A kind of fluorescein conjugate and its synthesis method and application

A synthetic method, fluorescein technology, applied in the direction of chemical instruments and methods, methods based on microorganisms, biochemical equipment and methods, etc., can solve problems such as complex operations, unsatisfactory effects, and insignificant specificity, and achieve safety high effect

Active Publication Date: 2021-07-09
HEPAITECH (BEIJING) BIOPHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other identification methods or complex operations, or insignificant specificity, the effect is not very satisfactory

Method used

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  • A kind of fluorescein conjugate and its synthesis method and application
  • A kind of fluorescein conjugate and its synthesis method and application
  • A kind of fluorescein conjugate and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of embodiment 1 fluorescein conjugate I-1

[0056] Synthesis of fluorescein conjugate I-1:

[0057]

[0058] Compound 2 (4.8mg, 12.3μmol, 1eq) and 1 (5.6mg, 12.3μmol, 1eq) were dissolved in water (1.5mL)), and triethylamine (8.5μL, 61.5μmol, 5eq) was added at room temperature, and stirred for 10 hours, Purification by HPLC gave 3 (2.3 mg, 2.71 μmol, 22%) as a yellow solid.

[0059] 1 H NMR (400MHz,D 2 O)δ8.27(s,1H),7.97(s,1H),7.78(d,J=8.4Hz,1H),7.62(d,J=9.8Hz,2H),7.41(d,J=8.1Hz ,1H),7.35(d,J=2.0Hz,2H),7.17(dd,J=9.2,2.0Hz,2H),4.48(t,J=5.6Hz,2H),4.36(d,J=5.7Hz ,1H),4.12(t,J=6.4Hz,1H),4.08(t,J=6.4Hz,1H),3.64–3.56(m,2H),3.50–3.38(m,4H),2.72–2.57( m,2H),2.48–2.33(m,2H),2.29–2.16(m,2H),2.03–1.93(m,2H),1.65–1.56(m,2H)( Figure 9 ); 13 C NMR (239MHz,D 2 O / CD 3 CN)δ180.8,176.2,171.3,170.8,170.2,168.7,166.0,156.7,141.0,140.7,131.8,129.8,129.6,128.5,124.9,117.3,114.4,102.9,100.0,62.8,60.3 44.0, 29.9, 27.1, 26.6, 25.5, 25.2, 25.1 ( Figure 10 ); IR(neat)ν m...

Embodiment 2

[0060] Synthesis of Example 2 Fluorescein Conjugate I-2

[0061] Synthesis of Fluorescein Conjugate I-2:

[0062]

[0063] Compound 1 (3.5mg, 6.4μmol, 1eq) and sodium bicarbonate (2.7mg, 32μmol, 5eq) were dissolved in water (1mL), and acetonitrile (1mL) and compound 4 (6.0mg, 7.7μmol, 1.2eq) were added at room temperature, After stirring for 2 hours, the green solid 5 (3.8 mg, 3.0 μmol, 47%) was obtained by gel column purification.

[0064] 1 H NMR (600MHz,D 2 O / 30%CD 3 CN)δ8.66(s,1H),8.21–8.13(m,2H),8.11–8.04(m,5H),7.88–7.77(s,1H),7.55(d,J=30.5Hz,2H), 6.89–6.73(m,2H),6.53(dd,J=37.9,12.1Hz,2H),4.60(br.s,2H),4.33(br.s,2H),4.27(br.s,2H), 4.18(br.s,1H),3.96–3.82(m,2H),3.54(br.s,4H),3.33(br.s,2H),2.72(br.s,2H),2.41(br.s ,2H),2.08(br.s,2H),2.03(br.s,3H),1.93(s,12H),1.84(br.s,3H),1.67–1.50(m,9H)( Figure 11 ); 13 C NMR (151MHz,D 2 O / 30%CD 3 CN)δ175.9,172.8,172.7,172.3,172.2,156.7,152.6,151.8,144.6,144.0,142.0,141.6,141.5,140.2,139.9,139.8,126.9,126.8,126.7,1009.6,11,12 ...

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Abstract

The invention belongs to the technical field of bacteria identification materials, and in particular relates to a fluorescein conjugate and its synthesis method and application. The structure of the fluorescein conjugate is shown in general formula I, wherein R represents a fluorescein containing a negatively charged phenolic hydroxyl group or a sulfonic acid group; m is an integer of 1-10. The obtained fluorescein conjugate not only has selective specificity for Pseudomonas aeruginosa, but also has high stability, is easy to react in aqueous solution, and can be used as a fluorescein probe for identification of Pseudomonas aeruginosa. The synthesis method adopts a modular synthesis route, can be applied to the chemical synthesis of compounds with similar structures, and opens up a broad development space for novel bacterial diagnostic reagents.

Description

technical field [0001] The invention belongs to the technical field of bacteria identification materials, and specifically relates to a fluorescein conjugate and its synthesis method and application; further relates to a fluorescein conjugate coupled with a pseudopaline derivative with a specific stereo configuration and its synthesis method with application. Background technique [0002] Compared with Gram-positive bacteria, Gram-negative bacteria are more prone to drug resistance and more difficult to treat because of their outer membrane protection. The main reason for the emergence of drug resistance is that it is impossible to quickly identify what kind of bacteria is causing the infection, which leads to the selection of broad-spectrum antibiotics for clinical treatment, which leads to the emergence of cross-drug resistance. [0003] Pseudomonas aeruginosa is one of the three pathogenic bacteria with the most serious drug resistance. Currently, the clinical identifica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D405/12C07F5/02C09K11/06C12Q1/04C12R1/385
CPCC07D403/14C07D405/12C07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055C09K2211/1059C09K2211/1088C12Q1/04G01N2333/21
Inventor 雷晓光赵天湖张健
Owner HEPAITECH (BEIJING) BIOPHARMA TECH CO LTD
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