Iron(III) Complexes Derived From Azo-Containing Salicylaldoxime Ligands: Synthesis, Structures and Biological Evaluations

Year 2021, , 1184 - 1201, 30.09.2021

Kerim Serbest , Bayram Dural Melek Çol Ayvaz , Ali Zengin Mustafa Emirik

https://doi.org/10.31202/ecjse.905307

Abstract

Two novel mononuclear Fe(III) complexes derived from azo-containing salicylaldoxime ligands were synthesized and characterized by elemental analyses, spectroscopic data i.e. IR, 1H NMR, UV-Vis, electrospray ionization mass spectra, molar conductivity, and magnetic susceptibility measurements. Both the experimental and theoretical results strongly suggest that the ligands have a major contribution to the azo enol imine form instead of the hydrazo keto imine and azo keto amine forms in solution/solid-state. The electronic spectra of the ligands and their iron(III) complexes were calculated theoretically for the band assignments by using DFT and TD-DFT/CPCM methods. DNA binding, cleavage, and antioxidative activities of the investigated compounds were studied. It has been shown that the ligands and their iron (III) complexes tested bind to DNA via the intercalative mode. One of the most striking results among the antioxidant activity tests is that the hydroxyl radical scavenging activities of the ligands and complexes are higher than the standard antioxidant mannitol.

Keywords

Azo-oxime, Iron(III) complex, DNA interaction, Antioxidant activity, DFT

Supporting Institution

TUBİTAK

Project Number

112T526

Azo Grubu Içeren Salisilaldoksim Ligandlarından Türetilen Demir (III) Kompleksleri: Sentez, Karakterizasyon Ve Biyolojik Değerlendirmeler

Abstract

Azo grubu taşıyan salisilaldoksim türevi ligandlarından türetilen iki yeni mononükleer Fe (III) kompleksi sentezlendi ve elementel analizler, spektroskopik veriler, yani IR, 1H NMR, UV-Vis, elektrosprey iyonizasyon kütle spektrumları, molar iletkenlik ve manyetik duyarlılık ölçümleriyle karakterize edildi. Hem deneysel hem de teorik sonuçlar, çözelti / katı halde ligandların hidrazo keto imin ve azo keto amin formları yerine azo enol imin formunun daha büyük bir katkısı olduğunu güçlü bir şekilde göstermektedir. Ligandlar ve bunların demir(III) komplekslerinin elektronik spektrumları deneysel spektrumlardaki bant atamaları için, DFT ve TD-DFT / CPCM yöntemleri kullanılarak teorik olarak hesaplandı. Araştırılan bileşiklerin DNA bağlanması, bölünmesi ve antioksidatif aktiviteleri incelenmiştir. Test edilen ligandların ve bunların demir(III) komplekslerinin interkalasyon yaparak DNA'ya bağlandığı gösterilmiştir. Antioksidan aktivite testleri arasında en çarpıcı sonuçlardan biri, ligandların ve komplekslerin hidroksil radikal süpürücü aktivitelerinin standart antioksidan mannitole göre daha yüksek olmasıdır.

Keywords

Azo-oksim, Demir(III) kompleksi, DNA etkileşimi, Antioksidan aktivitesi, DFT

Project Number

112T526

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