Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

Agotegaray, Mariela; Boeris, Mónica Alejandra; Quinzani, Oscar V.

doi:10.1590/s0103-50532010001200017

Cited by 21 publications

(18 citation statements)

References 38 publications

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“…The pyridine-containing complexes exhibited the lowest affinity for CT-DNA and the lowest ability to displace EtBr from its EtBr·DNA complex. 16) were prepared. [11,91] The manganese(II) complex of niflumic acid -[Mn(nifl) 2 -(H 2 O) 4 ] (279, Scheme 35) -bound through an intercalative mode to CT-DNA.…”

Section: Concluding Remarks On the Complexes With Antiproliferative Amentioning

confidence: 99%

“…The selective inhibition index with COX-2 [IC 50 (COX-1)/IC 50 (COX-2)] of 9 was 3.3, whereas that of asp was 0.4. [11,16] The copper(II) ternary complexes of fenoprofen and either imidazole (im) or caffeine (caf ) -of formulae Cu(fen) 2 (im) 2 (11) and Cu 2 (fen) 4 (caf ) 2 (12) -enhanced and prolonged anti-inflammatory properties in mice relative to those of the parent drug calcium fenoprofenate. [11,15] The complex of fenoprofen (fen) of formula [Cu 2 (fen) 4 (DMF) 2 ] (10, Scheme 12) was tested in vivo for anti-inflammatory properties in comparison with fenoprofen.…”

Section: Introductionmentioning

confidence: 99%

“…[11,15] The complex of fenoprofen (fen) of formula [Cu 2 (fen) 4 (DMF) 2 ] (10, Scheme 12) was tested in vivo for anti-inflammatory properties in comparison with fenoprofen. [18] Compounds with ketoprofen of the general formula [M(ket) 3 ] {M = Gd (15), Tb (16), Dy (17), Ho (18), Er (19), Tm (20), Yb (21), Lu (22), Y (23), Scheme 13} were evaluated for their antiinflammatory activities. Oral administration of the compound inhibited the development of carrageenaninduced edema in mice.…”

Section: Introductionmentioning

confidence: 99%

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Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

2016

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The nonsteroidal anti-inflammatory drugs (NSAIDs) make up a great group of drugs that provide benefits in the prevention of cancers. Coordinated metal ions with NSAIDs provide advantages over the drugs themselves. The metal complexes of NSAIDs display a range of biological activities quite often inaccessible to the original NSAID ligands. NSAIDs-metal complexes have molecular properties different from those of the parent drugs. Thus, if a given NSAIDs-metal complex remains intact in the biological medium its biological target is [a] She is now a Postdoctoral Fellow of the National Scholarships Foundation of Greece-Siemens program with a fellowship of excellence. Her research interests are mainly focused on bioinorganic chemistry and particularly on the evaluation of the anticancer properties of metal complexes by studying their interaction with intracellular molecules. Sotiris K. Hadjikakou was born in Famagusta, Cyprus. He graduated from the Chemistry 3049 dentate, bidentate, or bridge ligands in polynuclear complexes.Compounds of NSAIDs with biometals exhibit better pharmacological activity than free NSAIDs. [11] The structural characteristics, medicinal/veterinary properties, superoxide dismutase (SOD) activity [SOD is an enzyme that catalyzes the dismutation of the superoxide (O 2 -) radical into both ordinary molecular oxygen (O 2 ) and hydrogen peroxide (H 2 O 2 ), thus being involved in the inflammation mechanism], anti-inflammatory, and ulcerogenic effects of Cu-NSAIDs have also been reviewed. [5] The review concluded that the mode of action of the Cu-NSAIDs is similar to that of the traditional NSAIDs and the complexes reduced gastrointestinal toxicity. Moreover, the stabilities of Cu-NSAIDs complexes are a critical determinant of their activity and toxicity. [5] This review summarizes the complexes of NSAIDs: (i) acetylsalicylic acid, diflunisal, salicylic acid (salicylic acid derivatives, Scheme 1), (ii) diclofenac, indometacin, sulindac, tolmetin (arylalkanoic acid derivatives, Scheme 2), (iii) ibuprofen, ketoprofen, Scheme 1. Salicylic acid derivatives.Scheme 2. Arylalkanoic acid derivatives. MicroreviewScheme 3. Arylpropionic acid derivatives (profens).Scheme 4. N-Arylanthranilic acid (fenamic acids). 3050Scheme 5. Other acid derivatives.Scheme 6. Oxicams. MicroreviewScheme 7. Aniline and p-aminophenol derivatives.Scheme 8. Sulfonamides. Discussion Metal Complexes of NSAIDs Exhibiting Anti-Inflammatory or Analgesic ActivityMn II -, Fe II -, Co II -, Ni II -, and Zn II -Schiff base complexes that contain anthranilic acid and aldoses in the Schiff base component are four-coordinate in the anhydrous state with the general formula ML 2 [M = Mn II (1), Fe II (2), Co II (3), Ni II (4), and Zn II (5), Scheme 9]. They were tested for their in vivo biological activities. The stability of the complexes in DMSO solution was confirmed by 1 H NMR spectroscopy. The relative toxicities of the metal complexes were determined with albino Wistar male rats; the LD 50 values followed the trend Ni < Mn < Co < Fe < Zn, w...

