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  • Half-sandwich ruthenium–arene complexes with thiosemicarbazones: synthesis and biological evaluation of [(η⁶-p-cymene)Ru(piperonal thiosemicarbazones)Cl]Cl complexes.

Half-sandwich ruthenium–arene complexes with thiosemicarbazones: synthesis and biological evaluation of [(η⁶-p-cymene)Ru(piperonal thiosemicarbazones)Cl]Cl complexes.

Journal of inorganic biochemistry (2011-06-15)
Floyd Beckford, Deidra Dourth, Michael Shaloski, Jacob Didion, Jeffrey Thessing, Jason Woods, Vernon Crowell, Nikolay Gerasimchuk, Antonio Gonzalez-Sarrías, Navindra P Seeram
ABSTRACT

The synthesis and characterization of a number of organometallic ruthenium(II) complexes containing a series of bidentate thiosemicarbazone ligands derived from piperonal is reported. The structure of compounds have been confirmed by spectroscopic analysis (IR and NMR) as well as X-ray crystallographic analysis of [(η⁶-p-cymene)Ru(pPhTSC)Cl]Cl (4) (pPhTSC is piperonal-N(4)-phenylthiosemicarbazone). The interaction of the complexes ([(η⁶-p-cymene)Ru(pEtTSC)Cl]Cl) (3) (pEtTSC is piperonal-N(4)-ethylthiosemicarbazone) and 4 with calf thymus DNA, human serum albumin (HSA) and pBR322 plasmid DNA were studied by spectroscopic, gel electrophoresis and hydrodynamic methods. The apparent binding constant for the interaction with DNA was determined to be 3.97×10³ M⁻¹ and 4.07×10³ M⁻¹ at 293 K for 3 and 4 respectively. The complexes bind strongly to HSA with binding constants of 2.94×10⁴ M⁻¹ and 12.2×10⁴ M⁻¹ at 296 K for 3 and 4 respectively. The in vitro anticancer activity of 3 and 4 has been evaluated against two human colon cancer cell line (HCT-116 and Caco-2) with IC50 values in the range of 26–150 μM. Both 3 and 4 show good activity as a catalytic inhibitor of human topoisomerase II at concentrations as low as 20 μM. The proficiency of 3 and 4 to act as antibacterial agents was also evaluated against six pathogenic bacterial strains with the best activity seen against Gram-positive strains.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Piperonal, 99%
Sigma-Aldrich
Piperonal, ≥99%, FCC, FG
Sigma-Aldrich
Piperonal, natural, 98%, FG