Title:
ALANINE AGGREGATION-INDUCED EMISSION FLUORESCENT PROBE, AND SYNTHESIS METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/092715
Kind Code:
A1
Abstract:
Provided are an alanine aggregation-induced emission fluorescent probe (TPAPy-D-Ala) having a structure as represented by formula (I), and a synthesis method therefor and the use thereof. The synthesis method for TPAPy-D-Ala comprises: firstly, synthesizing a first compound (TPAPy) as represented by formula (II); synthesizing a second compound (TPAPy-Butyne) as represented by formula (III) on the basis of the first compound; and finally, obtaining the TPAPy-D-Ala as represented by formula (I) on the basis of the second compound. A strategy for directly labeling a target with a fluorophore-D-amino acid is provided, wherein an amino acid is directly coupled with a fluorescent molecule, and participation in the metabolism of the target can be realized via the amino acid. Compared with bio-orthogonal labeling, this strategy can shun two-step operation and a complex catalyst required for a reaction, and achieve one-step direct labeling of a target.
Inventors:
ZHANG PENGFEI (CN)
CHEN GUANGRUI (CN)
XIANG CHUNBAI (CN)
LUO YUAN (CN)
CAI LINTAO (CN)
CHEN GUANGRUI (CN)
XIANG CHUNBAI (CN)
LUO YUAN (CN)
CAI LINTAO (CN)
Application Number:
PCT/CN2021/137813
Publication Date:
June 01, 2023
Filing Date:
December 14, 2021
Export Citation:
Assignee:
SHENZHEN INST ADV TECH (CN)
International Classes:
C07D249/04; C07D213/38; C09K11/06
Foreign References:
| CN109970630A | 2019-07-05 | |||
| CN111742034A | 2020-10-02 | |||
| US20210109024A1 | 2021-04-15 | |||
| CN110606859A | 2019-12-24 | |||
| CN110981742A | 2020-04-10 |
Other References:
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ZHANG YUYANG, WANG LIANKE, RAO QINGPENG, BU YINGCUI, XU TIANREN, ZHU XIAOJIAO, ZHANG JIE, TIAN YUPENG, ZHOU HONGPING: "Tuning the hydrophobicity of pyridinium-based probes to realize the mitochondria-targeted photodynamic therapy and mitophagy tracking", SENSORS AND ACTUATORS B: CHEMICAL, ELSEVIER BV, NL, vol. 321, 1 October 2020 (2020-10-01), NL , pages 128460, XP093068517, ISSN: 0925-4005, DOI: 10.1016/j.snb.2020.128460
WU WENBO, LIU BIN: "Two-photon Excitable Photosensitizers with Aggregation-induced Emission and Their Biomedical Applications", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, JILIN DAXUE, BEIJING, CN, vol. 41, no. 2, 20 February 2020 (2020-02-20), CN , pages 191 - 203, XP093068516, ISSN: 0251-0790, DOI: 10.7503/cjcu20190614
WANG TAO, MA LAMAOCAO; MA HENGCHANG: "Research Progress on Cell Imaging Based on the Aggregation-induced Emission Fluorescent Probes", CHINESE JOURNAL OF APPLIED CHEMISTRY - YINGYONG HUAXUE, KEXUE CHUBANSHE, CN, vol. 35, no. 10, 10 October 2018 (2018-10-10), CN , pages 1155 - 1165, XP093068515, ISSN: 1000-0518, DOI: 10.11944/j.issn.1000-0518.2018.10.170461
YANG ZENGMING, YIN WEIDONG, ZHANG SHAOXIONG, SHAH IMRAN, ZHANG BO, ZHANG SHENGJUN, LI ZHAO, LEI ZIQIANG, MA HENGCHANG: "Synthesis of AIE-Active Materials with Their Applications for Antibacterial Activity, Specific Imaging of Mitochondrion and Image-Guided Photodynamic Therapy", ACS APPLIED BIO MATERIALS, AMERICAN CHEMICAL SOCIETY, US, vol. 3, no. 2, 17 February 2020 (2020-02-17), US , pages 1187 - 1196, XP093068520, ISSN: 2576-6422, DOI: 10.1021/acsabm.9b01094
WANG JUNJUN, ZHU XIAOJIAO, ZHANG JIE, WANG HAIYAN, LIU GANG, BU YINGCUI, YU JIANHUA, TIAN YUPENG, ZHOU HONGPING: "AIE-Based Theranostic Agent: In Situ Tracking Mitophagy Prior to Late Apoptosis To Guide the Photodynamic Therapy", APPLIED MATERIALS & INTERFACES, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 2, 15 January 2020 (2020-01-15), US , pages 1988 - 1996, XP093068519, ISSN: 1944-8244, DOI: 10.1021/acsami.9b15577
ZHANG YUYANG, WANG LIANKE, RAO QINGPENG, BU YINGCUI, XU TIANREN, ZHU XIAOJIAO, ZHANG JIE, TIAN YUPENG, ZHOU HONGPING: "Tuning the hydrophobicity of pyridinium-based probes to realize the mitochondria-targeted photodynamic therapy and mitophagy tracking", SENSORS AND ACTUATORS B: CHEMICAL, ELSEVIER BV, NL, vol. 321, 1 October 2020 (2020-10-01), NL , pages 128460, XP093068517, ISSN: 0925-4005, DOI: 10.1016/j.snb.2020.128460
WU WENBO, LIU BIN: "Two-photon Excitable Photosensitizers with Aggregation-induced Emission and Their Biomedical Applications", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, JILIN DAXUE, BEIJING, CN, vol. 41, no. 2, 20 February 2020 (2020-02-20), CN , pages 191 - 203, XP093068516, ISSN: 0251-0790, DOI: 10.7503/cjcu20190614
WANG TAO, MA LAMAOCAO; MA HENGCHANG: "Research Progress on Cell Imaging Based on the Aggregation-induced Emission Fluorescent Probes", CHINESE JOURNAL OF APPLIED CHEMISTRY - YINGYONG HUAXUE, KEXUE CHUBANSHE, CN, vol. 35, no. 10, 10 October 2018 (2018-10-10), CN , pages 1155 - 1165, XP093068515, ISSN: 1000-0518, DOI: 10.11944/j.issn.1000-0518.2018.10.170461
Attorney, Agent or Firm:
BEIJING ZHONG XUN TONG DA INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
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