Title:
RATIOMETRIC POLYSULFANE FLUORESCENT PROBE, AND PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/015795
Kind Code:
A1
Abstract:
Disclosed are a ratiometric polysulfane fluorescent probe, and a preparation method therefor and the use thereof. The structural formula of the fluorescent probe is represented by formula (I). The fluorescent probe is obtained by reacting 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-methylene)malononitrile with a precursor compound to obtain a precursor having an aggregation-induced emission characteristic, and then linking an electrophilic recognition group 2-fluoro-5-nitrobenzoate. The ratiometric polysulfane fluorescent probe has the advantages of easy-access synthetic raw materials, simple synthesis, a high yield of a target compound, ratiometric response and the like, avoids the defects that conventional fluorescent probes are not suitable for detection at high concentrations and single emission is prone to be interfered by external factors such as concentration, temperature, pH value, and instruments during the detection process, has high fluorescence intensity, fast response, a high resolution and a strong anti-interference capability, can be used for qualitative and quantitative detection of polysulfane in cells and living bodies, and has good prospects for application.
Inventors:
GONG PING (CN)
XIANG CHUNBAI (CN)
CAI LINTAO (CN)
XIANG JINGJING (CN)
ZHANG PENGFEI (CN)
LUO YUAN (CN)
XIANG CHUNBAI (CN)
CAI LINTAO (CN)
XIANG JINGJING (CN)
ZHANG PENGFEI (CN)
LUO YUAN (CN)
Application Number:
PCT/CN2021/137297
Publication Date:
February 16, 2023
Filing Date:
December 12, 2021
Export Citation:
Assignee:
SHENZHEN INST OF ADV TECH CAS (CN)
International Classes:
C07D307/54; C07D455/04; C09K11/06; G01N21/64
Foreign References:
| CN113582950A | 2021-11-02 | |||
| CN102482504A | 2012-05-30 | |||
| CN110511742A | 2019-11-29 |
Other References:
ZHANG, CHANGLI ET AL.: "A BODIPY-based ratiometric probe for sensing and imaging hydrogen polysulfides in living cells", SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol. 223, 19 June 2019 (2019-06-19), XP085811763, ISSN: 1386-1425, DOI: 10.1016/j.saa.2019.117295
ZHAO LIMING, SUN QIAN, SUN CHUANZHI, ZHANG CHANGLI, DUAN WENZENG, GONG SHUWEN, LIU ZHIPENG: "An isophorone-based far-red emitting ratiometric fluorescent probe for selective sensing and imaging of polysulfides", JOURNAL OF MATERIALS CHEMISTRY. B, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 6, no. 43, 7 November 2018 (2018-11-07), GB , pages 7015 - 7020, XP093034695, ISSN: 2050-750X, DOI: 10.1039/C8TB01813H
LI CHUNBIN, JIANG GUOYU, LIU XIANG, LAI QINGFANG, KANG MIAOMIAO, WANG DONG, ZHANG PENGFEI, WANG JIANGUO, TANG BEN ZHONG: "An easily available ratiometric AIE probe for nitroxyl visualization in vitro and in vivo", MATERIALS CHEMISTRY FRONTIERS, vol. 5, no. 4, 23 February 2021 (2021-02-23), pages 1817 - 1823, XP093034698, DOI: 10.1039/D0QM00995D
LIU CHUNRONG, CHEN WEI, SHI WEN, PENG BO, ZHAO YU, MA HUIMIN, XIAN MING: "Rational Design and Bioimaging Applications of Highly Selective Fluorescence Probes for Hydrogen Polysulfides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 136, no. 20, 21 May 2014 (2014-05-21), pages 7257 - 7260, XP093034700, ISSN: 0002-7863, DOI: 10.1021/ja502968x
