Advances in fluorescence bioimaging are driven by advances in fluorophore design. Fluorophores need to be both bright and stable. Here we present the synthesis for methacrylate functionalized thiazole orange intercalating dye. A DNA scaffold will be used to concentrate multiple dye molecules without self-quenching, thereby increasing the brightness. The methacrylate moiety will be used to polymerize the dyes once self-assembled on a DNA template to increase the binding affinity and slow dissociation kinetics. Here we present the synthesis of the methacrylate modified thiazole orange starting from 2-(methylthio)benzothiazole. Absorbance and fluorescence data indicate the methacrylate functionalized dye is present in a monomeric state and binds to DNA via intercalation at a ratio of 0.5 dye molecules/base pair. Both benzoyl peroxide initiated and atom transfer radical polymerization (ATRP) conditions will be used to determine if the dye can both polymerize and remain fluorescent when bound to a DNA template. Polymerization of an intercalating dye on a DNA template will provide a new tool in the toolkit for the design of ultrabright fluorophores for bioimaging applications.

Synthesis of a methacrylate functionalized thiazole orange intercalating dye

ACS Spring Meeting 2021

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