N-Acetyl-S-farnesyl-L-cysteine (AFC) CAS: 135304-07-3
MF: C20H33NO3S
MW: 367.55
An inhibitor of S-farnesylcysteine methyl transferase.

N-Acetyl-S-farnesyl-L-cysteine (AFC) (CAS 135304-07-3)

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Sinónimo: AFC
Solicitud: An inhibitor of S-farnesylcysteine methyl transferase
Número de CAS: 135304-07-3
Pureza: ≥98%
Peso Molecular: 367.55
Fórmula Molecular: C20H33NO3S
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N-Acetyl-S-farnesyl-L-cysteine is a synthetically derivatized cysteine amino acid inhibitor of S-farnesylcysteine carboxyl methyltransferase enzymes. These enzymes recognize N-Acetyl-S-farnesyl-L-cysteine as a substrate through the farnesyl moiety, and occupation of the binding site blocks processing of farnesylated proteins by the enzyme. Carboxyl methylation of farnesylated proteins is an important modification that regulates protein function. Blockade of methyltransferase processing of platelet rap1 proteins by N-Acetyl-S-farnesyl-L-cysteine leads to inhibition of platelet aggregation. N-Acetyl-S-farnesyl-L-cysteine is also described to block the cellular movement and membrane adhesion of Ras proteins by interfering with carboxyl methylation processing. N-Acetyl-S-farnesyl-L-cysteine as a substrate for isoprenylated protein methyltransferase is described to block fMet-Leu-Phe-stimulated release of superoxide radical anion in neutrophil cells. Inhibition of neutrophil chemotaxis by N-Acetyl-S-farnesyl-L-cysteine also produces suppression of inflammatory response induced by 12-O-tereadecanoyl-phorbol-13-acetate and arachidonic acid.


References

1. Volker, C., et al. 1991. J. Biol. Chem. 266: 21515-21522. PMID: 1939182
2. Huzoor-Akbar, D.A., et al. 1991. J. Biol. Chem. 266: 4387-4391. PMID: 1900293
3. Pérez-Sala, D., et al. 1991. Proc. Natl. Acad. Sci. U.S.A. 88: 3043-3046. PMID: 1901651
4. Huzoor-Akbar, W., et al. 1993. Proc. Natl. Acad. Sci. U.S.A. 90: 868-872. PMID: 8430099
5. Philips, M.R., et al. 1993. Science. 259: 977-980. PMID: 8438158
6. Ding, J., et al. 1994. J. Biol. Chem. 269: 16837-16844. PMID: 8207006
7. Gordon, J.S., et al. 2008. J. Invest. Dermatol. 128: 643-654. PMID: 17882268

Apariencia :
Oil
Estado de Materia :
Liquid
Solubilidad :
Soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), DMF (~20 mg/ml), 0.1 M Na2CO3 (63 mg/ml), PBS (pH 7.2), and water (63 mg/ml) at 25° C.
ALMACENAMIENTO :
Store at -20° C
Densidad :
1.04 g/mL
Indice de Refracción :
n20D 1.52
Datos Ki :
S-farnesylcysteine methyl transferase: Ki= 20 µM
Valores de pK :
pKa: 3.31
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
3
PubChem CID :
1994
Número MDL :
MFCD00871540
SMILES :
CC(=CCCC(=CCCC(=CCSCC(C(=O)O)NC(=O)C)C)C)C

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