L685458
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    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.


Chemical Structure

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L685458
CAS# 292632-98-5

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

Size Price Shipping out time Quantity
1mg USD 330 2 Weeks
5mg USD 890 2 Weeks
10mg USD 1500 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-02. Prices are subject to change without notice.

L685458, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

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

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).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 672.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 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.



Additional Information