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Research Article Open access CC BY 4.0

1,5-Acrylodan: A Fluorescent Bioconjugate Sensor of Protic Environments

Jake Morrin, Matthew Petitt, Christopher Abelt

Organics · pp. 493–506 · Published 7 Nov 2024

10.3390/org5040026

Abstract

1,5-Acrylodan (1-(5-(dimethylamino)naphthalen-1-yl)prop-2-en-1-one) is prepared in six steps from 1-nitronaphthalene and 19% overall yield. The last three steps involve an aryllithium-directed nucleophilic addition, catalytic Kulinkovich cyclopropanation, and copper-catalyzed oxidative ring-opening to generate the acryloyl moiety. The fluorescent properties of 1,5-Acrylodan (AC) are reported. These include its solvatochromism and H-bond quenching by protic solvents. Its use as a bioconjugate sensor is demonstrated with Human Serum Albumin (HSA) through its covalent attachment to Human Serum Albumin (HSA) at the free cysteine-34 moiety. Unfolding studies with guanidinium chloride (GdmCl) and sodium dodecyl sulfate (SDS) are conducted to illustrate how the fluorophore responds to changes in both micropolarity and exposure to water.

Bioconjugation Fluorescence Nanotechnology Chemistry Combinatorial chemistry Materials science Physics Quantum mechanics

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