Rhenium(I) tricarbonyl compounds of bioactive thiosemicarbazones: Synthesis, characterization and activity against Trypanosoma cruzi

Arce, Esteban Rodríguez; Machado, Ignacio; Rodrı́guez, Belén; Lapier, Michel; Zúñiga, María del Carmén; Maya, Juan Diego; Olea‐Azar, Claudio; Otero, Lucı́a; Gambino, Dinorah

doi:10.1016/j.jinorgbio.2017.01.011

Cited by 32 publications

(12 citation statements)

References 54 publications

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“…Although the activity of compound 12 is somewhat lower (IC 50 = 0.54 μM for tulahuen and IC 50 = 0.82 μM for Y strains), the influence of the metal ion appears to be a determinant for the biological activity, independent of the fluorinated substituents of the complexes. Similar results have been found by Rodriguez and co-workers, who recently reported that rhenium(I) tricarbonyl complexes with bioactive thiosemicarbazones also showed a considerable activity against unproliferative forms of the Dm28c strain …”

Section: Resultssupporting

confidence: 90%

“…Similar results have been found by Rodriguez and co-workers, who recently reported that rhenium(I) tricarbonyl complexes with bioactive thiosemicarbazones also showed a considerable activity against unproliferative forms of the Dm28c strain. 46 In the present study, compounds 12, 11, and 4 were 17−46 times more active than benznidazole (BZ) (IC 50 = 14.0 ± 1.1 μM) on Y trypomastigotes forms and 26−64 times more active than BZ (IC 50 = 14.1 ± 4.6 μM) on Tulahuen strain. T. cruzi strains may respond differently in in vitro and in vivo drugs screening, since it is known that many of them have different profiles of susceptibility to the reference drugs benznidazole and nifurtimox.…”

Section: Synthesis Of the [Tco(l1)(l2)]mentioning

confidence: 50%

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Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

et al. 2019

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A series of 16 “3 + 2” mixed-ligand complexes of the general composition [ReO(L1)(L2)] (H2L1a–H2L1d = tridentate thiosemicarbazones having a phenyl group with 4-H, 4-F, 3,5-di-F, and 4-CF3 substituents; HL2a–HL2d = bidentate N,N-diethyl-N′-benzoylthioureas with 4-H, 4-F, 3,5-di-F, and 4-CF3 substituents at the benzoyl groups) have been synthesized and characterized by spectroscopic methods and X-ray diffraction. Irrespective of the individual fluorine substitution, the complexes are stable and possess the same general structure. Some systematic electronic effects of the fluorine-substitution patterns of the ligands have been found on the 13C NMR chemical shifts of the N–CN carbon atoms of the {L1}2– and the CO carbon atoms of the {L2}− ligands. Antiparasitic properties of the rhenium complexes have been tested against epimastigotes and trypomastigotes forms of two Trypanosoma cruzi strains and the amastigotes form of one of them. The results of this study indicate that the activity of the rhenium complexes can clearly be modulated by fluorine substitution of their ligands. Some of the fluorinated compounds show a high activity against epimastigotes and trypomastigotes forms of the parasites. Reactions between (NBu4)[TcOCl4] and two representatives of the fluorinated ligands (H2L1b, 4-F-substituted, and H2L1c, 4-CF3-substituted) form stable complexes of the composition [TcOCl(L1b)] and [TcOCl(L1c)]. Subsequent reactions of these products with HL2b (4-F-substituted) give the corresponding [TcO(L1)(L2)] mixed-ligand complexes. Also, the technetium compounds are stable as solids and in solutions and have structures corresponding to those of their rhenium analogues.

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Section: Resultssupporting

confidence: 90%

Section: Synthesis Of the [Tco(l1)(l2)]mentioning

confidence: 50%

Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

et al. 2019

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“…32 Our group has reported some earlier promising results on T. cruzi of Re(I) tricarbonyls of bioactive semicarbazones and thiosemicarbazones. 33,34 About the bioactive ligands, polypyridyl derivatives of 1,10phenanthroline and their metal complexes have shown biological activity. In particular, most of the selected bidentate NN ligands have shown activity on T. cruzi (Fig.…”

Section: Papermentioning

confidence: 99%

“…32 Our group has reported some earlier promising results on T. cruzi of Re( i ) tricarbonyls of bioactive semicarbazones and thiosemicarbazones. 33,34…”

Section: Introductionmentioning

confidence: 99%

Multifunctional organometallic compounds for the treatment of Chagas disease: Re(i) tricarbonyl compounds with two different bioactive ligands

et al. 2023

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“…Thiosemicarbazones can act as NS [37] bidentate, NN S [38] and ONS [39] tridentate or ONN S [40] tetradentate chelators, forming either neutral [41] or cationic [42,43], mononuclear [44,45] or polynuclear [46][47][48] systems with different metal ions. Complexes of V(IV) [49], Mn(II) [50], Fe(III) [38,51], Co(III) [52], Ni(II) [53][54][55][56], Cu(II) [28,57,58], Zn(II) [48], Ga(III) [59,60], Ru(II/III) [61][62][63][64][65][66][67][68][69], Pd(II) [70][71][72][73][74], In(III) [75], Re(I) [76,77], Pt(II) [78], Au(III) [79], Hg(II) [80], Ag(I) [81] and Sn(IV) [39] exhibit higher cytotoxicity and anti...…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones

et al. 2020

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Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (1, -NH2; 2, -NHMe; 3, -NHEt) have been prepared and characterized. In both the X-ray structures of 1 and 3, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in 1a and nitrate in 1b) or in the co-ligand (water in 3a and methanol in 3b). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes 1 and 3 confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes 2 and 3 exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes 2 and 3 also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.

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Rhenium(I) tricarbonyl compounds of bioactive thiosemicarbazones: Synthesis, characterization and activity against Trypanosoma cruzi

Cited by 32 publications

References 54 publications

Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

Effect of Fluorination on the Structure and Anti-Trypanosoma cruzyActivity of Oxorhenium(V) Complexes withS,N,S-Tridentate Thiosemicarbazones and Benzoylthioureas. Synthesis and Structures of Technetium(V) Analogues

Multifunctional organometallic compounds for the treatment of Chagas disease: Re(i) tricarbonyl compounds with two different bioactive ligands

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones

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