Fluorescent probe for detecting hydrogen peroxide and preparation method and application thereof

Abstract

The invention discloses a fluorescent probe for detecting hydrogen peroxide and a preparation method and application thereof. The structural formula of the fluorescent probe for detecting hydrogen peroxide is shown in the description, wherein any one or two of R1-R5 represents electron withdrawing groups. The fluorescent probe is novel in group response, good in selectivity and high in sensitivity; the excitation emission wavelength of the fluorescent probe is located in the range of near infrared waves, damage to tissue is small, the penetrating power is high, and the fluorescent probe can be used for living body imaging. The preparation method comprises the steps that 3-aminophenol and Cy.7.Cl are subjected to a substitution reaction, and Cy-Ph-NH2 is obtained; a retro-Knoevenagel reaction is conducted, and P-NH2 is obtained; P-NH2 and a derivative of phenylglyoxylic acid are subjected to the substitution reaction, and the product P-R is obtained, that is, the fluorescent probe for detecting hydrogen peroxide is obtained. The synthesizing method is simple and suitable for industrial production.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a new responsive group and a near-infrared dye fluorescent probe with good selectivity. The synthesis method and its application in detecting intracellular hydrogen peroxide belong to the technical field of detection. Background technique [0002] Most of the hydrogen peroxide in the cell is produced by the mitochondrial respiratory chain, first oxygen (O 2 ) is reduced to generate O 2 · , then O 2 · It is converted into hydrogen peroxide by the dismutation of superoxide dismutases (SODs). [0003] In living organisms, hydrogen peroxide is a major reactive oxygen species that plays an important role in cell signaling. Hydrogen peroxide can not only produce other active oxygen, but also is the product of other active oxygen oxidation reaction. Cells are stimulated to produce a burst of reactive oxygen species, which will affect several types of signaling proteins that can regulate cell...

AI Technical Summary

Problems solved by technology

[0006] In recent years, most probes for detecting hydrogen peroxide are based on boronic acid (NaamaKarton-Lifshin, EhudSegal, LioraOmer, MoshePortnoy, RonitSatchi-Fainaro, andDoronShaba, J.Am.Chem.Soc., 2011, 133, 10960–10965 ; LinYuan, WeiyingLin, ShengZhao, WenshaGao, BinChen, LongweiHe, and SasaZhu, J.Am.Chem.Soc., 2012, 134, 13510-13523) or borate esters (DuangkhaeSrikun, EvanW.Miller, DylanW.Domaille, and ChristopherJ.Chang , J.Am.Chem.Soc., 2008,130,4596-4597; Dickinson, B.C.; Huynh, C.; Chang, C.J., J.Am.Chem.Soc., 2010,132,5906) as hydrogen peroxide Responsive groups, but have been reported in articles (ThomasF.Brewer, FranciscoJ.Garcia, CarlS.Onak, KateS.Carroll, and ChristopherJ.Chang, Annu.Rev.Biochem., 2015, 84:765-790.), ONOO - It will cause interference to this type of response group. In addition, several articles published in recent years (SikoraA, ZielonkaJ, LopezM, JosephJ, KalyanaramanB, FreeRadic.Biol.Med., 2009, 47:1401–7; ZielonkaJ, SikoraA, HardyM , JosephJ, DrankaBP, KalyanaramanB., Chem.Res.Toxicol., 2012, 25:1793–99; JiZhou, YangLi, JiaoningShen, QiangLi, RuiWang, YufangXuandXuhongQian, RSCAdv., 2014, 4, 51589–51592) detailed introduction In addition, probes with boronic acid or boronate as the response group can also be used with ONOO - , ClO - react and cause a change in probe fluorescence, and with ONOO - The reaction rate is much faster than the reaction rate with hydrogen peroxide

Therefore, the selectivity of probes with boronic acid or boronic acid ester as the response group to hydrogen peroxide needs to be improved.

[0007] In addition, TetsuoNagano designed and synthesized a fluorescent probe for hydrogen peroxide using a new responsive group (MasahiroAbo, YasuteruUrano, KenjiroHanaoka, TakuyaTerai, ToruKomatsu, and TetsuoNagano, J.Am.Chem.Soc., 2011, 133, 10629– 10637), although this probe has the advantage of high sensitivity, but ONOO - 、TBHP will cause different degrees of interference to the probe, and the excitation and emission wavelength of the probe is not in the near infrared, so it cannot be used for in vivo imaging

[0008] In general, the above probes have the problem of poor selectivity, and the excitation and emission wavelengths of most probes are not in the near infrared, which will limit the application of the probes in organisms

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