Synthesis, spectroscopic and DFT structural characterization of two novel ruthenium(III) oxicam complexes. In vivo evaluation of anti-inflammatory and gastric damaging activities

Tamasi, Gabriella; Bernini, Caterina; Corbini, Gianfranco; Owens, Natalie F.; Messori, Luigi; Scaletti, Federica; Massai, Lara; Giudice, Pietro; Cini, Renzo

doi:10.1016/j.jinorgbio.2014.01.011

Cited by 26 publications

(22 citation statements)

References 24 publications

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“…Notably, ruthenium complexes such as RAPTA‐C and NAMI‐A have been shown to be non‐cytotoxic in vitro but exhibit high activity against metastasis in vivo . Moreover, Ru III complexes of piroxicam and tenoxicam showed anti‐inflammatory properties comparable to extant drugs while causing less gastric damage than the free oxicams . The low intrinsic toxicity of ruthenium presents an opportunity to develop compounds with lower side effects than caused by highly cytotoxic drugs.…”

Section: Resultsmentioning

confidence: 99%

“…[16b] Moreover,R u III complexes of piroxicam and tenoxicam showed anti-inflammatory properties comparable to extantd rugs while causing less gastric damaget han the free oxicams. [13] The low intrinsict oxicity of ruthenium presents an opportunity to develop compounds with lower side effects than caused by highly cytotoxic drugs.…”

Section: Resultsmentioning

confidence: 99%

“…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%

“…The 1 HNMR spectra for stability studies were recorded on aBruker AvanceA V300 MHz NMR spectrometers at ambient temperature. The measurement frequency for 1 HNMR was 400.13 and 300.13 MHz and for13 C{ 1 H} NMR was 100.61 MHz. The NMR solvents used were D 2 O, CDCl 3 ,a nd [D 6 ]DMSO.…”

mentioning

confidence: 99%

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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: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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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 steric–electronic parameters of N ‐donor complexes/materials must be modified by easily applied methods. Recently, ruthenium‐based catalysts have been used in various types of organic molecular synthesis such as reduction, transfer hydrogenation (TH), alkylation, etc …”

Section: Introductionmentioning

confidence: 99%

SBA‐15‐supported N‐coordinate ruthenium(II) materials bearing sulfonamide‐type ligands: Effect of ligand backbones on catalytic transfer hydrogenation of ketones and aldehydes

Dayan

Kayacı

Özpozan

et al. 2017

Applied Organom Chemis

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RuLCl(p-cymene)] (L = N-arylsulfonylphenylenediamine) complexes (2 a-d ) were synthesized from the reaction between [Ru(p-cymene)Cl 2 ] 2 and ligand. Additionally, SBA-15-[RuLCl(p-cymene)] derived catalysts (3 a-d ) were successfully immobilized onto mesoporous silica (SBA-15) by an easily accessible approach. The structural elucidations of 2 a-d and 3 a-d were carried out with various methods such as 1 H NMR, 13 C NMR and infrared spectroscopies, elemental analysis, thermogravimetric/differential thermal analysis, nitrogen adsorption-desorption and scanning electron microscopy/energy-dispersive X-ray analysis. The Ru(II) complexes and materials were found to be highly active and selective catalysts for the transfer hydrogenation (TH) reaction of aldehydes and ketones. The influence of various 1,2-phenylenediamines on the reactivity of the catalysts (complexes or materials) was studied and the catalysts (2 d and 3 d ) with a 4,5-dichlorophenylenediamine substituent showed the best activity (the maximum turnover frequencies are 2916 and 2154 h −1 for TH of 4-fluoroacetophenone, and 6000 and 4956 h −1 for TH of 4-chlorobenzaldehyde).

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Recent Advances in Biomimetic Metal Phenolates

Tamasi¹,

Cini²

2017

Patai's Chemistry of Functional Groups

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The review reports and critically comments on articles mostly published during the period 2012–2015, relevant to phenolate‐containing metal complexes, in the following fields: (i) antioxidants and O 2 activation (Section III; copper complexes as models for amine oxidase and phenol‐like antioxidants from the OXICAM family of nonsteroidal anti‐inflammatory therapeutics), and (ii) efficient hydrolysis of phosphate diester bonds (Section IV). Remarkably, the review includes several other tasks grouped in Section V about phenolic chelators of iron, models for halophenol scavenger systems, phenols and their metal complexes designed for DNA cleavage, and synthesis of phenolate–metal complexes via radical reactions. The comments focus on the synthesis of complexes and their structural aspects, on spectroscopy, on reaction mechanisms, on computational analyses, and on biological implications of the compounds.

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Synthesis, spectroscopic and DFT structural characterization of two novel ruthenium(III) oxicam complexes. In vivo evaluation of anti-inflammatory and gastric damaging activities

Cited by 26 publications

References 24 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

SBA‐15‐supported N‐coordinate ruthenium(II) materials bearing sulfonamide‐type ligands: Effect of ligand backbones on catalytic transfer hydrogenation of ketones and aldehydes

Recent Advances in Biomimetic Metal Phenolates

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