Development of novel copper(II) complexes of benzothiazole-N-sulfonamides as protective agents against superoxide anion. Crystal structures of [Cu(N–2-(4-methylbenzothiazole)benzenesulfonamidate)2(py)2] and [Cu(N–2-(6-nitrobenzothiazole)naphthalenesulfonamidate)2(py)2]

González‐Álvarez, Marta; Alzuet, Gloria; Borrás, Joaquı́n; Agudo, Lucasdel Castillo; Montejo-Bernardo, José; García-Granda, Santiago

doi:10.1007/s00775-002-0394-7

Cited by 30 publications

(17 citation statements)

References 34 publications

(51 reference statements)

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“…The IC 50 value for native Cu 2 Zn 2 SOD is 0.006 μΜ. Thus, the IC 50 values for both complexes are higher than the IC 50 value for native Cu 2 Zn 2 SOD but are similar to those of complexes with related sulfonamide ligands presented in the literature [ 43 , 44 , 45 , 46 ].…”

Section: Resultssupporting

confidence: 72%

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

et al. 2022

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Nowadays, the discovery of a new non-toxic metal complex with biological activity represents a very active area of research. Two Cu+2 complexes, [Cu(L1)2(H2O)3] (C1) (HL1= N-(5-(4-methylphenyl)-[1,3,4]–thiadiazole–2-yl)-naphtalenesulfonamide) and [Cu(L2)2(py)2(H2O)] (C2) (HL2= N-(5-ethyl-[1,3,4]–thiadiazole–2-yl)-naphtalenesulfonamide), with two new ligands were synthesized. The X-ray crystal structures of the complexes were determined. In both complexes, Cu+2 is five-coordinated, forming a CuN2O3 and CuN4O chromophore, respectively. The ligands act as monodentate, coordinating the metal ion through a single Nthiadiazole atom; for the C2 complex, the molecules from the reaction medium (pyridine and water) are also involved in the coordination of Cu+2. The complexes have a distorted square pyramidal square-planar geometry. The compounds were characterized by FT-IR, electronic EPR spectroscopy, and magnetic methods. The nuclease activity studies confirm the complexes’ capacity to cleave the DNA molecule. Using a xanthine-xanthine oxydase system, the SOD mimetic activity of the complexes was demonstrated. Cytotoxicity studies were carried out on two tumor cell lines (HeLa, WM35) and on a normal cell line (HFL1) using the MTT method, with cisplatin used as a positive control. The antibacterial activity of the complexes was investigated against two Gram-positive and two Gram-negative bacteria, and compared with Amoxicillin and Norfloxacin using the disk diffusion method. Both complexes showed in vitro biological activity but the C2 complex was more active. A lack of in vivo toxicity was demonstrated for the C2 complex by performing hepatic, renal, and hematological studies on Swiss mice.

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Section: Resultssupporting

confidence: 72%

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

et al. 2022

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“…To circumvent such limitations, there is considerable interest in developing synthetic SOD mimics that have low molecular weight, biological stability, membrane permeability, nontoxicity, and cost-effectiveness . The search for SOD mimics yielded a variety of chelates of transition metals such as copper. − In this study, we have published several papers describing the SOD mimic activity of copper complexes with N -substituted sulfonamides. − Other pharmacological properties have been reported in detail for a large number of metal complexes of sulfonamides …”

Section: Introductionmentioning

confidence: 99%

Comparison of Protective Effects against Reactive Oxygen Species of Mononuclear and Dinuclear Cu(II) Complexes with N-Substituted Benzothiazolesulfonamides

