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Maleimide propionyl piperazine heptamethine cyanine salt fluorescence carrier and preparation method and application thereof

A technology of maleimide propionylpiperazine and heptamethine salt, applied in the field of maleimide propionylpiperazine heptamethine salt fluorescent carrier and its preparation, can solve the problem of small Stokes shift, Light instability, fluorescent material leakage and other problems, to achieve high quantum efficiency and Stokes shift, ensure accuracy and precision, convenient and fast marking effect

Active Publication Date: 2016-08-24
重庆高晋生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Because ICG itself cannot be used as a carrier for other molecules, and at the same time, its quantum efficiency is relatively low, the light is unstable, and the Stokes shift is small, which greatly limits its application.
For example, when used as a tracer detection of a specific target such as a drug molecule, other materials need to be used for embedding, which may cause false positive results caused by leakage of fluorescent substances, and adverse situations such as side effects

Method used

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  • Maleimide propionyl piperazine heptamethine cyanine salt fluorescence carrier and preparation method and application thereof
  • Maleimide propionyl piperazine heptamethine cyanine salt fluorescence carrier and preparation method and application thereof
  • Maleimide propionyl piperazine heptamethine cyanine salt fluorescence carrier and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 The 2-(-2-(-2-(4-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propionyl)piperazine- 1-yl)-3-(-2-(1-ethyl-3,3-dimethylindol-2-ylidene)ethylene)cyclohex-1-en-1-yl)vinyl)- Synthesis of 1-ethyl-3,3-dimethyl-3H-indole iodide

[0039] method one:

[0040] This method synthetic example maleimide propionyl piperazine heptamethine iodide comprises the following steps:

[0041] S1: Add 327.01mg (3.80mM) of piperazine into a single-neck flask, add an appropriate amount of acetonitrile to dissolve, heat up to 40°C and stir, then weigh 240.40mg (0.38mM) of chloroheptamethine iodide, and add an appropriate amount of acetonitrile After dissolving, slowly add it dropwise into the piperazine solution, and monitor the reaction process by thin-layer chromatography. The reaction solution gradually changes from emerald green to blue. After 2-3 hours of complete reaction, remove the solvent by rotary evaporation, and use After extraction, the organic layers were combined, and the di...

Embodiment 2

[0047] Example 2 Covalent linkage of maleimide propionylpiperazine heptamethine iodide and mercaptododecaborane disodium salt (BSH)

[0048] Since the anion part of the maleimide propionyl piperazine heptamethine salt fluorescent carrier referred to in the present invention has no essential influence on the covalent chemical connection performance of the carrier, this example is mainly based on the maleimide propionyl piperazine Heptamethine iodide is the representative (code name CyP).

[0049] In this embodiment, the classic radioactive boron neutron capture therapeutic drug mercaptododecaborane disodium salt (BSH) containing a sulfhydryl group is selected as a nucleophile, and is covalently bound to the maleimide propionyl piperazine heptamethine salt Above, the formation of copolymer dodecaborane maleimide propionyl piperazine heptamethine sulfide salt (code name BS-CyP). This experiment proves that the maleimide propionylpiperazine heptamethine salt-based fluorescent car...

Embodiment 3

[0051] Embodiment 3 physicochemical properties experiment

[0052] Because the anion portion of the near maleimide propionylpiperazine heptamethine salt of the present invention has no essential influence on the fluorescence performance of the carrier, this example is mainly based on the maleimide propionyl piperazine heptamethine iodide (CyP) as the representative.

[0053] (1) Absorption spectra of near-infrared cyanine dyes ICG and CyP

[0054] ICG and the maleimide propionylpiperazine heptamethine iodide prepared in Example 1 were dissolved in methanol respectively to prepare a stock solution with a concentration of 1 mM, diluted to 3.13 μM, and scanned the ultraviolet absorption spectrum respectively to measure Its UV-Vis spectrum was obtained as figure 1 shown. Depend on figure 1 It can be seen that the maximum absorption wavelength of ICG in methanol is 790nm, with a small shoulder at 710nm. CyP presents obvious double absorption peaks, the maximum absorption wavel...

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Abstract

The invention belongs to the technical field of drug carriers, and discloses a maleimide propionyl piperazine heptamethine cyanine salt fluorescence carrier and a preparation method and application thereof. On the basis of near-infrared fluorescent cyanine dye, a maleimide structure is introduced, the carrier is obtained, the carrier can be effectively subjected to a Michael addition reaction with micromolecules, polypeptide, protein and the like which contain nucleophilic groups such as mercapto groups, fluorescence labeling is conducted on corresponding molecules, and in vitro detection and in vivo developing tracking on the micromolecules, polypeptide and the protein are achieved. The fluorescence carrier has good light stability, and compared with indocyanine green (ICG), the fluorescence carrier has higher quantum efficiency and larger Stokes shift and can be used for preparing a detection reagent or kit of the micromolecules, polypeptide and the protein which contain the nucleophilic groups.

Description

technical field [0001] The invention belongs to the technical field of drug carriers, and more specifically relates to a fluorescent carrier of maleimide propionylpiperazine heptamethine salt and its preparation method and application. Background technique [0002] Near-infrared light refers to electromagnetic waves with a wavelength of 700-900nm. In this wavelength range, the damage to cells caused by excitation light is greatly reduced, and at the same time, it can effectively avoid the interference of cell autofluorescence and background fluorescence, and improve the accuracy of detection. And sensitivity, in addition, near-infrared light has strong tissue penetration, and the theoretical calculation of near-infrared light penetration into the tissue reaches a depth of 7-14cm. [0003] Near-infrared fluorescent cyanine dyes can be used as fluorescent probes in biological analysis for nucleic acid staining or labeling, and derivatization or labeling of amino acids, peptide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C09K11/06G01N21/64G01N21/359
CPCC07D403/14C09K11/06C09K2211/1029C09K2211/1044G01N21/359G01N21/6402
Inventor 卜宪章杜军黄景温蔡绍晖陈道远
Owner 重庆高晋生物科技有限公司
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