N-alkylation of highly quaternized chitosan derivatives affects the paracellular permeation enhancement in bronchial epithelia in vitro

Benediktsdóttir, Berglind Eva; Guðjónsson, Þórarinn; Baldursson, Ólafur; Másson, Már

doi:10.1016/j.ejpb.2013.04.002

Cited by 38 publications

(19 citation statements)

References 54 publications

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“…Hank’s buffered salt solution (HBSS, pH 7.4) was used as the solution in the basolateral compartments. P app was calculated as follows: Where dQ / dt is the FD4 transfer rate, A is the surface area of the Transwell membrane, and C 0 is the initial concentration of FD4 in the apical compartment [ 36 ].…”

Section: Methodsmentioning

confidence: 99%

Caveolin-1 regulates the expression of tight junction proteins during hyperoxia-induced pulmonary epithelial barrier breakdown

Xue

You

et al. 2016

Respir Res

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BackgroundBronchopulmonary dysplasia (BPD) is a common complication in preterm infants that involves the downregulation of tight junction (TJ) proteins. However, the mechanism underlying downregulation of the expression of TJ proteins during at the early stages of hyperoxia-induced BPD remains to be understood. Here, we aimed to identify the role of caveolin-1 (Cav-1) in hyperoxia-induced pulmonary epithelial barrier breakdown.MethodsFirst, we established an in vitro pulmonary epithelial barrier models using primary type II alveolar epithelial cells (AEC-II) from newborn rats. AEC-II was assigned to the hyperoxic (85 % O2/5 % CO2) or normoxic (21 % O2/5 % CO2) groups. Second, AEC-II was transfected with Cav-1-siRNA to downregulate Cav-1 under normoxic exposure. Third, AEC-II was transfected with a cDNA encoding Cav-1 to upregulate Cav-1 expression under hyperoxic exposure. Then, expression levels of Cav-1 and TJ proteins were examined by immunofluorescence staining, reverse transcription-polymerase chain reaction, and Western blotting. The TJ structures visualized using a transmission electron microscope, and transepithelial resistance and apparent permeability coefficient of fluorescein isothiocyanate–dextran, which are indicators of barrier function, were measured.ResultsOur data showed that exposure to hyperoxia disrupted the structure and function of the pulmonary epithelial barrier and decreased the ZO-1, occludin, claudin-4, and Cav-1 expression levels. Moreover, Cav-1 knockdown attenuated the expression of the other three genes and disrupted pulmonary epithelial barrier structure and function under normoxic exposure. However, Cav-1 upregulation markedly antagonized the hyperoxia-induced pulmonary epithelial barrier destruction and TJ protein loss.ConclusionsThis is the first study to present evidence illustrating the novel role of Cav-1 downregulation-mediated TJ protein loss in pulmonary epithelial barrier destruction during BPD.Electronic supplementary materialThe online version of this article (doi:10.1186/s12931-016-0364-1) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Caveolin-1 regulates the expression of tight junction proteins during hyperoxia-induced pulmonary epithelial barrier breakdown

Xue

You

et al. 2016

Respir Res

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“…It is highly soluble in acidic solutions (pH < 6.5) due to the protonation of the primary amine [ 12 , 35 ]. After trimethylation of chitosan, chitosan derivative 1 showed higher water solubility because of the high hydrophilicity of its quaternary ammonium groups [ 16 , 31 ]. Meanwhile, the introduction of quaternary phosphonium moieties into chitosan derivative 1 further improves the water solubility, especially at alkaline pH (pH > 8.0).…”

Section: Resultsmentioning

confidence: 99%

“…As a most typical cationic chitosan, quaternary ammonium-functionalized chitosan derivatives have attracted increasing interest from both an academic and industrial point of view [ 12 , 13 , 14 ]. Among them, N , N , N -trimethylchitosan with good water solubility can be synthesized rapidly and effectively by peralkylation of free amine groups in the chitosan molecule with excess iodomethane [ 12 , 15 , 16 ], and have special appeal as substrates for the introduction of the other functional groups into the chitosan backbone. Recently, the compounds bearing quaternary phosphonium salts were reported to exhibit a higher antimicrobial activity compared with those with quaternary ammonium salts [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Novel Cationic Chitosan Derivatives Bearing Quaternary Ammonium and Phosphonium Salts and Assessment of Their Antifungal Properties

