CDs and CD inclusion complexes may self-assemble in aqueous solutions into nano or micro aggregates by means of weak hydrogen bonds and hydrophobic forces [ 11 , 15 , 16 , 17 ]. In the case of inclusion complexes, the size of the aggregates may range from 100 to 4000 nm, while the shape of the aggregates strongly depends on the guest nature.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments

et al. 2020

View full text Add to dashboard Cite

We have designed and synthesized a series of novel, supramolecular, long-lived fluorescent probes based on the host-guest inclusion complexes formation between fluorescent indolizinyl-pyridinium salts and β-cyclodextrin. Fluorescence and electrospray ionisation mass spectrometry experiments, supported by theoretical molecular docking studies, were utilized in the monitoring of the inclusion complexes formation, evidencing the appearance of corresponding 1:1 and 1:2 species. Additionally, the influence of the guest molecule over the aggregation processes of the cyclodextrin inclusion complexes was investigated by transmission electron microscopy. The absence of cytotoxicity, cellular permeability, long-lived intracellular fluorescence, and in time specific accumulation within acidic organelles identified the investigated supramolecular entities as remarkable candidates for intracellular fluorescence probes. Co-staining experiments using specific organelle markers revealed the fact that, after a 24-h incubation period, the inclusion complexes accumulate predominantly in lysosomes rather than in mitochondria. This study opens new possibilities for a broad range of fluorescent dyes with solubility and high toxicity issues, able to form inclusion complexes with β-cyclodextrin, to be tested as intracellular fluorescence probes.

show abstract

“…The aggregation of single CDs and CD-guest complexes, in water, has been described in a number of recent studies [2,3,13,31,37,40,41]. Despite the efforts for understanding the factors that govern inclusion/binding with guest molecules, the precise manner in which CD molecules aggregate and the cooperative effects underlying this phenomenon are much less studied and still far from consensual.…”

Section: Controversial Experimental Evidencementioning

confidence: 99%

Aggregation of Cyclodextrins: Fundamental Issues and Applications

Cova¹,

Cruz²,

Valente³

et al. 2018

Cyclodextrin - A Versatile Ingredient

View full text Add to dashboard Cite

The aggregation of cyclodextrins (CD) in aqueous solution is an old, yet still vastly unexplored topic that has been studied at least since the 1980s. At that time, few authors took into consideration the possibility of formation of aggregates for the interpretation of thermodynamic and thermophysical properties of CDs in aqueous solution. The aggregates appear at quite low CD concentrations and seem to encompass only a small number of CD molecules. They also occur in water in the presence of hydrophobic or amphiphilic moieties, including surfactants, assuming a preassembled state with the hydrophobic chains threading through one or two CDs. After a long period in which it has been neglected, CD aggregation is now a hot topic and one far from gathering consensus. In this chapter, a timely and critical review on the phenomenon of CD aggregation and the respective supramolecular properties, including some computational rationales, will be presented. A comprehensive summary of CD aggregates studied to date, indicating the formation conditions, characterization techniques, and applications, is also provided.

show abstract

Nanoaggregation of inclusion complexes of glibenclamide with cyclodextrins

Cited by 24 publications

References 35 publications

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments

Aggregation of Cyclodextrins: Fundamental Issues and Applications

Contact Info

Product

Resources

About