Haemolytic properties of some water-soluble para-sulphonato-calix-[n]-arenes

Silva, Éric Da; Shahgaldian, Patrick; Coleman, Anthony W.

doi:10.1016/j.ijpharm.2003.12.008

Cited by 96 publications

(54 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…SC4 and SC8 were not significantly haemolytic on hRBCs up to a concentration of 512 μM, in agreement with Da Silva et al [41], although 50 % haemolysis was reached on hRBCs with 141 μM SC6 (Table 1). Despite haemolytic activities not being observed so far, one cannot exclude an active contaminant in SC6.…”

Section: Assessment Of Scn Toxicity On Hrbcs and Hpmnssupporting

confidence: 90%

p-Sulfonato-calix[n]arenes inhibit staphylococcal bicomponent leukotoxins by supramolecular interactions

Laventie

Potrich

Atmanène

et al. 2013

Biochemical Journal

View full text Add to dashboard Cite

PVL (Panton-Valentine leukocidin) and other Staphylococcus aureus β-stranded pore-forming toxins are important virulence factors involved in various pathologies that are often necrotizing. The present study characterized leukotoxin inhibition by selected SCns (p-sulfonato-calix[n]arenes): SC4, SC6 and SC8. These chemicals have no toxic effects on human erythrocytes or neutrophils, and some are able to inhibit both the activity of and the cell lysis by leukotoxins in a dose-dependent manner. Depending on the type of leukotoxins and SCns, flow cytometry revealed IC50 values of 6-22 μM for Ca2+ activation and of 2-50 μM for cell lysis. SCns were observed to affect membrane binding of class S proteins responsible for cell specificity. Electrospray MS and surface plasmon resonance established supramolecular interactions (1:1 stoichiometry) between SCns and class S proteins in solution, but not class F proteins. The membrane-binding affinity of S proteins was Kd=0.07-6.2 nM. The binding ability was completely abolished by SCns at different concentrations according to the number of benzenes (30-300 μM; SC8>SC6≫SC4). The inhibitory properties of SCns were also observed in vivo in a rabbit model of PVL-induced endophthalmitis. These calixarenes may represent new therapeutic avenues aimed at minimizing inflammatory reactions and necrosis due to certain virulence factors.

show abstract

Section: Assessment Of Scn Toxicity On Hrbcs and Hpmnssupporting

confidence: 90%

p-Sulfonato-calix[n]arenes inhibit staphylococcal bicomponent leukotoxins by supramolecular interactions

Laventie

Potrich

Atmanène

et al. 2013

Biochemical Journal

View full text Add to dashboard Cite

show abstract

“…Water-soluble calixarenes are important in supramolecular chemistry because they allow the study of the host-guest recognition processes under conditions in which most biological processes occur (Arena et al 2004). In recent years, reports have described the recognition properties of water-soluble p-sulfonated calix[n]arenas (Zhou et al 2005) toward dyes (Yilmaz et al 2007;Akceylan, Bahadir, and Yılmaz 2009), native amino acids (Silva, Shahgaldian, and Coleman 2004;Stone et al 2002), quaternary ammonium ions (Nimse et al 2011;Arena et al 2004;Komura et al 2002), and small molecules (Arena et al 2000). The use of p-sulfonated calix[n]arenas has been investigated for biological and pharmaceutical applications (Millership et al 2001;Silva et al 2004;Gualbert, Shahgaldian, and Coleman 2003).…”

Section: Introductionmentioning

confidence: 99%

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

et al. 2014

View full text Add to dashboard Cite

The ability of p-sulfonated calix[n]arenes (n ¼ 4, 6, 8) to form complexes with tryptophan was studied. The electrochemical properties of these complexes immobilized on gold surfaces were examined by cyclic voltammetry. Parameters affecting the performance of the modified electrodes including the arene concentration, scan rate, applied potential, and pH were optimized. Under the optimal conditions, the method had a linear response to tryptophan between 1 Â 10 À7 M and 1 Â 10 À5 M with a detection limit of 3 Â 10 À8 M. The interaction of the tryptophan-p-sulfonated calix[4]arene complex was more stable than the tryptophanp-sulfonated calix[6]arene and p-sulfonated calix[8]arene complexes. Molecular modeling calculations indicated that electrostatic interactions and structural matching effects were predominant stabilizing factors. The modified electrodes demonstrated good reproducibility and high selectivity, illustrating their effectiveness for analytical measurements.

show abstract

“…Increased haemolysis is observed for the corresponding parasulfonatocalix [6]arene and para-sulfonatocalix [8]arene at the same concentration but this is much reduced for all sulfonated calixarenes at lower concentrations [41]. No haemolytic effects were observed for solid lipid nanoparticles derived from a series of amphiphilic calixarenes [42].…”

Section: Biocompatibility Of Calix[n]arenesmentioning

confidence: 99%

Simple Calix[n]arenes and Calix[4]resorcinarenes as Drug Solubilizing Agents

Hoskins

Curtis²

2015

JNMR

View full text Add to dashboard Cite

Many drug molecules have low solubility in aqueous media and, hence, poor bioavailability. The formation of a host-guest complex with some other compound which has a good solubility profile can facilitate solubilization of hydrophobic drugs. Complex formation relies upon the formation of non-covalent interactions between the host molecule and the drug guest. The use of calix[n]arenes, a wellcharacterized class of cyclic oligomers, has been investigated for their ability to form complexes with a variety of ionic and molecular species. This review highlights those studies which have demonstrated the potential of calix[n]arenes as host molecules in novel drug delivery systems.

show abstract

Haemolytic properties of some water-soluble para-sulphonato-calix-[n]-arenes

Cited by 96 publications

References 25 publications

p-Sulfonato-calix[n]arenes inhibit staphylococcal bicomponent leukotoxins by supramolecular interactions

p-Sulfonato-calix[n]arenes inhibit staphylococcal bicomponent leukotoxins by supramolecular interactions

Determination of Tryptophan using ap-Sulfonated Calix [4,6,8]arene Modified Gold Electrode

Simple Calix[n]arenes and Calix[4]resorcinarenes as Drug Solubilizing Agents

Contact Info

Product

Resources

About