L685458

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 500910

CAS#: 292632-98-5

Description: L685458 is a potent and selective γ -secretase inhibitor (IC50 = 17 nM) that displays > 50-fold selectivity over a range of aspartyl, serine and cysteine proteases. L685458 also exhibits equal potency for inhibition of A β 40 and A β 42 peptides (IC50 values are 48 and 67 nM respectively in human neuroblastoma cells). Also regulates CXCR4 and VEGFR2 expression through inhibition of Notch signaling in vitro.


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2g
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L685458 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 500910
Name: L685458
CAS#: 292632-98-5
Chemical Formula: C39H52N4O6
Exact Mass: 672.38869
Molecular Weight: 672.85
Elemental Analysis: C, 69.62; H, 7.79; N, 8.33; O, 14.27


Synonym: L685458; L-685458; L 685458; L685,458, L-685,458; L 685,458

IUPAC/Chemical Name: tert-butyl ((2S,3R,5R)-6-(((S)-1-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl)carbamate.

InChi Key: MURCDOXDAHPNRQ-ZJKZPDEISA-N

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+,33+,34-/m1/s1

SMILES Code: O=C(OC(C)(C)C)N[C@H]([C@H](O)C[C@@H](CC1=CC=CC=C1)C(N[C@@H](CC(C)C)C(N[C@@H](CC2=CC=CC=C2)C(N)=O)=O)=O)CC3=CC=CC=C3


Technical Data

Appearance:
Solid powder

Purity:
>98%

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

  
  
 
 


References

 1: Singh CR, Bakhru P, Khan A, Li QB, Jagannath C. Cutting edge: Nicastrin and related components of γ-secretase generate a peptide epitope facilitating immune recognition of intracellular mycobacteria, through MHC class II-dependent priming of T cells. J Immunol. 2011 Dec 1;187(11):5495-9. Epub 2011 Oct 28. PubMed PMID: 22039303; PubMed Central PMCID: PMC3221744.

2: Hiyama A, Skubutyte R, Markova D, Anderson DG, Yadla S, Sakai D, Mochida J, Albert TJ, Shapiro IM, Risbud MV. Hypoxia activates the notch signaling pathway in cells of the intervertebral disc: implications in degenerative disc disease. Arthritis Rheum. 2011 May;63(5):1355-64. doi: 10.1002/art.30246. PubMed PMID: 21305512.

3: Knappenberger KS, Tian G, Ye X, Sobotka-Briner C, Ghanekar SV, Greenberg BD, Scott CW. Mechanism of gamma-secretase cleavage activation: is gamma-secretase regulated through autoinhibition involving the presenilin-1 exon 9 loop? Biochemistry. 2004 May 25;43(20):6208-18. PubMed PMID: 15147205.

4: Tian G, Ghanekar SV, Aharony D, Shenvi AB, Jacobs RT, Liu X, Greenberg BD. The mechanism of gamma-secretase: multiple inhibitor binding sites for transition state analogs and small molecule inhibitors. J Biol Chem. 2003 Aug 1;278(31):28968-75. Epub 2003 Apr 28. PubMed PMID: 12719412.

5: Tian G, Sobotka-Briner CD, Zysk J, Liu X, Birr C, Sylvester MA, Edwards PD, Scott CD, Greenberg BD. Linear non-competitive inhibition of solubilized human gamma-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. J Biol Chem. 2002 Aug 30;277(35):31499-505. Epub 2002 Jun 18. PubMed PMID: 12072428.