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AFC

Basic information Safety Supplier Related

AFC Basic information

Product Name:
AFC
Synonyms:
  • AFC
  • AC-CYSTEINE(FARNESYL)-OH
  • AC-CYS(FARNESYL)-OH
  • ACETYL-S-FARNESYL-L-CYSTEINE
  • N-ACETYL-S-(3,7,11-TRIMETHYL-2E,6E,10-DODECATRIENYL)-L-CYSTEINE
  • N-ACETYL-S-FARNESYL-L-CYSTEINE
  • N-ALPHA-ACETYL-S-FARNESYL-L-CYSTEINE
  • n-acetyl-s-farnesylcysteine
CAS:
135304-07-3
MF:
C20H33NO3S
MW:
367.55
Mol File:
135304-07-3.mol
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AFC Chemical Properties

Boiling point:
566.1±50.0 °C(Predicted)
Density 
1.038±0.06 g/cm3(Predicted)
storage temp. 
-15°C
solubility 
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml)
pka
3.31±0.10(Predicted)
form 
Pale yellow oil.
color 
Yellow
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
LogP
5.860 (est)
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Safety Information

HazardClass 
IRRITANT
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AFC Usage And Synthesis

Description

N-acetyl-S-farnesyl-L-Cysteine is a synthetic substrate for the isoprenylated protein methyltransferase (also known as S-adenosylmethionine-dependent methyltransferase). Because it is able to serve as a substrate for the methyltransferase, it effectively functions as an inhibitor of methylation of endogenous isoprenylated proteins.

Chemical Properties

Yellow-red oil

Uses

Arazine is an FTS (trans-Farnesylthiosalicylic Acid) compound, which does not inhibit EJ cell growth and does not affect Ras.

Definition

ChEBI: Acetyl-farnesyl-cysteine is a sesquiterpenoid.

in vivo

Arazine (AFC) (2,000?μg/20?μl; applied on ear) produces a dose-dependent inhibition of the TPA-induced edema, with the maximal reduction of edema approaching 73%, with a 50% effective dose (ED50) of 55±12?μg/20?μl[1].

Animal Model:TPA-induced ear acute inflammation in mouse[1]
Dosage:2000?μg/20?μl
Administration:2000?μg/20?μl; Applied on ear
Result:Inhibited ear edema, as measured by ear weight.

References

[1] C VOLKER. Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction.[J]. The Journal of Biological Chemistry, 1991, 266 32: 21515-21522.
[2] Y XU. Inhibition of capacitative Ca2+ entry into cells by farnesylcysteine analogs.[J]. Molecular Pharmacology, 1996, 50 6: 1495-1501.
[3] J. ROSADO S S. Farnesylcysteine analogues inhibit store-regulated Ca2+ entry in human platelets: evidence for involvement of small GTP-binding proteins and actin cytoskeleton.[J]. The Ukrainian Biochemical Journal, 2000, 13 1: 183-192. DOI:10.1042/bj3470183
[4] JOEL S. GORDON . Topical N-acetyl-S-farnesyl-L-cysteine Inhibits Mouse Skin Inflammation, and Unlike Dexamethasone, its Effects Are Restricted to the Application Site[J]. Journal of Investigative Dermatology, 2008, 128 3: Pages 643-654. DOI:10.1038/sj.jid.5701061
[5] KATAYUN ADHAMI. N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells[J]. Experimental Dermatology, 2012, 21 9: 700-705. DOI:10.1111/j.1600-0625.2012.01562.x

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