Thiazole orange derivative, preparation and application thereof

A technology of orange derivatives and thiazoles, applied in the field of small molecule photothermal materials, can solve the problem of low photothermal conversion efficiency of mitochondrial photothermal probes

Pending Publication Date: 2020-10-20
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of this, this application provides a thiazole orange derivative with low biological toxicity and high photothermal conversion, which can effectively solve the technical problem of low photothermal conversion efficiency of existing mitochondrial photothermal probes

Method used

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  • Thiazole orange derivative, preparation and application thereof
  • Thiazole orange derivative, preparation and application thereof
  • Thiazole orange derivative, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The embodiment of the present application provides a thiazole orange derivative (I-b), the synthesis method of which comprises:

[0082] (1) Add 2,4-dimethylquinoline and methyl iodide to acetonitrile solvent at a molar ratio of 1:1, react at 60°C for 24 hours, cool to room temperature, add an appropriate amount of ethyl acetate dropwise, and solids precipitate out. Collect solid, purify, obtain product formula (Ⅴ-b);

[0083]

[0084] The NMR data of formula (Ⅴ-b) is: 1 H NMR (DMSO, 400Hz): δ8.13 (d, J = 8.4Hz, 1H), 8.04 (d, J = 8.4Hz, 1H), 7.68 (m, 2H), 6.92 (s, 1H), 4.33 ( s,3H), 2.68(s,3H), 2.59(s,3H); ESI-MS m / z299.02[M-I] + ;

[0085] (2) Dissolve the formula (V-b) and N,N'-diphenylformamidine in ethanol at a molar ratio of 1:2, and heat at reflux at 60°C for 1 hour. After cooling to room temperature, the precipitate was collected by filtration, washed three times with ethanol, and then dried in vacuo to obtain a brown solid product formula (VI-b);

[0086...

Embodiment 2

[0102] The embodiment of the present application provides the photothermal conversion performance test of the compound of the formula I-b structure in Example 1, including:

[0103] The formula (I-b) prepared in Example 1 and commercialized ICG (indocyanine green ICG is a kind of cyanine dye used in medical diagnosis) are diluted to 1mM, 2mM, 3mM, 4mM, 5mM with deionized water Concentration of five gradients, then irradiated with 808nm laser for 5 minutes, irradiation energy is 2J / cm 2 , detect the ambient temperature every 1 minute with a near-infrared temperature detector, and the control group uses deionized water to measure the formula (I-b) and commercial ICG prepared in Example 1 when the irradiation energy is 2J / cm 2 The temperature rise within 5 minutes under the irradiation of the 808nm laser, the results are as follows Figure 4 ~ Figure 5 as shown, Figure 4 The formula (I-b) and ICG provided for the embodiment of the application are 2J / cm at the irradiation energ...

Embodiment 3

[0105] The embodiment of the present application provides the cytotoxicity test of the compound of formula I-b structure in embodiment 1, including:

[0106] Cell culture: Inoculate tumor cells (human prostate cancer PC3, breast cancer MCF7, non-small cell lung cancer A549 and liver cancer HepG2 cell lines) and Hacat epidermal cells in cell culture flasks and place at 37°C, 5% CO 2 The medium is cultured in the environment, and the medium is 1640 medium containing 10% fetal bovine serum and 0.5% double antibody. Cell inoculation: Inoculate the cultured cells in a 96-well plate with a cell density of 8000 cells / mL, and continue to store at 37°C, 5% CO 2 Incubate in the environment for 48 hours. Add gradient compound solution: remove the medium in the 96-well plate, wash with pre-cooled PBS 3 times, add 1640 complete medium containing formula (I-b) of different gradient Example 1, and continue to store at 37°C, 5% CO 2 Incubate in the environment for 24 hours. Add MTT solutio...

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Abstract

The invention belongs to the technical field of small molecular photo-thermal materials, particularly relates to a thiazole orange derivative, preparation and application thereof, and provides a thiazole orange derivative, which has a structure represented by a formula I, wherein n is equal to 1, 2 or 3, X is I, Br or Cl, R1 is fatty acylamino, fatty carboxyl or fatty alkyl, and R2 is triphenyl phosphine or triphenyl amine. The invention also provides a preparation method of the thiazole orange derivative. The preparation method comprises the following steps: reacting a compound with a structure epresented by a formula IX with a compound with a structure represented by a formula VII to obtain a compound with a structure represented by a formula I, wherein n is equal to 1, 2 or 3, R2 is triphenyl phosphine or triphenyl amine, Y is I, Br or Cl, X is I, Br or Cl, and R1 is fatty acylamino, fatty carboxyl or fatty alkyl. The invention discloses an application of a thiazole orange derivative in preparation of a targeted photothermal therapy tumor drug or a targeted photoacoustic imaging signal drug.

Description

technical field [0001] The application belongs to the technical field of small molecule photothermal materials, and in particular relates to a thiazole orange derivative and its preparation and application. Background technique [0002] Due to its high sensitivity, low cost, easy operation, no damage to body tissues, and the ability to achieve real-time tracer imaging, fluorescein contrast imaging technology has made a lot of progress in the detection and diagnosis of early cancers in recent years. [0003] Mitochondria are important organelles for cell survival, the energy factory of cells, and play a key role in the process of cell apoptosis. The abnormal activity of mitochondria in tumor cells is closely related to the infinite proliferation ability of tumors. Therefore, mitochondria have been considered as ideal targets for anti-tumor therapy, including material transport, interpretation of genetic information, regulation of gene expression, and some important biocataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558A61K41/00A61K49/22A61P35/00
CPCC07F9/65583A61K41/0052A61K49/22A61P35/00
Inventor 龙威卢宇靖郑伯鑫佘梦婷黄玄贺陈翠翠张艺瀚钟冬晓张焜
Owner GUANGDONG UNIV OF TECH
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