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PROTAC Bcl2 degrader-1 - CAS 2378801-85-3

Inquiry

PROTAC Bcl2 degrader-1, a PROTAC based on Cereblon ligand, potently and selectively induces the degradation of Bcl-2 (IC50 = 4.94 μM, DC50 = 3.0 μM) and Mcl-1 (IC50 = 11.81 μM) by introducing the E3 ligase cereblon (CRBN)-binding ligand pomalidomide to Mcl-1/Bcl-2 dual inhibitor Nap-1.

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Molecular Formula

C45H45BrN6O10S

Molecular Weight

941.84

PROTAC Bcl2 degrader-1

- Specification
  - Purity
    
    ≥98%
    
    Solubility
    
    Soluble in DMSO (25 mg/mL, 26.54 mM, Need ultrasonic)
    
    Storage
    
    Store at -20°C, stored under nitrogen
    
    IUPAC Name
    
    N-[2-[6-(4-bromophenyl)sulfanyl-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl]-N'-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethyl]hexanediamide
    
    Synonyms
    
    Hexanediamide, N1-[2-[6-[(4-bromophenyl)thio]-1,3-dioxo-1H-benz[de]isoquinolin-2(3H)-yl]ethyl]-N6-[2-[2-[2-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]ethoxy]ethoxy]ethyl]-; BCL2 Degrader C5; N1-(2-(6-((4-Bromophenyl)thio)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)-N6-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)ethoxy)ethoxy)ethyl)adipamide; N-(2-{6-[(4-Bromophenyl)sulfanyl]-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl}ethyl)-N'-{2-[2-(2-{[2-(2,6-dioxo-3-piperidinyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]amino}ethoxy)ethoxy]ethyl}hexanediamide
- Properties
  - Boiling Point
    
    1158.2±65.0°C (Predicted)
    
    Density
    
    1.54±0.1 g/cm3 (Predicted)
    
    InChI Key
    
    IUSLKFLLLNNOGR-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C45H45BrN6O10S/c46-27-11-13-28(14-12-27)63-35-17-15-32-39-29(35)5-3-6-30(39)42(57)51(43(32)58)22-19-48-36(53)9-1-2-10-37(54)49-21-24-62-26-25-61-23-20-47-33-8-4-7-31-40(33)45(60)52(44(31)59)34-16-18-38(55)50-41(34)56/h3-8,11-15,17,34,47H,1-2,9-10,16,18-26H2,(H,48,53)(H,49,54)(H,50,55,56)
    
    Canonical SMILES
    
    C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)NCCOCCOCCNC(=O)CCCCC(=O)NCCN4C(=O)C5=C6C(=C(C=C5)SC7=CC=C(C=C7)Br)C=CC=C6C4=O
- Reference Reading
  - 1. Proteolysis targeting chimeras for the selective degradation of Mcl-1/Bcl-2 derived from nonselective target binding ligands.
    
    Wang, Z., He, N., Guo, Z., Niu, C., Song, T., Guo, Y., Cao, K., Wang, A., Zhu, J., Zhang, X. and Zhang, Z., 2019. Journal of Medicinal Chemistry, 62(17), pp.8152-8163.
    
    Proteolysis targeting chimera (PROTAC) recruits an E3 ligase to a target protein to induce its ubiquitination and subsequent degradation. We reported success in the development of two PROTACs (C3 and C5) that potently and selectively induce the degradation of Mcl-1 and Bcl-2 (DC50 = 0.7 and 3.0 μM), respectively, by introducing the E3 ligase cereblon-binding ligand pomalidomide to Mcl-1/Bcl-2 dual inhibitors S1-6 and Nap-1 with micromolar-range affinity. C3-induced Mcl-1 ubiquitination translated into much more lethality in Mcl-1-dependent H23 cells than the most potent Mcl-1 occupancy-based inhibitor A-1210477 with nanomolar-range affinity. Moreover, structure-activity relationship analysis and molecular dynamic simulations discovered the structural basis for turning nonselective or promiscuous Bcl-2 family ligands into selective PROTACs. C3 and C5 exhibited reversible depletion in living cells, which provides a new potent toolkit for gain-of-function studies to probe the dynamic roles of Bcl-2 and Mcl-1 in apoptosis networks.

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