SNIPER(AR)-51 - CAS 2113688-43-8

SNIPER(AR)-51 (AR-51), consists of a cIAP1 ligand and an androgen ligand, connected by a linker[1]. SNIPER(AR)-51 induces androgen receptor (AR) protein degradation[1].

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Molecular Formula
C55H65N7O8S
Molecular Weight
984.21

SNIPER(AR)-51

    • Specification
      • Storage
        Please store the product under the recommended conditions in the Certificate of Analysis.
        Shipping
        Room temperature in continental US; may vary elsewhere
        IUPAC Name
        (2S)-N-[(1S)-2-[(2S)-2-[4-[3-[2-[2-[2-[2-[4-[[3-cyano-4-(4-cyanophenyl)-2,5-dimethylpyrrol-1-yl]methyl]phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]benzoyl]-1,3-thiazol-2-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide
        Synonyms
        Propanamide, N-[(1S)-2-[(2S)-2-[4-[3-[2-[2-[2-[2-[4-[[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl]phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]benzoyl]-2-thiazolyl]-1-pyrrolidinyl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)-, (2S)-; (S)-N-((S)-2-((S)-2-(4-(3-(2-(2-(2-(2-(4-((3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl)methyl)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzoyl)thiazol-2-yl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)-2-(methylamino)propanamide
    • Properties
      • Boiling Point
        1105.3±65.0°C at 760 Torr
        Density
        1.26±0.1 g/cm3
        InChI Key
        YKLNRBANSQLMHA-JWWZLTTOSA-N
        InChI
        InChI=1S/C55H65N7O8S/c1-37(58-4)53(64)60-51(43-10-6-5-7-11-43)55(65)61-23-9-14-49(61)54-59-48(36-71-54)52(63)44-12-8-13-46(32-44)70-31-29-68-27-25-66-24-26-67-28-30-69-45-21-17-41(18-22-45)35-62-38(2)47(34-57)50(39(62)3)42-19-15-40(33-56)16-20-42/h8,12-13,15-22,32,36-37,43,49,51,58H,5-7,9-11,14,23-31,35H2,1-4H3,(H,60,64)/t37-,49-,51-/m0/s1
        Canonical SMILES
        N#CC1=CC=C(C=C1)C=2C(C#N)=C(N(C2C)CC3=CC=C(OCCOCCOCCOCCOC4=CC=CC(=C4)C(=O)C=5N=C(SC5)C6N(C(=O)C(NC(=O)C(NC)C)C7CCCCC7)CCC6)C=C3)C
    • Reference Reading
      • 1. Development of protein degradation inducers of androgen receptor by conjugation of androgen receptor ligands and inhibitor of apoptosis protein ligands.
        Shibata, N., Nagai, K., Morita, Y., Ujikawa, O., Ohoka, N., Hattori, T., Koyama, R., Sano, O., Imaeda, Y., Nara, H. and Cho, N., 2018. Journal of medicinal chemistry, 61(2), pp.543-575.
        Targeted protein degradation using small molecules is a novel strategy for drug development. We have developed hybrid molecules named specific and nongenetic inhibitor of apoptosis protein [IAP]-dependent protein erasers (SNIPERs) that recruit IAP ubiquitin ligases to degrade target proteins. Here, we show novel SNIPERs capable of inducing proteasomal degradation of the androgen receptor (AR). Through derivatization of the SNIPER(AR) molecule at the AR ligand and IAP ligand and linker, we developed 42a (SNIPER(AR)-51), which shows effective protein knockdown activity against AR. Consistent with the degradation of the AR protein, 42a inhibits AR-mediated gene expression and proliferation of androgen-dependent prostate cancer cells. In addition, 42a efficiently induces caspase activation and apoptosis in prostate cancer cells, which was not observed in the cells treated with AR antagonists. These results suggest that SNIPER(AR)s could be leads for an anticancer drug against prostate cancers that exhibit AR-dependent proliferation.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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