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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Cu(I) complexes with thiosemicarbazides derived from p-toluenesulfohydrazide: Structural, luminescence and biological studies

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Author(s):
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Borges, Alice P. [1] ; Carneiro, Zumira A. [2] ; Prado, Fernando S. [3] ; Souza, Jhonathan R. [3] ; Furlan e Silva, Leonardo H. [3] ; Oliveira, Carolina G. [4] ; Deflon, Victor M. [4] ; de Albuquerque, Sergio [2] ; Leite, Natalia Bueno [1] ; Machado, Antonio E. H. [3, 5] ; Patrocinio, Antonio O. T. [3] ; Maia, Pedro I. S. [1]
Total Authors: 12
Affiliation:
[1] Univ Fed Triangulo Mineiro, Nucleo Desenvolvimento Compostos Bioat NDCBio, Ave Dr Randolfo Borges 1400, BR-38025440 Uberaba, MG - Brazil
[2] Univ Sao Paulo, Dept Anal Clin Toxicol & Bromatol, FCFRP, Ave Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil
[3] Univ Fed Uberlandia, Lab Photochem & Mat Sci, Inst Quim, Ave Joao Naves de Avila 2121, BR-38400902 Uberlandia, MG - Brazil
[4] Univ Sao Paulo, Inst Quim Sao Carlos, Ave Trabalhador Sao Carlense 400, BR-13566590 Sao Carlos, SP - Brazil
[5] Univ Fed Goias, Doctoral Program Exact & Technol Sci, Catatao, Go - Brazil
Total Affiliations: 5
Document type: Journal article
Source: Polyhedron; v. 155, p. 170-179, NOV 15 2018.
Web of Science Citations: 2
Abstract

Reactions of thiosemicarbazide ligands (L-R: R = cyclohexyl (Cy) or phenyl (Ph)) with {[}CuCl(PPh3)(3)] led to the formation of colorless Cu(I) complexes of composition {[}CuCl(PPh3)(2)(L-R)]. Both complexes were characterized by spectroscopic methods and further studied by single crystal X-ray diffractometry. The crystal structures confirmed the tetrahedral geometry for the Cu(I) metal center, which is coordinated by a chlorido, two triphenylphosphane and by the thiosemicarbazide as a neutral S-donor monodentate ligand. Photophysical studies revealed that the complexes exhibit emission at room temperature with maxima around 480 nm. At 77 K, the emission is shifted to higher energy, a characteristic behavior of MLCT emitters. The main low lying molecular orbitals were calculated by TD-DFT and confirmed that the S-0 -> S-1 transitions have mainly MLCT character as well as that the peripheral groups in the thiosemicarbazide ligand play an important role on this transition. Moreover, the emission bands are considerably suppressed in the presence of O-2, indicating the triplet character of the emitter excited states. The intersystem crossing process is also suggested by the energy diagrams built through TD-DFT calculations. Overall, both experimental and theoretical analysis suggest (MLCT)-M-3 radiative decays occurrence for the complexes. Furthermore, biological assays showed that the complexes are active on the intracellular amastigote form of Trypanosoma cruzi (Tulahuen Lac-Z strain), and present a significant cytotoxic effect against metastatic melanoma cells. Finally, no significant toxicity to LLC-MK2 cells was observed, resulting in a therapeutic index of about 30 for one of the complexes, in the same order of magnitude as that of the standard drug benznidazole. (C) 2018 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process: 09/54011-8 - Acquisition of a single-crystal X-ray diffractometer for the structural analysis of small molecules and proteins
Grantee:Victor Marcelo Deflon
Support Opportunities: Multi-user Equipment Program