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L1790 Sigma-Aldrich

L-685,458

>96% (HPLC), solid

Synonym: (5S)-(t-Butoxycarbonylamino)-6-phenyl-(4R)hydroxy-(2R)benzylhexanoyl)-L-leu-L-phe-amide

  • CAS Number 292632-98-5

  • Empirical Formula (Hill Notation) C39H52O6N4

  • Molecular Weight 672.85

  •  MDL number MFCD03093402

  •  PubChem Substance ID 329817393

  •  NACRES NA.77

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Fluorination Ready Pharma-Developed Compounds,
assay   >96% (HPLC)
form   solid
color   white
solubility   DMSO: >10 mg/mL
originator   Merck & Co., Inc., Kenilworth, NJ
storage temp.   −20°C
SMILES string   O[C@@H]([C@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O)C[C@@H](CC2=CC=CC=C2)C(N[C@@H](CC(C)C)C(N[C@@H](CC3=CC=CC=C3)C(N)=O)=O)=O
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+,33+,34-/m1/s1
InChI key   MURCDOXDAHPNRQ-ZJKZPDEISA-N
Gene Information   human ... APH1A(51107), APH1B(83464), NCSTN(23385), NOTCH1(4851), NOTCH2(4853), NOTCH3(4854), NOTCH4(4855), PSEN1(5663), PSEN2(5664), PSENEN(55851)
mouse ... Aph1a(226548), Aph1b(208117), Ncstn(59287), Notch1(18128), Notch2(18129), Notch3(18131), Notch4(18132), Psen1(19164), Psen2(19165), Psenen(66340)
rat ... Aph1a(365872), Aph1b(300802), Ncstn(289231), Notch1(25496), Notch2(29492), Notch3(56761), Notch4(406162), Psen1(29192), Psen2(81751), Psenen(292788)

Description

Application

L-685,458 has been used to attenuate Notch signalling in ovary culture. It has also been used to analyze the specificity of the γ-secretase activity in brain tissue samples.

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

L-685,458 mimics the transition state in aspartyl protease. It possesses an IC50 of 17nM with respect to inhibition of Aβ synthesis. It is known to block Notch (neurogenic locus notch homolog protein) signaling, which in turn reduces ERK (extracellular signal regulated kinase) phosphorylation by EGF (epidermal growth factor). L-685,458 targets the active site and substrate binding site of the enzyme.

L-685,458 is a potent, selective, structurally novel γ-secretase inhibitor; equipotent inhibitor of both Aβ1-42 and Aβ1-40 production.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Manufactured and sold under license from Merck & Co., Inc., Kenilworth, NJ

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Cancer Stem Cells: New Targets for Cancer Therapy

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Keywords: Cancer, Cell attachment, Cell culture, Cell proliferation, Gastrointestinal, Gene expression, Transcription, transformation

Peer-Reviewed Papers
15

References

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