Spectral, thermal, kinetic, molecular modeling and eukaryotic DNA degradation studies for a new series of albendazole (HABZ) complexes

doi:10.1016/j.saa.2010.09.021

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

Volume 78, Issue 1, January 2011, Pages 196-204

https://doi.org/10.1016/j.saa.2010.09.021 Get rights and content

Abstract

This work represents the elaborated investigation for the ligational behavior of the albendazole ligand through its coordination with, Cu(II), Mn(II), Ni(II), Co(II) and Cr(III) ions. Elemental analysis, molar conductance, magnetic moment, spectral studies (IR, UV–Vis and ESR) and thermogravimetric analysis (TG and DTG) have been used to characterize the isolated complexes. A deliberate comparison for the IR spectra reveals that the ligand coordinated with all mentioned metal ions by the same manner as a neutral bidentate through carbonyl of ester moiety and NH groups. The proposed chelation form for such complexes is expected through out the preparation conditions in a relatively acidic medium. The powder XRD study reflects the amorphous nature for the investigated complexes except Mn(II). The conductivity measurements reflect the non-electrolytic feature for all complexes. In comparing with the constants for the magnetic measurements as well as the electronic spectral data, the octahedral structure was proposed strongly for Cr(III) and Ni(II), the tetrahedral for Co(II) and Mn(II) complexes but the square–pyramidal for the Cu(II) one. The thermogravimetric analysis confirms the presence or absence of water molecules by any type of attachments. Also, the kinetic parameters are estimated from DTG and TG curves. ESR spectrum data for Cu(II) solid complex confirms the square–pyramidal state is the most fitted one for the coordinated structure. The albendazole ligand and its complexes are biologically investigated against two bacteria as well as their effective effect on degradation of calf thymus DNA.

Introduction

Ligands containing heterocyclic aromatic units and their metal complexes have extensive applications in many types of technology [1], [2]. Many heterocyclic compounds containing benzimidazoles, which are the nucleolus of albendazole are a subject of interest to medicinal chemistry because of the broad spectrum of their biological and pharmaceutical properties. Benzimidazole complexes have been investigated for their antifungal, antibacterial [3], [4], antimicrobial [5], [6], antiamoebic [7], [8], antiparasitic [9] and antitumor activities [10], [11]. Although the presence of many studies on benzimidazole complexes but the pharmacological or coordinative information about albendazole and some of its complexes is absent in the literature. A considerable number of metal complexes containing benzimidazole molecules is widely used in industry such Cu(II)-methylene-bis(N-methyl) benzimidazole is used in homopolimerization and co-polymerization of olefins and acrylates [12], Mn–binuclear complexes as a model to catalyses [13]. Recently, Ru–phenanthroline complexes with chelate ligands containing benzimidazoles and sulfur were reported to have a strong DNA binding and high anti cancer activity, being more potent than cisplatin against melanoma A375, and less toxic to normal cells [14]. Also, some biological studies have shown how analogous of ketone are effective as inhibitors of cell death [15]. Through out the previous work we abstract the importance of benzimidazole moiety, so the addition of other sites for the coordination (S and O) represents in albendazole ligand may reveal an expected distinguish behavior in coordination and application. In this study, we concern the synthesis, structural characterization and molecular modeling for the complexes with some metal ions in the first raw [Cu, Co, Ni, Cr and Mn]. Furthermore, the antimicrobial activity of the free ligand and its complexes against various pathogenic microorganisms was evaluated.

Section snippets

Reagents

Albendazole used in our study was obtained from the Egyptian International Pharmaceutical Industrial Company (EIPICO). All chemicals used for the study were of analytically reagent grade, commercially available from Fulka and used without previous purification as CoCl₂·6H₂O, CrCl₃·6H₂O, MnCl₂·4H₂O, NiCl₂·6H₂O and, CuCl₂·4H₂O compounds, which represents the metal ions in concern for the complexation.

Synthesis of the complexes

The complexes were prepared by heating 1:1 molar ratio for the ligand (0.2653 g, 1 mmol) with each

Results and discussion

The elemental analysis and some physical characteristics are summarized in Table 2. All the isolated complexes are stable in air, having high melting points, insoluble in H₂O and most organic solvents except DMSO and DMF. They are completely soluble except the Cr(III) and Ni(II) complexes. The molar conductivity measurements for (1.0 × 10⁻³ mol) in DMSO solvent are found with the range of non-conducting feature. This elucidates the proposal of analysis data for the presence of conjugated anion

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Spectral, thermal, kinetic, molecular modeling and eukaryotic DNA degradation studies for a new series of albendazole (HABZ) complexes

Abstract

Introduction

Section snippets

Reagents

Synthesis of the complexes

Results and discussion

II Farmaco

Bioorg. Med. Chem. Lett.

Eur. J. Pharm. Sci.

Bioorg. Med. Chem.

Bioorg. Med. Chem. Lett.

J. Inorg. Nucl. Chem.

Polyhedron

Polyhedron

Thermochim. Acta

Thermochim. Acta

J. Inorg. Biochem.

Coord. Chem. Rev.

Struct. Bond. (Berl.)

Trans. Met. Chem.

Spectrochim. Acta. A55

Chem. Rev.

II Farmaco

II Farmaco

Med. Chem. Lett.

J. Pharm. Chem.

J. Chem. Soc. Dalton Trans.

Macromolecules

Inorg. Chem.