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An Aromatic Micelle‐Based Saccharide Cluster with Changeable Fluorescent Color and its Protein Interactions

Haruna Narita, Lorenzo Catti, Michito Yoshizawa

2021Angewandte Chemie International Edition22 citationsDOI

Abstract

Abstract To develop a new type of synthetic saccharide clusters with changeable fluorescent colors, we herein designed a multisaccharide‐coated aromatic micelle. The new cluster forms in water through the quantitative assembly of bent polyaromatic amphiphiles bearing three mannose groups. The spherical assembly, with a 2 nm‐sized polyaromatic core and ca. 18 saccharide pendants, is stable even under high dilution conditions (up to 0.02 mM). The emission intensity and color of the saccharide cluster can be altered from moderate blue ( Φ F =19 %) to strong red, orange, and green ( Φ F up to 67 %) upon encapsulation of hydrophobic fluorescent dyes in water. Moreover, the present fluorescent clusters, both with and without the dyes, display selective interactions with mannose‐binding proteins in vitro.

Topics & Concepts

FluorescenceChemistryAmphiphileMicellePhotochemistryBiophysicsOrganic chemistryCopolymerAqueous solutionPolymerBiologyQuantum mechanicsPhysicsSupramolecular Self-Assembly in MaterialsSupramolecular Chemistry and ComplexesCarbohydrate Chemistry and Synthesis