Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents

Burmaoğlu, Serdar; Özcan, Şeyda; Balcıoğlu, Sevgi; Gencel, Melis; Noma, Samir Abbas Ali; Eşsiz, Şebnem; Ateş, Burhan; Algül, Öztekin

doi:10.1016/j.bioorg.2019.103149

Cited by 53 publications

(23 citation statements)

References 22 publications

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“…Inhibition of NO can lead to a variety of beneficial effects beyond urate lowering, as observed with the classical XO inhibitor allopurinol which presents also anticancer properties [81]. Anticancer XO inhibitors are actively searched [82]. LBT has revealed a cardioprotective activity, with an anti-arrhythmic activity demonstrated in experimental models [83].…”

Section: Other Bioactivities Of Lobetyolin: Antioxidant and Cardiopromentioning

confidence: 99%

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

Bailly

2020

Nat. Prod. Bioprospect.

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Lobetyolin (LBT) is a polyacetylene glycoside found in diverse medicinal plants but mainly isolated from the roots of Codonopsis pilosula, known as Radix Codonopsis or Dangshen. Twelve traditional Chinese medicinal preparations containing Radix Codonopsis were identified; they are generally used to tonify spleen and lung Qi and occasionally to treat cancer. Here we have reviewed the anticancer properties of Codonopsis extracts, LBT and structural analogs. Lobetyolin and lobetyolinin are the mono- and bis-glucosylated forms of the polyacetylenic compound lobetyol. Lobetyol and LBT have shown activities against several types of cancer (notably gastric cancer) and we examined the molecular basis of their activity. A down-regulation of glutamine metabolism by LBT has been evidenced, contributing to drug-induced apoptosis and tumor growth inhibition. LBT markedly reduces both mRNA and protein expression of the amino acid transporter Alanine-Serine-Cysteine Transporter 2 (ASCT2). Other potential targets are proposed here, based on the structural analogy with other anticancer compounds. LBT and related polyacetylene glycosides should be further considered as potential anticancer agents, but more work is needed to evaluate their efficacy, toxicity, and risk–benefit ratio.

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Section: Other Bioactivities Of Lobetyolin: Antioxidant and Cardiopromentioning

confidence: 99%

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

Bailly

2020

Nat. Prod. Bioprospect.

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“…synthesized eight bis‐chalcone derivatives by Claisen–Schmidt condensation reaction. Among them, the ones with fluoro group at the 2 or 2,5‐position of B‐ring were found to be potent XO inhibitors with sevenfold higher inhibitory effects than allopurinol (Burmaoglu et al., 2019).…”

Section: Flavonoidsmentioning

confidence: 99%

Advances in structures required of polyphenols for xanthine oxidase inhibition

et al. 2020

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Polyphenols have been used as natural medicaments for the management of hyperuricemia for a long history. They have been attracted many interests because of the little side effects in curing hyperuricemia, which is an important advantage over the antihyperuricemic drugs. In this review, the structure-activity relationships for polyphenols as xanthine oxidase (XO) inhibitors were discussed. It is concluded that the presence of hydroxyl groups, which influences the inhibitory effects, is closely related to whether the substitutions increase the steric hindrance or disturb the interaction of flavonoid with the catalytic site of XO, and the increased size of the molecule after glycosylation may increase the steric hindrance between flavonoid and XO, and consequently reducing the competitive inhibition behaviors. However, there is no obtained simple general rule that can comprehensively describe the effects of structural alteration on the inhibition activity because the results are varied among different subclasses of polyphenols. In addition, the inhibition mechanisms are mainly assumed as polyphenol binding to the active site of XO and hindering the entrance of xanthine or the discharge of uric acid and diffusion of O 2− radical.

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“…The bis-chalcone with fluoro group at the 2 nd or 2, 5 th position of B-ring was found to be a potent inhibitor of the enzyme possessing IC 50 values in the low micromolar range. The activities of the compounds were found to be around seven times higher than the standard allopurinol [25].…”

Section: Anticancer Chalconesmentioning

confidence: 88%

Biological Role of Chalcones in Medicinal Chemistry

Tekale¹,

Mashele²,

Pooe³

et al. 2020

Vector-Borne Diseases - Recent Developments in Epidemiology and Control

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Chalcones are promising synthons and bioactive scaffolds of great medicinal interest due to their numerous pharmacological and biological activities. They are well recognized to possess antimicrobial, anticancer, antitubercular, antioxidant, anti-inflammatory, antileishmanial, and other significant biological activities. This chapter highlights recent updates and applications of chalcones as biologically, pharmacologically, and medicinally important entities.

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Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents

Cited by 53 publications

References 22 publications

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen)

Advances in structures required of polyphenols for xanthine oxidase inhibition

Biological Role of Chalcones in Medicinal Chemistry

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