Antiproliferative effect on HepaRG cell cultures of new calix[4]arenes. Part II

Latxague, Laurent; Gaboriau, François; Chassande, Olivier; Léger, Jean‐Michel; Pires, Viviane Silva; Rouge, Pascal; Dassonville‐Klimpt, Alexandra; Fardeau, Sylvain; Jarry, Christian; Lescoat, Gérard; Guillon, Jean; Sonnet, Pascal

doi:10.3109/14756366.2010.489898

Cited by 13 publications

(3 citation statements)

References 53 publications

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“…Rouge et al [44] used calix [4]arenes bearing alkyl ester and alkyl acid moieties at the lower rim, Pires et al [45] used calix [4]arenes bearing two hydrazide function or ornithine, glutamic/aspartic acid groups at the lower rim, and Latxague et al [46] used calix [4]arenes bearing diamino-tetraesters, diamino-tetraalcohols, diamino-tetraacid and tetraaryloxypentoxy groups at the lower rim. They compared their calixarene derivatives with 4-3,5-bis-(2-hydroxyphenyl)-1,2,4-triazol-1-yl-benzoic acid as a new oral chelator.…”

Section: Anti-mycobacterial and Anti-proliferativitymentioning

confidence: 99%

Applications of calixarene nano-baskets in pharmacology

Bahram

Pourabdollah

2011

J Incl Phenom Macrocycl Chem

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Calixarene nano-baskets enable to encapsulate the guest drugs and show different biological activities. This review deals with the behavior of calixarene-based drugs and illustrates their potentials in the pharmacological sciences. The role of calixarene's scaffolds and substitutions in aspects of anti-cancer, anti-mycobacterial, antiproliferativity, catalytic and inhibitory activities as well as solubility control, drug analysis, drug purification, drug supports and structural studies is reviewed.

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Section: Anti-mycobacterial and Anti-proliferativitymentioning

confidence: 99%

Applications of calixarene nano-baskets in pharmacology

Bahram

Pourabdollah

2011

J Incl Phenom Macrocycl Chem

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“…We have shown recently that calix[4]arenes 1 – 4 exhibit interesting antiproliferative activities close to the ICL670 reference, and the correlation between the cytostatic effect and iron depletion was established clearly for tetra-acid 4 . [18] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Physicochemical Studies, Molecular Dynamics Simulations, and Metal‐Ion‐Dependent Antiproliferative and Antiangiogenic Properties of Cone ICL670‐Substituted Calix[4]arenes

et al. 2012

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Iron chelators, through their capacity to modulate the iron concentration in cells, are promising molecules for cancer chemotherapy. Chelators with high lipophilicity easily enter into cells and deplete the iron intracellular pool. Consequently, iron-dependent enzymes, such as ribonucleotide reductase, which is over-expressed in cancer cells, become nonfunctional. A series of calix[4]arene derivatives substituted at the lower rim by ICL670, a strong FeIII chelator, have been synthesized. Physicochemical properties and antiproliferative, angiogenesis, and tumorigenesis effects of two calix[4]arenes mono- (5a) or disubstituted (5b) with ICL670 have been studied. These compounds form metal complexes in a ratio of one to two ligands per FeIII atom as shown by combined analyses of the protometric titration curves and ESIMS spectra. The grafting of an ICL670 group on a calix[4]arene core does not significantly alter the acid–base properties, but improves the iron-chelating and lipophilicity properties. The best antiproliferative and anti-angiogenic results were obtained with calix[4]arene ligand 5a, which possesses the highest corresponding properties. Analyses of molecular dynamics simulations performed on the two calix[4]arenes provide three-dimensional structures of the complexes and proved 5a to be the most stable upon complexation.

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“…[69] In comparison of results of both lower-and upper-rim-functionalized calix [4]arene iminosugar clusters 7 and 20, respectively, the former was found much more active than the later. Sonnet et al [86,87] have synthesized functionalized calix [4]arene podands 21-23 having diamino-tetraesters, diamino-tetraalcohols, and diamino-tetraacids groups, respectively, at the lower rim (Scheme 12) and reported their effect on cell proliferation, in comparison with the new oral chelator ICL670A (4-[3,5-bis-(2-hydroxyphenyl)-1,2,4 -triazol-1-yl]-benzoic acid). The results of the antiproliferative effect of these functionalized calix [4]arene derivatives (studied in the human hepatocarcinoma HepaRG cell cultures, using cell nuclei counting subsequent to staining with the DNA intercalating fluorescence dye, Hoechst 33342) showed that the podands 21-23 have comparable activity to that of ICL670.…”

Section: Upper-rim-functionalized Calix[4] Arenesmentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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Antiproliferative effect on HepaRG cell cultures of new calix[4]arenes. Part II

Cited by 13 publications

References 53 publications

Applications of calixarene nano-baskets in pharmacology

Applications of calixarene nano-baskets in pharmacology

Synthesis, Physicochemical Studies, Molecular Dynamics Simulations, and Metal‐Ion‐Dependent Antiproliferative and Antiangiogenic Properties of Cone ICL670‐Substituted Calix[4]arenes

Functionalized calix[4]arenes as potential therapeutic agents

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