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Synthesis, Crystal Structure, and Enhancement of the Efficacy of Metronidazole Against Entamoeba histolytica by Complexation with Palladium(II), Platinum(II), or Copper(II)
Author(s) -
Bharti Neelam,
Coles Simon J.,
Hursthouse Michael B.,
Mayer Thomas A.,
Gonzalez Garza M. T.,
CruzVega Delia E.,
MataCardenas Benito D.,
Naqvi Fehmida,
Maurya Mannar R.,
Azam Amir
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200209)85:9<2704::aid-hlca2704>3.0.co;2-x
Subject(s) - chemistry , monoclinic crystal system , octahedron , crystallography , stereochemistry , molecule , entamoeba histolytica , metal , crystal structure , organic chemistry , microbiology and biotechnology , biology
Reaction of trans ‐[PdCl 2 (DMSO) 2 ], cis ‐[PtCl 2 (DMSO) 2 ], and [Cu(OAc) 2 ]⋅H 2 O with metronidazole (mnz) leads to the formation of new complexes, i.e., trans ‐[PdCl 2 (mnz) 2 ] ( 1 ), trans ‐[PtCl 2 (mnz) 2 ] ( 2 ), and trans ‐[Cu 2 (OAc) 4 (mnz) 2 ] ( 3 ), respectively. Complexes 1 – 3 crystallize all in the centrosymmetric monoclinic space group P 2 1 / c with Z =8. Unit‐cell parameters for these complexes are: 1 , a =7.1328(14) Å, b =20.699(4) Å, c =7.1455(14) Å, and β =116.17(3)°; 2 , a =6.9169(14) Å, b =21.853(4) Å, c =6.7218(13) Å, and β =110.79(3)°; 3 , a =9.1663(18) Å, b =19.129(4) Å, c =8.9446(18) Å, and β =116.44(3)°. The complexes 1 and 2 maintain an ideal square‐planar geometry. In complex 3 , the H 2 O molecules of the starting complex are replaced by metronidazole while maintaining a dimeric structure of [Cu(OAc) 2 ]. Each Cu ion has an ideal octahedral structure, though distortion occurs in the equatorial position where the acetato ligands are attached. The CuCu separation of 2.6343(8) Å indicates considerable metal‐metal interaction. The testing of the antiamoebic activity of these complexes against the protozoan parasite Entamoeba histolytica suggests that compound 1 – 3 might be endowed with important antiamoebic properties since they showed IC 50 values in a μ M range better than metronidazole ( Table 2 ). Thus, compound 1 displayed more effective amoebicidal activity than metronidazole ( IC 50 values of 0.103 μ M vs. 1.50 μ M , resp.).