et al. 2005

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Copper(II) complexes of N-benzothiazolesulfonamides (HL1=N-2-(4-methylphenylsulfamoyl)-6-nitro-benzothiazole, HL2=N-2-(phenylsulfamoyl)-6-chloro-benzothiazole, and HL3=N-2-(4-methylphenylsulfamoyl)-6-chloro-benzothiazole) with ammonia have been synthesized and characterized. The crystal structures of the [Cu(L1)2(NH3)2].2MeOH, [Cu(L2)2(NH3)2], and [Cu(L3)2(NH3)2] compounds have been determined. Compounds and present a distorted square planar geometry. In both compounds the metal ion is coordinated by two benzothiazole N atoms from two sulfonamidate anions and two NH3 molecules. Complex is distorted square-pyramidal. The Cu(II) ion is linked to the benzothiazole N and sulfonamidate O atoms of one of the ligands, the benzothiazole N of another sulfonamidate anion, and two ammonia N atoms. We have tested the superoxide dismutase (SOD)-like activity of the compounds and compared it with that of two dinuclear compounds [Cu2(L4)2(OCH3)2(NH3)2] and [Cu2(L4)2(OCH3)2(dmso)2] (HL4=N-2-(phenylsulfamoyl)-4-methyl-benzothiazole). In vitro indirect assays show that the dimeric complexes are better SOD mimics than the monomeric ones. We have also assayed the protective action provided by the compounds against reactive oxygen species over Deltasod1 mutant of Saccharomyces cerevisiae. In contrast to the in vitro results, the mononuclear compounds were more protective to SOD-deficient S. cerevisiae strains than the dinuclear complexes.

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“…The spectrum of the (C 2 ) complex presents bands at 1125, 1087 and 730 cm -1 , which are attributed to the coordinated phenanthroline molecule [36]. In general, the IR spectra are similar to those for the other copper Nsulfonamide compounds [37]. The changes of the IR characteristic bands are mainly due to the sulfonamide deprotonation.…”

Section: Spectroscopic Propertiesmentioning

confidence: 65%

“…Complex (C 2 ) was more potent than (C 1 ); the IC 50 values were founded 0.115 µM (C 2 ) and 0.223 µM (C 1 ). These values are higher than that for native Cu 2 Zn 2 SOD (0.006 µÌ) (that means that the complexes are less active than native SOD) but similar to those of complexes with related sulfonamide ligands [18, 37,52].…”

Section: Dna Cleavagementioning

confidence: 97%

Synthesis, Characterization and Biological Activity of Two New Copper (II) Complexes with N-sulfonamide Ligand

2019

Rev.Chim.

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Despite the fact that a large number of chemotherapeutic anticancer agents have been discovered, cancer still remains a great cause of deaths worldwide. The purpose of our researches is to discover a new antitumor drug. In this aim, two new Cu(II) complexes, (C1) and (C2) with a new ligand, N-(5-trifluoromethyl-<1,3,4>-thiadiazole-2-yl)-benzensulfonamide(HL) were synthesized. The complexes were characterized by elemental analysis, spectral and magnetic determinations. The nuclease activity studies of the complexes confirm their capacity to cleavage the DNA molecule. Both complexes have in vitro antioxidant activity (DPPH, FRAP methods), in vitro (using xanthine /xanthine oxidase system) and in vivo (using S.cerevisiae)SOD mimetic activity.The results of MTT assay on two carcinoma cell lines (HeLa and WM35) indicate that both complexes have antitumor activity, but (C2) has a superior activity compared with (C1) and with Cisplatin. On normal fibroblast (HDFa), (C1) showed toxicity comparable with Cisplatin, but (C2) showed a lower one. Bacterial assays were also performed (by the disk diffusion method) and both complexes have antibacterial activity against S. aureus, E. coli, P. aeroginosa and B. cereus. All the biological studies are in concordance and show that both complexes have biologic activity but (C2)is much more active. Keywords: oxidative DNA cleavage, antioxidant capacity, SOD-mimetic activity, cytotoxicity, antibacterial properties

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Development of novel copper(II) complexes of benzothiazole-N-sulfonamides as protective agents against superoxide anion. Crystal structures of [Cu(N–2-(4-methylbenzothiazole)benzenesulfonamidate)2(py)2] and [Cu(N–2-(6-nitrobenzothiazole)naphthalenesulfonamidate)2(py)2]

Cited by 30 publications

References 34 publications

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

Comparison of Protective Effects against Reactive Oxygen Species of Mononuclear and Dinuclear Cu(II) Complexes with N-Substituted Benzothiazolesulfonamides

Synthesis, Characterization and Biological Activity of Two New Copper (II) Complexes with N-sulfonamide Ligand

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