Antimicrobial activities, DNA interactions, spectroscopic (FT-IR and UV-Vis) characterizations, and DFT calculations for pyridine-2-carboxylic acid and its derivates

Tamer, Ömer; Tamer, Sevil Arabacı; İdil, Önder; Avcı, Davut; Vural, Hatice; Atalay, Yusuf

doi:10.1016/j.molstruc.2017.09.100

Cited by 50 publications

(33 citation statements)

References 40 publications

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“…The natural charge of Cd (II) ion in complex 2 was found to be 1.49573. As a consequently, the natural charges of free Mn (II) and Cd (II) ions decreased in complexes 1 and 2 , and the reason of this fact that the charge transfers from 4mpic and dmbpy ligands to Mn (II) and Cd (II) ions dominate those occur in the opposite directions . The high energy interactions of LP O/N → LP*Mn/Cd were presented in Table .…”

Section: Resultsmentioning

confidence: 99%

“…Consequently, the logical design of the organic ligands and the selection of suitable metal ions play a key role in obtaining the coordination complexes with the desired properties . Among numerous organic ligands, carboxylic acid ligands having a multifaceted nature are of particular importance and have been widely used in the construction of various metal–organic coordination complexes …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of the first mixed ligand Mn (II) and Cd (II) complexes of 4‐methoxy‐pyridine‐2‐carboxylic acid, molecular docking studies and investigation of their anti‐tumor effects in vitro

Tamer

Mahmoody

Feyzioğlu

et al. 2019

Applied Organom Chemis

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The first mixed ligand Mn (II) and Cd (II) complexes containing 4‐methoxy‐pyridine‐2‐carboxylic acid (4‐mpic) and 4,4′‐dimethyl‐2,2′‐bipyridine (dmbpy) were synthesized in this study. The geometric structures of [Mn(4‐mpic)2(dmbpy)] (complex 1) and [Cd(4‐mpic)2(dmbpy)] (complex 2) were determined by single crystal X‐Ray diffraction method. FT‐IR and UV–Vis spectra were also recorded to investigate vibrational and electronic properties of complexes 1 and 2. Density functional theory (DFT) calculations were also carried out to provide a deep understanding in geometric, spectroscopic, electronic and nonlinear optical (NLO) properties of complexes 1 and 2. The first‐order hyperpolarizibility (β) parameter calculated as 332.9736 × 10−30 esu demonstrated that complex 1 is an extremely promising candidate to NLO materials. Natural bond orbital (NBO) analysis not only verified the distorted octahedral geometries of central metal ions, but also found out the high‐energy interactions responsible for biological activities for complexes 1 and 2. Anti‐cancer activities of complexes 1 and 2 were tested on human breast carcinoma cell line MCF‐7 (ER and PR positive, HER2 negative) and the triple negative breast carcinoma cell line MDA‐MB 231 (ER, PR and HER2 negative). Dose–response relationship derived from MTT assays indicates that complexes 1 and 2 are showing concentration‐dependent effects, which could suggest a potential use for these drug combinations in cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of the first mixed ligand Mn (II) and Cd (II) complexes of 4‐methoxy‐pyridine‐2‐carboxylic acid, molecular docking studies and investigation of their anti‐tumor effects in vitro

Tamer

Mahmoody

Feyzioğlu

et al. 2019

Applied Organom Chemis

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“…The construction of metal–organic frameworks (MOFs) with fascinating structural architectures and topologies has received great interest due to their potential applications in the fields of magnetism, catalysis, gas adsorption, ion exchange, conductivity, photochemistry, materials science and medicine . In recent years, a number of MOFs that contain copper, cobalt, zinc, nickel and manganese have been synthesized by selecting suitable ligands and metal ions which improve the functional properties and biological activities of the synthesized complexes.…”

Section: Introductionmentioning

confidence: 99%

Crystal growth, structural and spectroscopic characterization, antimicrobial activity, DNA cleavage, molecular docking and density functional theory calculations of Zn(II) complex with 2‐pyridinecarboxylic acid

