2,4-Dihidroksikinolinden Türetilen Bazı Disazo Boyalar ile Antikanser ve DNA Bağlanma Özellikleri Arasındaki İlişkinin Yoğunluk Fonksiyonel Teorisi ile Analizi

2,4-dihidroksi kinolin türevi diazo boyalarının bazı fiziksel ve kimyasal özellikleri teorik yöntemlerle incelenmiştir. Bileşiklerin solvatokromik davranışını ve absorpsiyonunu belirlemek için altı farklı çözücü kullanılmış ve deneysel veriler kuantum kimyasal hesaplamalardan elde edilen teorik verilerle karşılaştırılmıştır. Bileşiklerin geometrik, elektronik ve bazı kimyasal reaktivite parametrelerini elde etmek için DFT hesaplamaları yapılmıştır. Bileşiklerin elektronik özellikleri ile DNA bağlanma, HeLa ve PC3 kanser hücre hatlarına karşı sitotoksisite kapasitesi arasındaki ilişkiyi belirlemek için molekül içindeki atom, doğal bağ yörüngesi, durum yoğunluğu, kovalent olmayan etkileşim, Fukui fonksiyonu, elektron lokalizasyon fonksiyonu ve elektron delokalizasyon aralığı analizleri yapılmıştır. –Cl ve –NO2 sübstitüentlerine sahip bileşiklerin daha yüksek DNA bağlanmasına ve daha yüksek antikanser etkisine sahip olduğu görülmüştür. Sübstitüentlerin pozisyonlarının yanı sıra bağlardaki elektron yoğunluğu, delokalizasyon indexi değerleri ve nükleofilik ve elektrofilik saldırı bölgelerinin dağılımının bileşiklerin raktivitelerini belirleyen önemli faktörler arasında olduğu görülmüştür. Ayrıca, daha iyi DNA bağlanma özelliği gösteren bileşiklerin HOMO enerjilerinin durum yoğunlukları diğer bileşiklere göre daha yüksek hesaplanmıştır.

Anahtar Kelimeler:

DNA bağlanma, Antikanser, DFT, NCI, ELF, AIM

Analysis of Relationship Between Some Disazo Dyes Derived from 2,4-Dihydroxyquinoline and Its Anticancer and DNA Binding Properties by Density Functional Theory

It was studied some physical and chemical properties of 2,4-dihydroxy quinoline derivative diazo dyes by theoretical methods. Six different solvents were used to determine the solvatochromic behavior and absorption of the compounds, and the experimental results were compared with the theoretical data obtained from quantum chemical calculations. DFT calculations were carried out to obtain the geometric, electronic and some chemical reactivity parameters of the compounds. The atom in molecule, natural bond orbital, density of state, non-covalent interaction, Fukui function, electron localization function, and electron delocalization range analyzes of the compounds were performed to determine the relationship between the electronic properties and the DNA binding capacity and the cytotoxicity against HeLa and PC3 cancer cell lines. It was observed that the compounds substituted with –Cl and –NO2 had higher DNA binding and higher anticancer effect. Besides the positions of the substituents, the electron density in the bonds, the delocalization index values and the distribution of the nucleophilic and electrophilic attack sites are among the important factors determining the reactivity of the compounds. In addition, the HOMO energies of the compounds with better DNA binding properties were calculated higher than the other compounds.

Keywords:

DNA binding, Anticancer, DFT, NCI, ELF, AIM,

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