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

Fareeda Athar; Kakul Husain; Mohammad Abid; Subhash M. Agarwal; Simon J. Coles; Micheal B. Hursthouse; Mannar R. Maurya; Amir Azam

doi:10.1002/cbdv.200590104

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

Fareeda Athar
, Kakul Husain
, Mohammad Abid
, Subhash M. Agarwal
, Simon J. Coles
, Micheal B. Hursthouse
, Mannar R. Maurya
, Amir Azam

Research output: Contribution to journal › Review article › peer-review

40 Scopus citations

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(μ-Cl)(H₂O)]₂Cl₂ (4) were readily synthesized from [Au(PPh₃)Cl], RuCl₃ · 3 H₂O, and CuCl₂ · 2 H₂O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, ¹H-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 μM (Table 2), which makes these drugs, especially the Cu^II complex 4, considerably more potent than uncomplexed metronidazole (1; IC₅₀ - 1.81 μM), the current standard drug for the worldwide treatment of amoebiasis.

Original language	English
Pages (from-to)	1320-1330
Number of pages	11
Journal	Chemistry and Biodiversity
Volume	2
Issue number	10
DOIs	https://doi.org/10.1002/cbdv.200590104
State	Published - 2005
Externally published	Yes

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@article{13526177aa174430978e4f9312af0f37,

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

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(μ-Cl)(H2O)]2Cl2 (4) were readily synthesized from [Au(PPh3)Cl], RuCl3 · 3 H2O, and CuCl2 · 2 H2O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, 1H-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 μM (Table 2), which makes these drugs, especially the CuII complex 4, considerably more potent than uncomplexed metronidazole (1; IC50 - 1.81 μM), the current standard drug for the worldwide treatment of amoebiasis.",

author = "Fareeda Athar and Kakul Husain and Mohammad Abid and Agarwal, \{Subhash M.\} and Coles, \{Simon J.\} and Hursthouse, \{Micheal B.\} and Maurya, \{Mannar R.\} and Amir Azam",

year = "2005",

doi = "10.1002/cbdv.200590104",

language = "English",

volume = "2",

pages = "1320--1330",

journal = "Chemistry and Biodiversity",

issn = "1612-1872",

publisher = "Wiley-Blackwell",

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}

TY - JOUR

T1 - Synthesis and anti-amoebic activity of gold(I), ruthenium(II), and copper(II) complexes of metronidazole

AU - Athar, Fareeda

AU - Husain, Kakul

AU - Abid, Mohammad

AU - Agarwal, Subhash M.

AU - Coles, Simon J.

AU - Hursthouse, Micheal B.

AU - Maurya, Mannar R.

AU - Azam, Amir

PY - 2005

Y1 - 2005

N2 - 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(μ-Cl)(H2O)]2Cl2 (4) were readily synthesized from [Au(PPh3)Cl], RuCl3 · 3 H2O, and CuCl2 · 2 H2O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, 1H-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 μM (Table 2), which makes these drugs, especially the CuII complex 4, considerably more potent than uncomplexed metronidazole (1; IC50 - 1.81 μM), the current standard drug for the worldwide treatment of amoebiasis.

AB - 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(μ-Cl)(H2O)]2Cl2 (4) were readily synthesized from [Au(PPh3)Cl], RuCl3 · 3 H2O, and CuCl2 · 2 H2O, respectively. All complexes were thoroughly characterized by IR, UV/VIS, 1H-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 μM (Table 2), which makes these drugs, especially the CuII complex 4, considerably more potent than uncomplexed metronidazole (1; IC50 - 1.81 μM), the current standard drug for the worldwide treatment of amoebiasis.

UR - https://www.scopus.com/pages/publications/27844470117

U2 - 10.1002/cbdv.200590104

DO - 10.1002/cbdv.200590104

M3 - Review article

C2 - 17191933

AN - SCOPUS:27844470117

SN - 1612-1872

VL - 2

SP - 1320

EP - 1330

JO - Chemistry and Biodiversity

JF - Chemistry and Biodiversity

IS - 10

ER -

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

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