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Novel near-infrared fluorescent probe for detecting carboxypeptidase A

A fluorescent probe and near-infrared technology, applied in the field of analytical chemical detection, can solve the problems of carboxypeptidase imaging, etc., and achieve the effect of high synthesis yield, high sensitivity and long emission wavelength

Active Publication Date: 2019-06-25
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, for the detection of carboxypeptidase, high-performance liquid chromatography, absorption spectroscopy and coupling analysis are mainly used, but these detection methods are limited to the detection of carboxypeptidase in vitro, and it is not possible to detect carboxypeptidase in real time. imaging

Method used

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  • Novel near-infrared fluorescent probe for detecting carboxypeptidase A
  • Novel near-infrared fluorescent probe for detecting carboxypeptidase A
  • Novel near-infrared fluorescent probe for detecting carboxypeptidase A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Implementation Example 1: Preparation of Potassium Salt 1a

[0020] Take 1,8-naphtholactam (0.85g, 5mmol), potassium hydroxide (0.56g, 10mmol), dissolve in N-methyl-2-pyrrolidone (10ml), stir at room temperature for 30min, and then add butanol Sultone (0.75g, 5.5mmol) was heated to 90°C for 10h, cooled, and treated with acetone (35ml) to give product 1a (1.65g, 96%). 1 H NMR (400 MHz, DMSO-d6): 8.18 (d, J = 8.1 Hz, 1H), 8.07 (d, J = 8.3 Hz, 1H), 7.81 (t, J = 8.7Hz, 1H), 7.65 (d , J = 8.1 Hz, 1H), 7.55 (t, J = 8.7 Hz, 1H), 7.23 (d, J =7.5Hz, 1H), 3.91 (t, J = 7.2 Hz, 2H), 2.46 (m, 2H ), 1.79 (m, 2H), 1.62 (t, J =7.2 Hz, 2H).

Embodiment 2

[0021] Implementation example 2: the preparation of intermediate product 2

[0022] Take 1a (1.50g, 5mmol), tetrabutylammonium chloride (1.51g, 5.5mmol), dissolve in acetic acid (8ml), stir at 90°C for 0.5h, then add ethyl acetate dropwise, and then filter, Rotary evaporation gave product 2 (2.5 g, 94%) as viscous oil. 1 H NMR(400 MHz, DMSO-d6): 8.01 (t, J = 7.4 Hz, 1H) ,7.66 (t, J = 7.4 Hz, 1H), 7.51(m, 2H) 7.24 (d, J = 7.2 Hz, 1H), 7.17 (d, J = 7.1 Hz, 1H), 6.97 (d, J = 7.1Hz, 1H), 3.93 (t, J = 7.4Hz, 1H), 3.26 (t, J = 8.6 Hz, 8H) , 2.90 (m, 2H), 1.94 (m, 4H), 1.64 (m, 8H), 1.42 (m, 8H), 0.98 (t, J = 8.6 Hz, 12H).

Embodiment 3

[0023] Implementation Example 3: Preparation of Compound 3

[0024] Take product 2 (2.73g, 5mmol) and methylmagnesium chloride, dissolve in anhydrous tetrahydrofuran (20ml), heat to 60°C under nitrogen atmosphere, stir for 1h, then cool, add 1M hydrochloric acid for neutralization, and use ethanol ( 15ml) and diethyl ether (20ml), then cooled to 0°C overnight to give product 3 (2.58 g, 85%). 1 H NMR (D2O): 8.51 (d, J = 8.1 Hz, 1H), 8.43 (d, J = 8.1 Hz, 1H), 8.09 (m, 2H), 7.85 (t, J = 8.5 Hz, 1H), 7.73 (t, J = 8.2 Hz, 1H), 4.51, (t, J = 8.5 Hz, 2H), 3.02 (s, 3H), 2.85 (m, 2H), 2.04 (m, 2H), 1.78 (t, J = 8.2 Hz, 2H). MS (maldi) m / z: calcd. for[C 16 h 19 NO 3 S] + , 304.10; found 304.10.

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting carboxypeptidase A. The fluorescent probe is used for sensing detection of carboxypeptidase A in vivo and in vitro, and the probe is simple to synthesize, is cheap, is easy to obtain, can achieve fluorescence imaging in vivo, and has an excellent diagnostic function for pancreatic juice leakage. The fluorescent probe of the invention has a good selectivity and a high sensitivity; and more importantly, the fluorescent probe has excellent anti-fluorescence ability when the emission wavelength is in the near-infrared region.The probe has broad application prospects in analytical chemical detection and biomedicines.

Description

technical field [0001] The design of the invention belongs to the technical field of analytical chemistry detection, and specifically relates to a preparation method of a novel near-infrared probe for identifying carboxypeptidase A in pancreatic juice and its application in vivo and in vitro. Background technique [0002] Carboxypeptidases (CPs) are a class of proteases that split one or more amino acids from the C-terminus of polypeptides or proteins, commonly including carboxypeptidase A, carboxypeptidase B, carboxypeptidase C and carboxypeptidase Y four It plays an important role in physiological processes and various diseases. Carboxypeptidase A and carboxypeptidase B are mainly produced in the pancreas and play a role in the degradation of proteins, and the expression levels of carboxypeptidase in pancreatitis and pancreatic cancer are different, which is a good way to detect the leakage of pancreatic juice. offers the possibility. At present, for the detection of c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D405/06G01N21/64
Inventor 颜梅孙荣环张晶王平刘明霞于京华
Owner UNIV OF JINAN
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