Design, Synthesis And Properties Of Novel Hydrazine Fluorescent Probes

Hydrazine?N₂H₄?is an important chemical material and also a highly toxic water-soluble biochemical reagent.Hydrazine is highly toxic,invasive and destructive to organism through skin or via breathing directly during its manufacture,transport,utilisation and disposal.There is no endogenous hydrazine in human body,but it can produced by the metabolism of some drugs.The development of hydrazine fluorescent probes is very important for rapid and accurate monitoring of hydrazine in living organisms.So three hydrazine fluorescent probes have been designed and synthesized in this article.The spectral properties,cytotoxicity,and bioimaging were studied.1.A novel hydrazine fluorescent probe 5 based on pyrazole formation reaction has been designed and synthesized.The structure of the 5 was determined by NMR and mass spectrometry.The results of fluorescence spectrum experiments indicated that 5 has high selectivity and low limitation?0.398?M in the solution?.The results of cell experiment showed that 5 has low cytotoxicity and great potential for hydrazine detection in living cells.2.A novel seminaphthorhodafluor-based near-infrared hydrazine fluorescent probe 9 has been designed and synthesized.In the 9,a seminaphthorhodafluor dye?SNARF?act as the near-infrared fluorophore,and an acetate moiety act as the reaction site.The structure of the 9 was determined by NMR and mass spectrometry.The results of spectral experiments indicated that9 has high selectivity and low limitation?0.041?M in the solution?.In addition,the results of bioimaging showed that 9 has great potential for hydrazine detection in living cells and in vivo.3.A novel hepatocyte-targeting hydrazine fluorescent probe 20 based on Gabriel reaction has been designed and synthesized.N-acetylgalactosamine in the 20 was served as a hepatocyte-targeting group.The structure of the 20 was determined by NMR and mass spectrometry.The results of spectral experiments showed that 20 has high selectivity and low limitation?0.618?M in the solution?.The results of bioimaging indicated that 20 has great potential for hepatocyte targeting and detection isoniazid in situ released hydrazine.