The piroxicam complex of copper(II), trans-[Cu(Pir)2(THF)2], and its interaction with DNA

Hadadzadeh, Hassan; Salimi, Mona; Weil, Mat­thias; Jannesari, Zahra; Darabi, Farivash; Abdi, Khatereh; Khalaji, Aliakbar Dehno; Sardari, Soroush; Ahangari, Reza

doi:10.1016/j.molstruc.2012.04.094

Cited by 28 publications

(17 citation statements)

References 41 publications

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“…Meloxicam (H 2 mel; Scheme a) is a member of the oxicam family, and is used widely as an analgesic, anti‐inflammatory and anti‐heat agent . Chelation between H 2 mel and metal ions can provide improved drug activity due to the synergy between ligand and mineral properties . H 2 mel may be coordinated with metal ions in a monodentate manner via the pyridyl or thiazoyl nitrogen, or as a singly deprotonated chelation via the pyridyl or thiazolyl nitrogen and the amide oxygen and in a di‐anionic tridentate manner via the amide oxygen, nitrogen and the pyridyl nitrogen .…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic characterization, thermogravimetry, density functional theory and biological studies of some mixed‐ligand complexes of meloxicam and 2,2′‐bipyridine with some transition metals

Sadeek

El‐Hamid

Mohamed

et al. 2019

Applied Organom Chemis

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The mixed‐ligand Mn(II), Fe(III), Ni(II), Cu(II), Zn(II) and Zr(IV) complexes of meloxicam (H2mel) and 2,2′‐bipyridine (Bipy) were prepared and characterized. For all complexes, the analytical and spectroscopic results revealed that H2mel acts in a monobasic bidentate manner through the oxygen of the amide and nitrogen of the thiazole groups, whereas Bipy coordinates through the two nitrogen atoms with slightly distorted octahedral geometry. Thermodynamic parameters (E, ΔS*, ΔH* and ΔG*) were calculated using Coats–Redfern and Horowitz–Metzger methods. The geometries of H2mel and the complexes were carefully studied using density functional theory to predict the properties of materials performed using the hybrid density functional method B3LYP. All studied complexes are soft with respect to H2mel where η varies from 0.096 for Zn(II) complex to 0.067 for Fe(III) complex and σ varies from 10.42 to 14.93 eV, while η and σ for H2mel are 0.14 and 7.14 eV, respectively. The antibacterial activities of the ligands and metal complexes were investigated and the data show that the complexes are active against some bacterial species compared with H2mel.

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Section: Introductionmentioning

confidence: 99%

Spectroscopic characterization, thermogravimetry, density functional theory and biological studies of some mixed‐ligand complexes of meloxicam and 2,2′‐bipyridine with some transition metals

Sadeek

El‐Hamid

Mohamed

et al. 2019

Applied Organom Chemis

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“…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. Many of the metal complexes of oxicam‐based ligands have demonstrated biological applications, such as in DNA cleavage, or as antitumor agents …”

Section: Introductionmentioning

confidence: 99%

“…[9] In case of hard Sn IV ,p iroxicam coordinated as an O,O-chelatorv ia its eno- late and amidate oxygen atoms, [10] whereas the analogous benzothiazine lornoxicam coordinated as at ridentate N,N,Ochelator [11] by employing an enolate oxygen and pyridyla nd amide nitrogen donors. Many of the metal complexes of oxicam-based ligandsh ave demonstrated biological applications, such as in DNA cleavage, [7,9,12] or as antitumor agents. [6, 8a, 13] The remarkable successo fp latinum-based anticancer drugs and promisingr esults from clinicalt rials of Ru III drugs [14] have prompted the research of organometallic anticancer compoundso ften featuring ruthenium or osmium metal centers.…”

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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“…The method was validated using Copper(II)-Piroxicam, Cu(II)-Pix, being one of the most active anti-inflammatory and anti-arthritic species [48,49,50,51]. The crystal structure of the Cu(II)-Piroxicam complex is known [49].…”

Section: Introductionmentioning

confidence: 99%

Metal-Ligand Recognition Index Determination by NMR Proton Relaxation Study

et al. 2019

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In this study, we developed and validated a new proposed parameter quantifying the interaction strength between natural and/or synthetic molecules with paramagnetic metal ions. The Metal ion Recognition Index, Miri, is a quantitative parameter to describe the proton environment and to define their involvement in the inner and/or outer sphere of the paramagnetic metal ion. The method is based on the analysis of NMR proton spin-lattice relaxation rates of a specific ligand in both the diamagnetic and paramagnetic conditions. The proposed procedure is also useful to calculate the ligand proton spin-lattice relaxation rate in the paramagnetic bound conditions, which is typically very difficult to determine experimentally. Miri was used to compare the ligand proton involvement toward different paramagnetic species, in particular the Copper(II)-Piroxicam system. Copper(II)-Piroxicam complex is one of the most active anti-inflammatory and anti-arthritic species. Miri provides an opportunity to improve our knowledge of metal-ligand complexes that play a fundamental role in bioinorganic interactions.

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The piroxicam complex of copper(II), trans-[Cu(Pir)2(THF)2], and its interaction with DNA

Cited by 28 publications

References 41 publications

Spectroscopic characterization, thermogravimetry, density functional theory and biological studies of some mixed‐ligand complexes of meloxicam and 2,2′‐bipyridine with some transition metals

Spectroscopic characterization, thermogravimetry, density functional theory and biological studies of some mixed‐ligand complexes of meloxicam and 2,2′‐bipyridine with some transition metals

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

Metal-Ligand Recognition Index Determination by NMR Proton Relaxation Study

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