Cobalt (II), zirconium(IV), calcium(II) complexes with dipicolinic acid and imidazole derivatives: X-ray studies, thermal analyses, evaluation as in vitro antibacterial and cytotoxic agents

Abdolmaleki, Sara; Ghadermazi, Mohammad; Ashengroph, Morahem; Saffari, Andisheh; Sabzkohi, Salime Moradi

doi:10.1016/j.ica.2018.04.047

Cited by 55 publications

(16 citation statements)

References 62 publications

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“…DPA has been reported to be able to link to metals forming metallic complexes (Abdolmaleki et al, 2018). Here, the antifungal activity of 1 mM DPA in the presence of different metals, including iron(II), nickel(II), zinc(II), cobalt(II) and copper(II), was studied using V. pyri conidia at pH = 5 ( Figure 2D).…”

Section: Resultsmentioning

confidence: 96%

Antifungal Mechanism of Dipicolinic Acid and Its Efficacy for the Biocontrol of Pear Valsa Canker

Song

Han

et al. 2020

Front. Microbiol.

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Valsa pyri is a fatal canker pathogen that causes significant reduction of crop yield in pear orchards. V. pyri invades the trunk phloem, and is difficult to control by chemical treatment. In this work, it was found for the first time that Bacillus subtilis-produced dipicolinic acid (DPA) exhibits antifungal activity against different canker pathogens, including Alteraria alternata, Botryosphaeria dothidea, Rhizoctonia solani, and V. pyri. Growth inhibition of V. pyri was observed at less than 5 mM concentration (pH = 5.6). DPA showed the highest antifungal activity at acidic pH values and in the presence of bivalent metals, such as zinc(II), cobalt(II), and copper(II). Measurement of mRNA expression levels and scanning electron microscope (SEM) observations revealed that DPA causes V. pyri apoptosis via inhibition of chitin biosynthesis and subsequent cell lysis. Interestingly, DPA showed high stability in the pear bark and was able to cross the pear tree bark into the phloem, protecting the internal phases of the pear trunk. In preventive applications, DPA reduced the canker symptoms of V. pyri on Cuigan pear trees by 90%. Taken together, an efficient strategy for the management of V. pyricaused canker disease was developed using a novel antifungal agent, DPA, with strong antifungal activity and particular diffusion properties.

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Section: Resultsmentioning

confidence: 96%

Antifungal Mechanism of Dipicolinic Acid and Its Efficacy for the Biocontrol of Pear Valsa Canker

Song

Han

et al. 2020

Front. Microbiol.

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“…Many studies have proven that inorganic compounds were usually exhibited a more potent cytotoxic effect compared to their organic ligands on cancer cells. It seems that sometimes coordination can be effective in the improvement of anticancer properties of synthetic chemical compounds 30 , 31 .…”

Section: Resultsmentioning

confidence: 99%

Novel Tl(III) complexes containing pyridine-2,6-dicarboxylate derivatives with selective anticancer activity through inducing mitochondria-mediated apoptosis in A375 cells

