Synthesis And Characterization And Bioactivities Of Sulfonated Flavone-Metal Complexes

Objectiv In oder to improve the bioavailability and resolve the problem of poor water-solubility of flavone. In this article, through the reaction of sulfonate and complexing, weobtained sulfonated flavone-metal complexes. Lay the foundation to developing highbiological activity and water-soluble of flavonoids drug.Methods （1） Series of sulfonated flavone-metal complexes were prepared through theconventional methods used quercitin and luteolin with intermediates of flavonoidssulfonic acid sodium respectively with Zn²⁺, Cu²⁺, Co²⁺and Mn²⁺coordination.（2）Identify the structure with nuclear magnetic resonance （NMR） spectroscopy, massspectrum and infrared spectrum.（3） investigated the in vitro antibacterial activity oftest compounds by slip method.（4） complexes of antioxidant activity through theDPPH radical scavenger.（5） Use MTT method to filtrate inhibition of complexex withMCF-7cancer cells.Results （1）78%productivity of3.2g intermediates of quercetin sulfonic acid sodiu and71.25%productivity of2.85g intermediates of luteolin sulfonic acid sodiu were preparedthrough sulfonation reaction used quercetin and luteolin.46.94%⁶4.71%productivity of8target compound through complexing reaction.（2）8target compounds were identify ofsulfonated quercitin-zinc complexes （I）, sulfonated quercitin-copper complexes （II）,sulfonated quercitin-cobalt complexes （III）, sulfonated quercitin-manganese complexes （IV）,sulfonated luteolin-zinc complexes （V）, sulfonated luteolin-copper complexes （VI）,sulfonated luteolin-cobalt complexes （VII）, sulfonated luteolin-manganese complexes （VIII）,with nuclear magnetic resonance （NMR） spectroscopy, mass spectrum and infrared spectrumrespectively.（3） Antibacterial research shows that the inhibitory effect of staphylococcusaureus and escherichia coli through the increase of concentration and improve of Sulfonatedflavone-metal complexes, in the concentration of2.5mg·mL^-1, the bacteriostatic annulus ofstaphylococcus aureus size were1.60mm and3.52mm with complexes （I） and complexes（V）, the escherichia coli size were1.21mm with complexes （I）. In the concentration of5.0mg·mL^-1, the bacteriostatic annulus of staphylococcus aureus size were2.10mm and7.10mm with complexes （I） and complexes （V）, the escherichia coli of size were2.87mm with complexes （I）. In the concentration of7.5mg·mL^-1, the bacteriostatic annulus ofstaphylococcus aureus size were3.60mm,9.67mm,4.48mm and3.09mm, the escherichiacoli of size were3.79mm with complexes （I）.（4） Antioxidant research shows that Theclearance DPPH through the increase of concentration and improve of sulfonated luteolin-metal complexes, In the concentration of0.002mmoL^-1, the clearance rate of DPPH were38.24%,53.59%,38.02%,46.95%,42.13%,61.24%,28.37%and64.68%with complexes（I^VIII）. In the concentration of0.004mmoL^-1, the clearance rate of DPPH were41.05%,63.64%,40.14%,49.51%,43.03%,67.36%,39.29%and76.31%with complexes （I^VIII）.In the concentration of0.008mmoL^-1, the clearance rate of DPPH were42.97%,79.55%,43.23%,50.18%,45.13%,73.75%,40.66%and94.48%with complexes （I^VIII）. In theconcentration of0.020mmoL^-1, the clearance rate of DPPH were43.89%,89.99%,45.20%,58.18%,47.55%,76.14%,46.21%and97.08%with complexes （I^VIII）. In theconcentration of0.040mmoL^-1, the clearance rate of DPPH were47.55%,91.40%,46.74%,68.22%,51.70%,80.40%,48.32%and97.13%with complexes （I^VIII）.（5） Anticancerexperiment in vitro shows that the inhibitory effect of MCF-7cancer cells through theincrease of concentration and improve of sulfonated luteolin-metal complexes, through thedose screeing, In the concentration of50μg·mL^-1, IC50were150.72±12.30and134.8±10.57with sulfonated quercitin-metal complexes and sulfonated luteolin-metal complexes.Conclution The sulfonated flavone-metal complexes through the reaction of sulfonateand complexing have good water soluble, part of the complexes have stronger antimicrobialactivity and have cleared DPPH free radical activity, anticancer experiment in vitro showsthat part of the sulfonated flavone-metal complexes for human MCF-7inhibition slightlybetter than flavone ontology.