DT2216 - Moligand™, ≥98% , CAS No.2365172-42-3

CAS: 2365172-42-3 Cat. No.: D414272 Molecular Weight: 1542.36 PubChem CID: 139331475

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2S,4R)-1-((S)-2-(7-(4-((R)-3-(4-(N-(4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-(trifluoromethylsulfonyl)phenylamino)-4-(phenylthio)butyl)piperazin-1-yl)-7-oxoheptanamido)-3,3-dimethylbutanoyl)-4-hydro

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Application

PROTAC

Overview

Information

DT2216 DT2216 is a potent and selective degrader of BCL-XL based on PROTAC technology. DT2216 inhibits various BCL-XL-dependent leukemia and cancer cells but considerably less toxic to platelets.

Targets

BCL-XL

In vitro

DT2216 is a BCL-XL proteolysis targeting chimera (PROTAC) that targets BCL-XL to the Von Hippel-Lindau (VHL) E3 ligase for degradation. DT2216 is more potent against various BCL-XL-dependent leukemia and cancer cells but significantly less toxic to platelets than ABT263 in vitro because VHL is poorly expressed in platelets.

In vivo

DT2216 effectively inhibits the growth of several xenograft tumors as a single agent or in combination with other chemotherapeutic agents, without causing significant thrombocytopenia.

Cell Research(from reference)

Cell lines：MOLT-4, RS4;11, NCI-H146, MDA-MB-231, PC-3, HepG2, SW620, 786-O, WI-38, HEK 293T cells 

Concentrations：0.1 μM, 0.3 μM 

Incubation Time：24 h 

Specifications

Synonyms

(2S, 4R)-1-((S)-2-(7-(4-((R)-3-(4-(N-(4-(4-((2-(4-chlorophenyl)-5, 5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-(trifluoromethylsulfonyl)phenylamino)-4-(phenylthio)butyl)piperazin-1-yl)-7-oxoheptanamido)-3, 3-dimethylbutanoyl)-4-hydro

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

DT2216 is a potent and selective degrader of BCL-XL based on PROTAC technology. DT2216 inhibits various BCL-XL-dependent leukemia and cancer cells but considerably less toxic to platelets.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

DEGRADER

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=C(SC=N1)C2=CC=C(C=C2)C(C)NC(=O)C3CC(CN3C(=O)C(C(C)(C)C)NC(=O)CCCCCC(=O)N4CCN(CC4)CCC(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
• 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
• InChIKey: PXVFFBGSTYQHRO-REQIQPEASA-N
• 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
• Isomeric 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
• Alternate CAS: 2365172-42-3
• PubChem CID: 139331475
• MeSH Entry Terms: (2S,4R)-1-((S)-2-(7-(4-((R)-3-((4-(N-(4-(4-((4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-yl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-((trifluoromethyl)sulfonyl)phenyl)amino)-4-(phenylthio)butyl)piperazin-1-yl)-7-oxoheptanamido);DT2216
• Molecular Weight: 1542.36

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Valine and derivatives Proline and derivatives N-acyl-alpha amino acids and derivatives Phenylpiperazines N-arylpiperazines Alpha amino acid amides Benzenesulfonamides Aminobenzoic acids and derivatives Thiophenol ethers Pyrrolidinecarboxamides Phenylalkylamines N-acylpyrrolidines Dialkylarylamines Benzoyl derivatives Aniline and substituted anilines Secondary alkylarylamines N-alkylpiperazines Chlorobenzenes Alkylarylthioethers N-acyl amines Thiazoles Tertiary carboxylic acid amides Sulfonyls Organosulfonic acids and derivatives Heteroaromatic compounds Trihalomethanes Trialkylamines Secondary alcohols Sulfenyl compounds Azacyclic compounds Organopnictogen compounds Organofluorides Organochlorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-dipeptide - Valine or derivatives - Proline or derivatives - N-acyl-alpha amino acid or derivatives - N-arylpiperazine - Phenylpiperazine - Alpha-amino acid amide - Benzenesulfonamide - Aminobenzoic acid or derivatives - Alpha-amino acid or derivatives - Benzoic acid or derivatives - Aryl thioether - Phenylalkylamine - Aniline or substituted anilines - Dialkylarylamine - Thiophenol ether - Tertiary aliphatic/aromatic amine - Pyrrolidine-2-carboxamide - Pyrrolidine carboxylic acid or derivatives - N-acylpyrrolidine - Benzoyl - Alkylarylthioether - N-alkylpiperazine - Secondary aliphatic/aromatic amine - Halobenzene - Chlorobenzene - Fatty acyl - Benzenoid - Piperazine - N-acyl-amine - Fatty amide - 1,4-diazinane - Monocyclic benzene moiety - Heteroaromatic compound - Thiazole - Tertiary carboxylic acid amide - Sulfonyl - Organosulfonic acid or derivatives - Pyrrolidine - Azole - Trihalomethane - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Carboxamide group - Amino acid or derivatives - Azacycle - Organoheterocyclic compound - Sulfenyl compound - Thioether - Secondary amine - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Halomethane - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Organochloride - Organohalogen compound - Amine - Alkyl halide - Alkyl fluoride - Alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MOLT-4 (49676 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RS4-11 (1012 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H146 (92 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCL2 Tclin VHL/Apoptosis regulator Bcl-2 (38 Activities)

Discover Target: BCL2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 100 mg/mL (64.83 mM); Ethanol: 100 mg/mL (64.83 mM); Water: Insoluble
• Molecular Weight: 1542.400 g/mol
• XLogP3: 12.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 29
• Exact Mass: 1540.58 Da
• Monoisotopic Mass: 1540.58 Da
• Topological Polar Surface Area: 321.000 Ų
• Heavy Atom Count: 105
• Formal Charge: 0
• Complexity: 3130.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1