DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

Tunç, Turgay; Demirel, Nadir; Emir, Mahmut Emir Mahmut; Günel, Aslıhan; Çolak, Mehmet; Karacan, Nurcan

doi:10.29356/jmcs.v62i3.424

Cited by 2 publications

(3 citation statements)

References 38 publications

(48 reference statements)

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“…[73,74]), and N-salicyl-β-amino alcohol Schiff bases ((0.04-2.4) × 10 6 , ref. [75]). The possibility of π-π stacking interaction due to the presence of aromatic rings and extended electronic delocalization favors the binding of CuHHSB, CuHIN, and CuHTSC, as confirmed by the high K b values of the ligands ((3.7-6.9) × 10 6 , Table 1).…”

Section: Uv-vis Studies On the Dna Bindingmentioning

confidence: 99%

Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes

Pisanu,

Sykula,

Sciortino

et al. 2024

IJMS

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The interactions with calf thymus DNA (CT-DNA) of three Schiff bases formed by the condensation of hesperetin with benzohydrazide (HHSB or L1H3), isoniazid (HIN or L2H3), or thiosemicarbazide (HTSC or L3H3) and their CuII complexes (CuHHSB, CuHIN, and CuHTSC with the general formula [CuLnH2(AcO)]) were evaluated in aqueous solution both experimentally and theoretically. UV–Vis studies indicate that the ligands and complexes exhibit hypochromism, which suggests helical ordering in the DNA helix. The intrinsic binding constants (Kb) of the Cu compounds with CT-DNA, in the range (2.3–9.2) × 106, from CuHTSC to CuHHSB, were higher than other copper-based potential drugs, suggesting that π–π stacking interaction due to the presence of the aromatic rings favors the binding. Thiazole orange (TO) assays confirmed that ligands and Cu complexes displace TO from the DNA binding site, quenching the fluorescence emission. DFT calculations allow for an assessment of the equilibrium between [Cu(LnH2)(AcO)] and [Cu(LnH2)(H2O)]+, the tautomer that binds CuII, amido (am) and not imido (im), and the coordination mode of HTSC (O−, N, S), instead of (O−, N, NH2). The docking studies indicate that the intercalative is preferred over the minor groove binding to CT-DNA with the order [Cu(L1H2am)(AcO)] > [Cu(L2H2am)(AcO)] ≈ TO ≈ L1H3 > [Cu(L3H2am)(AcO)], in line with the experimental Kb constants, obtained from the UV–Vis spectroscopy. Moreover, dockings predict that the binding strength of [Cu(L1H2am)(AcO)] is larger than [Cu(L1H2am)(H2O)]+. Overall, the results suggest that when different enantiomers, tautomers, and donor sets are possible for a metal complex, a computational approach should be recommended to predict the type and strength of binding to DNA and, in general, to macromolecules.

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Section: Uv-vis Studies On the Dna Bindingmentioning

confidence: 99%

Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes

Pisanu,

Sykula,

Sciortino

et al. 2024

IJMS

View full text Add to dashboard Cite

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“…Çalışmada kullanılan ligantlar ve kompleksler literatüre göre aşağıdaki genel sentez yöntemine göre sentezlenmiştir [22,23].…”

Section: B Schiff Base Ligandlarının Ve Komplekslerin Senteziunclassified

“…Reaksiyon tamamlandıktan sonra, karışım soğumaya bırakıldı ve 2 gün oda sıcaklığında bekletildi. Yeşil katı madde süzüldü, iki kez soğuk metanol ile yıkandı ve vakum altında kurutuldu [23].…”

Section: Bakır Komplekslerinin Genel Senteziunclassified

Bakır(II) Komplekslerinin Glutatyon Redüktaz İnhibitor Çalışması

Tunç

2019

Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi

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z-(S)-(+)-fenilglisinol, (1S, 2R)-2-amino-1,2-difeniletanol'in ve (R)-(+)-2-amino-1,1,3-trifenilpropanol bazlı kiral Schiff bazlarının bakır (II) kompleksi sentezlendi. Bu bileşiklerin glutatyon redüktaz enzimi üzerindeki etkileri incelendi. En iyi inhibitör etkisinin kompleks 3'e ait olduğu belirlenmiştir. Anahtar Kelimeler-Schiff Baz, Bakır (II) Kompleksleri, Glutatyon Redüktaz. bstract-(S)-(+)-phenylglycinol, (1S, 2R)-2-amino-1, 2-diphenylethanol and (R)-(+)-2-amino-1, 1, 3triphenylpropanol based chiral copper (II) complex of Schiff bases were synthesized. The effects of these compounds on glutathione reductase enzyme were investigated. The best inhibitory effect was found to belong to complex 3.

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DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

Cited by 2 publications

References 38 publications

Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes

Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes

Bakır(II) Komplekslerinin Glutatyon Redüktaz İnhibitor Çalışması

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