Anticancer activity of Ru- and Os(arene) compounds of a maleimide-functionalized bioactive pyridinecarbothioamide ligand

Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

“…Therefore, we label this compound as 1d neutral .T his is in contrast to all other molecular structures of relatedR ua nd Os complexes in which the PCAl igand was neutral and ac omplex cation was formed. [25][26][27] The Os-cym centroid and Os-Cl distances were 1.671 and 2.442(4) ,r espectively,a nd therefore similar to those reported for related complexes. [25][26][27] The OsÀS1 and OsÀN1 bond lengths were 2.355(4) and 2.133(1) ,r espectively.T he C6ÀS1 bond (1.754(15) in 1d neutral )w as elongated as compared to 1.655(5) for 1,i ndicating greater single bond character.T he C6ÀN2 bond length of 1.251 (19) in 1d neutral was slightly shorter compared to ab ond length of 1.345(6) in 1, demonstrating the increased double bond character upon coordination of the Os to the Sa tom and deprotonation of the amide group.T he latter bond is hardly modified if PCA coordinates as aneutral ligand to ametal center.…”

“…[24] We have recently developed organometallic anticancer complexes of 2-pyridinecarbothioamide (PCA) ligands. [25][26][27][28][29] The Ru complex, termed plecstatin-1, demonstrated target selectivity for plectin in an invasive B16 melanoma tumor model. [28] Herein, we report the functionalization of the PCAs caffold with the sulfonamide pharmacophore and its coordination to Ru II /Os II -cym (cym = h 6 -p-cymene) organometallics.…”

Impact of the Metal Center and Leaving Group on the Anticancer Activity of Organometallic Complexes of Pyridine-2-carbothioamide

“…The spectra featured peaks at m/z values assignable to the [M − X] + ions while the base peak was attributed to the [M − 2X − H] + ions. A similar ionization behavior in ESI-MS was observed for other PCA-metal complexes [34,35,37,38]. The experimental m/z values as well as the isotopic distribution pattern closely resembled the calculated values.…”

“…Careful modifications at the phenyl ring of PCAs and their conversion to Ru(cym)Cl and Os(cym)Cl complexes led to the identification of potent antiproliferative agents [34,35,37]. In order to investigate the effect of different metal ions and halido ligands on the biological properties of PCA-based organometallics, we expanded on the compound class bearing the PCA ligand that resulted in the most cytotoxic Ru(cym)Cl complexes, i.e., 4-fluorosubstituted PCA 1 [34,35].…”

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

“…We intend here to combine within one molecule the structural specificity of a meso -fuorinated porphyrin/chlorin macrocycle and maleimide units to develop novel multifunctional compounds with improved properties for various applications. Maleimides are considered as a biologically important scaffold that possess almost all types of biological activities including antibacterial and antifungal activity [24], anticancer activity [25], cox-2 inhibitor and anti-inflammatory, antidiabetic activity [26] and photodynamic activity [27]. Attaching of the maleimide group with its rich biological activity to the tetrapyrrole macrocycles with their unique photophysical properties may result in new conjugates with improved chemical, biological and anticancer characteristics [28].…”