Binding interaction of pharmaceutical drug captopril with calf thymus DNA: a multispectroscopic and molecular docking study

Mukherjee, Abhijit; Singh, Bula

doi:10.1016/j.jlumin.2017.05.068

Cited by 56 publications

(16 citation statements)

References 61 publications

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“…This phenomenon suggested that the groove binding enhanced the base stacking and right‐handed helicity of ctDNA, and the DNA structure tended to a transformation from B‐form structure to A‐form conformation. Similar result involving the groove binding between the drug captopril and ctDNA was reported by Mukherjee et al …”

Section: Resultssupporting

confidence: 88%

“…In contrast, groove and electrostatic binding modes will not obviously alter the stability of DNA double helix, and thus T m is almost unchanged. 43 As shown in Fig. 3(B), the T m values of ctDNA and 5-HMF-ctDNA complex were 85 and 84 ∘ C, respectively.…”

Section: Melting Temperature Determinationmentioning

confidence: 76%

“…Intercalative binding is beneficial to the stability of DNA double helix and thus it is more difficult to melt and T m will increase by about 5 °C compared to ds ctDNA. In contrast, groove and electrostatic binding modes will not obviously alter the stability of DNA double helix, and thus T m is almost unchanged . As shown in Fig.…”

Section: Resultsmentioning

confidence: 97%

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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: Resultssupporting

confidence: 88%

Section: Melting Temperature Determinationmentioning

confidence: 76%

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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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“…[ 54 ] If a drug has the same binding mode as Hoechst 33258, the original fluorescence intensity of the Hoechst 33258–DNA complex solution decreases gradually after the drug has successively been added to this solution. [ 55 ] As observed in Figure 11, the fluorescence intensity of the Hoechst 33258–DNA solution decreased significantly because some Hoechst 33258 molecules were replaced by DNP in the DNA's groove. [ 11,50 ] The above results indicated that DNP interacts with DNA through a groove‐binding mode.…”

Section: Resultsmentioning

confidence: 99%

Exploring the binding mode of donepezil with calf thymus DNA using spectroscopic and molecular docking methods

et al. 2020

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Donepezil (DNP) is one of approved drugs to treat Alzheimer's disease (AD). However, the potential effect of DNP on DNA is still unclear. Therefore, the interaction of DNP with calf thymus DNA (DNA) was studied in vitro using spectroscopic and molecular docking methods. Steady‐state and transient fluorescence experiments showed that there was a clear binding interaction between DNP and DNA, resulting from DNP fluorescence being quenched using DNA. DNP and DNA have one binding site between them, and the binding constant (Kb) was 0.78 × 104 L·mol−1 at 298 K. In this binding process, hydrophobic force was the main interaction force, because enthalpy change (ΔH) and entropy change (ΔS) of DNP–DNA were 67.92 kJ·mol−1 and 302.96 J·mol−1·K−1, respectively. DNP bound to DNA in a groove‐binding mode, which was verified using a competition displacement study and other typical spectroscopic methods. Fourier transform infrared (FTIR) spectrum results showed that DNP interacted with guanine (G) and cytosine (C) bases of DNA. The molecular docking results further supported the results of spectroscopic experiments, and suggested that both Pi‐Sigma force and Pi‐Alkyl force were the major hydrophobic force functioning between DNP and DNA.

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“…The spectral changes represent a strong indication of that interaction process between the ctDNA and the evaluated ligands [38] . According to Mukherjee and Sing [39] , this phenomenon is called quenching, and can occur by different mechanisms, generally classified by dynamic quenching, which occurs when the fluorophores (piperidines) in the excited state (F ∗ ) are deactivated upon contact with a quencher molecule (Q = ctDNA) during the existence of the excited state. Static quenching refers to the formation of a non-fluorescent supramolecular complex (F-Q) in the ground state, being independent of diffusion processes or molecular collisions [40] .…”

Section: Resultsmentioning

confidence: 99%

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Das

Silva

et al. 2018

Journal of Advanced Research

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Binding interaction of pharmaceutical drug captopril with calf thymus DNA: a multispectroscopic and molecular docking study

Cited by 56 publications

References 61 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

Exploring the binding mode of donepezil with calf thymus DNA using spectroscopic and molecular docking methods

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

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