L 739749

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

MedKoo CAT#: 596684

CAS#: 156511-34-1

Description: L 739749 is a CAAX peptidomimetic; a farnesyl-protein transferase inhibitor.


Price and Availability

Size
Price

Size
Price

Size
Price

L 739749 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

img

Theoretical Analysis

MedKoo Cat#: 596684
Name: L 739749
CAS#: 156511-34-1
Chemical Formula: C24H41N3O6S2
Exact Mass: 531.2437
Molecular Weight: 531.72
Elemental Analysis: C, 54.21; H, 7.77; N, 7.90; O, 18.05; S, 12.06


Synonym: L 739749; L-739749; L739749; L-739,749; L 739,749; L739,749;

IUPAC/Chemical Name: methyl (2R)-2-((2-amino-3-mercaptopropyl)amino)-2-(N-(((S)-3-methylpentyl)oxy)-3-phenylpropanamido)-4-(methylsulfonyl)butanoate

InChi Key: NMDIHBJSLHSAMQ-LDEFDFMYSA-N

InChi Code: InChI=1S/C24H41N3O6S2/c1-5-19(2)13-15-33-27(22(28)12-11-20-9-7-6-8-10-20)24(23(29)32-3,14-16-35(4,30)31)26-17-21(25)18-34/h6-10,19,21,26,34H,5,11-18,25H2,1-4H3/t19-,21?,24+/m0/s1

SMILES Code: CS(CC[C@@](C(OC)=O)(NCC(N)CS)N(OCC[C@@H](C)CC)C(CCC1=CC=CC=C1)=O)(=O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

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

Shelf Life:
>2 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


References

1: Dazy S, Damiola F, Parisey N, Beug H, Gandrillon O. The MEK-1/ERKs signalling pathway is differentially involved in the self-renewal of early and late avian erythroid progenitor cells. Oncogene. 2003 Dec 18;22(58):9205-16. PubMed PMID: 14681680.

2: Xu Y, Chiamvimonvat N, Vázquez AE, Akunuru S, Ratner N, Yamoah EN. Gene-targeted deletion of neurofibromin enhances the expression of a transient outward K+ current in Schwann cells: a protein kinase A-mediated mechanism. J Neurosci. 2002 Nov 1;22(21):9194-202. PubMed PMID: 12417644.

3: Bulus NM, Sheng HM, Sizemore N, Oldham SM, Barnett JV, Coffey RJ, Beauchamp DR, Barnard JA. Ras-mediated suppression of TGFbetaRII expression in intestinal epithelial cells involves Raf-independent signaling. Neoplasia. 2000 Jul-Aug;2(4):357-64. PubMed PMID: 11005570; PubMed Central PMCID: PMC1550294.

4: Emanuel PD, Snyder RC, Wiley T, Gopurala B, Castleberry RP. Inhibition of juvenile myelomonocytic leukemia cell growth in vitro by farnesyltransferase inhibitors. Blood. 2000 Jan 15;95(2):639-45. PubMed PMID: 10627474.

5: Lebowitz PF, Casey PJ, Prendergast GC, Thissen JA. Farnesyltransferase inhibitors alter the prenylation and growth-stimulating function of RhoB. J Biol Chem. 1997 Jun 20;272(25):15591-4. PubMed PMID: 9188444.

6: Lebowitz PF, Sakamuro D, Prendergast GC. Farnesyl transferase inhibitors induce apoptosis of Ras-transformed cells denied substratum attachment. Cancer Res. 1997 Feb 15;57(4):708-13. PubMed PMID: 9044849.

7: Kim HA, Ling B, Ratner N. Nf1-deficient mouse Schwann cells are angiogenic and invasive and can be induced to hyperproliferate: reversion of some phenotypes by an inhibitor of farnesyl protein transferase. Mol Cell Biol. 1997 Feb;17(2):862-72. PubMed PMID: 9001241; PubMed Central PMCID: PMC231813.

8: Fukazawa H, Nakano S, Mizuno S, Uehara Y. Inhibitors of anchorage-independent growth affect the growth of transformed cells on poly(2-hydroxyethyl methacrylate)-coated surfaces. Int J Cancer. 1996 Sep 17;67(6):876-82. PubMed PMID: 8824562.

9: Prendergast GC, Davide JP, Lebowitz PF, Wechsler-Reya R, Kohl NE. Resistance of a variant ras-transformed cell line to phenotypic reversion by farnesyl transferase inhibitors. Cancer Res. 1996 Jun 1;56(11):2626-32. PubMed PMID: 8653708.

10: James G, Goldstein JL, Brown MS. Resistance of K-RasBV12 proteins to farnesyltransferase inhibitors in Rat1 cells. Proc Natl Acad Sci U S A. 1996 Apr 30;93(9):4454-8. PubMed PMID: 8633088; PubMed Central PMCID: PMC39559.

11: Lebowitz PF, Davide JP, Prendergast GC. Evidence that farnesyltransferase inhibitors suppress Ras transformation by interfering with Rho activity. Mol Cell Biol. 1995 Dec;15(12):6613-22. PubMed PMID: 8524226; PubMed Central PMCID: PMC230914.

12: Rak J, Mitsuhashi Y, Bayko L, Filmus J, Shirasawa S, Sasazuki T, Kerbel RS. Mutant ras oncogenes upregulate VEGF/VPF expression: implications for induction and inhibition of tumor angiogenesis. Cancer Res. 1995 Oct 15;55(20):4575-80. PubMed PMID: 7553632.

13: Kohl NE, Conner MW, Gibbs JB, Graham SL, Hartman GD, Oliff A. Development of inhibitors of protein farnesylation as potential chemotherapeutic agents. J Cell Biochem Suppl. 1995;22:145-50. Review. PubMed PMID: 8538192.

14: Kohl NE, Wilson FR, Mosser SD, Giuliani E, deSolms SJ, Conner MW, Anthony NJ, Holtz WJ, Gomez RP, Lee TJ, et al. Protein farnesyltransferase inhibitors block the growth of ras-dependent tumors in nude mice. Proc Natl Acad Sci U S A. 1994 Sep 13;91(19):9141-5. PubMed PMID: 8090782; PubMed Central PMCID: PMC44763.

15: Prendergast GC, Davide JP, deSolms SJ, Giuliani EA, Graham SL, Gibbs JB, Oliff A, Kohl NE. Farnesyltransferase inhibition causes morphological reversion of ras-transformed cells by a complex mechanism that involves regulation of the actin cytoskeleton. Mol Cell Biol. 1994 Jun;14(6):4193-202. PubMed PMID: 8196657; PubMed Central PMCID: PMC358785.