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Section: Concluding Remarks On the Complexes With Antiproliferative Amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

2016

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“…Frequency of ν as and ν s (C=O) vibration depends on the coordination of the metal ion with carboxyl group from ligands. On the basis of the FTIR spectra in ν(CO) vibration area information about ligand identicity can be obtained (monodentate, bidentate, bridge-ligand), mode of coordination to the metal ion, the type of donor atoms, as well as the type of the complex (mononuclear, binuclear and polynuclear) [29][30][31][32][33]. On the basis of these data the difference in frequency of 175 cm -1 between ν as and ν s (C=O) vibration in FTIR spectra of Cu-CMD shows that CMD carboxyl group is acting like a bidentate ligand and it is understandable that, due to electron delocalization, order of bonds is changing from ligand to the complex compound.…”

Section: Synthesis Of Complexesmentioning

confidence: 99%

Spectroscopic study of copper(II) complexes with carboxymethyl dextran and dextran sulfate

Glišić

Nikolić

Cakić

et al. 2015

Russ. J. Phys. Chem.

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The copper(II) ion complexes with carboxymethyl dextran (CMD) and dextran sulfate (DS) were studied by different methods. Content of copper was determined by atomic absorption spectroscopy. It was found that copper : ligand mole ratio (Cu : CMD) is 1 : 2, and Cu : DS is 1 : 1 by mole ratio method. Spectrophotometric parameters of synthesized compounds are characteristic for Cu(II) ion in octahedral (O h ) coordination. Analyzing of FTIR spectra in ν(C=O) vibration region has showed that -COOH group acts as bidentate ligand, while the compounds of Cu(II) with DS copper ions are in the region of four oxygen atoms of two adjacent sulfo groups. The presence of crystalline water was determined by isotopic substitution of H 2 O molecules with D 2 O molecules. Comparison of spectra recorded at room (RT) and liquid nitrogen temperature (LNT) has enabled detection bands of water molecules libration indicating that they are coordinated complementing coordination sphere of Cu(II) ions to six. The complexes are of Cu(II) · (CMD) 2 · (H 2 O) 2 or Cu(II) · DS · (H 2 O) 2 type. The similarities of the γ(C-H) range in a part of FTIR spectra indicate that there is no difference in the conformation of the 4 C 1 glucopyranose (Glc) unit CMD and DS synthesized Cu(II) complexes.

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“…Ternary copper(II) complexes of Fenoprofen are promising therapeutic agents against inflammatory diseases because of their enhanced anti-inflammatory and analgesic effects compared to the parent Fenoprofen calcium salt [ 16 , 17 ]. It was also demonstrated that two copper(II) complexes of Fenoprofen do not produce toxicological effects in mice after a subacute exposure, making this finding interesting for the potential employment of the formulations in possible clinical treatment.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Analgesic Properties and Reduced Ulcerogenic Effect of a Mononuclear Copper(II) Complex with Fenoprofen in Comparison to the Parent Drug: Promising Insights in the Treatment of Chronic Inflammatory Diseases

Agotegaray

Gumilar

Boeris

et al. 2014

BioMed Research International

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Analgesic and ulcerogenic properties have been studied for the copper(II) coordination complex of the nonsteroidal anti-inflammatory drug Fenoprofen and imidazole [Cu(fen)2(im)2] (Cu: copper(II) ion; fen: fenoprofenate anion from Fenoprofen, im: imidazole). A therapeutic dose of 28 mg/kg was tested for [Cu(fen)2(im)2] and 21 mg/kg was employed for Fenoprofen calcium, administered by oral gavage in female mice to compare the therapeutic properties of the new entity. The acetic acid induced writhing test was employed to study visceral pain. The percentage of inhibition in writhing and stretching was 78.9% and 46.2% for the [Cu(fen)2(im)2] and Fenoprofen calcium, respectively. This result indicates that the complex could be more effective in diminishing visceral pain. The formalin test was evaluated to study the impact of the drugs over nociceptive and inflammatory pain. The complex is a more potent analgesic on inflammatory pain than the parent drug. Ulcerogenic effects were evaluated using a model of gastric lesions induced by hypothermic-restraint stress. Fenoprofen calcium salt caused an ulcer index of about 79 mm2 while the one caused by [Cu(fen)2(im)2] was 22 mm2. The complex diminished the development of gastric mucosal ulcers in comparison to the uncomplexed drug. Possible mechanisms of action related to both therapeutic properties have been discussed.

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Significant anti-inflammatory properties of a copper(II) fenoprofenate complex compared with its parent drug: Physical and chemical characterization of the complex

Cited by 21 publications

References 38 publications

Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

Spectroscopic study of copper(II) complexes with carboxymethyl dextran and dextran sulfate

Enhanced Analgesic Properties and Reduced Ulcerogenic Effect of a Mononuclear Copper(II) Complex with Fenoprofen in Comparison to the Parent Drug: Promising Insights in the Treatment of Chronic Inflammatory Diseases

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