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Near-infrared two-region dye based on naphthalimide derivative as well as preparation and application of near-infrared two-region dye

A naphthalene diimide, near-infrared technology, applied in the field of nano-biomedical imaging materials, can solve the problems of fluorescence quenching, low tissue penetration depth, photobleaching, etc., to increase the variety and selection space, synthesis route and preparation simple method effect

Pending Publication Date: 2021-08-13
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, fluorescence imaging also has some key problems such as autofluorescence quenching, photobleaching, and low tissue penetration depth.

Method used

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  • Near-infrared two-region dye based on naphthalimide derivative as well as preparation and application of near-infrared two-region dye
  • Near-infrared two-region dye based on naphthalimide derivative as well as preparation and application of near-infrared two-region dye
  • Near-infrared two-region dye based on naphthalimide derivative as well as preparation and application of near-infrared two-region dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The structure of the small molecule in the second near-infrared region provided by this example is as follows:

[0041]

[0042] For the preparation method of this embodiment, see Figure 8 As shown, it specifically includes the following steps:

[0043] 1) Add 5g 1,4,5,8-naphthalene tetracarboxylic dianhydride (18.64mmol, 1equiv) and 75mL oleum in a 250mL round bottom flask, add catalytic amount of iodine to the reaction system, and then 1.72 mL of bromine (33.52 mmol, 1.8 equiv) was added slowly under low temperature, then heated to 50° C. and the reaction was stirred for 48 hours. After cooling, slowly add a saturated solution of sodium thiosulfate to remove excess bromine, then pour the reaction solution into ice water to form a yellow precipitate, filter and wash with water to obtain a bright yellow solid, which is 2,6-dibromo-1,4 , 5,8-naphthalene tetracarboxylic dianhydride, directly proceed to the next step reaction.

[0044] 2) Add 2g of 2,6-dibromo-1,4,5...

Embodiment 2

[0048] Small molecule contrast agent in the second near-infrared region

[0049] Dissolve 1 mg of the small molecule in the second near-infrared region (prepared in Example 1) in 1 mL of dichloromethane, and dissolve 6 mg of the amphiphilic lipid molecule DSPE-PEG5000 in 1 mL of aqueous solution, and mix the prepared dichloromethane solution and aqueous solution to obtain a mixed liquid , and then stirred overnight at room temperature to evaporate excess dichloromethane to obtain a small-molecule contrast agent in the second near-infrared region.

[0050] The obtained small molecule contrast agent in the second near-infrared region was characterized by transmission electron microscopy, and the results are as follows: Figure 5 As shown, the morphology is spherical and the size is about 50nm.

Embodiment 3

[0059] Compared with Example 1, most of them are the same, except adjusting the consumption of 4-(diphenylamino) phenylboronic acid pinacol ester, Aliquat 336, potassium carbonate, tetrakis (triphenylphosphine) palladium, so that N, N'-(2'-Ethyl)hexyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide, 4-(diphenylamino)phenylboronic acid pinacol ester, Aliquat 336, potassium carbonate, and tetrakis(triphenylphosphine)palladium are added in a ratio of 1 mmol: 2.1 mmol: 10 mg: 5 mmol: 0.05 mmol.

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Abstract

The invention relates to a near-infrared two-region dye based on a naphthalimide derivative as well as preparation and an application of the near-infrared two-region dye. The near-infrared two-region dye based on a naphthalimide structure is obtained by carrying out coupling reaction on naphthalimide serving as an acceptor structure unit and different donor units. Then the near-infrared second-region dye and amphiphilic lipid molecules DSPE-PEG5000 are subjected to self-assembly, and the obtained water-soluble nanoparticles have good fluorescence intensity in a near-infrared second region and can be used as a contrast agent to realize imaging application in the near-infrared second region.

Description

technical field [0001] The invention belongs to the technical field of nano biomedical imaging materials, and relates to a dye in the second near-infrared region based on naphthalene diimide derivatives and its preparation and application. Background technique [0002] Since fluorescence imaging does not require ionizing radiation, it can be developed as a non-invasive or minimally invasive technique, which is conveniently used in the study of biological phenomena. At the same time, fluorescence imaging also has some key problems such as autofluorescence quenching, photobleaching, and low tissue penetration depth. The near-infrared second region (NIR-II, 1000-1700 nanometers) has lower autofluorescence absorption and tissue scattering, which is different from traditional visible light fluorescence imaging and near-infrared first region (NIR-I, 650-900 nanometers) fluorescence imaging Compared with near-infrared second-region imaging, which has the smallest scattering and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06C09B57/08A61K49/00A61P35/00
CPCC07D471/06C09K11/06C09B57/08A61K49/0054A61K49/0021A61P35/00C09K2211/1044C09K2211/1007C09K2211/1014
Inventor 崔胜胜崔大祥刘岩磊金涵
Owner SHANGHAI JIAO TONG UNIV
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