Calatrava-Pérez, E, Delente, JM, Shanmugaraju, S, Hawes, CS, Williams, CD, Gunnlaugsson, T and Scanlan, EM (2019) Glycosylated naphthalimides and naphthalimide Tröger's bases as fluorescent aggregation probes for Con A. Organic & Biomolecular Chemistry, 17 (8). pp. 2116-2125. ISSN 1477-0539

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Herein we report the synthesis of fluorescent, glycosylated 4-amino-1,8-naphthalimide (Nap) 1, and the related 1,8-naphthalimides Tröger's bases (TBNap) 2 and 3, from 1,8-naphthalic anhydride precursors, the α-mannosides being introduced through the use of CuAAC mediated 'click' chemistry. We investigate the photophysical properties of these probes in buffered solution and demonstrate their ability to function as fluorescent probes for Concanavalin A (Con A) lectin. We show that both the Nap and TBNap structures self-assemble in solution. The formation of the resulting supramolecular structures is driven by head-to-tail π-π stacking and extended hydrogen bonding interactions of the Nap and the triazole moieties. These interactions give rise to spherical nano-structures (ca. 260 nm and 100 nm, for 1 and 3, respectively), which interact with the Con-A protein, the interaction being probed by using both luminescent and Scanning Electron Microscopy imaging as well as dynamic light scattering measurements. Finally, we show that these supramolecular assembles can be used as luminescent imaging agents, through confocal fluorescence imaging of HeLa cells of the per-acetylated version 2.

Item Type: Article
Additional Information: The final published version of this accepted manuscript is available online at!divAbstract - a further document including corrections is available from
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Related URLs:
Depositing User: Symplectic
Date Deposited: 05 Feb 2019 12:01
Last Modified: 01 Jan 2020 01:30

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