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

Abstract

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

Multi-Spectroscopic and Molecular Simulation Approaches to Characterize the Intercalation Binding of 1-Naphthaleneacetic Acid With Calf Thymus DNA

“…As seen from Figure 4 , the conformations with the highest number of binding times (45 times, −4.44 kcal mol −1 ) were obtained for final binding analysis ( Figure 4A ). It can be found that the lowest binding energy predicted by molecular simulation (−4.44 kcal mol −1 = −18.57 kJ mol −1 ) is slightly higher than that measured by thermodynamic experiments (−27.35 kJ mol −1 ), which may be due to the lack of desolvation energy in the vacuum environment of docking operation, similar results have been found in previous studies (Zhou et al, 2019 ). As seen from Figure 4B , NAA is bound with ctDNA in the groove region which is rich in G–C bases.…”

“…The preparation method of ctDNA (Sigma Chemical Reagent Co., Ltd., USA) reserve solution is as follows: dissolve the appropriate amount of ctDNA in 0.1 mol L −1 NaCl solution and shake it gently until it dissolves. Then determine the ratio of ultraviolet absorbance of ctDNA reserve solution at 260 and 280 nm to 1.91 ( A 260 / A 280 = 1.91>1.8), indicating that the purity of ctDNA concentrate meets the requirements (Zhou et al, 2019 ). Finally, the absorbance value of ctDNA solution at 260 nm was determined, and the concentration in the reserve solution was calculated to be 3.22 × 10 −3 mol L −1 by using molar absorbance coefficient ε 260 = 6,600 L mol −1 cm −1 .…”

Green alternative methods for pretreatment of whole jujube before the drying process

“…It is generally believed that HMF is formed by the thermal decomposition of carbohydrates. Recent studies have shown that the Maillard reaction is an important way for the production of HMF in food 34‐36 . Thus, a reduced level of HMF in food products could reduce the health risks to the consumer 37 .…”

“…Recent studies have shown that the Maillard reaction is an important way for the production of HMF in food. [34][35][36] Thus, a reduced level of HMF in food products could reduce the health risks to the consumer. 37 From Table 2, it is seen that the HMF content in dried jujubes varied with the variation of pretreatment.…”

Interaction behavior between bisphenol AP and pepsin: Insights from density functional theory, and spectroscopic and molecular dynamic simulation

“…The initial snapshot of the MD process is shown in Figure 8A. Root mean square deviation (RMSD) is an important indicator to calculate the deviation of Cα backbone atoms from the overlap of the instantaneous structures (Brogi et al, 2020;Wang et al, 2015a;Zhou et al, 2018). A smaller deviation represents a higher spatial equivalent of the compared structures.…”