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Fluorescein conjugate as well as synthesis method and application thereof

A synthetic method, fluorescein technology, applied in chemical instruments and methods, microorganism-based methods, biochemical equipment and methods, etc., can solve problems such as unsatisfactory effects, insignificant specificity, complicated operations, etc.

Active Publication Date: 2020-09-01
海湃泰克(北京)生物医药科技有限公司
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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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  • Fluorescein conjugate as well as synthesis method and application thereof
  • Fluorescein conjugate as well as synthesis method and application thereof
  • Fluorescein conjugate as well as synthesis method and application thereof

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 bacterial identification materials, and particularly relates to a fluorescein conjugate as well as a synthesis method and application thereof. The structure of the fluorescein conjugate is shown as a general formula I, wherein R represents fluorescein containing negatively charged phenolic hydroxyl groups or sulfonic acid groups, and m is an integerfrom 1 to 10. The obtained fluorescein conjugate not only has selective specificity on pseudomonas aeruginosa, but also is high in stability, is easy to react in an aqueous solution, and can be used as a fluorescein probe for identifying pseudomonas aeruginosa. The synthesis method adopts a modular synthesis route, can be applied to chemical synthesis of compounds with similar structures, and opens up a wide development space for novel bacterial diagnosis 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 Applications(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 海湃泰克(北京)生物医药科技有限公司
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