Effects of Cyclodextrins on Drug Delivery Through Biological Membranes

Loftsson, Þorsteinn; Vogensen, Stine B.; Brewster, Marcus E.; Konráðsdóttir, Fífa

doi:10.1002/jps.20992

Cited by 274 publications

(171 citation statements)

References 92 publications

Supporting

Mentioning

158

Contrasting

Unclassified

Order By: Relevance

“…In previous studies dimethyl-b-Cd and methyl-b-Cd modified cyclodextrins were shown to markedly reduce the viability of Caco-2 cells at concentrations greater than 50 mM. In our study, we found that Hp-b-Cd inclusion complexes were more cytotoxic against Caco-2 cells, consistent with previous results (Loftsson et al, 2007).…”

Section: Discussionsupporting

confidence: 92%

“…The external component of Cd, which contains many hydrophilic hydroxide groups, may improve the interaction between Cd and cells (Yunomae et al, 2003;Loftsson et al, 2007). Yang et al (2007) reported that the introduction of a-Cd decreased the cytotoxicity of polyether-imide (PEI).…”

Section: Discussionmentioning

confidence: 99%

“…(Loftsson et al, 2004(Loftsson et al, , 2007. The hydrophilic outer surface of Cd molecules forms a weak interaction with biological membranes (Yue et al, 2004;Abdelwahed et al, 2008).…”

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Cyclodextrin modulates the cytotoxic effects of chlorhexidine on microrganisms and cellsin vitro

et al. 2014

View full text Add to dashboard Cite

Section: Discussionsupporting

confidence: 92%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Cyclodextrin modulates the cytotoxic effects of chlorhexidine on microrganisms and cellsin vitro

et al. 2014

View full text Add to dashboard Cite

“…Various derivatives of cyclo- unstirred water layer on their surface which can be 100 mm thick 39 (Lennernas, 1998;Loftsson et al, 2007). Hydrophilic cyclodextrins 40 can increase the drug transport only if the resistance of UWL on 41 donor side is equal or higher than the resistance of membrane barrier Masson et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Endocytosis of fluorescent cyclodextrins by intestinal Caco-2 cells and its role in paclitaxel drug delivery

Réti-Nagy

Malanga

Fenyvesi

et al. 2015

International Journal of Pharmaceutics

View full text Add to dashboard Cite

Chemical compounds studied in this article: Cyclodextrins are widely used excipients in pharmaceutical formulations. They are mainly utilized as solubilizers and absorption enhancers, but recent results revealed their effects on cell membranes and pharmacological barriers. In addition to the growing knowledge on their interaction with plasma membranes, it was confirmed that cyclodextrins are able to enter cells by endocytosis. The number of the tested cyclodextrins was limited, and the role of this mechanism in drug absorption and delivery is not known. Our aim was to examine the endocytosis of fluorescently labeled hydroxypropyl-b-cyclodextrin, random methyl-b-cyclodextrin and soluble b-cyclodextrin polymer, and the cellular uptake of the fluorescent paclitaxel derivative-random methyl-b-cyclodextrin complex. The studied cyclodextrin derivatives were able to enter Caco-2 intestinal cells and localized in vesicles in the cytoplasm, while their permeability was very limited through Caco-2 monolayers. We demonstrated for the first time that the fluorescent paclitaxel derivative and rhodamine-labeled random methyl-b-cyclodextrin were detected in the same intracellular vesicles after treating cells with their inclusion complex. These results indicate that the endocytosis of cyclodextrin complexes can contribute to drug absorption processes.2015 Published by Elsevier B.V.

show abstract

“…This is achieved by making the drug available at the surface of the biological barrier, e.g., skin, mucosa, or the eye cornea, from where it partitions into the membrane without disrupting the lipid layers of the barrier [9]. In such cases, it is important to use just enough cyclodextrin to solubilise the drug in the aqueous vehicle since excess cyclodextrin may decrease the drug bioavailability [10]. In the case of water-soluble drugs e.g.…”

Section: Introductionmentioning

confidence: 99%

Complexation of Both Enantiomers of 2-Phenylpropionic Acid with Cyclodextrin: Determination of Binding Constant, Stoichiometry, Bioavailability and Co-Conformation

Dahab¹,

Smith²

2012

JEAS

View full text Add to dashboard Cite

Although enantiomers of 2-phenylpropionic acids (2-PPAs), or profens are important group of nonsteroidal anti-inflammatory drugs (NSAIDs) and have been in clinical use for many years, there is no literature covering its binding interaction in particular with cyclodextrins. NSAIDs are marketed as racemates, chiral discrimination and knowledge of enantiomeric bioavailability is essential. Circular dichroism (CD) spectroscopy is the technique of choice for elucidating chirality and monitoring and characterizing molecular recognition phenomena in solution. Methods employing the fundamentals of the simultaneous measurements of absorbance and CD and a novel efficient titration method have been developed to study the binding of β-Cyclodextrin (β-CyD) and the two enantiomers of 2-PPA as a function of pH. The effect on physicochemical properties and bioavailability was investigated. The binding constant, stoichiometry and pKa for both the free and the bound drugs were determined using a Levenburg-Marquadt non-linear equation. The exact nature of the enantiomer discriminating interactions by cyclodextrins (CyDs) is not well understood. In this work, the interactions and co-conformations of both enantiomers of 2-PPA with β-CyD were explained and estimated using spectroscopic variations upon complexation. The results indicated a change in the physicochemical properties of 2-PPAs upon complexation and highlighted the enantioselective binding of β-CyD as a function of pH. The charge on the guest molecule and its stereochemistry are of great importance in regulating the stability of the guest/β-CyD complexes; hence the bioavailability of drugs. This work elucidates 2-PPAs/β-CyD binding interactions and highlights the effect of β-CyD on drugs with an effective novel method for binding titration and the potential of the simultaneous measurements of absorbance and CD in future chiral drug interactions studies.

show abstract

Effects of Cyclodextrins on Drug Delivery Through Biological Membranes

Cited by 274 publications

References 92 publications

Cyclodextrin modulates the cytotoxic effects of chlorhexidine on microrganisms and cellsin vitro

Cyclodextrin modulates the cytotoxic effects of chlorhexidine on microrganisms and cellsin vitro

Endocytosis of fluorescent cyclodextrins by intestinal Caco-2 cells and its role in paclitaxel drug delivery

Complexation of Both Enantiomers of 2-Phenylpropionic Acid with Cyclodextrin: Determination of Binding Constant, Stoichiometry, Bioavailability and Co-Conformation

Contact Info

Product

Resources

About