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PROTAC B-Raf degrader 1 - CAS 2364367-27-9

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It is a B-Raf degrader, which can accelerate the degradation of B-Raf through recruitment of ubiquitin-proteasome system, and then affect the expression of Mcl-1 (a downstream protein of B-Raf).

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Molecular Formula

C36H37N5O12S

Molecular Weight

763.77

PROTAC B-Raf degrader 1

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    10 mM in DMSO
    
    Storage
    
    Store at -20°C, stored under nitrogen
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere
    
    IUPAC Name
    
    N-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]-2-oxoethyl]-2-[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]anilino]acetamide
    
    Synonyms
    
    (E)-N-(2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)-2-(2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetamido)acetamide; N-[2-Methoxy-5-({[(E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfonyl}methyl)phenyl]glycyl-N-[2-(2,6-dioxo-3-piperidinyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]glycinamide; Glycinamide, N-[2-methoxy-5-[[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]phenyl]glycyl-N-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-
- Properties
  - Boiling Point
    
    1136.9±65.0°C at 760 Torr
    
    Density
    
    1.451±0.06 g/cm3
    
    InChI Key
    
    AMOFJSISJOOLNX-OUKQBFOZSA-N
    
    InChI
    
    InChI=1S/C36H37N5O12S/c1-50-21-15-28(52-3)22(29(16-21)53-4)12-13-54(48,49)19-20-8-10-27(51-2)25(14-20)37-17-31(43)38-18-32(44)39-24-7-5-6-23-33(24)36(47)41(35(23)46)26-9-11-30(42)40-34(26)45/h5-8,10,12-16,26,37H,9,11,17-19H2,1-4H3,(H,38,43)(H,39,44)(H,40,42,45)/b13-12+
    
    Canonical SMILES
    
    COC1=C(C=C(C=C1)CS(=O)(=O)C=CC2=C(C=C(C=C2OC)OC)OC)NCC(=O)NCC(=O)NC3=CC=CC4=C3C(=O)N(C4=O)C5CCC(=O)NC5=O
- Reference Reading
  - 1. Pomalidomide hybrids act as proteolysis targeting chimeras: Synthesis, anticancer activity and B-Raf degradation.
    
    Chen, H., Chen, F., Pei, S. and Gou, S., 2019. Bioorganic chemistry, 87, pp.191-199.
    
    As the first intracellular signaling molecule and the most frequently mutated oncogene, B-Raf represents an important target in cancer therapy. Here we report several pomalidomide hybrids acting as proteolysis targeting chimeras (PROTACs) for the degradation of B-Raf. Due to its high expression of B-Raf, MCF-7 cells are sensitive to these compounds. Among them, compound 2 can effectively kill cancer cells via inducing cells apoptosis. As a B-Raf degrader, compound 2 can accelerate the degradation of B-Raf by recruiting ubiquitin-proteasome system, and further affects the expression of Mcl-1, a downstream protein of B-Raf. The anticancer mechanism of compound 2 is quite different from its mother compound and cancer cells seem to be more sensitive to the degrader, hinting that degradation of B-Raf by PROTAC is a potential way for cancer treatment.

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It is commonly abbreviated as: C₁V₁ = C₂V₂

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