Carbohydrate-Functionalized Anthracene Carboximides as Multivalent Ligands and Bio-Imaging Agents

George, A and Jayaraman, N (2024) Carbohydrate-Functionalized Anthracene Carboximides as Multivalent Ligands and Bio-Imaging Agents. In: Chemistry - A European Journal .

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Abstract

Anthracene carboximides (ACIs) conjugated with gluco-, galacto- and mannopyranosides are synthesized, by glycosylation of N-hydroxyethylanthracene carboximide acceptor with glycosyl donors. Glycoconjugation of anthracene carboximide increases the aq. solubility by more than 3-fold. The glycoconjugates display red-shifted absorption and emission, as compared to anthracene. Large Stokes shift (λabs/λem=445/525 nm) and high fluorescence quantum yields (Φ) of 0.86 and 0.5 occur in THF and water, respectively. The ACI-glycosides undergo facile photodimerization in aqueous solutions, leading to the formation of the head-to-tail dimer, as a mixture of syn and anti-isomers. Solution phase and solid-state characterizations by dynamic light scattering (DLS), microscopic imaging by atomic force (AFM) and transmission electron (TEM) microscopies reveal self-assembled vesicle structures of ACI glycosides. These self-assembled structures act as multivalent glycoclusters for ligand-specific lectin binding, as evidenced by the binding of Man-ACI to Con A, by fluorescence and turbidity assays. The conjugates do not show cellular cytotoxicity (IC50) till concentrations of 50 μM with HeLa and HepG2 cell lines and are cell-permeable, showing strong fluorescence inside the cells. These properties enable the glycoconjugates to be used in cell imaging. The non-selective cellular uptake of the glycoconjugates suggests a passive diffusion through the membrane. © 2024 Wiley-VCH GmbH.

Item Type:	Journal Article
Publication:	Chemistry - A European Journal
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc
Keywords:	Anthracene; Cell culture; Cells; Dynamic light scattering; Fluorescence; Isomers; Lanthanum compounds; Ligands; Proteins; Red Shift; Sugars, And self-assembly; Anthracene carboximide; Bio-imaging; Carboximide; Cell imaging; Functionalized; Glycoconjugates; Imaging agent; Lectin; Multivalent ligands, Self assembly
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	29 Jul 2024 09:14
Last Modified:	29 Jul 2024 09:14
URI:	http://eprints.iisc.ac.in/id/eprint/85211

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