Synthesis, characterisation and biological aspects of copper(II) dithiocarbamate complexes, [Cu{S2CNR(CH2CH2OH)}2], (R=Me, Et, Pr and CH2CH2OH)

Lima, Geraldo Μ. de; Menezes, Daniele C.; Cavalcanti, Camila A.; Santos, Jaqueline A.F. dos; Ferreira, Isabella P.; Paniago, Eucler B.; Wardell, Jámes L.; Wardell, Solange M. S. V.; Krambrock, Klaus; Mendes, Isolda C.; Beraldo, Heloísa

doi:10.1016/j.molstruc.2010.11.048

Cited by 43 publications

(16 citation statements)

References 47 publications

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“…It is thought that the diffusion and mobility of the silver compounds in the solid medium is restricted, leading to poor diffusion through agar medium and thus moderate zones of inhibition are observed. Similar observations were made for related tin dithiocarbamates [50].…”

Section: Determination Of Minimum Inhibitory Concentration (Mic) and Minimum Bactericidal Concentration (Mbc)supporting

confidence: 82%

“…However, the results showed 4, Cy 3 PAg[S 2 CN (Me)CH 2 CH 2 OH], with a less polar group (methyl), was most active. It is possible that the increased lipophilic character of 4 enables more efficient diffusion across the membrane into the cytoplasm of bacterial cells, before exhibiting its anti-bacterial effects [50].…”

Section: Determination Of Minimum Inhibitory Concentration (Mic) and Minimum Bactericidal Concentration (Mbc)mentioning

confidence: 99%

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In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

Tan

Yeo

et al. 2019

Journal of Inorganic Biochemistry

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Four binuclear phosphanesilver(I) dithiocarbamates, {cyclohexyl 3 PAg(S 2 CNRR′)} 2 for R = R′ = Et (1), CH 2 CH 2 (2), CH 2 CH 2 OH (3) and R = Me, R′ = CH 2 CH 2 OH (4) have been synthesised and characterised by spectroscopy and crystallography, and feature tri-connective, μ 2 -bridging dithiocarbamate ligands and distorted tetrahedral geometries based on PS 3 donor sets. The compounds were evaluated for anti-bacterial activity against a total of 12 clinically important pathogens. Based on minimum inhibitory concentration (MIC) and cell viability tests (human embryonic kidney cells, HEK 293), 1-4 are specifically active against Gram-positive bacteria while demonstrating low toxicity; 3 and 4 are active against methicillin resistant S. aureus (MRSA). Across the series, 4 was most effective and was more active than the standard anti-biotic chloramphenicol. Time kill assays reveal 1-4 to exhibit both time-and concentration-dependent pharmacokinetics against susceptible bacteria. Compound 4 demonstrates rapid (within 2 h) bactericidal activity at 1 and 2 × MIC to reach a maximum decrease of 5.2 log 10 CFU/mL against S. aureus (MRSA). While the R = Cy and Ph derivatives exhibited specific activity against Gram-positive bacteria, the R = Et compound showed broad range activity against both Gram-positive and Gram-negative bacteria [23]. Also, based on time kill studies the R = Cy and Ph compounds were bactericidal whereas the R = Et compound was bactericidal and

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Section: Determination Of Minimum Inhibitory Concentration (Mic) and Minimum Bactericidal Concentration (Mbc)supporting

confidence: 82%

Section: Determination Of Minimum Inhibitory Concentration (Mic) and Minimum Bactericidal Concentration (Mbc)mentioning

confidence: 99%

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

Tan

Yeo

et al. 2019

Journal of Inorganic Biochemistry

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“…They fall into three main types. Most common are dialkyl complexes, which can be symmetrically or unsymmetrically substituted or encompassed into a cyclic system, and a large number of these have been prepared [7,8,[14][15][16][17][18][19][20][21]. Over the past decade, an increasing number of alkyl-aryl complexes (Figure 1d) have been documented, also being prepared by the same simple method as described above [22][23][24].…”

Section: Copper(ii) Bis(dithiocarbamate) Complexesmentioning

confidence: 99%

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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“…The peak shifted to 1520 cm −1 in the other three curves, which may be caused by chelating reaction. According to Gao and Lima's work, a C-S band was reported in the region 962-989 cm −1 and 980−1000 cm −1 [23,25]. In the Fig.…”

Section: Effect Of External Heavy Metal Ionsmentioning

confidence: 72%

Removal of micro complex copper in aqueous solution with a dithiocarbamate compound

Yang

et al. 2012

Desalination and Water Treatment

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Synthesis, characterisation and biological aspects of copper(II) dithiocarbamate complexes, [Cu{S2CNR(CH2CH2OH)}2], (R=Me, Et, Pr and CH2CH2OH)

Cited by 43 publications

References 47 publications

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2

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

Removal of micro complex copper in aqueous solution with a dithiocarbamate compound

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