B581 Chemical Properties

Boiling point:

716.1±60.0 °C(Predicted)

Density 

1.161±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

H₂O: soluble

form 

solid

pka

3.04±0.10(Predicted)

color 

white

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

B581 Usage And Synthesis

Description

FTase inhibitor I is a potent inhibitor of farnesyltransferase (FTase; IC₅₀ = 21 nM) that is greater than 30-fold selective for FTase over geranylgeranyl transferase (GGTase; IC₅₀ = 790 nM). It prevents farnesylation of Ras and inhibits proliferation of cells transformed by Ras farnesylation. In a dog model of subarachnoid hemorrhage, it reduces GTP-Ras in spastic basilar arteries, decreases angiographic vasospasm, and improves clinical scores.

Uses

FTase Inhibitor I is a potent, selective, peptidomimetic FTase inhibitor.

Definition

ChEBI: A dipeptide obtained from the tetrapeptide Cys-Val-Phe-Met by reduction of the amide carbonyl groups of the Cys and Val residues.

Enzyme inhibitor

This cell-permeable CAAX peptidomimetic (FW = 470.70 g/mol; FWtrifluoracetate-salt = 583.71 g/mol; CAS 149759-96-6), named as N-[2(S)- (2(R)-2-amino-3-mercaptopropylamino)-3-methylbutyl]-L-phenylalanyl-L methionine), binds to and prevents protein farnesyltransferase (IC50 = 21 nM) from interacting with C-terminal L-Cys-L-Val-L-Phe-L-Met substrate recognition sequences that are present in its natural substrates. Otherwise hydrophilic proteins associate with membranes by means of enzymatic attachment of hydrophobic moieties to their C-termini. Whereas prenylation occurs in the cytosol, post-prenylation processing is accomplished on the cytoplasmic surface of the endoplasmic reticulum and Golgi apparatus. B581 inhibits prenylation and processing of H-ras and lamin A. B581 specifically blocks farnesylated, but not geranylgeranylated or myristylated, oncogenic ras signaling and transformation.

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