Tamer

Avcı

Çelikoğlu

et al. 2018

Applied Organom Chemis

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A Zn(II) complex with 2-pyridinecarboxylic acid was prepared, and its crystal structure characterization was carried out using X-ray diffraction analysis.The spectroscopic properties of the Zn(II) complex were determined by means of Fourier transform infrared, Raman and UV-visible spectroscopic techniques. The coordination sphere for the central Zn(II) ion was found to be a distorted octahedron. The C═O, C═C and C═N stretching vibrations were found highly active and strong, leading to intramolecular charge transfer within the Zn(II) complex. Density functional theory calculations were carried out to provide further understanding of structural, spectroscopic and nonlinear optical properties of the complex. The occurrence of hydrogen bonding interactions in the Zn(II) complex was explained by natural bond orbital analysis. According to obtained hyperconjugative interaction energies, metal-ligand charge transfer interactions occur in the Zn(II) complex. The antimicrobial activities were determined against standard Gram-positive and Gram-negative bacterial strains and yeasts using the minimum inhibitory concentration method. Having a significant effect against Candida albicans and Saccharomyces cerevisiae is important in that the complex can be used as a new antifungal agent. The calculated free binding energy of the interaction of the Zn(II) complex with DNA was found to be 6.72 kcal mol −1 , indicating a high binding affinity between the complex and DNA.

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“…induces cell death via apoptosis (12)(13)(14). In particular, PA showed high antimicrobial activity at concentrations as low as 8 g/liter (15)(16)(17).…”

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confidence: 99%

Identification and Characterization of a Novel pic Gene Cluster Responsible for Picolinic Acid Degradation in Alcaligenes faecalis JQ135

Qiu

Zhao

et al. 2019

J Bacteriol

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Picolinic acid (PA) is a natural toxic pyridine derivative. Microorganisms can degrade and utilize PA for growth. However, the full catabolic pathway of PA and its physiological and genetic foundation remain unknown. In this study, we identified a gene cluster, designated picRCEDFB4B3B2B1A1A2A3, responsible for the degradation of PA from Alcaligenes faecalis JQ135. Our results suggest that PA degradation pathway occurs as follows: PA was initially 6-hydroxylated to 6-hydroxypicolinic acid (6HPA) by PicA (a PA dehydrogenase). 6HPA was then 3-hydroxylated by PicB, a four-component 6HPA monooxygenase, to form 3,6-dihydroxypicolinic acid (3,6DHPA), which was then converted into 2,5-dihydroxypyridine (2,5DHP) by the decarboxylase PicC. 2,5DHP was further degraded to fumaric acid through PicD (2,5DHP 5,6-dioxygenase), PicE (N-formylmaleamic acid deformylase), PicF (maleamic acid amidohydrolase), and PicG (maleic acid isomerase). Homologous pic gene clusters with diverse organizations were found to be widely distributed in Alpha-, Beta-, and Gammaproteobacteria. Our findings provide new insights into the microbial catabolism of environmental toxic pyridine derivatives. IMPORTANCE Picolinic acid is a common metabolite of L-tryptophan and some aromatic compounds and is an important intermediate in organic chemical synthesis. Although the microbial degradation/detoxification of picolinic acid has been studied for over 50 years, the underlying molecular mechanisms are still unknown. Here, we show that the pic gene cluster is responsible for the complete degradation of picolinic acid. The pic gene cluster was found to be widespread in other Alpha-, Beta-, and Gammaproteobacteria. These findings provide a new perspective for understanding the catabolic mechanisms of picolinic acid in bacteria.

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Antimicrobial activities, DNA interactions, spectroscopic (FT-IR and UV-Vis) characterizations, and DFT calculations for pyridine-2-carboxylic acid and its derivates

Cited by 50 publications

References 40 publications

Synthesis of the first mixed ligand Mn (II) and Cd (II) complexes of 4‐methoxy‐pyridine‐2‐carboxylic acid, molecular docking studies and investigation of their anti‐tumor effects in vitro

Synthesis of the first mixed ligand Mn (II) and Cd (II) complexes of 4‐methoxy‐pyridine‐2‐carboxylic acid, molecular docking studies and investigation of their anti‐tumor effects in vitro

Crystal growth, structural and spectroscopic characterization, antimicrobial activity, DNA cleavage, molecular docking and density functional theory calculations of Zn(II) complex with 2‐pyridinecarboxylic acid

Identification and Characterization of a Novel pic Gene Cluster Responsible for Picolinic Acid Degradation in Alcaligenes faecalis JQ135

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