N- to O- Rearrangement of Cyanines: Synthesis of a Robust Near-IR Fluorophore

Wednesday, September 24, 2014 — Poster Session IV
10:00 a.m. –12:00 p.m.	FAES Academic Center	NCI	CHEMBIO-3

* FARE Award Winner

Authors

• R. R. Nani
• J. B. Shaum
• A. P. Gorka
• M. J. Schnermann

Abstract

Cyanine fluorophores are fundamental tools for biomedical research. Herein, we report a new method for the synthesis of previously inaccessible O-alkyl-substituted Cy7 fluorophores. N-Methylethanolamine-substituted Cy7 cyanines undergo a facile N to O rearrangement induced by a variety of electrophiles. The resulting fluorophores exhibit similar optical properties to the widely used phenol-substituted Cy7s but possess greater chemical stability. A folate-cyanine conjugate was synthesized and employed in an in vitro fluorescence microscopy experiment. Current work is focused on synthesis of fluorophore bioconjugates for targeted in vivo imaging and activity-based near-IR ratiometric imaging.

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