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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)

Synthesis, crystal structure, and enhancement of the efficacy of metronidazole against Entamoeba histolytica by complexation with palladium(II), platinum(II), or copper(II)
Synthesis, crystal structure, and enhancement of the efficacy of metronidazole against Entamoeba histolytica by complexation with palladium(II), platinum(II), or copper(II)
Reaction of trans-[PdCl2(DMSO)(2)]. cis-[PtCl2(DMSO)(2)]. and [Cu(OAc)(2)](H2O)-H-. with metronidazole (mnz) leads to the formation of new complexes, i.e., trans-[PdCl2(mnz)(2)] (1), trans-[PtCl2(mnz)(2)] (2). and trans-[Cu-2(OAc)(4)(mnz)(2)] (3), respectively. Complexes 1-3 crystallize all in the centrosymmetric monoclinic space group P2(1)/c with Z = 8. Unit-cell parameters for these complexes are: 1, a = 7.1328(14) Angstrom, b = 20.699(4) Angstrom, c = 7.1455(14) Angstrom, and beta = 116.17(3)degrees; 2, a = 9.9169(14) Angstrom, b = 21.853(4) Angstrom, c = 6.7218(13) Angstrom, and beta = 110.79(3)degrees: 3. a = 9.1663(18) Angstrom, b = 19.129(4) Angstrom, c = 8.9446(18) Angstrom, and beta = 116.44(3)degrees. The complexes 1 and 2 maintain an ideal square-planar geometry. In complex 3, the H2O 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 Cu-Cu separation of 2.6343(8) Angstrom 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 IC50 values in a muM range better than metronidazole (Table 2). Thus, compound 1 displayed more effective amoebicidal activity than metronidazole (IC50 values of 0.103 muM vs. 1.50 muM resp.).
cytotoxic activity, resistant, cancer
0018-019X
2704-2712
Bharti, Neelam
6afd8acf-b57c-46b9-99a3-cb44c5264b00
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Mayer, Thomas A.
59bc92dc-0703-4f38-b37d-6e04295371a1
Gonzalez Garza, M.T.
d7ff488c-40e7-4220-87a4-1ad705e9ac20
Cruz-Vega, Delia E.
4b69e489-0311-4400-9b43-0c7857d76486
Mata-Cardenas, Benito D.
521c32c5-8ac6-419c-898c-0d8da229073d
Naqvi, Fehmida
5a92ee40-a145-4107-ab58-bd99f7b51e68
Maurya, Mannar R.
e3e76244-b3a4-47db-9504-07873c357477
Azam, Amir
8147ff4d-c7b3-4bfa-a2e2-61541b5bc62f
Bharti, Neelam
6afd8acf-b57c-46b9-99a3-cb44c5264b00
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Mayer, Thomas A.
59bc92dc-0703-4f38-b37d-6e04295371a1
Gonzalez Garza, M.T.
d7ff488c-40e7-4220-87a4-1ad705e9ac20
Cruz-Vega, Delia E.
4b69e489-0311-4400-9b43-0c7857d76486
Mata-Cardenas, Benito D.
521c32c5-8ac6-419c-898c-0d8da229073d
Naqvi, Fehmida
5a92ee40-a145-4107-ab58-bd99f7b51e68
Maurya, Mannar R.
e3e76244-b3a4-47db-9504-07873c357477
Azam, Amir
8147ff4d-c7b3-4bfa-a2e2-61541b5bc62f

Bharti, Neelam, Coles, Simon J., Hursthouse, Michael B., Mayer, Thomas A., Gonzalez Garza, M.T., Cruz-Vega, Delia E., Mata-Cardenas, Benito D., Naqvi, Fehmida, Maurya, Mannar R. and Azam, Amir (2002) Synthesis, crystal structure, and enhancement of the efficacy of metronidazole against Entamoeba histolytica by complexation with palladium(II), platinum(II), or copper(II). Helvetica Chimica Acta, 85 (9), 2704-2712. (doi:10.1002/1522-2675(200209)85:9<2704::AID-HLCA2704>3.0.CO;2-X).

Record type: Article

Abstract

Reaction of trans-[PdCl2(DMSO)(2)]. cis-[PtCl2(DMSO)(2)]. and [Cu(OAc)(2)](H2O)-H-. with metronidazole (mnz) leads to the formation of new complexes, i.e., trans-[PdCl2(mnz)(2)] (1), trans-[PtCl2(mnz)(2)] (2). and trans-[Cu-2(OAc)(4)(mnz)(2)] (3), respectively. Complexes 1-3 crystallize all in the centrosymmetric monoclinic space group P2(1)/c with Z = 8. Unit-cell parameters for these complexes are: 1, a = 7.1328(14) Angstrom, b = 20.699(4) Angstrom, c = 7.1455(14) Angstrom, and beta = 116.17(3)degrees; 2, a = 9.9169(14) Angstrom, b = 21.853(4) Angstrom, c = 6.7218(13) Angstrom, and beta = 110.79(3)degrees: 3. a = 9.1663(18) Angstrom, b = 19.129(4) Angstrom, c = 8.9446(18) Angstrom, and beta = 116.44(3)degrees. The complexes 1 and 2 maintain an ideal square-planar geometry. In complex 3, the H2O 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 Cu-Cu separation of 2.6343(8) Angstrom 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 IC50 values in a muM range better than metronidazole (Table 2). Thus, compound 1 displayed more effective amoebicidal activity than metronidazole (IC50 values of 0.103 muM vs. 1.50 muM resp.).

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Published date: 2002
Keywords: cytotoxic activity, resistant, cancer

Identifiers

Local EPrints ID: 19676
URI: http://eprints.soton.ac.uk/id/eprint/19676
ISSN: 0018-019X
PURE UUID: a89af8af-7a2b-4d01-826d-968ddd3323a6
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 21 Feb 2006
Last modified: 18 Feb 2021 16:52

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Contributors

Author: Neelam Bharti
Author: Simon J. Coles ORCID iD
Author: Thomas A. Mayer
Author: M.T. Gonzalez Garza
Author: Delia E. Cruz-Vega
Author: Benito D. Mata-Cardenas
Author: Fehmida Naqvi
Author: Mannar R. Maurya
Author: Amir Azam

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