Effects of histidin-2-ylidene vs. imidazol-2-ylidene ligands on the anticancer and antivascular activity of complexes of ruthenium, iridium, platinum, and gold

Antiproliferative Activity of Functionalized Histidine‐derived Au(I) bis‐NHC Complexes for Bioconjugation

“…The activity of 3 b and 5 is superior to the known Au(I) histidinylidene complex, corroborating the previously reported correlation between lipophilicity of the wingtips and antiproliferative activity . Furthermore, both complexes 3 b and 5 show a comparable activity in the cisplatin resistant cell line A2780cisR and in the respective cisplatin sensitive cell line.…”

“…proposed histidine as a NHC precursor and synthesized Pd complexes . Further Ru, Rh, Pd and Ir complexes were reported for catalytic applications and only one Au(I) histidinylidene complex, with moderate IC 50 values against various cancer cell lines, has been considered for medicinal applications . It is a neutral Au(I) complex bearing a Boc‐protected α‐amino‐group, methyl wingtips and a methyl ester group, but neither the amino acid backbone was modified, nor the stability discussed …”

Organometallic Iridium Arene Compounds: The Effects ofC-Donor Ligands on Anticancer Activity

“…These systems were extended into poly-(propyleneimine) dendrimer scaffolds in which the octanuclear chelating iridium metallodendrimer (28) shows superior activity in cancerous cells, when compared to the analogous mononuclear complexes 27, however, they remain cytotoxic towards normal cell types. 112 Sadler et al have conducted research on the effect of the arene substituent. Interestingly, the cytotoxic values usually follow a trend, whereby the number of phenyl rings attached to the Cp x moiety increases the activity, Cp biph > Cp ph º Cp*.…”

Optically active histidin-2-ylidene stabilised gold nanoparticles

“…Thus metal-NHC compounds show promise for catalytic applications 14 and also in the biological field. 15,16 For similar reasons, NHCs have attracted much attention in the development of novel nanoparticles [17][18][19][20][21][22][23][24][25][26] as it is estimated that the Au-NHC bond strength is about double that of a corresponding Au-thiol bond, 27 and recent reports show that NHC functionalized AuNPs and gold surfaces outperformed their thiol based counterparts with regards to thermal and chemical stability. 24,27,28 Amongst AuNPs, those with chiral ligands are of particular interest due to their potential applications in optics, asymmetric catalysis and chiral discrimination.…”

“…Histidine was selected as the chiral NHC precursor due to the ease of converting the imidazole side chain into an imidazolium derivative. 15 Here we report a novel method of incorporating N-BOC-histidine-methyl ester as a ligand to stabilize gold nanoparticle and the characterization of the resulting AuNPs stabilized with both enantiomers. Methylation of commercially available L and D forms of BOCHis-OH, followed by a transmetallation procedure with Ag 2 O and Au(SMe 2 )Cl yielded chlorido (1,3-…”