Synthesis, X-ray crystal structure, anti-fungal and anti-cancer activity of [Ag2(NH3)2(salH)2] (salH2=salicylic acid)

Coyle, Barry; McCann, Malachy; Kavanagh, Kevin; Devereux, Michael; McKee, Vickie; Kayal, Nijhuma; Egan, Denise A.; Deegan, Carol; Finn, Greg

doi:10.1016/j.jinorgbio.2004.04.016

Cited by 84 publications

(42 citation statements)

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“…22 Against the same fungi, the Ag(I) salicylate complexes, [Ag 2 (salH) 2 ] and [Ag 2 (NH 3 ) 2 (salH) 2 ] (salH 2 = salicylic acid), had MIC 100 values of 5.0 and 0.5 μM, respectively. 23 Investigations into the effects of silver(I) ions on bacterial cells revealed that they interact with the respiratory chain of Escherichia coli 24 and can lower the content of phospholipid fatty acids in some metal-reducing bacteria. 25 Electron microscopy and X-ray microanalysis have shown that silver builds up as granules in the cell wall and in the cytoplasm of E. coli and Staphylococcus aureus, 26,27 inflicting damage to the RNA and DNA and also deactivating cellular proteins.…”

Section: Introductionmentioning

confidence: 99%

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

et al. 2012

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Ag 2 (9-aca) 2 ] (1) (9-acaH = 9-anthracenecarboxylic acid) reacts with a series of imidazoles to give [Ag(imidH) The mononuclear complex 3, hexanuclear 4-6, and polymeric 7, were all characterised using X-ray crystallography. While many of the complexes possess excellent in vitro antifungal and antibacterial activities they are, unanimously, more effective against fungal cells. The insect, Galleria mellonella, can survive high doses of the Ag(I) complexes administered in vivo, and a number of the complexes offer significant protection to larvae infected with a lethal dose of pathogenic Candida albicans cells. † Electronic supplementary information (ESI) available. CCDC reference numbers 782886-782890 (X-ray supplementary data for [Ag-(imidH) 2.3 (CH 3 CN) 0.7 ](9-aca) (3), [Ag 6 (imidH) 4 (9-aca) 6 (MeOH) 2 ] (4), {[Ag(1-Me-imid) 2 ] 2 [Ag 4 (9-aca) 6 ]} (5), {[Ag(1-Bu-imid) 2 ] 2 [Ag 4 (9aca) 6 ]} (6) and [Ag(apim)](9-aca)•H 2 O (7)). For ESI and crystallographic data in CIF or other electronic format see

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Section: Introductionmentioning

confidence: 99%

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

et al. 2012

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“…[4,22] Addition of salicylic acid to an aqueous solution stabilizes a dimeric configuration, as observed previously, and led to the desired product. [23] When a 1:1 aqueous ammonia/ benzene mixture is used in the hydrothermal synthesis, a novel isolated solvent-bridged silver (I) …”

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confidence: 99%

“…An additional calculation of the electrostatic energy by means of the SPDFG program, which evaluates the electrostatic repulsion in terms of the monomer charge distributions, [31] confirms that in both cases the electrostatic repulsion is very large (E el = 293.63 and 278. 23 …”

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The Nature of the Ag^I⋅⋅⋅Ag^IInteraction in Different Ag(NH₃)₂Dimers Embedded in Supramolecular Solids

