Characterization, photocleavage, molecular modeling, and DNA- and BSA-binding studies of Cu(II) and Ni(II) complexes with the non-steroidal anti-inflammatory drug meloxicam

Sanatkar, Tahereh Hosseinzadeh; Hadadzadeh, Hassan; Jannesari, Zahra; Khayamian, Taghi; Ebrahimi, Malihe; Rudbari, Hadi Amiri; Torkzadeh‐Mahani, Masoud; Anjomshoa, Marzieh

doi:10.1016/j.ica.2014.08.060

Cited by 34 publications

(19 citation statements)

References 88 publications

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“…These possible coordination sites of meloxicam and peroxicam are shown in Figure and their coordination chemistry has been explored. 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 .…”

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 first copper complex reported to show efficient DNA cleavage activity bis (1,10-phenanthroline) copper(I), and then the chemistry of metal complexes of 1,10 phenanthroline or modified ligand were developed as therapeutic agents [2] . In recent years, the coordination of drugs to transition metal ions has an important role in medicine and diagnostics [3] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and DNA binding of copper(II) complexes with mixed ligands of 1, 10-phenanthroline / 2-2’ bipyridyl, L-methionine and ethylamine: Studies on antimicrobial and anti-cancer activities

Ezhilarasan¹,

Krishnan²,

Arumugham³

2017

Int. J. Curr. Res. Chem. Pharm. Sci

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Ternary copper(II) complexes [Cu(phen)(L-met)EA)] 1 & [Cu(Bpy)(L-met)EA] 2 ( phen = 1,10-phenanthroline Bpy = bipyridyl, LMethionine and EA= Ethylamine), have been synthesized and characterized by CHN analysis, molar conductance, electronic absorption, IR and EPR spectral studies. They have been tested for their in vitro DNA binding activities by the spectroscopic methods such as UV-Visible, Cyclic volumetric and viscosity measurement. Further, complexes 1 and 2 displayed significant cytotoxicity when examined in-vitro on a panel of cancerous cell line -human liver cancer cell line -HepG-2 cells (IC50= 40.82 and 29.74 μg/ml). Further complexes 1 & 2 were tested for their antimicrobial activities and it was found to have good antimicrobial activities.

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“…In order to determine the preferred orientation of complexes 1 and 2 inside the DNA helix and to rationalize the spectroscopic results, molecular docking studies were carried out. Docking results of complex 1 revealed preferential binding within the wide A–T region of major groove of the DNA helix (Figure ) . Generally, electronegative A–T sequences provide better van der waals contacts & therefore expose better fitting pockets for small flexible molecule.…”

Section: Resultsmentioning

confidence: 98%

New Ionic Cu(II) and Co(II) DACH–Flufenamate Conjugate Complexes: Spectroscopic Characterization, Single X–Ray Studies and Cytotoxic Activity on Human Cancer Cell Lines

et al. 2018

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New ionic antitumor drug entities [{Cu(DACH) 2 (H 2 O)Cl}.(fluf)], 1 and [{Co(DACH) 2 (H 2 O)Cl}.(fluf)], 2 where DACH = 1,2-diamminocyclohexane and fluf = flufenamate anion were prepared and characterized by spectroscopic studies and single X-ray crystallography. In order to evaluate the potential of these complexes to act as antitumor drug candidates, in vitro binding studies of 1 and 2 with ct-DNA have been carried out by biophysical methods which revealed electrostatic binding mode of these drug entities with ct-DNA preferably by external surface or groove binding mode contrary to other nonsteroidal anti-inflammatory (NSAIDs) drugs which show intercalative binding. Comparative electron paramagnetic reso-nance (EPR) titrations were performed which revealed that there was no significant change in EPR spectra of complexes upon incubation with ct-DNA implicating that coordination geometry of metal ions does not alter. Validation of antitumor potential of 1 and 2 was done by cytotoxicity experiments against human cancer cell lines by Sulforhodamine B (SRB) assay. Complex 1 was active against all tested cell lines with an exceptionally low GI 50 value = 2.9 μg/ml against MCF-7 (breast cancer) cell line showing its preferential selectivity. On the contrary, complex 2 showed poor activity against all tested cancer cell lines.

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Characterization, photocleavage, molecular modeling, and DNA- and BSA-binding studies of Cu(II) and Ni(II) complexes with the non-steroidal anti-inflammatory drug meloxicam

Cited by 34 publications

References 88 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

Synthesis, characterization and DNA binding of copper(II) complexes with mixed ligands of 1, 10-phenanthroline / 2-2’ bipyridyl, L-methionine and ethylamine: Studies on antimicrobial and anti-cancer activities

New Ionic Cu(II) and Co(II) DACH–Flufenamate Conjugate Complexes: Spectroscopic Characterization, Single X–Ray Studies and Cytotoxic Activity on Human Cancer Cell Lines

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