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Ratiometric fluorescent probe compound for detecting hypobromous acid and application thereof
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A fluorescent probe, hypobromous acid technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problem of detecting the lack of hypobromous acid
Active Publication Date: 2018-12-07
TAIZHOU UNIV
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[0003] However, the method for detecting hypobromous acid is still very lacking at present, so it is of great significance to develop a new method for detecting hypobromous acid
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Embodiment 1
[0019] Accurately weigh 3-amino-4-bromo-1,8-naphthalic anhydride compound I (120mg, 0.41mmol), 4-(2-aminoethyl)morpholine (106mg, 0.82mmol), dissolve in 10mL ethanol , reflux and stir at 80°C for 6 hours. TLC detected that the reaction was complete, the reaction was stopped, cooled to room temperature, filtered with suction, washed with an appropriate amount of ethanol, and dried to obtain 133 mg of a light yellow solid (Compound II), with a yield of 80.2%. 1 H NMR (400MHz, d 6 -DMSO): δ8.20(d, J=8.4Hz, 1H), 8.15(d, J=7.2Hz, 1H), 8.11(s, 1H), 7.76(t, J=7.8Hz, 1H), 6.32 (s,2H),4.14(t,J=7.0Hz,2H),3.53(t,J=4.4Hz,4H),2.55(t,J=6.8Hz,2H),2.46(s,4H); 13 C NMR (400MHz, d 6 -DMSO): δ163.7, 163.5, 145.8, 132.0, 128.9, 126.3, 122.7, 122.4, 122.3, 121.7, 107.1, 66.7, 56.0, 53.9, 37.3; HR-ESI-MS m / z: [M+H] + calcd. for 404.0610 found 404.0609.
Embodiment 2
[0021] Compound II (80mg, 0.198mmol), 2-methylthiophenylboronic acid (50mg, 0.297mmol), Pd(dppf) 2 Cl 2 ·CH 2 Cl 2 (9mg, 0.01mmol), K 2 CO 3 (4M, 2mL), EtOH (0.6mL), and toluene (5mL) were added into a 50mL round bottom flask, and stirred at 80°C for 24 hours under nitrogen protection. TLC detected that the reaction was complete, the reaction was stopped, the solvent was distilled off under reduced pressure, and column chromatography was used to separate and purify to obtain 75.4 mg of a pale yellow solid product (compound Lyso-NpSN), with a yield of 85.1%. 1 HNMR (400MHz, CDCl 3 ):δ8.25(d,J=7.2Hz,1H),8.07(s,1H),7.47-7.32(m,4H),7.27-7.11(m,2H),4.28(t,J=7.0Hz, 2H), 3.92(s, 2H), 3.64(t, J=4.2Hz, 4H), 2.65(t, J=7.0Hz, 2H), 2.56(s, 4H), 2.29(s, 3H); 13 C NMR (400MHz, CDCl 3 ): δ164.6, 164.2, 142.8, 139.4, 132.6, 132.2, 130.8, 130.3, 129.6, 127.3, 127.2, 125.6, 125.0, 123.6, 123.2, 122.7, 122.5, 122.2, 65.0, 56.3, 53.8; HR-1 ESI-MS m / z:[M+H] + calcd. for 448.1695 found 44...
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Abstract
The invention belongs to the field of fluorescent probes in analytical chemistry and relates to a ratiometric fluorescent probe compound for detecting hypobromous acid and application thereof. The synthetic method comprises the following steps: reacting 3-amino-4-bromo-1,8-naphthalic anhydride and 4-(2-amino ethyl) morpholine to produce an intermediate product II, and carrying out a coupled reaction between the compound II and 2-methylthiophenylboronic acid, thereby obtaining the probe molecule. The probe is excellent in stability and simple in preparation method, response on the hypobromous acid has the advantages of being ratiometric, high in selectivity, rapid and sensitive, and other activated small molecules, ions and amino acids do not produce interference to detection of the hypobromous acid. The probe provides a novel method for detecting the hypobromous acid, and has excellent application prospects.
Description
technical field [0001] The invention relates to a novel ratio-type fluorescent probe compound for detecting hypobromous acid and its application. Background technique [0002] Hypobromous acid is an active oxide contained in living organisms, which has strong oxidizing ability. In organisms, hypobromous acid is produced by the peroxidation reaction of bromide ions and hydrogenperoxide under the catalysis of hemeperoxidase, which includes myeloperoxidase (MPO) or Acid granulocyteperoxidase (EPO). Hypobromous acid can react with many biomolecules, such as amino acids, proteins, antioxidants (including thiols), carbohydrates, lipids and DNA, so it plays an important role in the immune system. However, excessive hypobromous acid can cause tissue damage in the human body, which is closely related to many human inflammatory diseases, including cardiovascular disease, kidneydisease, intestinal inflammation, neurodegenerative disease, rheumatoid arthritis, Inflammatory tissue...
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