Title:
TETRAZINE COMPOUND, PREPARATION METHOD THEREFOR, AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/142534
Kind Code:
A1
Abstract:
Disclosed in the present invention are a tetrazine compound, a preparation method therefor, and an application thereof. The tetrazine compound provided by the present invention can be used for implementing selective tetrazine labeling of a mercapto-containing polypeptide, protein and biological material, and can be used for rapid, efficient and stable function derivatization of a substance having a tetrazine mark by using a bioorthogonal reaction. In addition, the tetrazine compound has high selectivity, when other functional groups are enriched in a body, the tetrazine compound can selectively bind to cysteine to generate a stable linked product, while no by-product is detected, and after formation of a linked product with mercapto, reaction power of dienophile and the linked product is rapid, which is significantly faster than a manner of using thiotetrazine as a tetrazine marker in the prior art, indicating that the tetrazine compound can be applied to in-vivo bioorthogonal pre-targeting and radiolabeling by a nanomolar concentration.
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Inventors:
WU HAOXING (CN)
MAO WUYU (CN)
SUN HONGBAO (CN)
HE XINYU (CN)
YANG HAOJIE (CN)
MAO WUYU (CN)
SUN HONGBAO (CN)
HE XINYU (CN)
YANG HAOJIE (CN)
Application Number:
PCT/CN2021/120831
Publication Date:
July 07, 2022
Filing Date:
September 27, 2021
Export Citation:
Assignee:
WEST CHINA HOSPITAL SICHUAN UNIV (CN)
International Classes:
C07D257/08; G01N33/68
Foreign References:
| CN112812074A | 2021-05-18 | |||
| CN106317112A | 2017-01-11 | |||
| US20180362504A1 | 2018-12-20 |
Other References:
WUYU MAO; WEI SHI; JIE LI; DUNYAN SU; XIAOMENG WANG; LYUYE ZHANG; LILI PAN; XIAOAI WU; HAOXING WU: "Organocatalytic and Scalable Syntheses of Unsymmetrical 1,2,4,5‐Tetrazines by Thiol‐Containing Promotors", ANGEWANDTE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 131, no. 4, 18 December 2018 (2018-12-18), DE , pages 1118 - 1121, XP071380229, ISSN: 0044-8249, DOI: 10.1002/ange.201812550
ROS ENRIC, PRADES AMPARO, FORSON DOMINIQUE, SMYTH JACQUELINE, VERDAGUER XAVIER, POUPLANA LLUÍS RIBAS DE, RIERA ANTONI: "Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazines via a Sonogashira-type cross-coupling reaction", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 56, no. 75, 22 September 2020 (2020-09-22), UK , pages 11086 - 11089, XP055948173, ISSN: 1359-7345, DOI: 10.1039/D0CC03482G
HAOXING WU, JUN YANG, JOLITA SECKUTE, NEAL K. DEVARAJ: "In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live-Cell Imaging Probes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, vol. 53, no. 23, 2 June 2014 (2014-06-02), pages 5805 - 5809, XP055164300, ISSN: 14337851, DOI: 10.1002/anie.201400135
ROS ENRIC, PRADES AMPARO, FORSON DOMINIQUE, SMYTH JACQUELINE, VERDAGUER XAVIER, POUPLANA LLUÍS RIBAS DE, RIERA ANTONI: "Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazines via a Sonogashira-type cross-coupling reaction", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 56, no. 75, 22 September 2020 (2020-09-22), UK , pages 11086 - 11089, XP055948173, ISSN: 1359-7345, DOI: 10.1039/D0CC03482G
HAOXING WU, JUN YANG, JOLITA SECKUTE, NEAL K. DEVARAJ: "In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live-Cell Imaging Probes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, vol. 53, no. 23, 2 June 2014 (2014-06-02), pages 5805 - 5809, XP055164300, ISSN: 14337851, DOI: 10.1002/anie.201400135
Attorney, Agent or Firm:
CHENGDU YOUNG ZONE INTELLECTUAL PROPERTY AGENCY (ORDINARY PARTNERSHIP) (CN)
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