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Review
. 2015 Jul 28;13(28):7584-98.
doi: 10.1039/c5ob00788g.

Cyanine polyene reactivity: scope and biomedical applications

Alexander P Gorka  1 , Roger R Nani, Martin J Schnermann
Affiliations
Review

Cyanine polyene reactivity: scope and biomedical applications

Alexander P Gorka et al. Org Biomol Chem. .

Abstract

Cyanines are indispensable fluorophores that form the chemical basis of many fluorescence-based applications. A feature that distinguishes cyanines from other common fluorophores is an exposed polyene linker that is both crucial to absorption and emission and subject to covalent reactions that dramatically alter these optical properties. Over the past decade, reactions involving the cyanine polyene have been used as foundational elements for a range of biomedical techniques. These include the optical sensing of biological analytes, super-resolution imaging, and near-IR light-initiated uncaging. This review surveys the chemical reactivity of the cyanine polyene and the biomedical methods enabled by these reactions. The overarching goal is to highlight the multifaceted nature of cyanine chemistry and biology, as well as to point out the key role of reactivity-based insights in this promising area.

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Figures

Fig. 1
Fig. 1
(A) Key background, (B) common commercial fluorophores, and (C) overview of cyanine polyene reactivity and applications (Cy3 and Cy5: GE Life Sciences, Alexa 647: Life Technologies, IR800-CW: LI-COR).
Fig. 2
Fig. 2
Cyanine polyene reactivity-based optical sensing approaches.
Fig. 3
Fig. 3
pH-Sensing approaches.
Fig. 4
Fig. 4
Thiol sensing methods.
Fig. 5
Fig. 5
(A) Coumarin/cyanine hybrid for H2S sensing and (B) in situ cyanine formation with engineered CRABPII protein.
Fig. 6
Fig. 6
(A) General scheme for switching-dependent super resolution microscopy and (B) cyanine switching reactivity.
Fig. 7
Fig. 7
(A) ICG photobleaching products and (B) general singlet-oxygen photooxidation mechanism.
Fig. 8
Fig. 8
Strategies for improving cyanine photostability.
Fig. 9
Fig. 9
(A) Near-IR cyanine uncaging mechanism, (B) caged compounds, and (C) applications.
See this image and copyright information in PMC

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