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ARD-266 - CAS 2666951-70-6

Inquiry

ARD-266 is a highly potent and VHL E3 ligase-based androgen receptor (AR) PROTAC degrader. ARD-266 effectively induces the degradation of AR protein in AR-positive LNCaP, VCaP, and 22Rv1 prostate cancer cell lines (DC50s = 0.2-1 nM).

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Molecular Formula

C52H59ClN6O7

Molecular Weight

915.51

ARD-266

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO
    
    Appearance
    
    Solid Powder
    
    Storage
    
    Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
    
    IUPAC Name
    
    (2S,4R)-N-[(1S)-3-[4-[2-[4-[[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl]ethynyl]piperidin-1-yl]-3-oxo-1-phenylpropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide
    
    Synonyms
    
    2-Pyrrolidinecarboxamide, N-[(1S)-3-[4-[2-[4-[[[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]ethynyl]-1-piperidinyl]-3-oxo-1-phenylpropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-5-isoxazolyl)-1-oxobutyl]-, (2S,4R)-; (2S,4R)-N-((S)-3-(4-((4-(((1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)ethynyl)piperidin-1-yl)-3-oxo-1-phenylpropyl)-4-hydroxy-1-((R)-3-methyl-2-(3-methylisoxazol-5-yl)butanoyl)pyrrolidine-2-carboxamide; (2S,4R)-N-[(1S)-3-[4-[2-[4-[[[trans-3-(3-Chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]ethynyl]-1-piperidinyl]-3-oxo-1-phenylpropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-5-isoxazolyl)-1-oxobutyl]-2-pyrrolidinecarboxamide
- Properties
  - Boiling Point
    
    1095.6±65.0°C at 760 Torr
    
    Density
    
    1.31±0.1 g/cm3
    
    InChI Key
    
    RTNONCBKGZNCJS-LJLQSONVSA-N
    
    InChI
    
    InChI=1S/C52H59ClN6O7/c1-31(2)45(43-25-32(3)57-66-43)48(64)59-30-38(60)26-42(59)47(63)55-41(35-11-9-8-10-12-35)28-44(61)58-23-21-34(22-24-58)14-13-33-15-17-36(18-16-33)46(62)56-49-51(4,5)50(52(49,6)7)65-39-20-19-37(29-54)40(53)27-39/h8-12,15-20,25,27,31,34,38,41-42,45,49-50,60H,21-24,26,28,30H2,1-7H3,(H,55,63)(H,56,62)/t38-,41+,42+,45-,49-,50-/m1/s1
    
    Canonical SMILES
    
    N#CC1=CC=C(OC2C(C)(C)C(NC(=O)C3=CC=C(C#CC4CCN(C(=O)CC(NC(=O)C5N(C(=O)C(C=6ON=C(C6)C)C(C)C)CC(O)C5)C=7C=CC=CC7)CC4)C=C3)C2(C)C)C=C1Cl
- Reference Reading
  - 1. Discovery of Highly Potent and Efficient PROTAC Degraders of Androgen Receptor (AR) by Employing Weak Binding Affinity VHL E3 Ligase Ligands
    
    Lijie Zhao, Jeanne Stuckey, Weiguo Xiang, Krishnapriya Chinnaswamy, Xin Han, Shaomeng Wang, Mi Wang, Bukeyan Miao, Chao-Yie Yang, Tianfeng Xu, Chong Qin J Med Chem . 2019 Dec 26;62(24):11218-11231. doi: 10.1021/acs.jmedchem.9b01393.
    
    Androgen receptor (AR) is a validated therapeutic target for the treatment of metastatic castration-resistant prostate cancer (mCRPC). We report herein our design, synthesis, and biological characterization of highly potent small-molecule proteolysis targeting chimera (PROTAC) AR degraders using a potent AR antagonist and E3 ligase ligands with weak binding affinities to VHL protein. Our study resulted in the discovery of11(ARD-266), which effectively induces degradation of AR protein in AR-positive (AR+) LNCaP, VCaP, and 22Rv1 prostate cancer cell lines with DC50values of 0.2-1 nM. ARD-266 is capable of reducing the AR protein level by >95% in these AR+ prostate cancer cell lines and effectively reduces AR-regulated gene expression suppression. For the first time, we demonstrated that an E3 ligand with micromolar binding affinity to its E3 ligase complex can be successfully employed for the design of highly potent and efficient PROTAC degraders and this finding may have a significant implication for the field of PROTAC research.

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