Novel triphenylantimony(V) and triphenylbismuth(V) complexes with benzoic acid derivatives: structural characterization, in vitro antileishmanial and antibacterial activities and cytotoxicity against macrophages.
Arshad Islam, Jeferson Gomes Da Silva, Filipe Moan Berbet, Sydnei Magno da Silva, Bernardo Lages Rodrigues, Heloisa Beraldo, Maria Norma Melo, Frédéric Frézard, Cynthia Demicheli
Author Information
Arshad Islam: Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. arshad.cgl@gmail.com.
Jeferson Gomes Da Silva: Department of Pharmacy, Federal University of Juiz de Fora (UFJF), Campus Governador Valadares, Av. Dr. Raimundo Monteiro de Rezende, 330, Centro, 35010-177 Governador Valadares, MG, Brazil. jefersonpi1@yahoo.com.br.
Filipe Moan Berbet: Department of Physiology and Biophysics, Institute of Biological Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. fmberbet@yahoo.com.br.
Sydnei Magno da Silva: Laboratory of Parasitology, Institute of Biomedical Sciences, Federal University of Uberlândia (UFU), Av Amazonas, s/n, , 38400-902 Uberlândia, Minas Gerais, Brazil. sydnei@icbim.ufu.br.
Bernardo Lages Rodrigues: Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. bernardo@mail.qui.ufmg.br.
Heloisa Beraldo: Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. hberaldo@ufmg.br.
Maria Norma Melo: Department of Parasitology, Institute of Biological Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. melo@icb.ufmg.br.
Frédéric Frézard: Department of Physiology and Biophysics, Institute of Biological Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. frezard@icb.ufmg.br.
Cynthia Demicheli: Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil. demichel@netuno.lcc.ufmg.br.
Two novel organoantimony(V) and two organobismuth(V) complexes of the type ML2 were synthesized, with L = acetylsalicylic acid (HL1) or 3-acetoxybenzoic acid (HL2) and M = triphenylantimony(V) (M1) or triphenylbismuth(V) (M2). Complexes, [M1(L1)2] (1), [M1(L2)2]∙CHCl3 (2), [M2(L1)2], (3) and [M2(L2)2] (4), were characterized by elemental analysis, IR and NMR. Crystal structures of triphenylantimony(V) dicarboxylate complexes 1 and 2 were determined by single crystal X-ray diffraction. Structural analyses revealed that 1 and 2 adopt five-coordinated extremely distorted trigonal bipyramidal geometries, binding with three phenyl groups in the equatorial position and two deprotonated organic ligands (L) in the axial sites. The metal complexes, their metal salts and ligands were evaluated in vitro for their activities against Leishmania infantum and amazonensis promastigotes and Staphylococcus aureus and Pseudomonas aeruginosa bacteria. Both the metal complexes showed antileishmanial and antibacterial activities but the bismuth complexes were the most active. Intriguingly, complexation of organobismuth(V) salt reduced its activity against Leishmania, but increased it against bacteria. In vitro cytotoxic test of these complexes against murine macrophages showed that antimony(V) complexes were the least toxic. Considering the selectivity indexes, organoantimony(V) complexes emerge as the most promising antileishmanial agents and organobismuth(V) complex 3 as the best antibacterial agent.
References
Am J Trop Med Hyg. 2005 Dec;73(6):1005-11
[PMID: 16354802]
