Studies of the tautomeric equilibrium of 1,3-thiazolidine-2-thione: Theoretical and experimental approaches

Abbehausen, Camilla; Paiva, Raphael Enoque Ferraz de; Formiga, André Luiz Barboza; Corbi, Pedro P.

doi:10.1016/j.chemphys.2012.09.019

Cited by 22 publications

(12 citation statements)

References 37 publications

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“…1) is present in the solid state [30]. However, two tautomeric forms can be found in aqueous and in organic solutions (i.e., 1,4-dioxane, CCl 4 , benzene, CHCl 3 , CH 2 Cl 2 , C 2 H 4 Cl 2s , EtOH, MeOH, CH 3 CN, DMF and DMSO) [31,32]. Given this promising outlook and considering the different coordination sites of the tzdtH [33][34][35], this work aimed to study the reactivity of this ligand with Ru(II) phosphine precursors.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Corrêa

Silva

Graminha

et al. 2016

Journal of Inorganic Biochemistry

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Three new mixed and mononuclear Ru(II) complexes containing 1,3-thiazolidine-2-thione (tzdtH) were synthesized and characterized by spectroscopic analysis, molar conductivity, cyclic voltammetry, high-resolution electrospray ionization mass spectra and X-ray diffraction. The complexes presented unique stereochemistry and the proposed formulae are: [Ru(tzdt)(bipy)(dppb)]PF6 (1), cis-[Ru(tzdt)2(PPh3)2] (2) and trans-[Ru(tzdt)(PPh3)2(bipy)]PF6 (3), where dppb=1,4-bis(diphenylphosphino)butane and bipy=2,2'-bipyridine. These complexes demonstrated strong cytotoxicity against cancer cell lines when compared to cisplatin. Specifically, complex 2 was the most potent cytotoxic agent against MCF-7 breast cells, while complexes 1 and 3 were more active in DU-145 prostate cells. Binding of complexes to ctDNA was determined by UV-vis titration and viscosity measurements and revealed binding constant (Kb) values in range of 1.0-4.9×10(3)M(-1), which are characteristic of compounds possessing weak affinity to ctDNA. In addition, these complexes presented antiparasitic activity against Trypanosoma cruzi. Specifically, complex 3 demonstrated strong potency, moderate selectivity index and acted in synergism with the approved antiparasitic drug, benznidazole. Additionally, complex 3 caused parasite cell death through a necrotic process. In conclusion, we demonstrated that Ru(II) complexes have powerful pharmacological activity, while the metal-free tzdtH does not provoke the same outcome.

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Section: Introductionmentioning

confidence: 99%

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Corrêa

Silva

Graminha

et al. 2016

Journal of Inorganic Biochemistry

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“…This result is in agreement with the experimental results. [15,17,28] The tautomeries forms of T2T are shown in Figure 1. As it can be seen, the optimized structures agree well with the experimental crystal structures.…”

Section: Geometrical Parameters Vibrational Frequencies and Energiesmentioning

confidence: 99%

Theoretical study of interaction of thiazolidine-2-thione as an anti-thyroid agent with iodine

Makiabadi

2015

Journal of Sulfur Chemistry

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Quantum chemical calculations were used to investigate the interaction of tautomer forms of thiazolidine-2-thione (T2T) with iodine in the gas and solution phases. The calculations show that the planar complexes are more stable than the perpendicular complexes. Also in the perpendicular complexes, the thione form is more stable than the thiol form. The calculated thermodynamic parameters in the solution phase indicate that the stability of the formed complexes increases as the dielectric constant of the solvent is increased. This result is in good agreement with the experimental results. The NBO results predict that the LP(S) → σ *(I−I) and LP(S) → σ *(N−H) charge transfer (CT) interactions are very important in the stabilizing of the planar complexes with respect to the perpendicular complexes. In all complexes, CT takes place from T2T to I 2 . Therefore, it is predicted that the donor properties of T2T are the origin of its anti-thyroid action. The atoms in molecule (AIM) analysis shows that the interactions in the planar complexes are stronger than the perpendicular complexes.

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“…This molecule exhibits a tautomeric equilibrium in solution with the sulfur in thiol or thione forms ( Figure 1B). [25] The coordination of 2-mercaptothiazoline to transition metals can be modulated by the trans ligand and complexes with metal bound by the heterocycle nitrogen and/or the exocyclic sulfur are known. [26] The reaction of mtz with K[Au(CN) 2 ] in acidic conditions results in the nitrogen coordinated complex [NCAu(N-mtz)] (1, Figure 1A).…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Effects of coordination mode of 2-mercaptothiazoline on reactivity of Au(I) compounds with thiols and sulfur-containing proteins

Abbehausen

Manzano

Corbi

et al. 2016

Journal of Inorganic Biochemistry

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Studies of the tautomeric equilibrium of 1,3-thiazolidine-2-thione: Theoretical and experimental approaches

Cited by 22 publications

References 37 publications

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Ruthenium(II) complexes of 1,3-thiazolidine-2-thione: Cytotoxicity against tumor cells and anti-Trypanosoma cruzi activity enhanced upon combination with benznidazole

Theoretical study of interaction of thiazolidine-2-thione as an anti-thyroid agent with iodine

Effects of coordination mode of 2-mercaptothiazoline on reactivity of Au(I) compounds with thiols and sulfur-containing proteins

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