New affinity-based probes for capturing flavonoid-binding proteins

Carrié, Hélène; Tran, Dong Tien; Rousseau, Sabrina; Chaignepain, Stéphane; Schmitter, Jean‐Marie; Deffieux, Denis; Quideau, Stéphane

doi:10.1039/c4cc04557b

Cited by 11 publications

(22 citation statements)

References 28 publications

(8 reference statements)

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“…The previously reported reactions differ from our approach since they consider; 1) modifications through the Vilsmeier-Haack and Homer-Wadsworth-Emmons (HWE) reactions, forming a lactone group in the flavanol A ring with the objective to couple the flavonoid to a polyethylene glycol resin with free amino groups [23,24], 2) modifications on EC by the addition of propargyl groups at C3 position in order to couple the flavonoid to an agarose matrix with azide [25].…”

Section: Discussionmentioning

confidence: 95%

“…The proposed reaction considered the EC's structural characteristics: no double bond between C2 and C3 carbons, a carbonyl group on C ring, a hydroxyl group in C3 carbon and acidic hydrogens (as is required for Mannich reaction) in the A and B rings. These reasons make this project different compared to another previously synthetized columns [23,24].…”

Section: Discussionmentioning

confidence: 95%

“…On this regard, some attempts had been implemented to search proteins that can interact with EC as example: exchange columns to determine structural identifiers of EC and (þ)-catechin required for their interaction with an specific flavonoid enzyme in vegetal extracts, highlighting the importance of chiral centers [23,24]. Similarly, in the recent past our group developed an affinity column with EC to isolate proteins, using a methodology which blocks the C3 hydroxyl group; this approach allowed the isolation of GPER from endothelial cells [25].…”

Section: Introductionmentioning

confidence: 99%

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PXR is a target of (-)-epicatechin in skeletal muscle

Ortiz-Flores

Portilla-Martínez

Cabrera-Pérez

et al. 2020

Heliyon

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Epicatechin (EC) is a flavanol that has shown numerous biological effects such as: decrease risk of cardiovascular dysfunction, metabolism regulation, skeletal muscle (SkM) performance improvement and SkM cells differentiation induction, among others. The described EC acceptor/receptor molecules do not explain the EC's effect on SkM. We hypothesize that the pregnane X receptor (PXR) can fulfill those characteristics, based on structural similitude between EC and steroidal backbone and that PXR activation leads to similar effects as those induced by EC. In order to demonstrate our hypothesis, we: 1) analyzed the possible EC and mouse PXR interaction through in silico strategies, 2) developed an EC's affinity column to isolate PXR, 3) evaluated, in mouse myoblast (C2C12 cells) the inhibition of EC-induced PXR's nucleus translocation by ketoconazole, a specific blocker of PXR and 4) analyzed the effect of EC as an activator of mouse PXR, evaluating the expression modulation of cytochrome 3a11 (Cyp3a11) gen and myogenin protein. (-)-Epicatechin interacts and activates PXR, promoting this protein translocation to the nucleus, increasing the expression of Cyp3a11, and promoting C2C12 cell differentiation through increasing myogenin expression. These results can be the base of further studies to analyze the possible participation of PXR in the skeletal muscle effects shown by EC.

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Section: Discussionmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

PXR is a target of (-)-epicatechin in skeletal muscle

Ortiz-Flores

Portilla-Martínez

Cabrera-Pérez

et al. 2020

Heliyon

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“…Another set of interesting natural products belong to the class of flavonoids, as they are among the most studied bioactive plant polyphenols but with a limited knowledge about their binding targets. Aiming at shedding some light on this aspect, a series of probes to investigate flavonoid‐protein specific interactions (Figure 10C) have been reported [61] …”

Section: Biomedical Applicationsmentioning

confidence: 99%

“…Aiming at shedding some light on this aspect, a series of probes to investigate flavonoid-protein specific interactions ( Figure 10C) have been reported. [61]…”

Section: Use Of Probes For Finding the Molecular Target Of Natural Prmentioning

confidence: 99%

Chemistry for the Identification of Therapeutic Targets: Recent Advances and Future Directions

et al. 2021

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The increasing availability of chemical probes for specific applications in chemical biology and medicinal chemistry is extensively facilitating our knowledge of biological systems. This understanding has fundamental implications in the development of new efficacious therapeutic strategies. Nowadays, successful drug discovery programs consider identification, engagement, and endogenous levels of the intended therapeutic target from the earliest preclinical stages. All these aspects are addressed with the use of chemical probes, compounds that rely on the use of a particular chemical reaction to give an answer to a specific biological question. In this review we will describe the underlying chemistry and the most recent advances experienced in the field together with their most important biomedical applications.

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Real‐Time Analysis of Polyphenol–Protein Interactions by Surface Plasmon Resonance Using Surface‐Bound Polyphenols

López

Tran

Viault

et al. 2021

Chemistry A European J

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As election of bioactive polyphenols of different structural classes, such as the ellagitannins vescalagin and vescalin, the flavanoidsc atechin, epicatechin,e pigallocatechin gallate (EGCG), and procyanidin B2, and the stilbenoids resveratrol and piceatannol, were chemically modified to bear ab iotin unit for enabling their immobilization on streptavidin-coateds ensor chips. These sensorc hips were used to evaluate in real time by surfacep lasmon resonance(SPR) the interactionso fthree different surface-bound polyphenolic ligandsp er sensorc hip with variousp rotein analytes, including human DNA topoisomerase IIa,f lavonoid leucoanthocyanidin dioxygenase, B-cell lymphoma 2a poptosis regulator protein,a nd bovine serum albumin. The types and levels of SPR responses unveiled major differences in the association,o rl ack thereof,a nd dissociation between ag iven protein analyte and different polyphenolic ligands. Thus,t his multi-analysis SPR technique is av aluablem ethodology to rapidly screena nd qualitatively compare various polyphenol-protein interactions.

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New affinity-based probes for capturing flavonoid-binding proteins

Cited by 11 publications

References 28 publications

PXR is a target of (-)-epicatechin in skeletal muscle

PXR is a target of (-)-epicatechin in skeletal muscle

Chemistry for the Identification of Therapeutic Targets: Recent Advances and Future Directions

Real‐Time Analysis of Polyphenol–Protein Interactions by Surface Plasmon Resonance Using Surface‐Bound Polyphenols

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