Evaluation of Flavonoids Binding to DNA Duplexes by Electrospray Ionization Mass Spectrometry

• Published in: Journal of the American Society for Mass Spectrometry Vol. 19; no. 7; pp. 914 - 922
• Main Authors: Wang, Zhaofu, Cui, Meng, Song, Fengrui, Lu, Lin, Liu, Zhiqiang, Liu, Shuying
• Format: Journal Article
• Language: English
• Published: New York Elsevier Inc 01.07.2008; Springer-Verlag; Elsevier Science
• Subjects: Analytical Chemistry; Bioinformatics; Biological and medical sciences; Biotechnology; Chemistry; Chemistry and Materials Science; DNA - chemistry; Flavonoids - chemistry; Fundamental and applied biological sciences. Psychology; Humans; Interactions. Associations; Intermolecular phenomena; Molecular biophysics; Oligonucleotides - chemistry; Organic Chemistry; Proteomics; Spectrometry, Mass, Electrospray Ionization - methods; Baicalein; Naringin; Electrospray Ionization Mass Spectrometry; Flavonoid; Flavone; Tandem mass spectrometry; Collisional activation; Molecular interaction; Glycosylation; Duplex; Electrospray; Biological fixation; DNA; Non covalent binding; Negative ion; Oligonucleotide; Oligodeoxyribonucleotide; Mass spectrometry
• ISSN: 1044-0305; 1879-1123
• DOI: 10.1016/j.jasms.2008.04.018

In this study, electrospray ionization mass spectrometry (ESI-MS) was used to investigate the binding interactions of ten flavonoid aglycones and ten flavonoid glycosides with DNA duplexes. Relative binding affinities of the flavonoids toward DNA duplexes were estimated based on the fraction of bound DNA. The results revealed that the 4′-OH group of flavonoid aglycones was essential for their DNA-binding properties. Flavonoid glycosides with sugar chain linked on ring A or ring B showed enhanced binding toward the duplexes over their aglycone counterparts, whereas glycosylation of the flavonol quercetin on ring C exhibited a less pronounced effect. The aglycone skeletons and other hydroxyl substitutions on the aglycone also have an effect on the fractions of bound DNA. Upon collision-induced dissociation, the complexes containing flavonoid aglycones underwent the predominant ejection of a neutral ligand molecule, suggesting an intercalative DNA-binding mode. However, for complexes containing flavonoid glycosides, the loss of nucleobase increased to different extents, indicating a stronger binding or different binding mode. The results may provide not only a deeper insight into the DNA-binding properties of flavonoids but also a useful guideline for the design of efficient DNA-binding agents for chemotherapy.