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Hydrogen Bonding and Anticancer Properties of Water‐Soluble Chiral p ‐Cymene Ru II Compounds with Amino‐Oxime Ligands
Author(s) -
Benabdelouahab Yosra,
MuñozMoreno Laura,
Frik Malgorzata,
de la CuevaAlique Isabel,
El Amrani Mohammed Amin,
Contel María,
Bajo Ana M.,
Cuenca Tomás,
Royo Eva
Publication year - 2015
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201500097
Subject(s) - chemistry , ruthenium , p cymene , oxime , hydrogen bond , stereochemistry , medicinal chemistry , cytotoxicity , molecule , organic chemistry , in vitro , biochemistry , catalysis
An investigation into the effects of hydrogen bonding on the aggregation tendency of ruthenium compounds [(η 6 ‐ p ‐cymene)Ru(κNHR,κNOH)Cl]Cl {R = Ph ( 1a ), Bn ( 1b )} and [(η 6 ‐ p ‐cymene)Ru(κ 2 NH(2‐ pic ),κNOH)][PF 6 ] 2 ( 1c ), [(η 6 ‐ p ‐cymene)Ru(κNHBn,κNO)Cl] ( 2b ), and [(η 6 ‐ p ‐cymene)Ru(κNBn,κ 2 NO)] ( 3b ) has been performed by means of concentration‐dependence 1 H NMR chemical shift and DOSY experiments. The synthesis and full characterization of new compounds 1c , [(η 6 ‐ p ‐cymene)Ru(κNPh,κ 2 NO)] ( 3a ) and 3b are also reported. The effect of the water‐soluble ruthenium complexes 1a – c on cytotoxicity, cell adhesion, and cell migration of the androgen‐independent prostate cancer PC3 cells have been assessed by MTT, adhesion to type‐I‐collagen, and recovery of monolayer wounds assays, respectively. Interactions of 1a – c with DNA and human serum albumin have also been studied. Together, the properties reported herein suggest that ruthenium compounds 1a – c have considerable potential as anticancer agents against advanced prostate cancer.