Molecules 2014, 19(5), 6009-6030; doi:10.3390/molecules19056009
Article

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages

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Received: 10 April 2014; in revised form: 30 April 2014 / Accepted: 5 May 2014 / Published: 12 May 2014
(This article belongs to the Section Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: organoantimony(V); organobismuth(V); carboxylate; crystal structure; cytotoxicity; antileishmanial; antibacterial
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MDPI and ACS Style

Islam, A.; Da Silva, J.G.; Berbet, F.M.; da Silva, S.M.; Rodrigues, B.L.; Beraldo, H.; Melo, M.N.; Frézard, F.; Demicheli, C. Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages. Molecules 2014, 19, 6009-6030.

AMA Style

Islam A, Da Silva JG, Berbet FM, da Silva SM, Rodrigues BL, Beraldo H, Melo MN, Frézard F, Demicheli C. Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages. Molecules. 2014; 19(5):6009-6030.

Chicago/Turabian Style

Islam, Arshad; Da Silva, Jeferson G.; Berbet, Filipe M.; da Silva, Sydnei M.; Rodrigues, Bernardo L.; Beraldo, Heloisa; Melo, Maria N.; Frézard, Frédéric; Demicheli, Cynthia. 2014. "Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages." Molecules 19, no. 5: 6009-6030.

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