Calix[4]arene-α-hydroxyphosphonic acids. Synthesis, stereochemistry, and inhibition of glutathione S-transferase

Cherenok, S. O.; Yushchenko, O.A.; Tanchuk, Vsevolod Yu.; Mischenko, I. M.; Samus, Nataliya V.; Ruban, Olexander V.; Matvieiev, Yuriy; Karpenko, Julia A.; Kukhar, V. P.; Vovk, А. I.; Kаlchеnkо, Vitaly I.

doi:10.3998/ark.5550190.0013.421

Cited by 24 publications

(9 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to previous studies, the anticancer activities of calixarene-based compounds are related to their enzyme inhibition potential (Cherenok et al, 2006, 2012), inhibiting tumor angiogenesis (Dings et al, 2006) and DNA replication of cancer cells (Consoli et al, 2007). The cytotoxicity of the ligand and complexes was studied against the MCF-7 and Saos-2 cell lines by MTT assay.…”

Section: Resultsmentioning

confidence: 99%

Design of a Thiosemicarbazide-Functionalized Calix[4]arene Ligand and Related Transition Metal Complexes: Synthesis, Characterization, and Biological Studies

et al. 2019

View full text Add to dashboard Cite

In this study, we synthesized a new thiosemicarbazide-functionalized calix[4]arene L and its Co2+, Ni2+, Cu2+, and Zn2+ transition metal complexes. For characterization several techniques were employed: Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), 13C-NMR, 15N-NMR, correlation spectroscopy (COZY), nuclear Overhauser enhancement spectroscopy (NOESY), electrospray ionization (ESI)–mass spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), and elemental analysis. To explore the capability of the thiosemicarbazide function hosted on a calix[4]arene scaffold for growth inhibition of bacteria, fungi, and cancerous tumor cells, a series of biological evaluations were performed. For L, the antimicrobial tests revealed a higher antibacterial activity against gram-positive Bacillus subtilis and a lower activity against gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), whereas the gram-positive Staphylococcus aureus shows resistance. All examined metal derivatives show an enhancement of the antibacterial activity against gram-negative E. coli bacteria, with a more significant improvement for the Ni2+ and Zn2+ complexes. MTT assays showed a considerable in vitro anticancer activity of Co2+, Ni2+, and Cu2+ complexes against Saos-2 bone cancer cell lines. The activity is ascribable to the inorganic ions rather than calixarene ligand. Hemolysis assay results demonstrated that all compounds have high blood compatibility.

show abstract

Section: Resultsmentioning

confidence: 99%

Design of a Thiosemicarbazide-Functionalized Calix[4]arene Ligand and Related Transition Metal Complexes: Synthesis, Characterization, and Biological Studies

et al. 2019

View full text Add to dashboard Cite

show abstract

“…CXs are perfect host molecules for a wide variety of therapeutic guest molecules due to their exceptional structure, which encompasses an upper rim with para-substituent of a phenolic ring, a lower rim with a phenolic hydroxyl group, and a hydrophobic π electron-rich core cavity. The water solubility of CXs is improved by the attachment of some functional groups, including sulfonates and carboxylates at the para -position of their phenolic units [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ]. Among the various functionalized CX derivatives, the para -sulfonatocalix[n]arenes [n = 4 and 6, ( p -SC4 and-SC6)] demonstrated significant water solubility (>0.1 mol/L), safety, and outstanding biocompatibility to human cells where they show negligible adverse effects at in vivo doses up to 100 mg/kg ( Figure 1 C,D).…”

Section: Introductionmentioning

confidence: 99%

Host-Guest Complexation of Oxaliplatin and Para-Sulfonatocalix[n]Arenes for Potential Use in Cancer Therapy

et al. 2020

View full text Add to dashboard Cite

P-sulfonatocalix[n]arenes have demonstrated a great potential for encapsulation of therapeutic drugs via host-guest complexation to improve solubility, stability, and bioavailability of encapsulated drugs. In this work, guest-host complexes of a third-generation anticancer drug (oxaliplatin) and p-4-sulfocalix[n]arenes (n = 4 and 6; p-SC4 and p-SC6, respectively) were prepared and investigated, using 1H NMR, UV, Job’s plot analysis, and DFT calculations, for use as cancer therapeutics. The peak amplitude of the prepared host-guest complexes was linearly proportional to the concentration of oxaliplatin in the range of 1.0 × 10−5 M−1 to 2.1 × 10−4 M−1. The reaction stoichiometry between either p-SC4 or p-SC6 and oxaliplatin in the formed complexes was 1:1. The stability constants for the complexes were 5.07 × 104 M−1 and 6.3 × 104 M−1. These correspond to complexation free energy of −6.39 and −6.52 kcal/mol for p-SC4 and p-SC6, respectively. Complexation between oxaliplatin and p-SC4 or p-SC6 was found to involve hydrogen bonds. Both complexes exhibited enhanced biological and high cytotoxic activities against HT-29 colorectal cells and MCF-7 breast adenocarcinoma compared to free oxaliplatin, which warrants further investigation for cancer therapy.

show abstract

“…Among them, calix [4]arene-based phosphonic acids were found to inhibit alkaline phosphatases [17][18][19] and protein tyrosine phosphatases [20][21][22][23]. We previously demonstrated that calix [4]arenes functionalized by α-hydroxyphosphonic acid group exhibited inhibitory effects towards GSTs from the equine liver and human placenta [24,25].…”

Section: Introductionmentioning

confidence: 99%

Inhibition of glutathione S-transferases by calix[4]arene-based phosphinic acids

et al. 2022

View full text Add to dashboard Cite

Calix[4]arene-, thiacalix[4]arene- and sulfonylcalix[4]arene-based derivatives with upper rim phosphinic acid groups were studied as inhibitors of glutathione S-transferases. It was found that the macrocyclic compounds can exhibit good to potent activity against GST from equine liver and human recombinant GSTA1-1, while being selective over the enzyme from human placenta and GSTP1-1. The thiacalix[4]arene phosphinic acid was the most active inhibitor of equine liver GST and GSTA1-1 with IC50 values of 85 nM and 50 nM, respectively. Kinetic studies revealed that the inhibition was of non-competitive type concerning both enzyme substrates, glutathione, and 1-chloro-2,4-dinitrobenzene. Molecular docking was carried out to predict possible binding sites for thiacalix[4]arene-based phosphinic acid on the surface of homodimeric GSTA1-1

show abstract

Calix[4]arene-α-hydroxyphosphonic acids. Synthesis, stereochemistry, and inhibition of glutathione S-transferase

Cited by 24 publications

References 35 publications

Design of a Thiosemicarbazide-Functionalized Calix[4]arene Ligand and Related Transition Metal Complexes: Synthesis, Characterization, and Biological Studies

Design of a Thiosemicarbazide-Functionalized Calix[4]arene Ligand and Related Transition Metal Complexes: Synthesis, Characterization, and Biological Studies

Host-Guest Complexation of Oxaliplatin and Para-Sulfonatocalix[n]Arenes for Potential Use in Cancer Therapy

Inhibition of glutathione S-transferases by calix[4]arene-based phosphinic acids

Contact Info

Product

Resources

About