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

Anal Chim Acta. 2015 Sep 17:893:84-90. doi: 10.1016/j.aca.2015.08.041. Epub 2015 Sep 1.

Abstract

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.

Keywords: Cell imaging; Chemodosimetric probe; Hydrazine; Rhodamine; “Turn-on” fluorescence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / toxicity
  • Humans
  • Hydrazines / chemistry*
  • MCF-7 Cells
  • Microscopy, Fluorescence
  • Molecular Conformation
  • Nitriles / chemical synthesis
  • Nitriles / chemistry*
  • Nitriles / toxicity
  • Quantum Theory
  • Rhodamines / chemistry
  • Spectrometry, Fluorescence
  • Xanthenes / chemical synthesis
  • Xanthenes / chemistry*
  • Xanthenes / toxicity

Substances

  • 4-(2-((3',6'-bis(diethylamino)-3-oxospiro(isoindoline-1,9'-xanthene)-2-yl)ethylimino)methyl)benzonitrile
  • Fluorescent Dyes
  • Hydrazines
  • Nitriles
  • Rhodamines
  • Xanthenes
  • hydrazine