Products for Research Use Only

DT2216

CAT: 0013-GTR19242576-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19242576-02Size:5 mg
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Description
DT2216 is a VHL-recruiting PROTAC that selectively degrades BCL-XL. It demonstrates potent activity against BCL-XL-dependent leukemia and cancer cell lines in vitro and in vivo, while showing reduced on-target toxicity to platelets compared to traditional inhibitors.
CAS Number
2365172-42-3
Product Name Alternative
Apoptosis, DT 2216, DT2216, DT-2216, PROTAC, VHL
Field of Research
Cell Biology, Pharmacology & Drug Discovery
Purity
99.52% (May vary between batches)
Solubility
H2O:< 0.1 mg/mL (insoluble) ; DMSO:25 mg/mL (16.21 mM) ;10% DMSO+90% Corn Oil:2 mg/mL (1.3 mM)
Smiles
CC1 (C) CCC (C2=CC=C (Cl) C=C2) =C (C1) CN3CCN (C4=CC=C (C (NS (=O) (C5=CC (S (C (F) (F) F) (=O) =O) =C (N[C@@H] (CSC6=CC=CC=C6) CCN7CCN (C (CCCCCC (N[C@@H] (C (C) (C) C) C (N8[C@@H] (C[C@@H] (O) C8) C (N[C@H] (C9=CC=C (C%10=C (N=CS%10) C) C=C9) C) =O) =O) =O) =O) CC7) C=C5) =O) =O) C=C4) CC3
Molecular Formula
C77H96ClF3N10O10S4
Molecular Weight
1542.36
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Dt-2216

Bcl-XL Proteolysis Targeting Chimera DT2216 is an anti-apoptotic protein B-cell lymphoma-extra large (Bcl-XL) targeted protein degrader, using the proteolysis targeting chimera (PROTAC) technology, with potential pro-apoptotic, immunomodulating and antineoplastic activities. DT2216 is composed of a Bcl-XL ligand attached to a Von Hippel-Lindau (VHL) E3 ligase ligand. Upon administration of DT2216, the Bcl-XL binding moiety specifically targets and binds to Bcl-XL which is expressed on tumor-infiltrating regulatory T-cells (Tregs) in the tumor microenvironment (TME) and cancer cells that are dependent on Bcl-XL for their survival, such as certain Bcl-XL-dependent T-cell malignancies. In turn, the VHL E3 ligase ligand is recruited to the endoplasmic reticulum (ER) and Bcl-XL is tagged by ubiquitin. This causes ubiquitination and proteasome-mediated degradation of Bcl-XL. The degradation of Bcl-XL leads to an inhibition of the anti-apoptotic activity of Bcl-XL and restores apoptotic processes in and causes depletion of Bcl-XL-expressing Tregs and Bcl-XL-dependent cancer cells. Reduction of Tregs may activate anti-tumor CD8-positive-mediated immune responses. This leads to the inhibition of tumor growth. Bcl-XL, a protein belonging to the Bcl-2 family, plays an important role in the negative regulation of apoptosis. Their expression in tumors is associated with increased Tregs survival. Tregs play a key role in cancer progression and tumor immunosuppression. Compared to other Bcl-XL inhibitors, DT2216 does not cause platelet toxicity as the VHL E3 ligase is not highly expressed in platelets.

CAS Number2365172-42-3
PubChem CID139331475
IUPAC Name(2S,4R)-1-[(2S)-2-[[7-[4-[(3R)-3-[4-[[4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]benzoyl]sulfamoyl]-2-(trifluoromethylsulfonyl)anilino]-4-phenylsulfanylbutyl]piperazin-1-yl]-7-oxoheptanoyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide
Molecular FormulaC77H96ClF3N10O10S4
Molecular Weight1542.4
XLogP12.8
Topological Polar Surface Area321
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count20
Rotatable Bond Count29
Heavy Atom Count105
Formal Charge0
Complexity3130
SMILES
CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCC(=O)N4CCN(CC4)CC[C@H](CSC5=CC=CC=C5)NC6=C(C=C(C=C6)S(=O)(=O)NC(=O)C7=CC=C(C=C7)N8CCN(CC8)CC9=C(CCC(C9)(C)C)C1=CC=C(C=C1)Cl)S(=O)(=O)C(F)(F)F)O
InChI
InChI=1S/C77H96ClF3N10O10S4/c1-51(53-18-20-55(21-19-53)70-52(2)82-50-103-70)83-73(96)66-44-61(92)48-91(66)74(97)71(75(3,4)5)85-68(93)16-12-9-13-17-69(94)90-42-36-87(37-43-90)35-33-59(49-102-62-14-10-8-11-15-62)84-65-31-30-63(45-67(65)104(98,99)77(79,80)81)105(100,101)86-72(95)56-24-28-60(29-25-56)89-40-38-88(39-41-89)47-57-46-76(6,7)34-32-64(57)54-22-26-58(78)27-23-54/h8,10-11,14-15,18-31,45,50-51,59,61,66,71,84,92H,9,12-13,16-17,32-44,46-49H2,1-7H3,(H,83,96)(H,85,93)(H,86,95)/t51-,59+,61+,66-,71+/m0/s1
InChIKey
PXVFFBGSTYQHRO-REQIQPEASA-N
Chemical Structure
2D Structure
2D structure of Dt-2216
CAS: 2365172-42-3
CID: 139331475
Formula: C77H96ClF3N10O10S4
MW: 1542.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight1542.4
XLogP312.8
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count20
Rotatable Bond Count29
Exact Mass1540.5834362
Monoisotopic Mass1540.5834362
Topological Polar Surface Area321 Ų
Heavy Atom Count105
Formal Charge0
Complexity3130
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes