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HDAC6 degrader 9c - CAS 2235382-05-3

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It is a bifunctional PROTAC molecule that can selectively degrade HDAC6 by conjugating a non-selective HDAC inhibitor with an E3 ubiquitin ligase ligand.

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Molecular Formula

C37H45N9O10

Molecular Weight

775.81

HDAC6 degrader 9c

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO
    
    Appearance
    
    Solid Powder
    
    Storage
    
    Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
    
    IUPAC Name
    
    N-[(E)-[4-[2-[2-[2-[4-[[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]methyl]triazol-1-yl]ethoxy]ethoxy]ethoxy]phenyl]methylideneamino]-N'-hydroxyoctanediamide
    
    Synonyms
    
    dHDAC6 9c; (E)-8-(2-(4-(2-(2-(2-(4-(((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)benzylidene)hydrazineyl)-N-hydroxy-8-oxooctanamide; 8-[(2E)-2-{4-[2-(2-{2-[4-({[2-(2,6-Dioxo-3-piperidinyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]amino}methyl)-1H-1,2,3-triazol-1-yl]ethoxy}ethoxy)ethoxy]benzylidene}hydrazino]-N-hydroxy-8-oxooctanamide; Octanoic acid, 8-(hydroxyamino)-8-oxo-, 2-[(1E)-[4-[2-[2-[2-[4-[[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]methyl]-1H-1,2,3-triazol-1-yl]ethoxy]ethoxy]ethoxy]phenyl]methylene]hydrazide; 8-(Hydroxyamino)-8-oxooctanoic acid (2E)-2-[[4-[2-[2-[2-[4-[[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]methyl]-1H-1,2,3-triazol-1-yl]ethoxy]ethoxy]ethoxy]phenyl]methylene]hydrazide
- Properties
  - Density
    
    1.44±0.1 g/cm3
    
    InChI Key
    
    MHILTYZXXFOWJH-WVKHYPTHSA-N
    
    InChI
    
    InChI=1S/C37H45N9O10/c47-31-15-14-30(35(50)40-31)46-36(51)28-6-5-7-29(34(28)37(46)52)38-23-26-24-45(44-41-26)16-17-54-18-19-55-20-21-56-27-12-10-25(11-13-27)22-39-42-32(48)8-3-1-2-4-9-33(49)43-53/h5-7,10-13,22,24,30,38,53H,1-4,8-9,14-21,23H2,(H,42,48)(H,43,49)(H,40,47,50)/b39-22+
    
    Canonical SMILES
    
    C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)NCC4=CN(N=N4)CCOCCOCCOC5=CC=C(C=C5)C=NNC(=O)CCCCCCC(=O)NO
- Reference Reading
  - 1. Development of the first small molecule histone deacetylase 6 (HDAC6) degraders.
    
    Yang, K., Song, Y., Xie, H., Wu, H., Wu, Y.T., Leisten, E.D. and Tang, W., 2018. Bioorganic & medicinal chemistry letters, 28(14), pp.2493-2497.
    
    Histone deacetylases (HDACs) decrease the acetylation level of histones and other non-histone proteins. Over expression of HDACs have been observed in cancers and other diseases. Targeted protein degradation by "hijacking" the natural ubiquitin-proteasome-system (UPS) recently emerged as a novel technology to "knock-out" endogenous disease-causing proteins. We applied this strategy to the development of the first small molecule degraders for zinc-dependent HDACs by conjugating non-selective HDAC inhibitors with E3 ubiquitin ligase ligands. Through cell-based assays, we discovered novel bifunctional molecules (dHDAC6) that could selectively degrade HDAC6. Further mechanistic studies indicated that HDAC6 was selectively removed by the UPS.

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It is commonly abbreviated as: C₁V₁ = C₂V₂

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