A comparative study of the metal binding behavior of alanine based bis-thiourea isomers

Abstract

Two new symmetrical bis-thiourea, 2,2′-[{(terephthaloylbis(azanediyl)bis(carbonothioyl) bis(azanediyl)}dipropanoic acid] (1A) and 3,3′-[{(terephthaloylbis(azanediyl)bis (carbonothioyl)bis(azanediyl)} dipropanoic acid] (1B) were synthesized by the reaction of terephthaloyl chloride with α- and β-alanine in good yields. Their binding properties were investigated with various metal cations using UV–Vis titration experiments. Both isomers exhibited effective binding with Ag+, Cu2+, Hg2+, Pb2+, Fe2+ and Fe3+ cations. However, in the presence of other cations, such as Na+, Ni2+, Co2+, Cd2+, Zn2+, Mn2+, Mg2+, Ca2+, Sn2+, Al3+, and anions tetrabutylammonium Cl− and H2PO4 −, no interaction occurred. Both isomers displayed similar trends towards binding with metal cations.

Iodide n,π-chelate complexes of platinum(II) based on N-allyl substituted thioureas and their effect on the activity of hepatobiliary system enzymes in comparison with chloride analogs

“…These absorption bands undergo both bathochromic and hypsochromic shifts of +20/21 and - (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) nm relative to their chloride counterparts (green curves in Fig. 2) studied in our previous publications [17,19].…”

“…A recent trend in the development of new metal-based anticancer drugs is the use of biologically active ligands capable of inhibiting the growth of malignant tumors with different mechanisms of action [10,11]. Promising ligands for the development of new potential drugs are thiourea derivatives, which, having high antitumor activity [12], are able to coordinate many metal ions as N,S donor agents [13][14][15]. In previous studies, we found that a number of π-coordination complexes of Pt(II) and Pd(II) with N-allylthiourea derivatives showed a high affinity to DNA with cytostatic and proapoptotic effects which was superior to that of cisplatin [16][17][18][19].…”

Synthesis and Binding Behaviour of New Isomers of Bis-Thiourea

“…Derivative 1A, however, showed no excellent biological activity against various bacteria. It is assumed from the structure of similar bis-thiourea derivative (Fakhar et al 2017) that the thiourea moiety is not planar because of intermolecular attractions hence offering steric hindrance. The occurrence of steric hindrance creates a force that obstructs the contact between active sites in the compound with receptor site of the bacteria (Fernandez et al 2005).…”

Synthesis of Thiourea Derivatives and Binding Behavior Towards the Mercury Ion

“…The band at 370 nm shows a hyperchromic effect with an increasing amount of Hg 2+ . Based on the UV-Vis titration, we were able to calculate the stoichiometry of the binding interaction between ligand 3b and Hg 2+ through the molar-ratio curve method (Figure 4) [19]. The binding ratio of 3b-Hg 2+ was 1:1 and the binding constant (K d ) was calculated using the nonlinear regression equation using Sigma Plot 12.0 software.…”