Ru(II)-based complexes with N-(acyl)-N′,N′-(disubstituted)thiourea ligands: Synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells

Abstract

Four ruthenium(II)-based complexes with N-(acyl)-N',N'-(disubstituted)thiourea derivatives (Th) were obtained. The compounds, with the general formula trans-[Ru(PPh3)2(Th)(bipy)]PF6, interact with bovine serum albumin (BSA) and DNA. BSA-binding constants, which were in the range of 3.3-6.5×10(4) M(-1), and the thermodynamic parameters (ΔG, ΔH and ΔS), suggest spontaneous interactions with this protein by electrostatic forces due to the positive charge of the complexes. Also, binding constant by spectrophotometric DNA titration (Kb = 0.8-1.8×10(4) M(-1)) and viscosity studies indicate weak interactions between the complexes and DNA. Cytotoxicity assays against DU-145 (prostate cancer) and A549 (lung cancer) tumour cells revealed that the complexes are more active in tumour cells than in normal (L929) cells, and that they present high cytotoxicity (low IC50 values) compared with the reference metallodrug, cisplatin.

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

“…To the best our knowledge, there is no paper published related to the octanoyl thiourea. However, Correa et al (2015) reported the BSA-and DNAbinding studies of thiourea complexes against lung and prostate tumor cells. The antimicrobial activities of thioureas were reported in which few derivatives were found to be good against E. coli (Zhong et al, 2008).…”

Polypyridyl Ruthenium Complexes: Novel DNA-Intercalating Agents against Human Breast Tumor

“…The distances for the Ru-Cl, Ru-P and Ru-N bonds lengths and bond angles found for the compound is within the normal range for similar ruthenium(II) complexes. 12,25,27 In Figure 2A the six rings of the dpqQX ligand labeled (a-f) are depicted. Rings a and b are connected with the ruthenium(II), while rings c-f (tetraaza center) are in the outer-coordination sphere responsible for intermolecular interactions.…”

“…Complexes 1 and 2 are also active, presenting IC 50 values comparable with other ruthenium(II)/phosphine complexes. 11,12,27 The isomer cis-[RuCl 2 (dppb)(dpqQX)] (2) is more active than the trans-[RuCl 2 (dppb)(dpqQX)] (1) one. Probably, due to the lability of the chlorine ligand trans to a phosphorus atom, forming the cationic species [RuCl(L)(dppb)(dpqQX)] + (where L = solvent), such as occur in analogous complexes.…”

“…Recently, we have synthesized several classes of phosphine ruthenium(II) complexes with N-heterocyclic ligands and we have evaluated their cytotoxicity against tumor cancer cells, in which promising results have been obtained. 11,12 Therefore, as part of our ongoing research to obtain new compounds with potential cytotoxic effects, three neutral complexes were obtained with the general formula [RuCl 2 (P-P)(dpqQX)], where P-P is dppb (1,4-bis(diphenylphosphino)butane) or (PPh 3 ) 2 (triphenylphosphine) and dpqQX = dipyrido[3,2-a:2',3'-c] quinoxaline [2,3-b]quinoxaline, a planar heteroaromatic ligand with high electronic conjugation. Also, an ionic compound ct-[RuCl(CO)(dppb)(dpqQX)]PF 6 was synthesized by exchange of a chorine trans to phosphorus to one carbonyl ligand (Scheme 1).…”

Discotic Liquid Crystals Based on Cu(I) Complexes with Benzoylthiourea Derivatives Containing a Perfluoroalkyl Chain

“…ese benzoylthiourea derivatives (BTU) proved to have excellent properties to bind to various metal ions due to the very strong donor groups (carbonyl and thioamide) that yield various transition metal complexes. e BTU ligands can give neutral homoleptic or heteroleptic complexes either with S-and Ocoordination, when the ligand is coordinated in monoanionic bidentate form by deprotonation or with only S-coordination if the ligand is bound in neutral form to the metal center [22][23][24][25][26][27][28][29][30][31][32].…”