Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine

Agotegaray, Mariela; Dennehy, Mariana; Boeris, Mónica Alejandra; Grela, M. A.; Burrow, Robert A.; Quinzani, Oscar V.

doi:10.1016/j.poly.2011.12.005

Cited by 48 publications

(30 citation statements)

References 56 publications

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“…随着保泰松(Phenylbutazone)、吲哚美辛(Indomethacin)和布诺芬(Ibuprofen)等药物的出现, 非甾体消炎药引起了人们的广泛关注, 其中有大量的工作致力于唑类络合物超分子消炎药的研究 [395,396] . [397] . 络合物超分子消炎活性高, 而且三个烃基取代的比双烃基取代络合物超分子消炎活性高 [398] .…”

Section: 唑类超分子作为消炎药物unclassified

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Cheng¹,

Wang²,

Addla³

et al. 2016

Chin. J. Org. Chem.

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Noncovalent bond forces-based supramolecular chemistry grows quite rapidly and has been revealed to have extensively potential applications and huge development values in chemistry, physics, materials and information science, medicine and so on. Azole compounds such as imidazoles, thiazoles, oxazoles, pyrazoles, triazoles, tetrazoles and carbazoles containing special nitrogen aromatic heterocyclic structure, can exert non-covalent forces to form supramolecular complexes with inorganic and/or organic compounds and exhibit broad biological activity. In recent years, heterocyclic azole-based supramolecular complexes have been expeditiously expanding in the field of medicine, and have become a quite hot topic. Combined with our work and referring to other literature in recent 5 years, this paper systematically reviews the researches and applications of azole-based supermolecules as medicinal agents including anticancer, antibacterial, antifungal, antiparasitic, antidiabetic, antihypertensive, anti-inflammatory drugs and other ones. Finally, the perspectives of the future development of azole-based supermolecules as medicinal agents are also presented.

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Section: 唑类超分子作为消炎药物unclassified

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Cheng¹,

Wang²,

Addla³

et al. 2016

Chin. J. Org. Chem.

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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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“…The results suggest that 9 is a stronger inhibitor of COX-2, with activity seven times greater than that of aspirin. [17] Indomethacin (indo) complexes of formulae [Cu 2 (indo) 4 -(DMF) 2 ] (13) and [Zn 2 (indo) 4 (DMA) 2 ] (14, DMA = N,N-dimethylacetamide) were tested for in vitro SOD activity, in vivo antiinflammatory activity, and gastrointestinal ulcerogenic properties (Scheme 12) in male Sprague-Dawley rats. The stability of the complex in solution was suggested by UV/Vis.…”

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%

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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Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine

Cited by 48 publications

References 56 publications

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

Current Researches and Applications of Azole-BasedSupermolecules as Medicinal Agents

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

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

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