The Nature of Phosphorylated Chrysin−Protein Interactions Involved in Noncovalent Complex Formation by Electrospray Ionization Mass Spectroscopy

Chen, Xiaolan; Qu, Lingbo; Zhang, Ting; Liu, Hongxia; Yu, Fei; Yu, Youzhu; Liao, Xincheng; Zhao, Yufen

doi:10.1021/ac035027q

Cited by 36 publications

(19 citation statements)

References 25 publications

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“…Chrysin is a member from the flavone subgroup of flavonoid and has shown antiviral activity in our previous assay against enterovirus 71 (Wang et al, 2014b). As phosphorylated flavonoids usually demonstrated relatively stronger binding affinities and enhanced activity compared with non-phosphorylated forms (Chen et al, 2004(Chen et al, , 2007. In the present study, we tested anti-DENV activity for CPI, the phosphate ester for chrysin.…”

Section: Discussionmentioning

confidence: 99%

Inhibition of dengue virus replication by diisopropyl chrysin-7-yl phosphate

Chen

Zhang

et al. 2016

Sci. China Life Sci.

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Dengue fever is a tropical disease and caused by dengue virus (DENV), which is transmitted by mosquitoes and infects about 400 million people annually. With the development of international trade and travel, China is facing a growing threat. Over 40 thousands of people were infected during the 2014 DENV outbreak in Guangdong. Neither licensed vaccine nor therapeutic drug has been available. In this report, we isolated two clinical DENV strains. The full-length genome was sequenced and characterized. We also applied a flavonoid, CPI, into an anti-DENV assay. Replication of viral RNA and expression of viral protein was all strongly inhibited. These results indicated that CPI may serve as potential protective agents in the treatment of patients with chronic DENV infection.

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Section: Discussionmentioning

confidence: 99%

Inhibition of dengue virus replication by diisopropyl chrysin-7-yl phosphate

Chen

Zhang

et al. 2016

Sci. China Life Sci.

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“…Since its introduction by Yamashita and Fenn in 1984, [17] ESI-MS has been widely used in chemical and biological research, such as peptide sequencing, [18] phosphopeptide detection and phosphosite localization, [19] and interactions of non-covalent macromolecule-ligand. [20] Moreover, the development of ESI-MS has greatly enhanced the ability of chemists to study chemically active molecules in gas phase and opened the door to important new applications in conventional organic chemistry analysis. Although the molecular environment of gasphase reaction is different from that of liquid-phase system, gas-phase studies without the influences of solvent interferences 780 X. Gao et al…”

Section: Introductionmentioning

confidence: 99%

Formation of cyclic acylphosphoramidates in mass spectra of N‐monoalkyloxyphosphoryl amino acids using electrospray ionization tandem mass spectrometry

Gao

Bao

et al. 2010

J. Mass Spectrom.

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The fragmentation reactions of N-monoalkyloxyphosphoryl amino acids (N-MAP-AAs) were studied by electrospray ionization tandem mass spectrometry (ESI-MS). The sodiated cyclic acylphosphoramidates (CAPAs) were formed through a characteristic pentacoordinate phosphate participated rearrangement reaction in the positive-ion ESI-MS/MS and HR-MS/MS of N-MAP-AAs, in which the fragmentation patterns were clearly different from those observed in the corresponding ESI-MS/MS of N-dialkyloxyphosphoryl amino acids/peptides and N-phosphono amino acids. The formation of CAPAs depended on the chemical structures of N-terminal phosphoryl groups, such as alkyloxy group, negative charge and alkali metal ion. A possible integrated rearrangement mechanism for both P-N to P-O phosphoryl group migration and formation of CAPAs was proposed. The fragmentation patterns of CAPAs as novel intermediates in gas phase were also investigated. In addition, it was found that the formation of alpha-amino acid CAPAs was more favorable than beta- or gamma-CAPAs in gas phase, which was consistent with previous solution-phase experiments.

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“…It also prevented cytopathic effects (CPE). Phosphorylated flavonoids demonstrated relatively stronger binding affinities and enhanced activity compared with non-phosphorylated forms [30], [31]. Therefore, we generated diisopropyl chrysin-7-yl phosphate (CPI), the phosphate ester for CR, through a simplified Atheron-Todd reaction.…”

Section: Introductionmentioning

confidence: 99%

Anti-Enterovirus 71 Effects of Chrysin and Its Phosphate Ester

Wang

Zhang

et al. 2014

PLoS ONE

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Enterovirus 71 (EV71) can cause severe disease and even lead to death in children, and an effective antiviral drug is currently unavailable. The anti-EV71 effect of chrysin (5,7-dihydroxyflavone), a natural flavonoid commonly found in many plants, was tested in this report. By using the predicting program Autodock 4.0 and an in vitro protease inhibition assay, we found that chrysin could suppress viral 3Cpro activity. Replication of viral RNA and production of viral capsid protein and the infectious virion were strongly inhibited by chrysin, without noticeable cytotoxicity. Cytopathic effects on cells were also prevented. Diisopropyl chrysin-7-yl phosphate (CPI), the phosphate ester for chrysin, was generated through a simplified Atheron-Todd reaction to achieve stronger anti-viral activity. CPI was also able to bind with and inhibit viral 3Cpro activity in vitro. As expected, CPI demonstrated more potent antiviral activity against EV71.

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The Nature of Phosphorylated Chrysin−Protein Interactions Involved in Noncovalent Complex Formation by Electrospray Ionization Mass Spectroscopy

Cited by 36 publications

References 25 publications

Inhibition of dengue virus replication by diisopropyl chrysin-7-yl phosphate

Inhibition of dengue virus replication by diisopropyl chrysin-7-yl phosphate

Formation of cyclic acylphosphoramidates in mass spectra of N‐monoalkyloxyphosphoryl amino acids using electrospray ionization tandem mass spectrometry

Anti-Enterovirus 71 Effects of Chrysin and Its Phosphate Ester

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