Effect of glucosamine conjugation to zinc(II) complexes of a bis-pyrazole ligand: Syntheses, characterization and anticancer activity

Bhattacharyya, S.; Sarkar, Amrita; Dey, Satyahari; Mukherjee, Arindam

doi:10.1016/j.jinorgbio.2014.07.009

Cited by 22 publications

(7 citation statements)

References 67 publications

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“…Similarly, the planes passing through the acetylamido linker and each pyrazolyl ring makes with equatorial plane angles of 90 and 44.5°, respectively. A search in the CCDC repository , showed some Cu(II) complexes of bis-pyrazolyl acetate, − among which few bis-pyrazolyl acetamide derivatives; other bis-pyrazolyl acetamide ligands, including the one present in the above-named aluminum complex are also known. − With one exception, reported bis-pyrazolyl acetate copper derivatives share a trans-fac coordination of the tridentate ligand with mean values of the O–Cu–O and O–Cu–N angles of 179.7 and 94.8°, similar to those found in this work. Likewise, the mean values of the Cu–N and Cu–O bonds are 2.055 and 2.276 Å; in 3 these bonds are 0.035 and 0.070 Å shorter than such means, respectively, but within the known ranges (1.972–2.438 Å for Cu–N and 1.936–2.540 Å for Cu–O).…”

Section: Resultsmentioning

confidence: 67%

“…The C1−N1 and N1− C8 distances (1.316(4) and 1.481(4) Å, respectively), typical of an amide linkage, agree well with the mean values found for pyrazolyl acetamide ligands 51−59 (1.330, 1.457 Å) and even better if considering the same values specifically pertaining to acetamide ligands involved in coordination (1.322, 1.463 Å). 45,52,55,59 Notably, the amide nitrogen N1 establishes a hydrogen bond with the O3 oxygen of a water molecule (w1) (Figure 2b). At an average distance of 2.15 Å from w1, an undefined ring of electron density is positioned on a 2-fold proper rotation axis and a mirror plane.…”

Section: Resultsmentioning

confidence: 99%

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Copper-Based Complexes with Adamantane Ring-Conjugated bis(3,5-Dimethyl-pyrazol-1-yl)acetate Ligand as Promising Agents for the Treatment of Glioblastoma

Morelli,

Caviglia,

Santini

et al. 2024

J. Med. Chem.

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The new ligand L 2Ad , obtained by conjugating the bifunctional species bis(3,5-dimethylpyrazol-1-yl)-acetate and the drug amantadine, was used as a chelator for the synthesis of new Cu complexes 1−5. Their structures were investigated by synchrotron radiation-induced X-ray photoelectron spectroscopy (SR-XPS), near-edge X-ray absorption fine structure (NEXAFS) spectroscopy, and by combining X-ray absorption fine structure (XAFS) spectroscopy techniques and DFT modeling. The structure of complex 3 was determined by single-crystal X-ray diffraction analysis. Tested on U87, T98, and U251 glioma cells, Cu(II) complex 3 and Cu(I) complex 5 decreased cell viability with IC 50 values significantly lower than cisplatin, affecting cell growth, proliferation, and death. Their effects were prevented by treatment with the Cu chelator tetrathiomolybdate, suggesting the involvement of copper in their cytotoxic activity. Both complexes were able to increase ROS production, leading to DNA damage and death. Interestingly, nontoxic doses of 3 or 5 enhanced the chemosensitivity to Temozolomide.

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Section: Resultsmentioning

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Copper-Based Complexes with Adamantane Ring-Conjugated bis(3,5-Dimethyl-pyrazol-1-yl)acetate Ligand as Promising Agents for the Treatment of Glioblastoma

Morelli,

Caviglia,

Santini

et al. 2024

J. Med. Chem.

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“…This is due to the importance of palladium complexes in cancer therapy because they induce tumor-cell death and zinc metal ions are well-managed by human physiology, cause minor side effects in comparison to other non-essential metalbased complexes. [52,53] This is in addition to zinc is significantly non-toxic even at higher doses than other metals, [54,55] the (Sb-Zn-Cipro) and (Pd 2 -Sb) complexes were chosen to examine their anticancer activity.…”

Section: Anticancer Activitymentioning

confidence: 99%

Theoretical calculations for new coumarin Schiff base complexes as candidates for in vitro and in silico biological applications

