Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N3S2 Schiff base ligand and its [CuN3S2]2+ complexes

Ismail Warad; Hadeel Suboh; Nabil Al-Zaqri; Ali Alsalme; Fahad A. Alharthi; Meshari M. Aljohani; Abdelkader Zarrouk

doi:10.1039/D0RA04323K

Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes

Ismail Warad,

*^a Hadeel Suboh,^b Nabil Al-Zaqri,

^cd Ali Alsalme,

^c Fahad A. Alharthi,

^c Meshari M. Aljohani^e and Abdelkader Zarrouk^f

Author affiliations

* Corresponding authors

^a Department of Chemistry and Earth Sciences, Qatar University, PO Box 2713, Doha, Qatar
E-mail: ismail.warad@qu.edu.qa

^b Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus, Palestine

^c Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

^d Department of Chemistry, College of Science, Ibb University, P.O. Box 70270, Ibb, Yemen

^e Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk-71491, Saudi Arabia

^f Laboratory of Materials, Nanotechnology and Environment, Faculty of Sciences, Mohammed V University, Av. Ibn Battouta, Box 1014, Agdal-Rabat, Morocco

Abstract

A new N₃S₂ pentadentate Schiff base ligand derived from 5-bromothiophene-2-carbaldehyde, (E)-N1-((5-bromothiophen-2-yl)methylene)-N2-(2-((E)-((5-bromothiophen-2-yl)-methylene amino) ethyl ethane-1,2-diamine, is prepared. The ligand and its complexes are subjected to extensive physical and theoretical analyses and the results are consistent with their predicted compositions. Dicationic Cu(II) complexes ([CuN₃S₂]X₂) with a coordination number of 5 are proposed on the basis of the spectral data with N₃S₂ serving as a pentadentate ligand. The prepared complexes display a square pyramidal geometry around the Cu(II) center. TG shows different thermal behavior for the N₃S₂ ligand and its complexes. Solvatochromism of the complexes is promoted by the polarity of the solvent used. A one-electron transfer Cu(II)/Cu(I) reversible redox reaction is promoted by CV. SEM and EDS of the free ligand and its complexes support the morphology and composition changes observed upon the complexation of Cu(II). As an outstanding goal to develop anticancer new metal chemotherapy, preliminary studies of the binding of the desired complexes with DNA were carried out, as it is through judging the strength of interactions that a future drug can be designed and synthesized. The viscosity and absorption results obtained for complex 1 indicated its enhanced CT-DNA binding properties as compared to those of complex 2 with K_b values of 3.2 × 10⁵ and 2.5 × 10⁵ M⁻¹, respectively.

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Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes

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Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes

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