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Synthesis and anti-amoebic activity of gold(I), ruthenium(II), and copper(II) complexes of metronidazole

Synthesis and anti-amoebic activity of gold(I), ruthenium(II), and copper(II) complexes of metronidazole
Synthesis and anti-amoebic activity of gold(I), ruthenium(II), and copper(II) complexes of metronidazole
A series of Au, Ru, and Cu complexes of metronidazole (= [1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole; 1) were prepared as highly potent anti-amoebic drugs. The complexes [Au(PPh3)(1)]PF6 (2), [Ru(1)(2)(Cl)(2)(H2O)(2)] (3), and [CU(1)(2)(mu-Cl)(H2O)](2)Cl-2 (4) were readily synthesized from [Au(PPh3)Cl], RuCl(3)center dot 3H(2)O, and CuCl(2)center dot 2H(2)O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, H-1-NMR, FAB-MS, elemental and thermogravimetric analyses, and, in the case of 4, also by X-ray crystallography (Fig. 1). All complexes were evaluated in vitro as growth inhibitors of Entamoeba histolytica (HM1 : IMSS strain). Their IC50 values were in the range of 0.10 - 0.51 mu m (Table 2), which makes these drugs, especially the Cu-11 complex 4, considerably more potent than uncomplexed metronidazole (1: IC50 = 1.81 mu M) the current standard drug for the worldwide treatment of amoebiasis.
entamoeba-histolytica, crystal-structure, in-vitro, coordination, derivatives, efficacy, agents, drugs, donor
1612-1872
1320-1330
Athar, Fareeda
3ba79da5-63d8-4a3c-a0fd-531de9e50381
Husain, Kakul
044b990b-5f6d-4413-ad9a-a4195e5cb3de
Abid, Mohammad
3401fafc-56b5-476e-9030-91c58b16b316
Agarwal, Subhash M.
397d0419-2297-4833-a1ec-3b2e7a9e8d12
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Maurya, Mannar R.
e3e76244-b3a4-47db-9504-07873c357477
Azam, Amir
8147ff4d-c7b3-4bfa-a2e2-61541b5bc62f
Athar, Fareeda
3ba79da5-63d8-4a3c-a0fd-531de9e50381
Husain, Kakul
044b990b-5f6d-4413-ad9a-a4195e5cb3de
Abid, Mohammad
3401fafc-56b5-476e-9030-91c58b16b316
Agarwal, Subhash M.
397d0419-2297-4833-a1ec-3b2e7a9e8d12
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Maurya, Mannar R.
e3e76244-b3a4-47db-9504-07873c357477
Azam, Amir
8147ff4d-c7b3-4bfa-a2e2-61541b5bc62f

Athar, Fareeda, Husain, Kakul, Abid, Mohammad, Agarwal, Subhash M., Coles, Simon J., Hursthouse, Michael B., Maurya, Mannar R. and Azam, Amir (2005) Synthesis and anti-amoebic activity of gold(I), ruthenium(II), and copper(II) complexes of metronidazole. Chemistry & Biodiversity, 2 (10), 1320-1330.

Record type: Article

Abstract

A series of Au, Ru, and Cu complexes of metronidazole (= [1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole; 1) were prepared as highly potent anti-amoebic drugs. The complexes [Au(PPh3)(1)]PF6 (2), [Ru(1)(2)(Cl)(2)(H2O)(2)] (3), and [CU(1)(2)(mu-Cl)(H2O)](2)Cl-2 (4) were readily synthesized from [Au(PPh3)Cl], RuCl(3)center dot 3H(2)O, and CuCl(2)center dot 2H(2)O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, H-1-NMR, FAB-MS, elemental and thermogravimetric analyses, and, in the case of 4, also by X-ray crystallography (Fig. 1). All complexes were evaluated in vitro as growth inhibitors of Entamoeba histolytica (HM1 : IMSS strain). Their IC50 values were in the range of 0.10 - 0.51 mu m (Table 2), which makes these drugs, especially the Cu-11 complex 4, considerably more potent than uncomplexed metronidazole (1: IC50 = 1.81 mu M) the current standard drug for the worldwide treatment of amoebiasis.

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More information

Published date: 2005
Keywords: entamoeba-histolytica, crystal-structure, in-vitro, coordination, derivatives, efficacy, agents, drugs, donor

Identifiers

Local EPrints ID: 20705
URI: https://eprints.soton.ac.uk/id/eprint/20705
ISSN: 1612-1872
PURE UUID: fb1abfb4-49ba-4ca3-807e-34daa533938b
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 28 Feb 2006
Last modified: 06 Jun 2018 12:54

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