Zheng

Volkov

Nygren

et al. 2007

Chemistry A European J

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An isolated silver(I) ammonia monomer, a dimer, and a novel dimer containing an intercalated water molecule have been embedded as guests in supramolecular frameworks, [Ag(NH3)2][(H2thpe)(H3thpe)].MeCN (1), [{Ag(NH3)2}2][(H2thpe)2]4.25 H2O (2), and [{Ag(NH3)2}-H2O-{Ag(NH3)2}][(H2thpe)(2)]benzene (3) (H3THPE=tris(hydroxyphenyl)ethane). The [{Ag(NH3)2}2]2+ dimer is not stable as an isolated entity, but is stabilized by hydrogen bonding in the supramolecular framework. The water-intercalated silver(I) ammonia dimer, which constitutes a novel species, is also subject by hydrogen bonding in concentrated solutions. The destabilization energy of the dimer relative to isolated monomers is calculated to be approximately 300 kJ mol(-1) by both perturbation methods and DFT theory. For the water-intercalated dimer it is calculated to be approximately 200 kJ mol(-1) according to the BSSE-corrected MP2 calculation. The different aggregate states show a dramatic variation of absorption and emission properties, in accordance with the concentration dependent red-shift observed in solutions. Natural-bond-orbital analysis shows that the disilver-ammonium-aquo "sandwich" cation in 3 is stabilized by interaction between the pi lone pair orbital on the oxygen atom of the water molecule and Ag(I)--N sigma antibonding molecular orbital.

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“…Apart from a low toxicity, copper complexes can potentially inhibit cellular proteasomal activity, enhance apoptosis and DNA binding activities (Gopalakrishnan et al, 2014). Benzimidazole and its derivatives exhibit anticancer (Rodríguez-Solano et al, 2011), antifungal (Coyle et al, 2004), anti-inflammatory (Są czewski et al, 2006, antirheumatism (Rowan et al, 2009) or insect-repellent activities (Rowan et al, 2009), and are widely used in metal-organic chemistry. In the current project we have combined copper and a benzimidazole derivative together with 2,2 0 -bipyridine as a co-ligand to yield the title complex, [Cu 2 (C 20 H 12 N 4 )(C 10 H 8 N 2 )] n .…”

Section: Structure Descriptionmentioning

confidence: 99%

Poly[(2,2′-bipyridine-κ²N,N′)[μ₄-2,2′-(1,3-phenylene)bis(imidazol-1-yl)-κ⁴N:N′:N′′:N′′′]dicopper(I)]

Zhou

Meng

2016

IUCr Data

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Two CuIatoms are present in the asymmetric unit of the polymeric title complex, [Cu2(C20H12N4)(C10H8N2)]n. One of the cations is located on an inversion centre and is linearly coordinated by the N atoms of benzimidazolyl moieties of the 1,2-bis(2-benzimidazolium)benzene ligand, whereas the second cation is located on a twofold rotation axis and is tetrahedrally coordinated by two N atoms of a chelating 2,2′-bipyridine ligand and two other N atoms of the benzimidazolyl moieties. The bridging character of the 1,2-bis(2-benzimidazolyl)benzene leads to the formation of a three-dimensional framework structure.

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Synthesis, X-ray crystal structure, anti-fungal and anti-cancer activity of [Ag2(NH3)2(salH)2] (salH2=salicylic acid)

Cited by 84 publications

References 20 publications

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

The Nature of the Ag^I⋅⋅⋅Ag^IInteraction in Different Ag(NH₃)₂Dimers Embedded in Supramolecular Solids

Poly[(2,2′-bipyridine-κ²N,N′)[μ₄-2,2′-(1,3-phenylene)bis(imidazol-1-yl)-κ⁴N:N′:N′′:N′′′]dicopper(I)]

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Synthesis, X-ray crystal structure, anti-fungal and anti-cancer activity of [Ag2(NH3)2(salH)2] (salH2=salicylic acid)

Cited by 84 publications

References 20 publications

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

Silver(i) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

The Nature of the AgI⋅⋅⋅AgIInteraction in Different Ag(NH3)2Dimers Embedded in Supramolecular Solids

Poly[(2,2′-bipyridine-κ2N,N′)[μ4-2,2′-(1,3-phenylene)bis(imidazol-1-yl)-κ4N:N′:N′′:N′′′]dicopper(I)]

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The Nature of the Ag^I⋅⋅⋅Ag^IInteraction in Different Ag(NH₃)₂Dimers Embedded in Supramolecular Solids

Poly[(2,2′-bipyridine-κ²N,N′)[μ₄-2,2′-(1,3-phenylene)bis(imidazol-1-yl)-κ⁴N:N′:N′′:N′′′]dicopper(I)]