Spectroscopic and molecular modeling methods to investigate the interaction between 5-Hydroxymethyl-2-furfural and calf thymus DNA using ethidium bromide as a probe.
In this work, the interaction of 5-Hydroxymethyl-2-furfural (5-HMF) with calf thymus DNA (ctDNA) under simulated physiological conditions (Tris-HCl buffer of pH 7.40), was explored by UV absorption spectroscopy, fluorescence spectroscopy and molecular modeling method, using ethidium bromide (EB) as a fluorescence probe of DNA. The fluorescence quenching mechanism of EB-ctDNA by 5-HMF was confirmed to be a static quenching, which derived from the formation of a new complex. The binding constants of 5-HMF with DNA in the presence of EB were calculated to be 2.17×10(3), 4.24×10(3) and 6.95×10(3) L mol(-1) at 300, 305 and 310 K, respectively. The calculated thermodynamic parameters, enthalpy change ΔH and entropy change ΔS, suggested that both hydrophobic interactions and hydrogen bonds played a predominant role in the binding of 5-HMF to DNA. According to the UV absorption spectroscopy and melting temperature (Tm) curve results, the binding mode of 5-HMF with DNA was indicative of a non-intercalative binding, which was supposed to be a groove binding. The molecular modeling results showed that 5-HMF could bind into the hydrophobic region of ctDNA and supported the conclusions obtained from the above experiments.
Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, China. Electronic address: zhujinhua0528@163.com.
Jinhua
J
Zhu
Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, China.
Lanlan
L
Chen
Key Lab of Natural Drug and Immune Engineering of Henan Province, Kaifeng, Henan 475004, China.
Yingying
Y
Dong
School of Pharmacy, Lanzhou University, Donggang West Road 199, 730000 Lanzhou, China.
Jiazhong
J
Li
Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, China; Key Lab of Natural Drug and Immune Engineering of Henan Province, Kaifeng, Henan 475004, China.
Xiuhua
X
Liu
D000818:Animals; D002417:Cattle; D004247:DNA / Q000378:metabolism*; D015342:DNA Probes / Q000378:metabolism*; D004996:Ethidium / Q000378:metabolism*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D008958:Models, Molecular; D009691:Nucleic Acid Denaturation; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature
D015342:DNA Probes; C008046:5-hydroxymethylfurfural; D004247:DNA; C427203:calf thymus DNA; D005662:Furaldehyde; D004996:Ethidium
5-Hydroxymethyl-2-furfural; Calf thymus DNA; Ethidium bromide; Molecular modeling; Spectroscopy