Tan

Dong

et al. 2017

Molecules

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Chitosan is an abundant and renewable polysaccharide, its derivatives exhibit attractive bioactivities and the wide applications in various biomedical fields. In this paper, two novel cationic chitosan derivatives modified with quaternary phosphonium salts were successfully synthesized via trimethylation, chloride acetylation, and quaternization with tricyclohexylphosphine and triphenylphosphine. The structures and properties of synthesized products in the reactions were characterized by FTIR spectroscopy, 1H-NMR, 31P-NMR, elemental and thermogravimetric analysis. The antifungal activities of chitosan derivatives against four kinds of phytopathogens, including Phomopsis asparagi, Watermelon fusarium, Colletotrichum lagenarium, and Fusarium oxysporum were tested using the radial growth assay in vitro. The results revealed that the synthesized cationic chitosan derivatives showed significantly improved antifungal efficiency compared to chitosan. It was reasonably suggested that quaternary phosphonium groups enabled the obviously stronger antifungal activity of the synthesized chitosans. Especially, the triphenylphosphonium-functionalized chitosan derivative inhibited the growth of Phomopsis asparagi most effectively, with inhibitory indices of about 80% at 0.5 mg/mL. Moreover, the data demonstrated that the substituted groups with stronger electron-withdrawing ability relatively possessed greater antifungal activity. The results suggest the possibility that cationic chitosan derivatives bearing quaternary phosphonium salts could be effectively employed as novel antifungal biomaterials for application in the field of agriculture.

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“…Chitosan has been one of the most studied polysaccharides for this purpose. To provide additional properties and applications to chitosan, the synthesis and characterization of new derivatives has been extensively explored through its functionalization with hydrophobic and hydrophilic groups (Benediktsdóttir, Gudjónsson, Baldursson, & Másson, 2014;Huo et al, 2010). Special attention has been given to its use in antimicrobial coatings (Kong, Chen, Xing, & Park, 2010;Rabea, Badawy, Stevens, Smagghe, & Steurbaut, 2003), fungicides (Rabea et al, 2005;Radulescu et al, 2015), bactericides (Li et al, 2011;Seo, King, Prinyawiwatkul, & Janes, 2008), packaging materials (González-Aguilar et al, 2009), and crop protection (Bautista-Baños et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

Martins

Nasário²,

Silva-Gonçalves

et al. 2018

Carbohydrate Polymers

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The antimicrobial activity of chitosan and derivatives to human and plant pathogens represents a high-valued prospective market. Presently, two low molecular weight derivatives, endowed with hydrophobic and cationic character at different ratios were synthesized and characterized. They exhibit antimicrobial activity and increased performance in relation to the intermediate and starting compounds. However, just the derivative with higher cationic character showed cytotoxicity towards human cervical carcinoma cells. Considering cell membranes as targets, the mode of action was investigated through the interaction with model lipid vesicles mimicking bacterial, tumoral and erythrocyte membranes. Intense lytic activity and binding are demonstrated for both derivatives in anionic bilayers. The less charged compound exhibits slightly improved selectivity towards bacterial model membranes, suggesting that balancing its hydrophobic/hydrophilic character may improve efficiency. Observing the aggregation of vesicles, we hypothesize that the "charge cluster mechanism", ascribed to some antimicrobial peptides, could be applied to these chitosan derivatives.

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N-alkylation of highly quaternized chitosan derivatives affects the paracellular permeation enhancement in bronchial epithelia in vitro

Cited by 38 publications

References 54 publications

Caveolin-1 regulates the expression of tight junction proteins during hyperoxia-induced pulmonary epithelial barrier breakdown

Caveolin-1 regulates the expression of tight junction proteins during hyperoxia-induced pulmonary epithelial barrier breakdown

Preparation and Characterization of Novel Cationic Chitosan Derivatives Bearing Quaternary Ammonium and Phosphonium Salts and Assessment of Their Antifungal Properties

Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

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