Abdolmaleki

Ghadermazi

Aliabadi

2021

Sci Rep

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Three novel Tl(III) complexes (C1), (C2) and (C3) were synthesized using the one-pot reactions of pyridine dicarboxylic acid derivatives, 2-aminobenzimidazole and/or 4-aminopyridine, and also thallium(III) nitrate trihydrate metal salt. The structure of all three complexes was determined by the single-crystal X-ray diffraction. C1 and C2 were realized to be isostructural with disordered square anti-prismatic geometry and for C3 arrangement of the distorted tricapped triangular prism was proposed. Cyclic voltammetry measurements on the complexes exhibited that formal potential values are more positive for C1 (E0ˊ 0.109 V) and C3 (E0ˊ 0.244 V) compared to C2 (E0ˊ –0.051 V), versus Ag/AgCl under argon. Moreover, cytotoxicity of the compounds was evaluated in vitro against two cancer cell lines including a human melanoma (A375), a human colon adenocarcinoma (HT29), and also one normal cell human foreskin fibroblast (HFF). The selective and potent cytotoxicity effect was exhibited by C1 and C3 on cancer cell lines. The apoptosis through a caspase-dependent mitochondrion pathway was confirmed by ROS production, MMP reduction, p53 activation, Bax up-regulation, and Bcl-2 down-regulation, cytochrome c release, procaspase-9, and 3 expression, for A375 cells treated to C1 and C3. According to similar cellular uptake of the complexes in A375 cell line, the generation of ROS was considered as an effective agent to justify the inhibition effect C1 and C3 on mentioned cells. Furthermore, arresting the cell cycle in the G2-M phase and inducing apoptosis were indicated by these two complexes.

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“…The melting points were found to range between 248-250 ο C and 186-188°C for 2,6-H 2 pdc and 2,3-H 2 pdc ligands respectively. The results of the thermal analysis show that the compounds are more thermally stable than some metal coordination compounds of pyridinedicarboxylate [9,12]. However, the thermal stability of beyond 400 ο C was reported for some calcium coordination compounds [19,34].…”

Section: Thermal Analysismentioning

confidence: 97%

“…In the same way, ligands with mixed-functionalities such as pyridinecarboxylate, pyrazinecarboxylate, imidazolecarboxylate have been reported to favours the design of diverse structure of coordination compounds with fascinating potential application [9][10][11]. Furthermore, these ligands are known to possess strong and weak hydrogen bonding (such as O-H•••O and C-H••••O) and π-π stacking interactions, which in uences their biological properties [12][13][14][15].…”

Section: Introductionmentioning

confidence: 96%

Calcium coordination compounds of dipicolinic and quinolinic acids: synthesis, characterization, crystal structures and DFT studies

Tella

Oladipo

Olayemi

et al. 2022

Preprint

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In the past two decades various N-heterocyclic carboxylate coordination compounds have been synthesized with intriguing architectures and potential applications as functional materials. In this regard, two novel calcium coordination compounds [Ca(2,6-Hpdc)2(H2O)2] 1 and [Ca2(2,3-pdc)2(H2O)6]n 2 (where 2,6-H2pdc = 2,6-pyridinedicarboxylic acid and 2,3-H2pdc = 2,3-pyridinedicarboxylic acid) were grown at room temperature. The compounds were characterized using elemental analysis, Fourier Transform infrared (FT-IR) spectroscopy, thermogravimetric analysis, powder X-ray diffraction and single crystal X-ray crystallographic analysis. Compounds 1 and 2 crystallize in orthorhombic space group Pccn and monoclinic space group Pc, respectively. The structures of both compounds are stabilized by a network of hydrogen bonds arising from coordinated water molecules and carboxylate groups. Computational analysis revealed that compound 1 has a large energy gap (9.221 eV) suggesting high excitation energies and chemical hardness making it a better electron acceptor while compound 2 displayed a smaller energy gap (5.156 eV) which is indicative of a softer molecule with better polarizability and reactivity.

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Cobalt (II), zirconium(IV), calcium(II) complexes with dipicolinic acid and imidazole derivatives: X-ray studies, thermal analyses, evaluation as in vitro antibacterial and cytotoxic agents

Cited by 55 publications

References 62 publications

Antifungal Mechanism of Dipicolinic Acid and Its Efficacy for the Biocontrol of Pear Valsa Canker

Antifungal Mechanism of Dipicolinic Acid and Its Efficacy for the Biocontrol of Pear Valsa Canker

Novel Tl(III) complexes containing pyridine-2,6-dicarboxylate derivatives with selective anticancer activity through inducing mitochondria-mediated apoptosis in A375 cells

Calcium coordination compounds of dipicolinic and quinolinic acids: synthesis, characterization, crystal structures and DFT studies

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