Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

Donnier-Maréchal, Marion; Abdullayev, Shuay; Bauduin, Marvin; Pascal, Yoann; Fu, Meng-Qi; He, Xiao‐Peng; Gillon, Émilie; Imberty, Anne; Kipnis, Éric; Dessein, Rodrigue; Vidal, Sébastien

doi:10.1039/c8ob02035c

Cited by 29 publications

(27 citation statements)

References 31 publications

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“…Dimethoxy‐TPE [16] 2 was demethylated then propargylated and conjugated with azido‐functionalized glycosides (β‐galactose, β‐glucose, α‐mannose and α‐fucose) through azide‐alkyne click chemistry (Scheme 2). After deprotection under MeOH/H 2 O/Et 3 N solution, divalent TPE‐based glycoclusters ( TPE‐Gly 2 ) were obtained, while the tetravalent TPE‐based glycoclusters ( TPE‐Gly 4 ) were previously reported by us [14] …”

Section: Resultsmentioning

confidence: 90%

“…After deprotection under MeOH/H 2 O/Et 3 Ns olution, divalent TPE-based glycoclusters (TPE-Gly 2 )w ere obtained, while the tetravalentT PE-based glycoclusters (TPE-Gly 4 )w erepreviously reported by us. [14] Fluorescence properties of the DM probes…”

Section: Synthesis Of Dm-based Fluorescent Probesmentioning

confidence: 99%

“…Te traphenylethene (TPE) is af luorogen with aggregation-induced emission properties, and TPE-basedg lycoclustersh ave been developed for lectin sensing. [14] The amphiphilic TPEbased glycoclustersi nP BS buffer,m ight well self-assemble with the hydrophobic DM probes. The corresponding glycodots with satisfying water solubility were monitored for their response peroxynitrite in PBS buffer.T herefore, we have designed two DM-boronatef luorescent probes( DMB1 and DMB2)f or peroxynitrite detection.…”

Section: Introductionmentioning

confidence: 99%

“…Tetraphenylethene (TPE) is a fluorogen with aggregation‐induced emission properties, and TPE‐based glycoclusters have been developed for lectin sensing [14] . The amphiphilic TPE‐based glycoclusters in PBS buffer, might well self‐assemble with the hydrophobic DM probes.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular Assembly of TPE‐Based Glycoclusters with Dicyanomethylene‐4H‐pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Dong

Liu

et al. 2020

Chemistry A European J

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Twor ed-emitting dicyanomethylene-4H-pyran (DM) based fluorescent probesw ere designeda nd used for peroxynitrite (ONOO À)d etection. Nevertheless, the aggregation-caused quenching effect diminished the fluorescence and restricted their further applications. To overcomet his problem, tetraphenylethylene (TPE) based glycoclusters were used to self-assemblewith these DM probes to obtain supramolecular water-soluble glyco-dots. This self-assemblys trat-egy enhanced the fluorescencei ntensity,l eading to an enhanced selectivity and activity of the resulting glyco-dot comparing to DM probes alone in PBS buffer.T he glyco-dots also exhibitedb etter results during fluorescences ensing of intracellular ONOO À than the probes alone, thereby offering scope for the development of others imilars upramolecular glyco-systemsf or chemical biologicals tudies.

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Section: Resultsmentioning

confidence: 90%

Section: Synthesis Of Dm-based Fluorescent Probesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Supramolecular Assembly of TPE‐Based Glycoclusters with Dicyanomethylene‐4H‐pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Dong

Liu

et al. 2020

Chemistry A European J

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“…On this basis, He and workmates designed a supramolecular AIE glyconanoparticle for the ratiometric detection of β‐amyloid and discernment from lectins . In addition, in 2017, He and co‐workers reported a AIEgens‐based glycoclusters as a high‐affinity ligand for LecA and LecB bacterial lectins …”

Section: Biomolecule‐conjugated Aiegens Via Single Click Reactionmentioning

confidence: 99%

Rational Fabrication and Biomedical Application of Biomolecule‐Conjugated AIEgens through Click Reaction

et al. 2019

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Recently, the issue of cancer has attracted extensive attention. Early diagnosis and timely therapy are important for cancer treatment. And lots of advanced fluorescent probes have been applied to cancer theranostics. However, the further development of these probes is limited by the disadvantages of poor targeting, weak sensitivity and photobleaching. Fortunately, the emergence of biomolecule-conjugated fluorescent probes with aggregationinduced emission properties has taken innovative impetus to the cancer theranostics. This review summarizes the rational fabrication and biomedical applications of biomolecule-conjugated AIE luminogens (AIEgens) based on "click reaction" over the past decade. In the meantime, the challenges of biomolecule-conjugated AIEgens in the field of biomedicine are also discussed.

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Modified Galacto‐ or Fuco‐Clusters Exploiting the Siderophore Pathway to Inhibit the LecA‐ or LecB‐Associated Virulence of Pseudomonas aeruginosa

et al. 2020

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Galacto-and fuco-clusters conjugated with one to three catechol or hydroxamate motifs were synthesised to target LecA and LecB lectins of Pseudomonas aeruginosa (PA) localised in the outer membrane and inside the bacterium. The resulting glycocluster-pseudosiderophore conjugates were evaluated as Trojan horses to cross the outer membrane of PA by iron transport. The data suggest that glycoclusters with catechol moieties are able to hijack the iron transport, whereas those with hydroxamates showed strong nonspecific interactions. Mono-and tricatechol galactoclusters (G1C and G3C) were evaluated as inhibitors of infection by PA in comparison with the free galactocluster (G0). All of them exhibited an inhibitory effect between 46 to 75 % at 100 μM, with a higher potency than G0. This result shows that LecA localised in the outer membrane of PA is involved in the infection mechanism.

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Tetraphenylethylene-based glycoclusters with aggregation-induced emission (AIE) properties as high-affinity ligands of bacterial lectins

Abstract: TPE-based glycoclusters are fluorescent through aggregation induced emission (AIE) in water.

Cited by 29 publications

References 31 publications

Supramolecular Assembly of TPE‐Based Glycoclusters with Dicyanomethylene‐4H‐pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Supramolecular Assembly of TPE‐Based Glycoclusters with Dicyanomethylene‐4H‐pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Rational Fabrication and Biomedical Application of Biomolecule‐Conjugated AIEgens through Click Reaction

Modified Galacto‐ or Fuco‐Clusters Exploiting the Siderophore Pathway to Inhibit the LecA‐ or LecB‐Associated Virulence of Pseudomonas aeruginosa

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