XIANG CHUNBAI, LI CHUNBIN, XIANG JINGJING, LUO YUAN, PENG JIAOFENG, DENG GUANJUN, WANG JIANGUO, KOLEMEN SAFACAN, LI HONGCHUN, ZHAN: "An easily available lysosomal-targeted ratiometric fluorescent probe with aggregation induced emission characteristics for hydrogen polysulfide visualization in acute ulcerative colitis", MATERIALS CHEMISTRY FRONTIERS, vol. 5, no. 20, 11 October 2021 (2021-10-11), pages 7638 - 7644, XP093034701, DOI: 10.1039/D1QM01043C
ZHONG KELI, CHEN LIN, PAN YONGXIN, YAN XIAOMEI, HOU SHUHUA, TANG YIWEI, GAO XUE, LI JIANRONG, TANG LIJUN: "A colorimetric and near-infrared fluorescent probe for detection of hydrogen sulfide and its real multiple applications", SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, ELSEVIER, AMSTERDAM, NL, vol. 221, 1 October 2019 (2019-10-01), AMSTERDAM, NL, pages 117135, XP093034703, ISSN: 1386-1425, DOI: 10.1016/j.saa.2019.117135
ZHAO LIMING, SUN QIAN, SUN CHUANZHI, ZHANG CHANGLI, DUAN WENZENG, GONG SHUWEN, LIU ZHIPENG: "An isophorone-based far-red emitting ratiometric fluorescent probe for selective sensing and imaging of polysulfides", JOURNAL OF MATERIALS CHEMISTRY. B, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 6, no. 43, 7 November 2018 (2018-11-07), GB , pages 7015 - 7020, XP093034695, ISSN: 2050-750X, DOI: 10.1039/C8TB01813H
LI CHUNBIN, JIANG GUOYU, LIU XIANG, LAI QINGFANG, KANG MIAOMIAO, WANG DONG, ZHANG PENGFEI, WANG JIANGUO, TANG BEN ZHONG: "An easily available ratiometric AIE probe for nitroxyl visualization in vitro and in vivo", MATERIALS CHEMISTRY FRONTIERS, vol. 5, no. 4, 23 February 2021 (2021-02-23), pages 1817 - 1823, XP093034698, DOI: 10.1039/D0QM00995D
LIU CHUNRONG, CHEN WEI, SHI WEN, PENG BO, ZHAO YU, MA HUIMIN, XIAN MING: "Rational Design and Bioimaging Applications of Highly Selective Fluorescence Probes for Hydrogen Polysulfides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 136, no. 20, 21 May 2014 (2014-05-21), pages 7257 - 7260, XP093034700, ISSN: 0002-7863, DOI: 10.1021/ja502968x
XIANG CHUNBAI, LI CHUNBIN, XIANG JINGJING, LUO YUAN, PENG JIAOFENG, DENG GUANJUN, WANG JIANGUO, KOLEMEN SAFACAN, LI HONGCHUN, ZHAN: "An easily available lysosomal-targeted ratiometric fluorescent probe with aggregation induced emission characteristics for hydrogen polysulfide visualization in acute ulcerative colitis", MATERIALS CHEMISTRY FRONTIERS, vol. 5, no. 20, 11 October 2021 (2021-10-11), pages 7638 - 7644, XP093034701, DOI: 10.1039/D1QM01043C
ZHONG KELI, CHEN LIN, PAN YONGXIN, YAN XIAOMEI, HOU SHUHUA, TANG YIWEI, GAO XUE, LI JIANRONG, TANG LIJUN: "A colorimetric and near-infrared fluorescent probe for detection of hydrogen sulfide and its real multiple applications", SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, ELSEVIER, AMSTERDAM, NL, vol. 221, 1 October 2019 (2019-10-01), AMSTERDAM, NL, pages 117135, XP093034703, ISSN: 1386-1425, DOI: 10.1016/j.saa.2019.117135
Attorney, Agent or Firm:
BEIJING ZHONG XUN TONG DA INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
Download PDF:
Previous Patent: SWEEPING ROBOT
Next Patent: METHOD, APPARATUS AND SYSTEM FOR CONTROLLING MAGNETORHEOLOGICAL SEMI-ACTIVE SUSPENSION
Next Patent: METHOD, APPARATUS AND SYSTEM FOR CONTROLLING MAGNETORHEOLOGICAL SEMI-ACTIVE SUSPENSION