149759-96-6

Basic information

• Product Name: B581
• Synonyms: N-[(S)-2-((R)-2-AMINO-3-MERCAPTO-PROPYLAMINO)-3-METHYL-BUTYL]-PHE-MET-OH;N-[2(S)-(2(R)-2-AMINO-3-MERCAPTOPROPYLAMINO)-3-METHYLBUTYL]-L-PHENYLALANYL-L-METHIONINE;N-[2(S)-[2(R)-AMINO-3-MERCAPTOPROPYLAMINO]-3-METHYL-BUTYL]-PHE-MET;N-[2(S)-[2(R)-AMINO-3-MERCAPTOPROPYLAMINO]-3-METHYLBUTYL]-PHE-MET-OH;CYS-((R))-VAL-((R))-PHE-MET;FTASE INHIBITOR I;H-CYS-(R)-VAL-(R)-PHE-MET-OH;B581
• CAS NO: 149759-96-6
• Molecular Formula: C22H38N4O3S2
• Molecular Weight: 470.69
• Mol File: 149759-96-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 716.1°Cat760mmHg
• Flash Point: 386.9°C
• Appearance: white/solid
• Density: 1.161g/cm³
• Vapor Pressure: 1.6E-21mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: −20°C
• Solubility: H2O: soluble
• PKA: 3.04±0.10(Predicted)
• CAS DataBase Reference: B581(CAS DataBase Reference)
• NIST Chemistry Reference: B581(149759-96-6)
• EPA Substance Registry System: B581(149759-96-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 149759-96-6(Hazardous Substances Data)

Usage

Description

B581, also known as FTase Inhibitor I, is a potent and selective peptidomimetic inhibitor of farnesyltransferase (FTase). It is derived from the tetrapeptide Cys-Val-Phe-Met by reduction of the amide carbonyl groups of the Cys and Val residues. B581 exhibits greater than 30-fold selectivity for FTase over geranylgeranyl transferase (GGTase) and plays a crucial role in preventing the farnesylation of Ras, which in turn inhibits the proliferation of cells transformed by Ras farnesylation.

Uses

Used in Pharmaceutical Industry:
B581 is used as an FTase inhibitor for preventing the farnesylation of Ras, which is a key process in the proliferation of cells transformed by Ras farnesylation. This makes it a potential therapeutic agent in the treatment of various diseases associated with abnormal Ras activity.
Used in Cardiovascular Applications:
In a dog model of subarachnoid hemorrhage, B581 is used as a therapeutic agent to reduce GTP-Ras in spastic basilar arteries, decrease angiographic vasospasm, and improve clinical scores. This highlights its potential application in treating cardiovascular conditions related to vasospasm and other complications arising from subarachnoid hemorrhage.
Used in Cancer Research:
B581 is used as a research tool in cancer biology to study the role of farnesyltransferase in the development and progression of cancer. By inhibiting FTase, B581 can help researchers understand the underlying mechanisms of cancer cell proliferation and the potential for targeted therapies against cancer cells with abnormal Ras activity.

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.

InChI:InChI=1/C22H38N4O3S2/c1-15(2)20(24-12-17(23)14-30)13-25-19(11-16-7-5-4-6-8-16)21(27)26-18(22(28)29)9-10-31-3/h4-8,15,17-20,24-25,30H,9-14,23H2,1-3H3,(H,26,27)(H,28,29)/t17-,18+,19+,20-/m1/s1