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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Synonym AFC
Anwendungen An inhibitor of S-farnesylcysteine methyl transferase
CAS Nummer: 135304-07-3
Reinheit: ≥98%
Molekulargewicht: 367.55
Summenformel: 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.


Literaturhinweise

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

Erscheinung :
Oil
Aggregatzustand :
Liquid
Löslichkeit :
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.
LAGERUNG: :
Store at -20° C
Dichte :
1.04 g/mL
Brechungsindex :
n20D 1.52
Ki-Daten :
S-farnesylcysteine methyl transferase: Ki= 20 µM
pK Werte :
pKa: 3.31
Ausschließlich für Forschungszwecke. Nicht Geeignet für Verwendung in Diagnostik oder Therapie.
Deutsche WGK :
3
PubChem CID :
1994
MDL-Nummer :
MFCD00871540
SMILES :
CC(=CCCC(=CCCC(=CCSCC(C(=O)O)NC(=O)C)C)C)C

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