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Carbohydrate-Functionalized Anthracene Carboximides as Multivalent Ligands and Bio-Imaging Agents
Anne George1, Narayanaswamy Jayaraman1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, India.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 3, 2024
Summary
Anthracene carboximide glycosides enhance solubility and fluorescence, forming self-assembled vesicles. These novel glycoconjugates act as multivalent clusters for lectin binding and show potential for cell imaging.
Area of Science:
- Carbohydrate Chemistry
- Supramolecular Chemistry
- Fluorescent Probes
Background:
- Anthracene carboximides (ACIs) are fluorescent molecules with limited aqueous solubility.
- Glycoconjugation is a strategy to improve solubility and introduce biological recognition.
- Developing novel fluorescent probes for biological applications is an ongoing area of research.
Purpose of the Study:
- To synthesize and characterize novel anthracene carboximide-glycoside conjugates.
- To investigate the photophysical properties, self-assembly behavior, and biological interactions of these glycoconjugates.
- To evaluate their potential for cell imaging applications.
Main Methods:
- Synthesis of ACIs conjugated with glucose, galactose, and mannose via glycosylation.
- Spectroscopic analysis (absorption, emission, quantum yield) and solubility measurements.
- Dynamic light scattering (DLS), atomic force microscopy (AFM), and transmission electron microscopy (TEM) for structural characterization.
- Lectin binding assays (Con A) using fluorescence and turbidity.
- Cellular cytotoxicity and cell permeability studies using HeLa and HepG2 cell lines.
Main Results:
- Glycoconjugation increased aqueous solubility by over 3-fold.
- The glycoconjugates exhibited red-shifted absorption/emission with large Stokes shifts and high fluorescence quantum yields (up to 0.86 in THF, 0.5 in water).
- ACI-glycosides self-assembled into vesicle structures, forming multivalent glycoclusters.
- Man-ACI demonstrated specific binding to Concanavalin A (Con A).
- The conjugates showed no cytotoxicity up to 50 μM and were cell-permeable, enabling intracellular fluorescence imaging.
Conclusions:
- Novel anthracene carboximide-glycosides were successfully synthesized and characterized.
- These glycoconjugates possess favorable photophysical properties and self-assembly capabilities.
- The multivalent nature of the self-assembled structures facilitates ligand-specific lectin binding.
- The non-toxic, cell-permeable nature and fluorescence make them promising candidates for cell imaging applications.
