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TL13-12 - CAS 2229037-04-9

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TL13-12 is a potent PROTAC® degrader targeting anaplastic lymphoma kinase (ALK) with an IC50 value of 0.69 nM, consisiting of a cereblon E3 ligase ligand Pomalidomide conjugated to an ALK inhibitor by a linker.

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Molecular Formula

C45H53ClN10O10S

Molecular Weight

961.48

TL13-12

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO
    
    Appearance
    
    Yellow Solid
    
    Storage
    
    Store at -20°C
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    N-[2-[2-[2-[4-[4-[[5-chloro-4-(2-propan-2-ylsulfonylanilino)pyrimidin-2-yl]amino]-3-methoxyphenyl]piperazin-1-yl]ethoxy]ethoxy]ethyl]-2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetamide
    
    Synonyms
    
    TL 13-12; TL-13-12; Acetamide, N-[2-[2-[2-[4-[4-[[5-chloro-4-[[2-[(1-methylethyl)sulfonyl]phenyl]amino]-2-pyrimidinyl]amino]-3-methoxyphenyl]-1-piperazinyl]ethoxy]ethoxy]ethyl]-2-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]-; N-(2-(2-(2-(4-(4-((5-Chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperazin-1-yl)ethoxy)ethoxy)ethyl)-2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)acetamide
- Properties
  - Density
    
    1.4±0.1 g/cm3
    
    InChI Key
    
    WXNUIPVZMJMPNM-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C45H53ClN10O10S/c1-28(2)67(62,63)37-10-5-4-8-33(37)50-41-31(46)26-49-45(53-41)51-32-12-11-29(25-36(32)64-3)55-18-16-54(17-19-55)20-22-66-24-23-65-21-15-47-39(58)27-48-34-9-6-7-30-40(34)44(61)56(43(30)60)35-13-14-38(57)52-42(35)59/h4-12,25-26,28,35,48H,13-24,27H2,1-3H3,(H,47,58)(H,52,57,59)(H2,49,50,51,53)
    
    Canonical SMILES
    
    COC1=C(C=CC(N2CCN(CC2)CCOCCOCCNC(CNC3=C4C(N(C(C4=CC=C3)=O)C5CCC(NC5=O)=O)=O)=O)=C1)NC6=NC=C(C(NC7=C(S(=O)(C(C)C)=O)C=CC=C7)=N6)Cl
    
    Pub Chem ID
    
    138108740
- Reference Reading
  - 1. Chemically induced degradation of anaplastic lymphoma kinase (ALK).
    
    Powell, C.E., Gao, Y., Tan, L., Donovan, K.A., Nowak, R.P., Loehr, A., Bahcall, M., Fischer, E.S., Jänne, P.A., George, R.E. and Gray, N.S., 2018. Journal of medicinal chemistry, 61(9), pp.4249-4255.
    
    We present the development of the first small molecule degraders that can induce anaplastic lymphoma kinase (ALK) degradation, including in non-small-cell lung cancer (NSCLC), anaplastic large-cell lymphoma (ALCL), and neuroblastoma (NB) cell lines. These degraders were developed through conjugation of known pyrimidine-based ALK inhibitors, TAE684 or LDK378, and the cereblon ligand pomalidomide. We demonstrate that in some cell types degrader potency is compromised by expression of drug transporter ABCB1. In addition, proteomic profiling demonstrated that these compounds also promote the degradation of additional kinases including PTK2 (FAK), Aurora A, FER, and RPS6KA1 (RSK1).
- Preparing Stock Solutions
  - ConcentrationVolumeMass 1 mg 5 mg 10 mg
    
    1 mM 1.04 mL 5.2 mL 10.4 mL
    
    5 mM 0.21 mL 1.04 mL 2.08 mL
    
    10 mM 0.1 mL 0.52 mL 1.04 mL
    
    50 mM 0.02 mL 0.1 mL 0.21 mL

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	1.04 mL	5.2 mL	10.4 mL
5 mM	0.21 mL	1.04 mL	2.08 mL
10 mM	0.1 mL	0.52 mL	1.04 mL
50 mM	0.02 mL	0.1 mL	0.21 mL

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