Hydrazine selective dual signaling chemodosimetric probe in physiological conditions and its application in live cells

• A selective rhodamine–cyanobenzene conjugate is synthesized.
• The conjugate is a selective dual signaling chemodosimetric probe towards hydrazine.
• Spirolactam ring opening of the probe, followed by its hydrolysis, is the sensing mechanism.
• The probe detects hydrazine in the human breast cancer cells MCF-7 imaging.

A rhodamine–cyanobenzene conjugate, (E)-4-((2-(3′,6′-bis(diethylamino)-3-oxospiro[isoindoline-1,9′-xanthene]-2-yl)ethylimino)methyl)benzonitrile (1), which structure has been elucidated by single crystal X-ray diffraction, was synthesized for selective fluorescent “turn-on” and colorimetric recognition of hydrazine at physiological pH 7.4. It was established that 1 detects hydrazine up to 58 nM. The probe is useful for the detection of intracellular hydrazine in the human breast cancer cells MCF-7 using a fluorescence microscope. Spirolactam ring opening of 1, followed by its hydrolysis, was established as a probable mechanism for the selective sensing of hydrazine.

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