Azo-PROTAC: Novel Light-Controlled Small-Molecule Tool for Protein Knockdown

Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-mole...

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Published inJournal of medicinal chemistry Vol. 63; no. 9; pp. 4644 - 4654
Main Authors Jin, Yu-Hui, Lu, Meng-Chen, Wang, Yan, Shan, Wen-Xin, Wang, Xuan-Yu, You, Qi-Dong, Jiang, Zheng-Yu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.05.2020
Amer Chemical Soc
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Science & Technology
OPTICAL CONTROL
SPATIOTEMPORAL CONTROL
DESIGN
GLUTAMATE
PHOTOCHROMIC AGONIST
IN-VIVO
DEGRADATION
RECEPTOR
PROTEOLYSIS
PROTEASOME INHIBITORS
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Abstract Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-molecule tools for protein knockdown in cells. The light-induced configuration change can switch the active state to induce protein degradation activity, which can be reversely controlled by light exposure in intact cells. We compared the protein degradation abilities of Azo-PROTACs with different configurations and linker lengths. Using the stable form with the best degradation ability against the BCR-ABL fusion and ABL proteins in myelogenous leukemia K562 cells, we showed that Azo-PROTAC combines the potent protein knockdown and facile cell uptake properties of the small-molecule PROTAC with a reversible photoswitchability, offering a promising chemical knockdown strategy based on the light-induced reversible on/off properties.
AbstractList Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-molecule tools for protein knockdown in cells. The light-induced configuration change can switch the active state to induce protein degradation activity, which can be reversely controlled by light exposure in intact cells. We compared the protein degradation abilities of Azo-PROTACs with different configurations and linker lengths. Using the stable form with the best degradation ability against the BCR-ABL fusion and ABL proteins in myelogenous leukemia K562 cells, we showed that Azo-PROTAC combines the potent protein knockdown and facile cell uptake properties of the small-molecule PROTAC with a reversible photoswitchability, offering a promising chemical knockdown strategy based on the light-induced reversible on/off properties.
Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-molecule tools for protein knockdown in cells. The light-induced configuration change can switch the active state to induce protein degradation activity, which can be reversely controlled by light exposure in intact cells. We compared the protein degradation abilities of Azo-PROTACs with different configurations and linker lengths. Using the stable form with the best degradation ability against the BCR-ABL fusion and ABL proteins in myelogenous leukemia K562 cells, we showed that Azo-PROTAC combines the potent protein knockdown and facile cell uptake properties of the small-molecule PROTAC with a reversible photoswitchability, offering a promising chemical knockdown strategy based on the light-induced reversible on/off properties.Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-molecule tools for protein knockdown in cells. The light-induced configuration change can switch the active state to induce protein degradation activity, which can be reversely controlled by light exposure in intact cells. We compared the protein degradation abilities of Azo-PROTACs with different configurations and linker lengths. Using the stable form with the best degradation ability against the BCR-ABL fusion and ABL proteins in myelogenous leukemia K562 cells, we showed that Azo-PROTAC combines the potent protein knockdown and facile cell uptake properties of the small-molecule PROTAC with a reversible photoswitchability, offering a promising chemical knockdown strategy based on the light-induced reversible on/off properties.
Author Jiang, Zheng-Yu
You, Qi-Dong
Lu, Meng-Chen
Shan, Wen-Xin
Jin, Yu-Hui
Wang, Xuan-Yu
Wang, Yan
AuthorAffiliation State Key Laboratory of Natural Medicines and Jiang Su Key Laboratory of Drug Design and Optimization
Department of Medicinal Chemistry, School of Pharmacy
AuthorAffiliation_xml – name: State Key Laboratory of Natural Medicines and Jiang Su Key Laboratory of Drug Design and Optimization
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  organization: Department of Medicinal Chemistry, School of Pharmacy
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  fullname: Shan, Wen-Xin
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/32153174$$D View this record in MEDLINE/PubMed
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Keywords OPTICAL CONTROL
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PHOTOCHROMIC AGONIST
IN-VIVO
DEGRADATION
RECEPTOR
PROTEOLYSIS
PROTEASOME INHIBITORS
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Snippet Reversibly altering endogenous protein levels are persistent issues. Herein, we designed photoswitchable azobenzene-proteolysis targeting chimeras...
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SubjectTerms Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Science & Technology
Title Azo-PROTAC: Novel Light-Controlled Small-Molecule Tool for Protein Knockdown
URI http://dx.doi.org/10.1021/acs.jmedchem.9b02058
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