Abdel-Kader

Moustafa

El-Ansary

et al. 2022

Applied Organom Chemis

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The Schiff base (Sb) formed by the condensation of 8-acetyl-7-hydroxy-4-methyl coumarin and sulfaclozine was used for the preparation of [Cu 2 plexes. Also, the mixed ligand zinc complex, [(Sb)Zn(Cipro)]Á4H 2 O, (Sb-Zn-Cipro) was prepared from (Sb) and ciprofloxacin. Many tools of analysis as elemental and spectral studies, in addition to thermogravimetry (TG), molar conductance, magnetic moment, X-ray diffraction (XRD), energy dispersive X-ray (EDX), scanning electron microscope (SEM), and electron spin resonance (ESR) measurements, were used to prove the complexes' composition. The morphology studies confirm the nanostructure of copper and palladium complexes. At the B3LYP/GENECP level, the optimal structure of the complexes was estimated using the 6-31G++(d, p) basis set for C, H, N, S, and O atoms and the Los Alamos National Laboratory double zeta (LANL2DZ) basis set for metal atoms. A distorted square planar geometry is presumed for (Pd 2 -Sb), and distorted tetrahedral geometry is presumed for (Cu 2 -Sb) and (Sb-Zn-Cipro).The in vitro examination of the antimicrobial activity of the complexes was performed. The cytotoxic effects of the (Pd 2 -Sb) and (Sb-Zn-Cipro) against MCF-7 (breast cancer) and HCT-116 (colon cancer) cell lines were achieved in vitro. The results showed that (Sb-Zn-Cipro) has the best biological activity. In view of this, the in silico binding mode of (Sb-Zn-Cipro) complex with Escherichia coli (KAS I-PDB ID-1FJ4), Staphylococcus aureus tyrosyl-tRNA synthetase (PDB id: 1JIJ), yeast-specific serine/threonine protein phosphatase (PPZ1) of Candida albicans (PDB ID: 5JPE), breast cancer mutant oxidoreductase (PDB ID: 3HB5), and colon cancer human cyclin-dependent kinase 2; CDK2 (PDB ID: 6GUE) was performed using molecular docking.

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“…14 However, we found that conjugation of methionine to a bis-pyrazolyl ligand and formation of its Zn(II) complex did not render a higher toxicity. 15 Hence, although it is found that methionine based PET CT imaging agents are taken up more by cancer cells, in therapeutics this concept needs to be probed more for a generalization.…”

Section: Introductionmentioning

confidence: 99%

“…23 From our group, we found that even when we conjugate acetylated glucosamine to a Zn(II) bis-pyrazolyl complex, the intake of the complex increases in MCF-7 cell line. 15 Nonetheless, all of these facts suggest that functionalization with cell absorbable and cheaper compounds like methionine or glucosamine might be very useful options for designing chemotherapeutic agents. However, more compounds are to be designed with such conjugations to understand the effect of conjugation in a broader aspect.…”

Section: Introductionmentioning

confidence: 99%

Effect of methionine and glucosamine conjugation on the anticancer activity of aromatic dinitrobenzamide mustards

2016

Self Cite

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Certain nutrients viz., glucose and methionine are consumed more by cancer cells. Hence, an anticancer agent conjugated to them may render more toxicity in cancer cells due to higher uptake. To probe this effect, methionine and glucosamine were conjugated to a series of well-known aromatic dinitrobenzamide mustards. The in vitro cytotoxicity studies performed to probe the effect of such conjugation showed that the conjugation of methionine and glucosamine to one of the dinitrobenzamide mustard led to more toxicity selectively in human breast adenocarcinoma (MCF-7) cell lines. However, effect of functionalization cannot be generalized. Hypoxia based studies showed that IC 50 value did not show much change from normoxic condition which is encouraging as many drugs deactivate in hypoxia. Among the glucosamine and methionine conjugated dinitrobenzamide mustards, the methionine conjugated aromatic dinitrobenzamide mustard of 2-chlorobenzoic acid is the most effective one. It acts by inducing apoptosis through G2/M phase arrest and encouragingly, is much less toxic to nontumorigenic human embryonic kidney (HEK-293T) and mouse embryonic fibroblast (NIH 3T3) cell lines in vitro.

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Effect of glucosamine conjugation to zinc(II) complexes of a bis-pyrazole ligand: Syntheses, characterization and anticancer activity

Cited by 22 publications

References 67 publications

Copper-Based Complexes with Adamantane Ring-Conjugated bis(3,5-Dimethyl-pyrazol-1-yl)acetate Ligand as Promising Agents for the Treatment of Glioblastoma

Copper-Based Complexes with Adamantane Ring-Conjugated bis(3,5-Dimethyl-pyrazol-1-yl)acetate Ligand as Promising Agents for the Treatment of Glioblastoma

Theoretical calculations for new coumarin Schiff base complexes as candidates for in vitro and in silico biological applications

Effect of methionine and glucosamine conjugation on the anticancer activity of aromatic dinitrobenzamide mustards

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