Synthesis of 4'-(2-ferrocenyl)-2,2':6'2''-terpyridine: characterization and antiprotozoal activity of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes

Annu Juneja; Tais Soares Macedo; Diogo Rodrigo Magalhaes Moreira; Milena Botelho Pereira Soares; Ana Cristina Lima Leite; Juliana Kelle de Andrade Lemoine Neves; Valeria Rego Alves Pereira; Fernando Avecilla; Amir Azam

doi:10.1016/j.ejmech.2014.01.051

Synthesis of 4'-(2-ferrocenyl)-2,2':6'2''-terpyridine: characterization and antiprotozoal activity of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes

Eur J Med Chem. 2014 Mar 21:75:203-10. doi: 10.1016/j.ejmech.2014.01.051. Epub 2014 Jan 31.

Authors

Annu Juneja¹, Tais Soares Macedo², Diogo Rodrigo Magalhaes Moreira³, Milena Botelho Pereira Soares³, Ana Cristina Lima Leite⁴, Juliana Kelle de Andrade Lemoine Neves⁵, Valeria Rego Alves Pereira⁵, Fernando Avecilla⁶, Amir Azam⁷

Affiliations

¹ Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India.
² Centro de Pesquisas Gonçalo Moniz, Fundação Oswaldo Cruz, Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, BA, Brazil.
³ Centro de Pesquisas Gonçalo Moniz, Fundação Oswaldo Cruz, Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, BA, Brazil; Centro de Biotecnologia e Terapia Celular, Hospital São Rafael. Av. São Rafael, 2152, São Marcos, 41253-190 Salvador, BA, Brazil.
⁴ Department of Pharmaceutical Sciences, Centre for Health Sciences, Federal University of Pernambuco, 50740-520 Recife, PE, Brazil.
⁵ Departamento de Imunologia, Centro de Pesquisas Aggeu Magalhães, Fundação Oswaldo Cruz, 50670-420 Recife, PE, Brazil.
⁶ Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira s/n, 15071 A Coruña, Spain.
⁷ Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India. Electronic address: amir_sumbul@yahoo.co.in.

PMID: 24534536
DOI: 10.1016/j.ejmech.2014.01.051

Abstract

A terpyridine ligand Fctpy was reacted with divalent metals (Cu, Co, Mn, Ni and Zn), yielding five complexes of general formula [Metal(Fctpy)2][PF6]2. The structure of Fctpy was determined by single crystal X-ray diffraction studies. The complexes characterized using various spectroscopic techniques suggested an octahedral geometry around the central metal ion. These complexes were screened for their antiamoebic, trypanocidal and antimalarial activities. It was found that, complexes 2 and 3 showed better IC50 values than metronidazole against HM1:IMSS strain of Entamoeba histolytica. A substantial parasitic inhibition was not observed for the trypanocidal activity. However, for the erythrocytic stage of W2 strain of Plasmodium falciparum, the complexes inhibited β-hematin formation. At the concentration of 10 μg/mL, these complexes did not display toxicity.

Keywords: Amoebiasis; Ferrocenyl; Malaria; Metal complexes; Terpyridine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antiprotozoal Agents / chemical synthesis
Antiprotozoal Agents / chemistry
Antiprotozoal Agents / pharmacology*
Coordination Complexes / chemical synthesis
Coordination Complexes / chemistry
Coordination Complexes / pharmacology*
Entamoeba histolytica / drug effects*
Entamoebiasis / drug therapy
Ferrous Compounds / chemical synthesis
Ferrous Compounds / chemistry
Ferrous Compounds / pharmacology*
Humans
Malaria, Falciparum / drug therapy
Metals, Heavy / chemical synthesis
Metals, Heavy / chemistry
Metals, Heavy / pharmacology*
Mice
Mice, Inbred BALB C
Models, Molecular
Plasmodium falciparum / drug effects*
Pyridines / chemical synthesis
Pyridines / chemistry
Pyridines / pharmacology*

Substances

4'-ferrocenyl-2,2':6',2' '-terpyridine
Antiprotozoal Agents
Coordination Complexes
Ferrous Compounds
Metals, Heavy
Pyridines