The piroxicam complex of cobalt(II): Synthesis in two different ionic liquids, structure, DNA- and BSA interaction and molecular modeling

Darabi, Farivash; Hadadzadeh, Hassan; Ebrahimi, Malihe; Khayamian, Taghi; Rudbari, Hadi Amiri

doi:10.1016/j.ica.2013.09.035

Cited by 69 publications

(32 citation statements)

References 75 publications

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“…For example meloxicam acted as monodentate nitrogen donor ligand to Pt II , and coordinated in a bidentate fashion to Ni II through the thiazole nitrogen and amidate oxygen atoms . Similarly, piroxicam coordinated monodentately to Ru II (arene), by its pyridyl nitrogen, and it can act also as an N,O ‐chelator through its amidate oxygen and pyridyl nitrogen to metal ions such as Co II , Ru II , Cu II , and Zn II . In case of hard Sn IV , piroxicam coordinated as an O,O ‐chelator via its enolate and amidate oxygen atoms, whereas the analogous benzothiazine lornoxicam coordinated as a tridentate N , N,O ‐chelator by employing an enolate oxygen and pyridyl and amide nitrogen donors.…”

Section: Introductionmentioning

confidence: 99%

Anti‐Inflammatory Oxicams as Multi‐donor Ligand Systems: pH‐ and Solvent‐Dependent Coordination Modes of Meloxicam and Piroxicam to Ru and Os

Aman

Hanif

Kubanik

et al. 2017

Chemistry A European J

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The nitrogen- and sulfur-containing 1,2-benzothiazines meloxicam and piroxicam are widely used as nonsteroidal anti-inflammatory drugs. Intrigued by the presence of multiple donor atoms and therefore potentially rich coordination chemistry, we prepared a series of organometallic Ru and Os compounds with meloxicam and piroxicam featuring either as mono- or bidentate ligand systems. The choice of the solvent and the pH value was identified as the critical parameter to achieve selectively mono- or bidentate coordination. The coordination modes were confirmed experimentally by NMR spectroscopy and single crystal X-ray diffraction analysis. Using DFT calculations, it was established that complexes in which meloxicam acts as a bidentate N,O donor are energetically more favorable than coordination as O,O and S,O donor systems. Since meloxicam and piroxicam derivatives have shown anticancer activity in the past, we aimed to compare the complexes with mono- and bidentate ligands on their in vitro anticancer activity. However, stability studies revealed that only the latter complexes were stable in [D ]DMSO/D O (5:95) and therefore no direct comparisons could be made. The meloxicam complexes 1 and 2 showed moderate cytotoxicity, whereas the piroxicam derivatives 5 and 6 were hardly active against the utilized cell lines.

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Section: Introductionmentioning

confidence: 99%

Anti‐Inflammatory Oxicams as Multi‐donor Ligand Systems: pH‐ and Solvent‐Dependent Coordination Modes of Meloxicam and Piroxicam to Ru and Os

Aman

Hanif

Kubanik

et al. 2017

Chemistry A European J

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“…The emission intensity of EB bound DNA was measured, which is used to find out the binding ability of metal complexes. Using classical Stern‐Volmer equation,

F_{0} / F = 1 + K_{sv} ([], Q) = 1 + K_{q} normalτ ([], Q)

where F 0 and F is the emission intensity in the absence presence of quencher, K sv is the Stern‐Volmer quenching constant, K q is DNA quenching rate constant and τ is DNA average lifetime without quencher, which is equal to 10 −8 s for bio‐macromolecules, the quenching constant ( K sv ) value is obtained as a slope from the plot of F 0 / F vs. [Q]. The K b and n can be calculated from the equation,

log ((), F_{0} - F) / F = log K_{b} + nlog ([], Q)

where K b is the binding constant and n is the number of binding sites in DNA base pairs.…”

Section: Methodsmentioning

confidence: 99%

DNA/BSA binding interactions and VHPO mimicking potential of vanadium(IV) complexes: Synthesis, structural characterization and DFT studies

Neelakantan

Balakrishnan

Selvarani

et al. 2017

Applied Organom Chemis

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Vanadium(IV) Schiff base complexes (VOL1‐VOL3) were synthesized and characterized by elemental analysis, various spectral methods and single crystal XRD studies. Structural analysis of VOL2 reveals that the central vanadium ion in the complex is six coordinate with distorted octahedral geometry. Density functional theory (DFT) and time dependent (TD‐DFT) studies were used to understand the electronic transitions observed in the complexes in UV–Vis spectra. The electrochemical behavior of the complexes was investigated in acetonitrile medium exhibit quasi‐reversible one electron transfer. The DNA and BSA protein binding interaction of vanadium complexes has been explored by UV–Vis and fluorescence spectral methods and viscosity measurements reveal that the complexes interact with CT‐DNA through intercalation mode and follows the order VOL1 < VOL3 < VOL2. The complexes exhibit binding interactions with BSA protein. The complexes act as chemical nuclease and cleave DNA in the presence of H2O2. The 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) assay was used to evaluate the radical scavenging activity demonstrate the antioxidant property of the complexes. The antimicrobial activity was screened for several microorganisms, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli. The mimicking of vanadium haloperoxidase was investigated by the bromination of the organic substrate phenol red by vanadium complexes in the presence of bromide and H2O2.

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“…Coupling of the π orbitals which are also partially filled by electrons, reduces the transition probability and thus results in a hypochromism [23,24]. In the case of groove binding, sometimes a hypochromism that is manifested in terms of a small decline in absorbance and either no or only minor changes in λ max are observed [25,26].…”

Section: Titration Of Ole With the Dnamentioning

confidence: 99%

“…From the shifts observed in peak potential separation (∆E p ) and formal potential (E˚f) of the electroactive species after interacting with DNA, one can explain the binding mechanism [25]. Typical cyclic voltammetric behavior of Ole in the absence and presence of the DNA was studied.…”

Section: Electrochemical Studiesmentioning

confidence: 99%

Spectroscopic and electrochemical studies of the interaction between oleuropein, the major bio-phenol in olives, and salmon sperm DNA

Mohamadi

Afzali

Esmaeili‐Mahani

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The piroxicam complex of cobalt(II): Synthesis in two different ionic liquids, structure, DNA- and BSA interaction and molecular modeling

Cited by 69 publications

References 75 publications

Anti‐Inflammatory Oxicams as Multi‐donor Ligand Systems: pH‐ and Solvent‐Dependent Coordination Modes of Meloxicam and Piroxicam to Ru and Os

Anti‐Inflammatory Oxicams as Multi‐donor Ligand Systems: pH‐ and Solvent‐Dependent Coordination Modes of Meloxicam and Piroxicam to Ru and Os

DNA/BSA binding interactions and VHPO mimicking potential of vanadium(IV) complexes: Synthesis, structural characterization and DFT studies

Spectroscopic and electrochemical studies of the interaction between oleuropein, the major bio-phenol in olives, and salmon sperm DNA

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