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Indocyanine green derivative and preparaiton method

A technology of indocyanine green and derivatives, which is applied in the field of indole derivatives, can solve the problems of easy leakage of ICG and unstable nanoparticle structure, and achieve the effect of expanding the scope of application

Inactive Publication Date: 2018-07-10
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] like figure 1 As shown, since there is no active functional group in the structure of ICG, in some researches, such as the process of constructing the nano-diagnosis and treatment system, ICG is often encapsulated by physical coating, the structure of the formed nanoparticles is unstable, and ICG is easy to leak

Method used

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  • Indocyanine green derivative and preparaiton method
  • Indocyanine green derivative and preparaiton method
  • Indocyanine green derivative and preparaiton method

Examples

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Embodiment 1

[0034] Synthesis of Compound 3

[0035] Add compound 1 (345.0g, 1.0mol) and compound 2 (313.0g, 1.1mol) into boiling acetic anhydride (2L) under stirring conditions, stir for 30min, cool to room temperature, filter with suction, filter cake with acetone After washing and drying, a blue-black solid was obtained, which was Compound 3 (460.7 g, 85%).

Embodiment 2

[0037] Synthesis of compound 6

[0038] Compound 4 (5.7g, 27.2mmol) and compound 5 (6.90g, 35.4mmol) were dissolved in 240ml of acetonitrile and heated at 80°C for 16 hours. The reaction solution was concentrated under reduced pressure, 500ml of ether was added, and then filtered, and the residue was After washing with ether, the filter cake was dried to obtain compound 6 (9.8 g, 74.4%).

Embodiment 3

[0040] Synthesis of compound 7

[0041] Compound 3 (300mg, 0.553mmol) and compound 6 (179mg, 0.553mmol) were dissolved in 5ml of pyridine, stirred at 50°C for 1 hour; the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 10ml of water, and the solution was After the pH value was adjusted to 3, the solvent was removed by rotary evaporation under reduced pressure, and the eluent was passed through a silica gel column with chloroform / methanol (10:1) to obtain a dark green solid, which was compound 7 (105 mg, 25.9%).

[0042] The mass spectrum data of the synthesized compound 7 is as follows: HRMS (ESI) [M+H] 731.3507, [M+Na] 753.3264, the spectrum is as follows figure 1 shown.

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Abstract

The invention discloses an indocyanine green derivative and a preparaiton method. The indocyanine green derivative has the structure shown in the formula a (the formula is shown in the description). In the formula a, R1 is C1-C10 linear or branched alkyl or cycloalkyl or substituted cycloalkyl or aryl or substituted aryl with or without heteroatoms; R2 is -NH2 or -COOH or _COOCH3 or -COOEt or -OH;R3 is a metal cation. Independent active groups exist in the indocyanine green derivative so that a biological material can easily modify indocyanine green and the indocyanine green derivative, and the application range of the ndocyanine green and the indocyanine green derivative is expanded.

Description

technical field [0001] The invention relates to the technical field of indole derivatives, in particular to an indocyanine green derivative and a preparation method thereof. Background technique [0002] Indocyanine green (ICG for short) is a near-infrared fluorescent dye with the molecular formula C 43 h 47 N 2 NaO 6 S 2 , its absorption peak and emission peak (805nm and 835nm respectively), is currently the only near-infrared imaging reagent approved by the US Food and Drug Administration (FDA) for clinical use: in 1956, the US FDA approved ICG in the cardiovascular system and liver The application of functional assessment; in 1975, the US FDA supplemented its approval for ophthalmic angiography; in 2002, the US FDA approved ICG for the study of intraoperative cerebral angiography. The incidence of side effects of ICG is 0.05% to 0.2%, manifested as hypotension, arrhythmia, anaphylactic shock, nausea, itching, syncope or rash. [0003] ICG not only has extremely high...

Claims

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Application Information

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IPC IPC(8): C07D209/60C09K11/06G01N21/64A61K41/00A61P35/00
Inventor 蔡林涛孟晓青龚萍李三朋孙枝红周理华张佳丽邓冠军李文军郑明彬
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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