Novel water soluble morpholine substituted Zn(II) phthalocyanine: Synthesis, characterization, DNA/BSA binding, DNA photocleavage and topoisomerase I inhibition

Barut, Burak; Demirbaş, Ümit; Özel, Arzu; Kanteki̇n, Hali̇t

doi:10.1016/j.ijbiomac.2017.07.072

Cited by 55 publications

(29 citation statements)

References 54 publications

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“…Their migration speeds are considered to be in the order Form I > Form III > Form II. 55 As shown in Fig. 7, with increasing concentration of 5-HMF from 0 to 4.52 × 10 −2 mol L −1 , the brightness of Form I decreased gradually.…”

Section: Ftir Spectral Analysismentioning

confidence: 75%

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Exploring the binding interaction of Maillard reaction by‐product 5‐hydroxymethyl‐2‐furaldehyde with calf thymus DNA

Zhou

Zhang

et al. 2019

J Sci Food Agric

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BACKGROUND 5‐Hydroxymethyl‐2‐furaldehyde (5‐HMF), a by‐product of the Maillard reaction, usually present in fried and baked food, may cause potential harm to the human body. Here, the interaction between 5‐HMF and calf thymus DNA (ctDNA) under physiological buffer (pH 7.4) was studied using multi‐spectroscopic methods combined with multivariate curve resolution–alternating least squares (MCR‐ALS) chemometrics and molecular simulation techniques. RESULTS The concentration profiles and pure spectra of the three components (5‐HMF, ctDNA and 5‐HMF–ctDNA complex) were extracted from highly overlapping spectra using MCR‐ALS analysis, which verified the formation of 5‐HMF–ctDNA complex. The binding constant being of the order of 103 L mol−1 at four temperatures (292, 298, 304 and 310 K) indicated a weak affinity in the binding of 5‐HMF to ctDNA. The binding interaction was mainly driven by hydrogen bonds and van der Waals forces. Viscosity analysis, melting assay, ionic strength effect and competitive fluorescence studies ascertained that 5‐HMF bound to ctDNA through groove binding, and it tended to bind to guanine–cytosine rich region of ctDNA which was characterized using Fourier transform infrared spectra and molecular docking. Circular dichroism spectral analysis and DNA cleavage assays indicated that the ctDNA conformation was altered from B to A form and 5‐HMF caused DNA damage at higher concentration. CONCLUSIONS The results suggested that 5‐HMF bound to ctDNA through groove binding and caused DNA damage. This research may contribute to understand the binding mechanism of 5‐HMF to ctDNA and to the assessment of the toxicological effect of 5‐HMF in biological processes. © 2018 Society of Chemical Industry

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Section: Ftir Spectral Analysismentioning

confidence: 75%

“…Circular plasmid DNA shows only one form, named Form I, in gel electrophoresis, but when DNA is damaged, an open circular form (Form II) and a linear form (Form III) may be observed. Their migration speeds are considered to be in the order Form I > Form III > Form II . As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Exploring the binding interaction of Maillard reaction by‐product 5‐hydroxymethyl‐2‐furaldehyde with calf thymus DNA

Zhou

Zhang

et al. 2019

J Sci Food Agric

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“…According to Barut, studying water soluble morpholine substituted Zn(II) phthalocyanine compound showed that the compound interacts with DNA via intercalation binding mode . The experimental results of another study demonstrated that cationic phthalocyanine compounds binds to DNA via electrostatic interaction .…”

Section: Resultsmentioning

confidence: 99%

Studies on DNA Interaction with 2(3),9(10), 16(17), 23(24)‐Tetrakis 2((4‐Phenoxyphenyl) Diazeylbenzoic acid)phthalocyaninato Zinc (II) Compound

Arslantaş

Ağırtaş

2018

ChemistrySelect

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In this study, 2(3), 9(10), 16(17), 23(24)‐tetrakis 2((4‐phenoxyphenyl) diazeylbenzoic acid)phthalocyaninato zinc (II) compound was chosen to study DNA binding activities. The binding activities of zinc (II) phthalocyanine compound bearing 2(3),9(10), 16(17), 23(24)‐tetrakis 2((4‐Phenoxyphenyl) diazeylbenzoic acid) ligand with Calf Thymus (CT)‐DNA was investigated using absorption titration, fluorescence spectroscopy, cyclic voltammetry and thermal melting profile in a Tris‐HCl buffer system at pH 7.0. In addition to these methods, gel electrophoresis and viscosity measurements were also carried out to determine DNA binding activities with compound 6 in a buffer solution. The results indicated that compound 6 interacts with CT‐DNA through partial intercalation binding mode.

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“…Recently, the literature has reported tetracationic zinc and metal‐free phthalocyanines containing 4‐((7‐(trifluoromethyl)quinolin‐4‐yl)oxy) units on the periphery. [ 25] A study indicated that water‐soluble quaternized zinc and metal‐free phthalocyanines showed powerful DNA binding activity . According to Barut, studying water soluble morpholine substituted Zn(II) phthalocyanine compound showed that the compound binded to CT‐DNA through intercalation mode .…”

Section: Resultsmentioning

confidence: 99%

Investigation of DNA‐Binding Activities of Zinc(II) and Cobalt(II) Phthalocyanine Compounds with 3,4,5‐Trimethoxybenzyloxy Substituents

Arslantaş

Ağırtaş

2017

ChemistrySelect

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In this study, DNA‐binding activities of previously synthesized tetrakis(3,4,5‐trimethoxybenzyloxy)‐substituted Zn(II) and Co(II) phthalocyanines (Pc4 and Pc5) have been chosen for the study. The interaction of synthesized tetrakis(3,4,5‐trimethoxybenzyloxy)‐substituted Zn(II) and Co(II) phthalocyanine compounds with CT‐DNA was investigated by using UV/Vis titrimetric method, fluorescence spectroscopy, cyclic voltammetry, thermal denaturation profile, gel electrophoresis and viscosty measurement in a Tris‐HCI buffer at pH 7.0. The results indicated that tetrakis(3,4,5‐trimethoxybenzyloxy)‐substituted Zn(II) and Co(II) phthalocyanines (Pc4 and Pc5) can interact with CT‐DNA via intercalation binding mode.

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Novel water soluble morpholine substituted Zn(II) phthalocyanine: Synthesis, characterization, DNA/BSA binding, DNA photocleavage and topoisomerase I inhibition

Cited by 55 publications

References 54 publications

Exploring the binding interaction of Maillard reaction by‐product 5‐hydroxymethyl‐2‐furaldehyde with calf thymus DNA

Exploring the binding interaction of Maillard reaction by‐product 5‐hydroxymethyl‐2‐furaldehyde with calf thymus DNA

Studies on DNA Interaction with 2(3),9(10), 16(17), 23(24)‐Tetrakis 2((4‐Phenoxyphenyl) Diazeylbenzoic acid)phthalocyaninato Zinc (II) Compound

Investigation of DNA‐Binding Activities of Zinc(II) and Cobalt(II) Phthalocyanine Compounds with 3,4,5‐Trimethoxybenzyloxy Substituents

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