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Evans blue complex as well as preparation method and application thereof

A technology of Evans blue and complexes, applied in copper organic compounds, chemical instruments and methods, fluorescence/phosphorescence, etc., can solve the problems of increasing surgeons to distinguish sentinel lymph nodes, signal interference, etc.

Active Publication Date: 2018-01-26
SHANGHAI THERANOSTICS BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the rapid spread of NEB, it spreads to the sentinel lymph nodes and secondary lymph nodes within a short time after local injection, so that the secondary lymph nodes will interfere with the signal of the sentinel lymph nodes during surgery, which increases the difficulty for surgeons to distinguish the sentinel lymph nodes
At the same time, this problem is also a common problem in other SLNs imaging methods.

Method used

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  • Evans blue complex as well as preparation method and application thereof
  • Evans blue complex as well as preparation method and application thereof
  • Evans blue complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1. Preparation of Evans blue derivative ligand (compound 13)

[0073] Synthesis of Compound 2:

[0074] Compound 1 (3,3'-dimethylbenzidine, 4.25 g, 20.0 mmol) and 50 mL of dry dichloromethane were respectively put into a 250 mL flask to obtain a pale yellow solution. 20 mL of di-tert-butyl dicarbonate (4.36 g, 20.0 mmol) in dichloromethane was slowly dropped into the flask. After stirring at room temperature for 24 h, the solvent was spin-dried to obtain a yellow solid. The residue was purified by silica gel column (petroleum ether / ethyl acetate=1:3) to obtain light yellow compound 2 with a yield of 50%. 1 H NMR (300MHz, CDCl 3)δ7.79(d, J=8.0Hz, 1H), 7.35(d, J=8.5Hz, 1H), 7.31(s, 1H), 7.24(d, J=3.7Hz, 1H), 6.71(d, J=7.9Hz,1H),6.27(s,1H),3.63(s,2H),2.28(s,3H),2.21(s,3H),1.53(s,9H).

[0075] Synthesis of compound 3:

[0076] Under ice bath condition, 15 mL of iced 2.0 M HCl was added dropwise to 40 mL of compound 2 (3.12 g, 10.0 mmol) in acetonitrile. St...

Embodiment 2～20

[0096] The N(EB) of embodiment 2-20 2 The compound structure is shown in the following formula (I), wherein, R can be a linking group shown in the following formula (II), the selection of each part of the group in the formula (II) is listed in Table 1 below, and their preparation method All can refer to embodiment 1:

[0097]

[0098] Table 1

[0099]

[0100]

Embodiment 21

[0101] Example 21. Radioactivity 18 Preparation of F-labeled Evan's blue complex

[0102] 1. Radioactivity 18 Preparation of F-labeled freeze-dried kit (take the preparation of 100 as an example)

[0103] Weigh 10 mg of compound 13 prepared in Example 1 and dissolve it in 10 mL of 0.5 mol / L acetic acid-sodium acetate buffer solution (pH=4), then add 0.1 mg of aluminum chloride (AlCl 3 ) was dissolved in 10 mL of 0.5 mol / L acetic acid-sodium acetate buffer solution (pH=4), and the two were evenly mixed. After sterile filtration, it is divided into 100 controlled antibiotic vials, and then placed in a freeze dryer for 24 hours to freeze-dry, and then sealed with a stopper to obtain a freeze-dried medicine box. According to the output of the kit and the requirements for the content of the components in each kit, the amount of compound 13 and aluminum chloride can be adjusted so that the mass ratio is in the range of 20-100:1.

[0104] 2. 18 Preparation of F-labeled Evan's bl...

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Abstract

The invention provides an Evans blue complex which is of formula (I) as shown in the specification. The Evans blue complex structurally comprises two serum albumin combined groups and one macrocyclicpolyamine chelated group NOTA. The invention further provides a marking complex prepared from the Evans blue complex after radionuclide marking. The marked complex provided by the invention is simpleto mark and biological property; biological test results show that the complex has a property of distinguishing sentinel nodes from secondary lymphatic glands. The invention further relates to a preparation method and application of the complex in preparing organ and tissue photographic developers of human beings or animals.

Description

technical field [0001] The invention relates to a class of radioactive complexes, a preparation method thereof and the application of the complexes as sentinel lymph node imaging agents and blood pool imaging agents. Background technique [0002] Metastasis and spread of solid tumors usually pass through lymphatic vessels, and tumor cells secrete lymphatic growth factors (such as VEGF-C and VEGF-D) to stimulate the formation of new lymphatic vessels at the tumor margin and inside, thereby promoting the spread of tumor cells to lymph nodes through lymphatic vessels. The first-level lymph nodes, Sentinel Lymph Nodes (SLNs), are the first stop for tumor metastasis and spread. Therefore, clinically, the degree of malignancy of the tumor and the corresponding treatment methods can be determined by detecting whether tumor metastasis has occurred in the sentinel lymph nodes (SLNs) . Currently, SLNs biopsy results are the gold standard for judging tumor metastasis, which has become...

Claims

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Application Information

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IPC IPC(8): C07D255/02C07F1/08G01N21/64A61K51/04
CPCC09B35/029
Inventor 陈小元郎立新牛刚田蕊
Owner SHANGHAI THERANOSTICS BIOTECH CO LTD
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