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Issue 40, 2019
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Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging

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Abstract

Molecular probes that enable high-contrast photoacoustic (PA) imaging of cellular processes are valuable tools for in vivo studies. Design of activatable PA probes with high contrast remains elusive. We develop a new NIR rhodol derivative, Rhodol-NIR, with a large extinction coefficient, low quantum yield and structural switching from a ‘ring-open’ form to a ‘closed’ spirolactone upon esterification. This structural transition, together with the ideal photophysical properties, enables the development of activatable probes for high-contrast PA imaging via a target-specific de-esterification reaction. This strategy is demonstrated using a PA probe designed for a tumor biomarker, human NAD(P)H: quinone oxidoreductase isozyme 1 (hNQO1), which affords high contrast and excellent sensitivity for PA detection and imaging of hNQO1 in living cells and animals. The strategy can provide a new paradigm for engineering activatable PA probes for high-contrast imaging.

Graphical abstract: Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging

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Supplementary files

Article information


Submitted
06 Jun 2019
Accepted
16 Aug 2019
First published
16 Aug 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 9257-9264
Article type
Edge Article

Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging

F. Liu, X. Shi, X. Liu, F. Wang, H. Yi and J. Jiang, Chem. Sci., 2019, 10, 9257
DOI: 10.1039/C9SC02764E

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