Determination of SOD-Like activity of Copper(II) complexes with α-Amino acid dithiocarbamates

Cao, Roberto; Travieso, Nadina; Fragoso, Alex; Villalonga, Reynaldo; Diaz, A. F.; Martínez, Miguel E.; Alpízar, Jesús; West, Douglas X.

doi:10.1016/s0162-0134(96)00175-4

Cited by 18 publications

(7 citation statements)

References 19 publications

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“…Superoxide dismutase (SOD) is a copper-containing enzyme that catalyses the conversion of superoxide to oxygen and peroxide via a Cu(II)-Cu(I) redox couple. The SOD-like activity of Cu(II) dithiocarbamate complexes has been extensively studied by Cao and co-workers [293][294][295][296][297][298] and others [267]. In order to enhance their water solubility, they prepared a range of cyclodextrin [293,297] and α-amino-acid [295] functionalised dithiocarbamates and their Cu(II) complexes.…”

Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

“…The SOD-like activity of Cu(II) dithiocarbamate complexes has been extensively studied by Cao and co-workers [293][294][295][296][297][298] and others [267]. In order to enhance their water solubility, they prepared a range of cyclodextrin [293,297] and α-amino-acid [295] functionalised dithiocarbamates and their Cu(II) complexes. For the latter, structure-activity relationships were established between −log IC 50 values and the molar refraction of the amino acid substituents, and also the Cu(II)-Cu(I) redox potentials.…”

Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

“…For the latter, structure-activity relationships were established between −log IC 50 values and the molar refraction of the amino acid substituents, and also the Cu(II)-Cu(I) redox potentials. The complex derived from L-glutamic acid showed especially high SOD-like activity interpreted on the basis of EPR spectroscopy to its distorted ground-state geometry [295].…”

Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

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Copper Dithiocarbamates: Coordination Chemistry and Applications in Materials Science, Biosciences and Beyond

Hogarth

Onwudiwe

2021

Inorganics

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Copper dithiocarbamate complexes have been known for ca. 120 years and find relevance in biology and medicine, especially as anticancer agents and applications in materials science as a single-source precursor (SSPs) to nanoscale copper sulfides. Dithiocarbamates support Cu(I), Cu(II) and Cu(III) and show a rich and diverse coordination chemistry. Homoleptic [Cu(S2CNR2)2] are most common, being known for hundreds of substituents. All contain a Cu(II) centre, being either monomeric (distorted square planar) or dimeric (distorted trigonal bipyramidal) in the solid state, the latter being held together by intermolecular C···S interactions. Their d9 electronic configuration renders them paramagnetic and thus readily detected by electron paramagnetic resonance (EPR) spectroscopy. Reaction with a range of oxidants affords d8 Cu(III) complexes, [Cu(S2CNR2)2][X], in which copper remains in a square-planar geometry, but Cu–S bonds shorten by ca. 0.1 Å. These show a wide range of different structural motifs in the solid-state, varying with changes in anion and dithiocarbamate substituents. Cu(I) complexes, [Cu(S2CNR2)2]−, are (briefly) accessible in an electrochemical cell, and the only stable example is recently reported [Cu(S2CNH2)2][NH4]·H2O. Others readily lose a dithiocarbamate and the d10 centres can either be trapped with other coordinating ligands, especially phosphines, or form clusters with tetrahedral [Cu(μ3-S2CNR2)]4 being most common. Over the past decade, a wide range of Cu(I) dithiocarbamate clusters have been prepared and structurally characterised with nuclearities of 3–28, especially exciting being those with interstitial hydride and/or acetylide co-ligands. A range of mixed-valence Cu(I)–Cu(II) and Cu(II)–Cu(III) complexes are known, many of which show novel physical properties, and one Cu(I)–Cu(II)–Cu(III) species has been reported. Copper dithiocarbamates have been widely used as SSPs to nanoscale copper sulfides, allowing control over the phase, particle size and morphology of nanomaterials, and thus giving access to materials with tuneable physical properties. The identification of copper in a range of neurological diseases and the use of disulfiram as a drug for over 50 years makes understanding of the biological formation and action of [Cu(S2CNEt2)2] especially important. Furthermore, the finding that it and related Cu(II) dithiocarbamates are active anticancer agents has pushed them to the fore in studies of metal-based biomedicines.

