2-Acetylpyridine- and 2-benzoylpyridine-derived hydrazones and their gallium(III) complexes are highly cytotoxic to glioma cells

Despaigne, Angel A. Recio; Parrilha, Gabrieli L.; Izidoro, Jans Bastos; Costa, Pryscila R. Da; Santos, Raquel Gouvêa dos; Piro, Oscar E.; Castellano, Eduardo E.; Rocha, Willian R.; Beraldo, Heloísa

doi:10.1016/j.ejmech.2012.01.051

Cited by 60 publications

(30 citation statements)

References 38 publications

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“…The intramolecular N4-H⋯N2 hydrogen bond probably hinders rotation around C4-N3 contributing to the stability of the Z configuration. This conformation was also observed by us in 2-benzoylpyridine-derived hydrazones [30]. The crystal packing of 11a is dominated by N-H⋯N and N-H⋯O hydrogen bonds (see Table 2).…”

Section: Characterization Of the Hydrazone Derivativesmentioning

confidence: 56%

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

et al. 2013

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New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehydepara-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-paranitrobenzoyl hydrazone (4(5)ImpNO 2 Ph), 4-(imidazole-1-yl)acetophenone-para-chlorobenzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitrobenzoylhydrazone (4ImAcpNO 2 Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO 2 Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

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Section: Characterization Of the Hydrazone Derivativesmentioning

confidence: 56%

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

et al. 2013

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“…The absorption of the added DNA was accounted for by adding an equal amount to a cuvette containing buffer. The values of the intrinsic binding constant K b , illustrating the binding strength of the complexes with ct-DNA< were determined from the following equation [14]:…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic gallium complexes containing thiosemicarbazones derived from 9-anthraldehyde: Molecular docking with biomolecules

Beckford

Brock

González‐Sarrías

et al. 2016

Journal of Molecular Structure

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We have synthesized a trio of gallium complexes bearing 9-anthraldehyde thiosemicarbazones. The complexes were assessed for their anticancer activity and their biophysical reactivity was also investigated. The three complexes displayed good cytotoxic profiles against two human colon cancer cell lines, HCT-116 and Caco-2. The IC50 ranged from 4.7 – 44.1 μM with the complex having an unsubstituted amino group on the thiosemicarbazone being the most active. This particular complex also showed a high therapeutic index. All three complexes bind strongly to DNA via intercalation with binding constants ranging from 7.46 × 104 M-1 to 3.25 × 105 M-1. The strength of the binding cannot be directly related to the level of anticancer activity. The complexes also bind strongly to human serum albumin with binding constants on the order of 104 – 105 M-1 as well. The complexes act as chemical nucleases as evidenced by their ability to cleave pBR322 plasmid DNA. The binding constants along with the cleavage results may suggest that the extent of DNA interaction is not directly correlated with anticancer activity. The results of docking studies with DNA, ribonucleotide reductase and human serum albumin, however showed that the complex with the best biological activity had the largest binding constant to DNA.

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“…Gürsoy et al .,[63] reported the anticancer activity of thiazolohydrazides (67) against prostate cancer. Despaigne et al .,[64] have described acetylpyridine and benzoylpyridine derived hydrazones (68, 69) as agents against brain tumor [Figure 3]. …”

Section: Biological Activitymentioning

confidence: 99%

A review exploring biological activities of hydrazones

et al. 2014

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The development of novel compounds, hydrazones has shown that they possess a wide variety of biological activities viz. antimicrobial, anticonvulsant, antidepressant, anti-inflammatory, analgesic, antiplatelet, antimalarial, anticancer, antifungal, antitubercular, antiviral, cardio protective etc., Hydrazones/azomethines/imines possess-NHN = CH- and constitute an important class of compounds for new drug development. A number of researchers have synthesized and evaluated the biological activities of hydrazones. This review aims at highlighting the diverse biological activities of hydrazones.

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2-Acetylpyridine- and 2-benzoylpyridine-derived hydrazones and their gallium(III) complexes are highly cytotoxic to glioma cells

Cited by 60 publications

References 38 publications

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

Cytotoxic gallium complexes containing thiosemicarbazones derived from 9-anthraldehyde: Molecular docking with biomolecules

A review exploring biological activities of hydrazones

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