Novel silver(I)– and gold(I)–N-heterocyclic carbene complexes. Synthesis, characterization and evaluation of biological activity against tumor cells

Sanchez, Oriel; González, Sorenlis; Fernández, Mercedes; Higuera-Padilla, Ángel R.; León, Yokoy; Coll, David S.; Vidal, Alba B.; Taylor, Peter; Urdanibia, Izaskun; Goite, María C.; Castro, William

doi:10.1016/j.ica.2015.08.017

Cited by 23 publications

(12 citation statements)

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“…The observed lipophilicity values are higher than those for the previously reported Ag(I), Au(I), Ru(II), Ga(III) and Pt(II) complexes. [46][47][48][49] DNA binding. Electronic absorption spectra of complexes (1-6) with varying amount of CT-DNA solution showed hypochromic effect in the intra-ligand (n-p*) region with a signicant red shi (4-6 nm), indicating the strong intercalative mode of binding of the complexes with DNA (Fig.…”

Section: Biological Signicancementioning

confidence: 99%

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

et al. 2018

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Section: Biological Signicancementioning

confidence: 99%

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

et al. 2018

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“…Compound 65 ( Figure 12 ) was synthesized and is proposed to interact with DNA mainly through non-covalent interactions as π-π stacking contacts, inducing a conformational change in the structure of DNA [ 86 ]. The Ag(I)-NHC complex showed similar activity to cisplatin against prostate (PC3) and colon (HT29) cancerous cell lines.…”

Section: Antitumor Activity Of Silver Nhc Complexesmentioning

confidence: 99%

“… Structures of Ag(I)-NHC complexes from Garner et al ( 62 ) [ 84 ], Bjørsvik et al ( 63 and 64 ) [ 85 ], and Sanchez et al ( 65 ) [ 86 ]. …”

Section: Figurementioning

confidence: 99%

Recent Developments in the Medicinal Applications of Silver-NHC Complexes and Imidazolium Salts

2017

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Because of their great structural diversity and multitude of chemical properties, N-heterocyclic carbenes (NHCs) have been utilized in a variety of capacities. Most recently, NHCs have been utilized as carrier molecules for many transition metals in medicinal chemistry. Specifically, Ag(I)-NHCs have been investigated as potent antibacterial agents and chemotherapeutics and have shown great efficacy in both in vitro and in vivo studies. Ag(I)-NHC compounds have been shown to be effective against a wide range of both Gram-positive and Gram-negative bacterial strains. Many compounds have also shown great efficacy as antitumor agents demonstrating comparable or better antitumor activity than standard chemotherapeutics such as cisplatin and 5-fluorouracil. While these compounds have shown great promise, clinical use has remained an unattained goal. Current research has been focused upon synthesis of novel Ag(I)-NHC compounds and further investigations of their antibacterial and antitumor activity. This review will focus on recent advances of Ag(I)-NHCs in medicinal applications.

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“…All organometallic compounds were prepared under a nitrogen atmosphere. The imidazolium salts L 1 ·2HCl, L 2 ·2HCl, 55,56 and L 3 ·4HCl 57 were prepared according to literature procedures, and the Au III complexes [Au 2 (L 1 ) 2 X 4 ]X 2 (X = Cl, Br) and [Au 2 (L 2 ) 2 Br 4 ]Br 2 were prepared in the same way as the corresponding hexafluorophosphate salts. 8,47 Synthesis of Au III -NHC complexes Complex 2, [Au(L 1 ) 2 Cl 2 ]Cl.…”

Section: General Proceduresmentioning

confidence: 99%

Stable Au^III complexes with four N-heterocyclic carbene groups can be prepared in high yield directly from KAuCl₄

2017

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Gold(iii) N-heterocyclic carbene (NHC) complexes of form [Au(NHC)Cl]Cl were synthesized by reaction of KAuCl with bis- and tetrakis(imidazolium) salts in the presence of a mild base. Treatment of these complexes with KPF afforded four-coordinate Au complexes of form [Au(NHC)](PF). X-Ray crystallography showed the [Au(NHC)] cations in the hexafluorophosphate salts to have a square planar Au(NHC) moiety [AuC 2.024(4)-2.082(7) Å]. In the [Au(NHC)Cl] cations in the chloride salts, coordination about Au was tetragonally-distorted octahedral, the axial Au-Cl bonds being substantially longer [AuCl 3.148(2)-3.693(1) Å] than the equatorial Au-C bonds [AuC 2.024(4)-2.082(7) Å]. NMR and conductance studies suggested that the structures of the complexes seen in the solid state persisted in DMSO solution, except in one case where a chlorido ligand dissociated from [Au(NHC)Cl] to form [Au(NHC)Cl]. The Au(NHC) unit was surprisingly robust. An Au complex was found to undergo H/D exchange reactions in DO solution at 100 °C with no signs of decomposition detectable by H NMR spectroscopy.H NMR studies showed that various complexes containing Au(NHC) moieties underwent little or no decomposition when heated at 120 °C in DMSO-d for extended periods.

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Novel silver(I)– and gold(I)–N-heterocyclic carbene complexes. Synthesis, characterization and evaluation of biological activity against tumor cells

Cited by 23 publications

References 98 publications

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Recent Developments in the Medicinal Applications of Silver-NHC Complexes and Imidazolium Salts

Stable Au^III complexes with four N-heterocyclic carbene groups can be prepared in high yield directly from KAuCl₄

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Novel silver(I)– and gold(I)–N-heterocyclic carbene complexes. Synthesis, characterization and evaluation of biological activity against tumor cells

Cited by 23 publications

References 98 publications

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Recent Developments in the Medicinal Applications of Silver-NHC Complexes and Imidazolium Salts

Stable AuIII complexes with four N-heterocyclic carbene groups can be prepared in high yield directly from KAuCl4

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Stable Au^III complexes with four N-heterocyclic carbene groups can be prepared in high yield directly from KAuCl₄