Synthesis, structural characterization and study of antioxidant and anti-PrPSc properties of flavonoids and their rhenium(I)–tricarbonyl complexes

IF 2.7 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY JBIC Journal of Biological Inorganic Chemistry Pub Date : 2023-01-25 DOI:10.1007/s00775-022-01986-9
Pigi Glykofridi, Vassiliki-Eleni Tziouri, Konstantinos Xanthopoulos, Maria-Eirini Vlachou, Susana Correia, Anna-Lisa Fischer, Katrin Thüne, Antonios Hatzidimitriou, Inga Zerr, Matthias Schmitz, Theodoros Sklaviadis, Dimitra Hadjipavlou-Litina, Dionysia Papagiannopoulou
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引用次数: 1

Abstract

This study aims at the synthesis and initial biological evaluation of novel rhenium–tricarbonyl complexes of 3,3′,4′,5,7-pentahydroxyflavone (quercetin), 3,7,4΄-trihydroxyflavone (resokaempferol), 5,7-dihydroxyflavone (chrysin) and 4΄,5,7-trihydroxyflavonone (naringenin) as neuroprotective and anti-PrP agents. Resokaempferol was synthesized from 2,2΄,4-trihydroxychalcone by H2O2/NaOH. The rhenium–tricarbonyl complexes of the type fac-[Re(CO)3(Fl)(sol)] were synthesized by reacting the precursor fac-[Re(CO)3(sol)3]+ with an equimolar amount of the flavonoids (Fl) quercetin, resokaempferol, chrysin and naringenin and the solvent (sol) was methanol or water. The respective Re–flavonoid complexes were purified by semi-preparative HPLC and characterized by spectroscopic methods. Furthermore, the structure of Re–chrysin was elucidated by X-ray crystallography. Initial screening of the neuroprotective properties of these compounds included the in vitro assessment of the antioxidant properties by the DPPH assay as well as the anti-lipid peroxidation of linoleic acid in the presence of AAPH and their ability to inhibit soybean lipoxygenase. From the above studies, it was concluded that the complexes’ properties are mainly correlated with the structural characteristics and the presence of the flavonoids. The flavonoids and their respective Re-complexes were also tested in vitro for their ability to inhibit the formation and aggregation of the amyloid-like abnormal prion protein, PrPSc, by employing the real-time quaking-induced conversion assay with recombinant PrP seeded with cerebrospinal fluid from patients with Creutzfeldt–Jakob disease. All the compounds blocked de novo abnormal PrP formation and aggregation.

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黄酮类化合物及其铼(I) -三羰基配合物的合成、结构表征及抗氧化和抗prpsc性能研究
本研究旨在合成和初步生物学评价新型的3,3 ',4 ',5,7-五羟黄酮(槲皮素),3,7,4΄-trihydroxyflavone(山奈酚),5,7-二羟黄酮(菊花素)和4΄,5,7-三羟黄酮(柚皮素)的三羰基配合物作为神经保护和抗prp药物。以2,2΄,4-三羟基查尔酮为原料,用H2O2/NaOH催化合成了山奈酚。以fac-[Re(CO)3(sol)3]+为前驱体,以等摩尔量的黄酮类化合物(Fl)槲皮素、山奈酚、菊花素和柚皮素为溶剂(sol),合成了fac-[Re(CO)3(Fl)(sol)]型铼-三羰基配合物。采用半制备高效液相色谱法对其进行纯化,并用波谱法对其进行表征。并用x射线晶体学对其结构进行了表征。这些化合物的神经保护特性的初步筛选包括通过DPPH测定体外抗氧化特性的评估,以及AAPH存在下亚油酸的抗脂质过氧化作用和它们抑制大豆脂氧合酶的能力。综上所述,配合物的性能主要与结构特征和黄酮类化合物的存在有关。通过实时振动诱导的方法,将重组PrP植入克雅氏病患者脑脊液中,在体外测试了黄酮类化合物及其各自的re -复合物对淀粉样异常朊蛋白PrPSc形成和聚集的抑制能力。所有化合物都阻断了新生异常PrP的形成和聚集。图形抽象
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来源期刊
JBIC Journal of Biological Inorganic Chemistry
JBIC Journal of Biological Inorganic Chemistry 化学-生化与分子生物学
CiteScore
5.90
自引率
3.30%
发文量
49
审稿时长
3 months
期刊介绍: Biological inorganic chemistry is a growing field of science that embraces the principles of biology and inorganic chemistry and impacts other fields ranging from medicine to the environment. JBIC (Journal of Biological Inorganic Chemistry) seeks to promote this field internationally. The Journal is primarily concerned with advances in understanding the role of metal ions within a biological matrix—be it a protein, DNA/RNA, or a cell, as well as appropriate model studies. Manuscripts describing high-quality original research on the above topics in English are invited for submission to this Journal. The Journal publishes original articles, minireviews, and commentaries on debated issues.
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