ChemicalBook > CAS DataBase List > B581

B581

Product Name
B581
CAS No.
149759-96-6
Chemical Name
B581
Synonyms
FTASE INHIBITOR I;B581;B581 USP/EP/BP;H-Cys-()-Val-()-Phe-Met-OH;CYS-((R))-VAL-((R))-PHE-MET;H-CYS-(R)-VAL-(R)-PHE-MET-OH;H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH;N-[(S)-2-((R)-2-Amino-3-mercapto-propylamino)-3-me;H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH trifluoroacetate salt;N-[2(S)-[2(R)-AMINO-3-MERCAPTOPROPYLAMINO]-3-METHYL-BUTYL]-PHE-MET
CBNumber
CB6454713
Molecular Formula
C22H38N4O3S2
Formula Weight
470.69
MOL File
149759-96-6.mol
More
Less

B581 Property

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
Water Solubility 
water: 1mg/mL
DMSO: 5mg/mL
More
Less

Safety

Safety Statements 
22-24/25
WGK Germany 
3
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Cayman Chemical
Product number
22755
Product name
FTase Inhibitor I
Purity
≥95%
Packaging
500μg
Price
$73
Updated
2024/03/01
Cayman Chemical
Product number
22755
Product name
FTase Inhibitor I
Purity
≥95%
Packaging
1mg
Price
$138
Updated
2024/03/01
TRC
Product number
F810353
Product name
FTaseInhibitorI
Packaging
1mg
Price
$145
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC111045
Product name
H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH trifluoroacetate salt
Packaging
500ug
Price
$95
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC111045
Product name
H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH trifluoroacetate salt
Packaging
1mg
Price
$166
Updated
2021/12/16
More
Less

B581 Chemical Properties,Usage,Production

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.

References

[1] A M GARCIA. Peptidomimetic inhibitors of Ras farnesylation and function in whole cells.[J]. The Journal of Biological Chemistry, 1993, 268 25: 18415-18418.
[2] A D COX. The CAAX peptidomimetic compound B581 specifically blocks farnesylated, but not geranylgeranylated or myristylated, oncogenic ras signaling and transformation.[J]. The Journal of Biological Chemistry, 1994, 269 30: 19203-19206.
[3] MITSUO YAMAGUCHI. Ras protein contributes to cerebral vasospasm in a canine double-hemorrhage model.[J]. Stroke, 2004, 35 7: 1750-1755. DOI: 10.1161/01.str.0000129898.68350.9f

B581 Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

B581 Suppliers

China 56 Germany 2 India 1 Japan 2 South Korea 1 Switzerland 2 United Kingdom 2 United States 19 Global 85
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42934
Advantage
64
Chemsky (shanghai) International Co.,Ltd
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
15402
Advantage
60
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
12952
Advantage
65
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4720
Advantage
55
BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9803
Advantage
58
Alabiotech Inc.
Tel
001-619-354-5251
Fax
001-855-855-6087
Email
sales@alabiotech-e.com
Country
United States
ProdList
972
Advantage
60
Hangzhou Peptidego Biotech Co.,Ltd.
Tel
0571-87213919
Email
Eric@peptidego.com
Country
China
ProdList
7408
Advantage
58
Alpha Biopharmaceuticals Co., Ltd
Tel
0411-39042497
Fax
0411-39042693
Email
sales@alphabiopharm.com
Country
China
ProdList
1951
Advantage
58
Shanghai Han-Xiang Chemical Co., Ltd.
Tel
15971444841
Fax
18327183813
Email
amber@biochempartner.com
Country
China
ProdList
3061
Advantage
58

149759-96-6, B581Related Search:

avicelrc58 ci58 ICI 581,pp58 dh58 Indole-3-butyric acid Glycidyl acrylate C11-BODIPY(581-591) SDZ 220-581 FTASE INHIBITOR III B581 GP140 (581-600) GP41 (581-597) EE 581 MICROCRYSTALLINE CELLULOSE RC581 transparent silicone adhesive for aircraft GN-581 corrosion inhibitor 581 Reactive Turquoise Blue 581 Am-581

  • CYS-((R))-VAL-((R))-PHE-MET
  • FTASE INHIBITOR I
  • H-CYS-(R)-VAL-(R)-PHE-MET-OH
  • B581
  • 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
  • N-[(S)-2-((R)-2-AMino-3-Mercapto-propylaMino)-3-Methyl-butyl]-Phe-Met-OH, B581
  • (2S)-2-({(2S)-2-[((2S)-2-{[(2R)-2-aMino-3-sulfanylpropyl]aMino}-3-Methylbutyl)aMino]-3-phenylpropanoyl}aMino)-4-(Methylsulfanyl)butanoic acid
  • H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH
  • H-Cys-()-Val-()-Phe-Met-OH
  • N-[(S)-2-((R)-2-Amino-3-mercapto-propylamino)-3-me
  • N-[2(S)-(2(R)-2-Amino-3-mercaptopropylamino)-3-methylbutyl]-L-phenylalanyl-L-methionine trifluoroacetate salt
  • H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH trifluoroacetate salt
  • L-Methionine, N-[(2S)-2-[[(2R)-2-amino-3-mercaptopropyl]amino]-3-methylbutyl]-L-phenylalanyl-
  • B581 USP/EP/BP
  • 149759-96-6
  • C22H38N4O3S2
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • G Proteins and Cyclic Nucleotides
  • G Protein Function
  • Post-translational Modification