Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay

Nishizaki, Yosuke; Ishimoto, Yoichi; Hotta, Yudai; Hosoda, Akira; Yoshikawa, Hiromichi; Akamatsu, Miki; Tamura, Hiroto

doi:10.1016/j.bmcl.2009.06.073

Cited by 25 publications

(12 citation statements)

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“…Flavonoids are a naturally occurring subclass of polyphenols based on a C6‐C3‐C6 phenyl‐benzopyran backbone . The high versatility of the flavonoid scaffold provides them with promiscuous affinity towards a plethora of biological targets, which in turn influence a number of cancer‐related processes, such as cellular proliferation, differentiation, apoptosis, metastasis and reversal of multidrug‐resistance . Flavopiridol (Alvocidib) and P276–00 are two new antitumour agents bearing a flavonoid scaffold undergoing clinical development.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity studies, DNA interaction and protein binding of new Al (III), Ga (III) and In (III) complexes with 5‐hydroxyflavone

Arbănași

Badea

Olar

et al. 2018

Applied Organom Chemis

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We report the synthesis and characterization of three new complexes of the natural flavonoid 5-hydroxyflavone (primuletin) and Al (III), Ga (III), In (III), respectively. The physico-chemical properties and structural features of these three novel compounds have been investigated by elemental and thermogravimetric analysis, molar conductance and several spectroscopic techniques, including FT-IR, UV-Vis and mass spectra. Based on the experimental data, the general chemical formula of the complexes iswhere M is the cation and n = 2 for Al (III), n = 0 for Ga (III), n = 1, for In (III); each one of the three 5-hydoxyflavone molecules acts as a monoanionic bidentate chelate ligand in the complexes. DFT calculations further sustain the proposed structures of the complexes. Cytotoxicity was studied using MTS assay on cervical, breast, colon and ovary adenocarcinoma cell lines.The central metal ions exert cytotoxic effects in a disparate manner: Al (III) enhances, while Ga (III) and In (III) decrease the cytotoxicity of the ligand.As a means to investigate the mechanism underlying the cytotoxic effects of the complexes, interactions with calf thymus DNA, human serum albumin and transferrin were also carried out.This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Section: Introductionmentioning

confidence: 99%

Cytotoxicity studies, DNA interaction and protein binding of new Al (III), Ga (III) and In (III) complexes with 5‐hydroxyflavone

Arbănași

Badea

Olar

et al. 2018

Applied Organom Chemis

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“…In comparison to other flavonoids, the biological activity of 5-hydroxyflavone (5-HOF) is yet poorly explored. To date, it has been reported that 5-HOF acts as an agonist of calcium-activated and ATP-sensitive potassium channels [27], and has strong vasorelaxing and androgen receptor antagonistic activity [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Investigation of New Bio-Relevant Complexes of Lanthanides with 5-Hydroxyflavone: DNA Binding and Protein Interaction Studies

et al. 2016

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Abstract:In the present work, we attempted to develop new metal coordination complexes of the natural flavonoid 5-hydroxyflavone with Sm(III), Eu(III), Gd(III), Tb(III). The resultant hydroxo complexes have been characterized by a variety of spectroscopic techniques, including fluorescence, FT-IR, UV-Vis, EPR and mass spectral studies. The general chemical formula of the complexes is [Ln(C 15 H 9 O 3 ) 3 (OH) 2 (H 2 O) x ]·nH 2 O, where Ln is the lanthanide cation and x = 0 for Sm(III), x = 1 for Eu(III), Gd(III), Tb(III) and n = 0 for Sm(III), Gd(III), Tb(III), n = 1 for Eu(III), respectively. The proposed structures of the complexes were optimized by DFT calculations. Theoretical calculations and experimental determinations sustain the proposed structures of the hydroxo complexes, with two molecules of 5-hydroxyflavone acting as monoanionic bidentate chelate ligands. The interaction of the complexes with calf thymus DNA has been explored by fluorescence titration and UV-Vis absorption binding studies, and revealed that the synthesized complexes interact with DNA with binding constants (K b )~10 4 . Human serum albumin (HSA) and transferrin (Tf) binding studies have also been performed by fluorescence titration techniques (fluorescence quenching studies, synchronous fluorescence spectra). The apparent association constants (K a ) and thermodynamic parameters have been calculated from the fluorescence quenching experiment at 299 K, 308 K, and 318 K. The quenching curves indicate that the complexes bind to HSA with smaller affinity than the ligand, but to Tf with higher binding affinities than the ligand.

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“…3,4) We have already reported that some flavonoids act as a novel androgen receptor ligand which interacts with the receptor in a different manner from known androgen receptor ligands. 5) We also disclosed that 5-hydroxyflavone have extremely high AR antagonistic activity, and that the hydroxyl group at the 5-position plays an important role in the interaction with the AR. Furthermore, the introduction of hydroxyl group at the 4Ј-position increases AR antagonistic activity as well.…”

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confidence: 87%

An Effective Synthesis of 5,4'-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction

Matsugi

Takeda

Takahashi

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay

Cited by 25 publications

References 9 publications

Cytotoxicity studies, DNA interaction and protein binding of new Al (III), Ga (III) and In (III) complexes with 5‐hydroxyflavone

Cytotoxicity studies, DNA interaction and protein binding of new Al (III), Ga (III) and In (III) complexes with 5‐hydroxyflavone

Synthesis and Structural Investigation of New Bio-Relevant Complexes of Lanthanides with 5-Hydroxyflavone: DNA Binding and Protein Interaction Studies

An Effective Synthesis of 5,4'-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction

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