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Near infrared fluorescent dye taking fluorophore of cyanine dye as parent skeleton structure and preparation method and application thereof

A technology of fluorescent groups and fluorescent dyes, which is applied in the field of near-infrared fluorescent dyes and their preparation, can solve the problems of rare, viral carrier limitations, and low transfection efficiency, and achieve improved photostability, high yield, The effect of high fluorescence intensity

Active Publication Date: 2017-10-20
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Considering safety, viral vectors are greatly limited in clinical application
Non-viral vectors, such as polymer micelles, liposomes, and dendrimers, have the disadvantage of lower transfection efficiency than viral vectors
On the other hand, at present, there are not many carriers that can well realize the integration of diagnosis and treatment.

Method used

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  • Near infrared fluorescent dye taking fluorophore of cyanine dye as parent skeleton structure and preparation method and application thereof
  • Near infrared fluorescent dye taking fluorophore of cyanine dye as parent skeleton structure and preparation method and application thereof
  • Near infrared fluorescent dye taking fluorophore of cyanine dye as parent skeleton structure and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of near-infrared fluorescent dyes with cyanine dye fluorescent groups as the parent skeleton structure

[0054] (1) The synthetic route of compound 1 is as follows:

[0055]

[0056] Specific steps: In a 100 mL sealed tube, dissolve 10 g (63 mmol, 1 eq) of 2,3,3-trimethylindole in 30 mL of toluene, and then add 7.72 g (63 mmol, 1 eq) of 1- bromopropane. React at 130°C for 72 h, after cooling, let it stand for a while, and pour off the upper layer solution. The red solid in the lower layer was washed twice with ether, spin-dried, and weighed to obtain 15 g of compound 1 with a yield of 84.7%, which was sealed and stored in a -20°C refrigerator.

[0057] (2) The synthetic route of compound 2 is as follows:

[0058]

[0059] Specific steps: In a 250 mL round bottom flask, mix 40 mL of DMF and 20 mL of dichloromethane in an ice-water bath, then add the mixture of 20 mL of dichloromethane and 37 mL of phosphorus oxychloride dropwise into the above soluti...

Embodiment 2

[0070] Preparation of Linker Molecules Containing Reduction Sensitive Bonds

[0071] The synthetic route of compound 6 is as follows:

[0072]

[0073] Specific steps: In a 1 L round bottom flask, dissolve 8 g (35 mmol, 1 eq) of cystamine dihydrochloride in 300 mL of methanol, and then add 7.07 g (70 mmol, 2 eq) of triethylamine. Then dissolve 6.7 g (31 mmol, 0.88eq) of di-tert-butyl dicarbonate in 200 mL of methanol, under stirring, in an ice-water bath, slowly drop the methanol solution of di-tert-butyl dicarbonate into cystamine di Hydrochloride in methanol solution. React overnight at 30°C, then use a rotary evaporator to spin off the methanol, and add 100 mL of dichloromethane to redissolve. Wash twice with 50 mL of saturated NaCl solution, dry with anhydrous sodium sulfate, filter with suction, and spin dry. Weighed to obtain 7.2 g of crude product, the crude yield was 92.3%. Purify with a silica gel column, using dichloromethane / methanol system as eluent, and iso...

Embodiment 3

[0075] Preparation of Second Generation Lysine-Arginine Dendrimers

[0076] (1) The synthetic route of compound 7 is as follows:

[0077]

[0078] Specific steps: Boc-Arg(Pbf)-OH 11.3 g (21.45mmol, 2.5 eq) and benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) 9.76 g (25.74mmol, 3eq) were dissolved in 20 mL N,N-dimethylformamide (DMF), mixed in a 250 mL round bottom flask, and N,N-diisopropylethylamine (DIEA) was added 3.33 g (25.74mmol, 3eq) were reacted for a while. Dissolve 2 g (8.58 mmol, 1 eq) of L-lysine methyl ester hydrochloride in 20 mL DMF, and add it dropwise to the above reaction solution while stirring. 30°C, N 2 Reacted for 48 h under protection. After the reaction, use a rotary evaporator to spin off the DMF, and add 200 mL of dichloromethane to redissolve. With 100 mL saturated sodium bicarbonate (NaHCO 3 ), 100 mL saturated sodium dihydrogen phosphate (NaH 2 PO 4 ) and 100 mL of saturated sodium chloride solution (NaCl) were washe...

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Abstract

The invention discloses a near infrared fluorescent dye taking a fluorophore of a cyanine dye as a parent skeleton structure and a preparation method and the application of the near infrared fluorescent dye, and belongs to the field of biomedical materials. The photostability of the near infrared fluorescent dye is better and the fluorescence quantum yield of the near infrared fluorescent dye is high as a cyclic hydrocarbon group is inserted into a long methenyl chain. The near infrared fluorescent dye can serve as a hydrophobic end to be combined with a hydrophilic molecule with good biocompatibility through an environment sensitive bond and self-assembled to form a nanoscale lipidosome or a micelle or a vesicle. An obtained lipid material can be mixed with a medicine and\or a gene and self-assembled to form the lipidsome or the micelle or the vesicle, and the medicine and\or the gene are\is coated inside to form a carrier system. The carrier system at the luminescence quenching state enters a target cell, the environment sensitive bond on the material is fractured and disassembled in the specific environment, the medicine and\or the gene are\is released to play a role in treatment, moreover, the cyanine dye gathered inside is also released, the fluorescence is recovered. Therefore, the fluorescence switching function is realized, and the integration of diagnosis and treatment is further realized.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and relates to a class of near-infrared fluorescent dyes with a cyanine dye fluorescent group as a parent skeleton structure, a preparation method and an application thereof. technical background [0002] With the development of imaging technology, near-infrared fluorescence imaging has been widely used in the field of biological imaging due to its advantages of less damage to organisms, strong tissue penetration ability, and low biological background interference. Organic dyes used as near-infrared fluorescence detection mainly include cyanine dyes (such as Cy series), BODIPY, rhodamine, squaraine, and porphyrin, etc. Cyanine dyes have the characteristics of wide spectral range, high molar absorptivity, high fluorescence quantum yield, high sensitivity and low cytotoxicity. Among them, indocyanine green (ICG), as the only FDA-approved near-infrared fluorescent dye, has been widely used in cli...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06A61K9/107A61K9/127A61K49/00A61K47/34
CPCA61K9/1075A61K9/127A61K47/34A61K49/0032A61K49/0082A61K49/0084A61K49/0086C09B23/107C09K11/06C09K2211/1029
Inventor 聂宇梁鸿柯博文陈晓冰
Owner SICHUAN UNIV
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