Novel triphenylantimony(V) and triphenylbismuth(V) complexes with benzoic acid derivatives: structural characterization, in vitro antileishmanial and antibacterial activities and cytotoxicity against macrophages.
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.
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.
Arshad
A
Islam
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.
Jeferson Gomes
JG
Da Silva
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.
Filipe Moan
FM
Berbet
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.
Sydnei Magno
SM
da Silva
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.
Bernardo Lages
BL
Rodrigues
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.
Heloisa
H
Beraldo
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.
Maria Norma
MN
Melo
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.
Frédéric
F
Frézard
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.
Cynthia
C
Demicheli
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000965:Antimony / Q000737:chemistry / Q000494:pharmacology*; D019817:Benzoic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018314:Leishmania infantum / Q000187:drug effects; D008024:Ligands; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013730:Terphenyl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D008024:Ligands; D009942:Organometallic Compounds; D013730:Terphenyl Compounds; D019817:Benzoic Acid; D000965:Antimony; C076672:triphenyl bismuth