PubReading [134] - Tethering Carbohydrates to the Vinyliminium Ligand of Antiproliferative Organometallic Diiron Complexes - S. Schoch, M. Dalla Pozza, G. Gasser, F. Marchetti et al

Four propargyl O-glycosides derivatized with mannose, glucose, and fructose moieties were synthesized and then incorporated within a diiron structure as part of a vinyliminium ligand. Hence, six glycoconjugated diiron complexes, [2−5]CF3SO3 (see Scheme 1) and the nonglycosylated analogues [6a−b]CF3SO3, were obtained in high yields and unambiguously characterized by elemental analysis, mass spectrometry, and IR and multinuclear NMR spectroscopies. All compounds exhibited a significant stability in DMSO-d6/D2O solution, with 63−89% of the complexes unaltered after 72 h at 37 °C and also in the cell culture medium. The cytotoxicity of [2−6]CF3SO3, as well as that of previously reported 7 and 8, was assessed on CT26 (mouse colon carcinoma), U87 (human glioblastoma), MCF-7 (human breast adenocarcinoma), and RPE-1 (human normal retina pigmented epithelium) cell lines. In general, the IC50 values correlate with the hydrophobicity of the compounds (measured as octanol−water partition coefficients) and do not show an appreciable level of selectivity against cancer cells with respect to the nontumor ones.

doi.org/10.1021/acs.organomet.1c00519 - 2022