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Near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, preparation method and application thereof

A thiopylate and near-infrared technology, which is applied in the field of preparation of thiopylate fluorescent compounds, can solve the problems of difficult post-modification, poor bioavailability, complex synthesis process, etc., achieve good photostability, reduce energy gap, The effect of simple synthesis process

Active Publication Date: 2020-12-29
SHENZHEN RES INST OF WUHAN UNIVERISTY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the shortcomings of existing near-infrared second-region dyes such as complex synthesis process, difficult post-modification, and poor bioavailability, the present invention provides a near-infrared second-region fluorescent molecule that can target mitochondrial thiopylate salts. Simple process, high yield, good photostability, easy to post-modify and connect various biomarkers to construct functional molecular probes

Method used

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  • Near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, preparation method and application thereof
  • Near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, preparation method and application thereof
  • Near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, preparation method and application thereof

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Embodiment 1

[0063] The features and advantages of the present invention can be further understood through the following detailed description in conjunction with the accompanying drawings. The examples provided are only illustrative of the method of the present invention and do not limit the rest of the present disclosure in any way. Example 1] Synthesis and characterization of thiopyran compounds LQQ-1, LQQ-2, LQQ-3, LQQ-4 and LQQ-5

[0064] The thiopyran compounds LQQ-1, LQQ-2, LQQ-3, LQQ-4 and LQQ-5 (as shown below), all compounds were characterized by NMR and high-resolution mass spectrometry,

[0065]

[0066] Wherein, the synthesis route and steps of thiopyran compound LQQ-1 are as follows

[0067]

[0068] Synthesis of compound 3: KOH aqueous solution (50% w / w, 70 mL) was added to 4-hydroxyacetophenone 2 (100 mmol, 13.6 g) in 200 mL of MeOH in an ice bath. After stirring for 10 min, a solution of benzaldehyde 1 (100 mmol, 10.6 g) in 30 mL of MeOH was added dropwise over 1 h....

Embodiment 2

[0087] [Example 2] the ultraviolet absorption emission spectrum of dyestuff LQQ-1~LQQ-5

[0088] Weigh the dyes LQQ-1~LQQ-5 and dissolve them in DCM solvent at a concentration of 0.1~1mol / L, place them under a Shimadzu UV spectrometer to measure the absorption spectra of different dyes, and then perform normalized mapping. Then place the corresponding samples under a fluorescence spectrometer to measure their respective emission spectra, select 808nm as the excitation wavelength, and normalize their jinx respectively to obtain figure 2 , according to the spectrum, it can be seen that as more electron-donating groups are introduced into the molecule, the corresponding absorption-emission spectrum shifts bluer, and the more electron-withdrawing groups are introduced, the corresponding absorption-emission spectrum of the dye corresponds to redshift.

Embodiment 3

[0089] [Example 3] Preparation scheme of the near-infrared second region probe PEG-Glu

[0090]Weigh glucose hydrochloride (2.35mg, 0.01mmol) and N 3 -PEG 8 -NHS (6mg, 0.01mmol) was dissolved in 1mL of anhydrous DMF, then DIPEA (14mg, 0.1mmol) was added, and reacted overnight at room temperature. After the reaction was completed, the reaction solution was added to 50mL of ether and placed in a -80°C refrigerator The precipitate was precipitated, and then centrifuged to remove the upper ether clear liquid to obtain the crude product PEG-Glu, and the obtained crude product was directly put into the next step without purification. Its synthetic route is attached image 3 .

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Abstract

The invention discloses a near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, a preparation method and application thereof. According to the invention, a thiapyransalt heterocyclic structure is modified, different modification groups are introduced, and the emission wavelength of the thiapyran salt heterocyclic structure can be redshifted to a near-infrared IIregion (1000-1200 nm); the compound has good light stability, is easy for post-modification, can be connected with different biomarkers (polypeptide, antibody, PEG, folic acid and the like) through chemical bonding, improves the water solubility and targeting property, reduces the biotoxicity, and improves the bioavailability; and the compound can be used for mitochondrial imaging, drug efficacy evaluation, solid tumor imaging for breast cancer, osteosarcoma, glioma and other solid tumors, and vascular imaging, can also be used for surgical navigation, early diagnosis of diseases, intraoperative real-time monitoring, photothermal therapy, photodynamic therapy and other biological applications, and has good industrial production values and biomedical application prospects.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dye preparation, and relates to the combined treatment of tumor imaging, photothermal and chemotherapy in the field of biomedicine, in particular to a preparation method and application of a thiopylate fluorescent compound with fluorescence emission in the second near-infrared region. Background technique [0002] Acute myeloid leukemia (AML) is a heterogeneous and complex hematological malignancy that affects about 1 million people worldwide every year. At present, molecular targeted chemotherapy, allogeneic hematopoietic stem cell transplantation (HSCT) and other treatment methods have been widely used in the clinical treatment of acute myeloid leukemia. However, the 5-year survival rate of AML patients over 20 years old is still very low (~25%). Compared with traditional solid tumors, acute myeloid leukemia is prone to drug resistance and Escape, leading to unsatisfactory treatment effect....

Claims

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Application Information

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IPC IPC(8): C07D409/06C07D409/14C07H13/04C09K11/06G01N21/64A61K41/00A61K49/00A61P35/00A61P35/02
CPCC07D409/06C07D409/14C09K11/06C07H13/04A61K41/0057A61K49/0032A61P35/00A61P35/02G01N21/6428C09K2211/1092C09K2211/1029C09K2211/1059C09K2211/1088
Inventor 肖玉玲李芊芊洪学传
Owner SHENZHEN RES INST OF WUHAN UNIVERISTY
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