Oxazine compound and application thereof

Patent metadata

Field	Value
Publication number	US-11639360-B2
Application number	US-201917053042-A
Country	US
Kind code	B2
Filing date	Apr 22, 2019
Priority date	May 4, 2018
Publication date	May 2, 2023
Grant date	May 2, 2023

Abstract

Disclosed are an oxazine compound and an application thereof. The oxazine compound has a structure of a general formula F. The oxazine compound described in the disclosure is a photo/acoustic dynamic active organic molecule with near-infrared absorption-emission function as well as photosensitivity and acoustic sensitivity. Maximum absorption and emission wavelengths of the compound are both greater than 660 nanometers, and a triplet-state conversion rate of the compound is high; and under illumination or ultrasound, the compound can produce reactive oxygen species with high efficiency, which has a good killing effect on cancer cells and cancer tissues, and almost has no toxic or side effects on normal tissues while achieving photo/acoustic dynamic therapy on tumors.

First claim

What is claimed is:

1. An oxazine compound having a structural formula F:

wherein,
A is selenium;
R 1 , R 2 , and R 3 are each independently selected from hydrogen, substituted C 1-20 alkyl, and unsubstituted C 1-20 alkyl;
the substituted C 1-20 alkyl is substituted by one or more functional groups selected from halogen, hydroxyl, alkoxy, aldehyde, carbonyl, amino, carboxyl, ester, acylamino, nitro, and sulfonic acid group; and
X is selected from phosphate radical, sulfate, bisulfate, nitrate, chlorine anion, bromine anion, iodine anion, and perchlorate.

2. The oxazine compound according to claim 1 , wherein R 1 , R 2 , and R 3 are each independently selected from hydrogen, substituted C 1-14 alkyl, and unsubstituted C 1-14 alkyl.

3. The oxazine compound according to claim 2 , wherein R 1 , R 2 , and R 3 are each independently selected from hydrogen, substituted C 1-6 alkyl, and unsubstituted C 1-6 alkyl.

4. The oxazine compound according to claim 3 , wherein one of R 1 and R 2 is hydrogen.

5. The oxazine compound according to claim 3 , wherein R 3 is hydrogen.

6. The oxazine compound according to claim 1 , wherein the compound is selected from

7. A photosensitizer, comprising the oxazine compound according to claim 1 .

8. The photosensitizer according to claim 7 , wherein the photosensitizer sensitizer is a near-infrared long-wavelength fluorescent probe.

9. The photosensitizer according to claim 8 , wherein the photosensitizer comprising self-assembled nanoparticles having particle sizes of 1 to 1000 nanometers.

10. A method for inhibiting growth of cancer cells, comprising:
activating the photosensitizer of claim 7 using a 660-wavelength red light to generate singlet oxygen; and
exposing the cancer cells to the singlet oxygen.

11. An acoustic sensitizer, comprising the oxazine compound according to claim 1 .

12. The acoustic sensitizer according to claim 11 , comprising self-assembled nanoparticles having particle sizes of 1 to 1000 nanometers.

13. A method for inhibiting growth of cancer cells, comprising:
activating the acoustic sensitizer of claim 11 using ultrasound to generate singlet oxygen; and exposing the cancer cells to the singlet oxygen.

Assignees

• Univ Dalian Tech
• Dalian Chromas Bioscience Co Ltd

Inventors

• Fan Jiangli
• Yao Qichao
• Li Haidong
• Bian Yana
• Li Mingle
• Wang Jingyun
• Peng Xiaojun

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C07D517/16 Primary

  Peri-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• G01N2021/6439

  with indicators, stains, dyes, tags, labels, marks · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title