A γ-secretase inhibitor
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L-685,458

Item No. 14926

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2R,4R,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-L-phenylalaninamide
CAS Number
292632-98-5
Synonyms
  • γ-Secretase Inhibitor X
Molecular Formula
C39H52N4O6
Formula Weight
672.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/ml
SMILES
CC(OC(N[C@H]([C@@H](C[C@H](C(N[C@H](C(N[C@H](C(N)=O)CC1=CC=CC=C1)=O)CC(C)C)=O)CC2=CC=CC=C2)O)CC3=CC=CC=C3)=O)(C)C
InChi Code
InChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31+,32
InChi Key
MURCDOXDAHPNRQ-ZJKZPDEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $109

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    5 mg

    $355

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    10 mg

    $654

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    Product Description

    L-685,458 is an inhibitor of γ-secretase (IC50 = 17 nM).1 It is selective for γ-secretase over HIV-1, cathepsin D, trypsin, HepC3 NS3, papain, and calpain I proteases (IC50s = >1,000 nM). L-685,458 inhibits production of amyloid-β (1-40) (Aβ40; Item No. 21617) and Aβ42 (Item No. 20574) in Neuro2A cells transfected with human amyloid precursor protein (APP; IC50s = 402 and 775 nM, respectively). It is also an inhibitor of Notch signaling that blocks hypoxia-induced activity of the Notch-responsive reporters 12xCSL and CBF1 in isolated rat intervertebral disc cells.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shearman, M.S., Beher, D., Clarke, E.E., et al. L-685,458, an aspartyl protease transition state mimic, is a potent inhibitor of amyloid β-protein precursor γ-secretase activity. Biochemistry 39(30), 8698-8704 (2000).

    2. Hiyama, A., Skubutyte, R., Markova, D., et al. Hypoxia activated the Notch signaling pathway in cells of the intervertebral disc: Implications in degenerative disc disease. Arthritis Rheum. 63(5), 1355-1364 (2011).