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Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

Section: Antimicrobial Antibacterial Antioxidant and Sod-like Activitymentioning

confidence: 99%

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Copper Dithiocarbamates: Coordination Chemistry and Applications in Materials Science, Biosciences and Beyond

Hogarth

Onwudiwe

2021

Inorganics

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“…Bis(dithiocarbamato)copper(II) complexes (CuDTC 2 ) are highly stable and can scavenge superoxide and nitric oxide, two radicals of biological importance. − With this in mind, a CuDTC 2 complex was built LbL on gold surfaces. In order to achieve this goal, 4-piperidinemethanethiol (pipSH) was synthesized for the first time.…”

Section: Introductionmentioning

confidence: 99%

Building Layer-by-Layer a Bis(dithiocarbamato)copper(II) Complex on Au{111} Surfaces

et al. 2007

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A bis(dithiocarbamato)copper(II) complex (CuDTC2) was built on Au{111} surfaces (sheets and electrode beads) using different building blocks in a layer-by-layer (LbL) procedure. The process was followed by AFM and cyclic voltammetry. Initially 4-piperidinemethanethiol, which was synthesized here for the first time, was self-assembled on a gold surface and a highly organized array was obtained. The resulting monolayer was treated with CS2 and NH3 to transform the NH groups of piperidine into dithiocarbamate groups (DTC) with the formation of an amphiphilic ligand (DTCpipS) with thiolate and DTC terminal anionic groups. Two reductive desorption peaks were observed in the cyclic voltammogram of self-assembled DTCpipS, a more intense peak at -0.87 V (thiolate group) and a broader, less intense peak at -0.68 V, corresponding to the desorption of the DTC group bound to the gold surface after the ligand made a approximately 180 degrees flip on the surface. Copper(II) and the morpholyldithiocarbamate anion were associated with self-assembled DTCpipS in order to complete the formation of the CuDTC2 complex on the gold surface. In the voltammogram of the LbL self-assembled CuDTC2 complex the reductive desorption peak at -0.68 V disappeared and one single peak was observed at -0.85 V. This corresponds to the reorientation of all of the DTCpipS dianions in order to coordinate to copper(II) through the DTC groups, leaving the self-assembly only through the thiolate groups. The complete formation of the LbL self-assembled CuDTC2 complex was confirmed by XPS and ToF SIMS, with a detected fragment corresponding to the whole complex.

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“…Various strategies have been developed for solving these difficulties, including: Liposomal encapsulation of the protein [11], synthesis of metal complexes with SOD-like activity [12][13][14], as well as the chemical modification of the enzyme by macromolecular substances [15][16][17][18][19][20][21][22][23]. Among these, the latter appears as the most promissory strategy for improving the pharmacokinetic behavior of this protein, but it is often unsuccessful for protecting SOD against H 2 O 2 inactivation.…”

Section: Introductionmentioning

confidence: 99%

Improved Pharmacological Properties for Superoxide Dismutase Modified with Carboxymethycellulose

Domínguez¹,

Valdivia²,

Caballero³

et al. 2005

Journal of Bioactive and Compatible Polymers

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Superoxide dismutase (SOD) was chemically modified with carboxymethylcellulose through two different synthetic procedures: Reductive alkylation with the periodate-oxidized polymer (SOD-CMCox), and the formation of amide linkages through a carbodiimide catalyzed reaction (SODCMCedac). The SOD-CMCox and SOD-CMCedac conjugates contained about 1.8-1.2 mol of polymer per mol of protein, and retained 68-78% of the initial catalytic activity, respectively. The glycosidated enzymes were more resistant to inactivation with H 2 O 2 and their plasma half-life times were prolonged to 34.7 h -6.6 h when compared with 4.8 min for native SOD. The anti-inflammatory activity of the enzyme was 2-2.4 times increased after conjugation with the polymer.

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Determination of SOD-Like activity of Copper(II) complexes with α-Amino acid dithiocarbamates

Cited by 18 publications

References 19 publications

Copper Dithiocarbamates: Coordination Chemistry and Applications in Materials Science, Biosciences and Beyond

Copper Dithiocarbamates: Coordination Chemistry and Applications in Materials Science, Biosciences and Beyond

Building Layer-by-Layer a Bis(dithiocarbamato)copper(II) Complex on Au{111} Surfaces

Improved Pharmacological Properties for Superoxide Dismutase Modified with Carboxymethycellulose

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