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Glycosylation near infrared dye as well as preparation method and application thereof

A near-infrared dye, glucose-based technology, applied in chemical instruments and methods, organic dyes, azo dyes, etc., can solve the problems of inconvenient derivatization and poor drug-like properties, and achieve the effect of being beneficial to biological detection and good drug-like properties.

Active Publication Date: 2016-06-15
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a kind of glucosylated near-infrared dye, to solve the problems of poor drug-like property and inconvenient derivatization in the prior art

Method used

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  • Glycosylation near infrared dye as well as preparation method and application thereof
  • Glycosylation near infrared dye as well as preparation method and application thereof
  • Glycosylation near infrared dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1.1 Synthesis of compound III

[0035]

[0036] 2.0g (16.1mmol) of compound II was dissolved in 20mL of DMSO, 1.25g of sodium azide (19.2mmol) was added thereto, and heated to about 50°C for 20h. Extract with ethyl acetate, wash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, and distill off the solvent under reduced pressure. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 1.54 g of light yellow liquid of Compound III, with a yield of 73.3%.

[0037] 1 HNMR (400MHz, CDCl 3 )δ3.69(t, J=4Hz, 2H), 3.63(t, J=4Hz, 2H), 3.55(t, J=4Hz, 2H), 3.36(t, J=6Hz, 2H), 2.67(s ,1H).

Embodiment 2

[0039] 1.2 Synthesis of compound IV

[0040]

[0041] 1.0g (8.0mmol) of compound III and 0.97mL (12.05mmol) of pyridine were dissolved in 20mL of DCM, and 1.8g (9.6mmol) of TsCl was added under ice-cooling, warmed to room temperature, and reacted for 20h. DCM extraction, dilute hydrochloric acid washing, water washing, saturated NaCl washing, anhydrous NaSO 4 After drying, the solvent was distilled off under reduced pressure. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 1.1 g of compound IV as a light yellow liquid, with a yield of 48.0%.

[0042] 1HNMR (400MHz, CDCl 3 )δ7.80(d, J=8.0Hz, 2H), 7.35(d, J=8.0Hz, 2H), 4.17(t, J=5.4, 4.1Hz, 2H), 3.70(t, J=5.3, 4.1 Hz, 2H), 3.60(t, J=5.0Hz, 2H), 3.32(t, J=5.0Hz, 2H), 2.45(s, 3H).

Embodiment 3

[0044] 1.3 Preparation of compound VI

[0045]

[0046]Dissolve 5.0g (36.2mmol) of compound V in 100mL of anhydrous acetone, under nitrogen protection, add 6.5g (47.1mmol) of potassium carbonate solid in batches, after the addition is complete, add 3.3mL (38.7mmol) of MOMCl in batches, and react at room temperature for 20h . After the reaction, add water, extract with ethyl acetate, wash with saturated sodium chloride solution, dry with anhydrous sodium sulfate, and distill under reduced pressure to remove the solvent. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 4.2 g of compound VI as a white solid, with a yield of 64.2%.

[0047] 1 HNMR (400MHz, CDCl 3 )δ6.12(s,2H),6.08–5.98(m,1H),5.96(s,1H),5.39(d,J=17.3Hz,1H),5.28(d,J=10.5Hz,1H), 4.65(s,2H),4.52(d,J=4.6Hz,2H),4.08(d,J=11.2Hz,2H),3.92(s,2H),3.85-3.75(m,8H),2.37-2.29 (m, 4H), 1.67-1.57 (m, 4H), 1.28 (m, 24H), 0.88 (t, J=5.9Hz, 6H).

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Abstract

The invention discloses glycosylation near infrared dye as well as a preparation method and application thereof, in particular relates to dye shown as a general formula I. The dye is finally obtained by respective synthesis of three fragments and substitution and condensation reaction. The dye has the functions of ultraviolet absorption and near-infrared emission, is easy for detection and has a derivatization site which can be used for connecting molecules with different target abilities. In addition, the dye is also provided with a fluorescent switch which can be used for connecting anoxia, pH, enzyme and redox sensitive groups, so that the effect of selectively fluorescing is realized; the dye is applied to visualized target administration (see the description).

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a derivatizable dye molecule and its preparation method and application. Background technique [0002] Cancer is a major disease that seriously threatens human life and social development. It is one of the main causes of death, and its incidence is increasing year by year, seriously endangering people's health. The prevention and treatment of cancer is the greatest challenge facing human medical health. Early diagnosis and discovery are the key to the treatment of cancer, but many tumors are secretive and have no obvious symptoms in the early stage. At the same time, there is still a lack of specific medical means for real-time monitoring of tumor occurrence, development, and metastasis. The bioluminescent imaging technology developed in recent years can realize the study of the pathogenesis of cancer at the molecular level, track the pathological process in real time...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07D405/12C09K11/06A61K49/00
CPCA61K49/0021A61K49/0052A61K49/0056A61K49/0082C07D405/12C09B57/00C09K11/06C09K2211/1059C09K2211/1088
Inventor 吕伟陈世光方艳芬章雄文
Owner EAST CHINA NORMAL UNIVERSITY
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