Development of a Highly Specific Rhodamine-Based Fluorescence Probe for Hypochlorous Acid and Its Application to Real-Time Imaging of Phagocytosis

The tetramethylrhodamine (TMR) fluorophore is a useful platform for fluorescence probes, being applicable, for example, to biological investigations utilizing fluorescence microscopy, owing to its excellent photochemical properties in aqueous media. We have developed new TMR derivatives that show di...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-06, Vol.129 (23), p.7313-7318
Main Authors: Kenmoku, Suguru, Urano, Yasuteru, Kojima, Hirotatsu, Nagano, Tetsuo
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Fluorescent Dyes - chemistry
Hypochlorous Acid - analysis
Hypochlorous Acid - chemistry
Hypochlorous Acid - metabolism
Microscopy, Fluorescence
Molecular Structure
Phagocytosis - physiology
Phagosomes - chemistry
Phagosomes - metabolism
Rhodamines - chemistry
Time Factors
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Summary:The tetramethylrhodamine (TMR) fluorophore is a useful platform for fluorescence probes, being applicable, for example, to biological investigations utilizing fluorescence microscopy, owing to its excellent photochemical properties in aqueous media. We have developed new TMR derivatives that show different dependences of their behavior upon the environment. Among them, HMTMR showed unique characteristics, and its putative spirocyclic structure was confirmed by X-ray crystallography. Utilizing this discovery, we have established a strategy to modulate the fluorescence of TMR by regulating the spirocyclization, and we have obtained a new fluorescence probe that can detect hypochlorous acid specifically. This probe, HySOx, can work in 99.9% aqueous solution at pH 7.4 and was confirmed to be able to detect hypochlorous acid being generated inside phagosomes in real time. HySOx is tolerant to autoxidation and photobleaching under bioimaging conditions. Regulation of the spirocyclization of rhodamines, as we describe here, provides a new approach to the rational development of novel fluorescence probes.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja068740g