ChemicalBook > CAS DataBase List > Bestatin

Bestatin

Product Name
Bestatin
CAS No.
58970-76-6
Chemical Name
Bestatin
Synonyms
UBENIMEX;nk421;BENIMEX;BESTATIN;NSC 265489;Bestatin D10;Bestatin, >=99%;Ubenimex Ubenimex;Bestatin Impurity;Bestatin free base
CBNumber
CB9324019
Molecular Formula
C16H24N2O4
Formula Weight
308.37
MOL File
58970-76-6.mol
More
Less

Bestatin Property

Melting point:
245 °C (dec.)(lit.)
alpha 
D20 -15.5° (c = 1.0 in 1N HCl)
Boiling point:
448.76°C (rough estimate)
Density 
1.0917 (rough estimate)
refractive index 
1.5800 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Aqueous Acid (Slightly, Sonicated), DMSO (Slightly, Heated)
pka
8.1, 3.1(at 25℃)
form 
Powder
color 
White
optical activity
[α]20/D 11°, c = 1 in 1 M NaOH
Water Solubility 
Soluble in water (<1 25), DMSO (2 mg/ml), methanol (5 mg/ml), 1eq. NaOH (50 mM), ethanol (<1 mg/ml at 25°C), acetic acid, aq. HCl, and alkaline solution. Insoluble in ethyl acetate, benzene, hexane, and chloroform.
Merck 
13,9910
InChIKey
VGGGPCQERPFHOB-RDBSUJKOSA-N
CAS DataBase Reference
58970-76-6(CAS DataBase Reference)
More
Less

Safety

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
OH2915000
HS Code 
29242998
Toxicity
LD50 in male, female mice, male, female rats (g/kg): 1.3, 1.9, 1.9, 2.1 s.c.; 0.19, 0.19, 0.90, 0.78 i.p.; >4.0, >4.0, >2.0, >2.0 orally (Sakakibara)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
200484-M
Product name
Bestatin - CAS 58970-76-6 - Calbiochem
Purity
Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.
Packaging
200484-10MG
Price
$195
Updated
2024/03/01
Sigma-Aldrich
Product number
200484-M
Product name
Bestatin
Purity
Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.
Packaging
200484-500MG
Price
$10260
Updated
2024/03/01
Sigma-Aldrich
Product number
200484-M
Product name
Bestatin
Purity
Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.
Packaging
200484-200MG
Price
$18700
Updated
2024/03/01
Sigma-Aldrich
Product number
482609
Product name
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
Purity
97%
Packaging
500mg
Price
$325
Updated
2024/03/01
Sigma-Aldrich
Product number
200484-M
Product name
Bestatin
Purity
Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.
Packaging
200484-250MG
Price
$18700
Updated
2024/03/01
More
Less

Bestatin Chemical Properties,Usage,Production

Description

Bestatin is an aminopeptidase inhibitor originally isolated from S. olivoreticuli. It inhibits aminopeptidase B (IC50 = 0.05 μg/ml), aminopeptidase N (IC50 = 16.9 μM), leucine aminopeptidase (IC50 = 0.01 μg/ml), and the aminopeptidase activity of leukotriene A4 (LTA4) hydrolase (Kapp = 172 nM). It is selective for these aminopeptidases over aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, and thermolysin. Bestatin inhibits the production of LTB4 in erythrocytes when used at a concentration of 70 μM. It increases the expression of Akt, inhibits proliferation, migration, and invasion, and induces autophagy and apoptosis in 5637 bladder cancer cells. Bestatin (5 and 15 mg/kg) decreases serum levels of LTB4 and reduces tumor growth in a patient-derived xenograft (PDX) mouse model of colorectal cancer.

Chemical Properties

white powder, soluble in methanol, ethanol, DMSO and other organic solvents, from Streptomyces olivoreticuli.

Originator

Inst. of Microbial Chem (Japan)

Uses

Ubenimex (also known as bestatin) is a competitive aminopeptidase B inhibitor with an IC50 of 100 mg/ml for K562 cells. Proliferation of all the cell lines except KG1 was inhibited by bestatin. P39/TSU, HL60 and U937 were highly sensitive, with 50% growth inhibitory concentration. It is useful in the treatment of non-lymphocytic leukemia. In other types of cancers ubenimex added to radiotherapy or chemotherapy following surgery significantly inmases survival time through immunopotentiation. It is being studied for use in the treatment of acute myelocytic leukemia.

Uses

Bestatin is "pseudo"-dipeptide isolated from Strepotmyces olivreticuli in 1976. Bestatin is a potent aminopeptidase B inhibitor with no carboxypeptidase activity. Bestatin acts as an immunomodulator by activating macrophages and T lymphocytes. Bestatin also exhibits good antitumour activity and is has been investigated in clinical trials.

Application

Bestatin can indirectly act on monocytes by inhibiting Aminopeptidase B, which in turn inhibits the catabolism of tuftsin. Bestatin has also been shown to inhibit Leukotriene A4 hydrolase. It can directly stimulate lymphocytes through its fixation on the cell surface. The agent has been used in multiple leukemia studies. Bestatin is an aminopeptidase inhibitor, inhibits enkephalin metabolism and leukotriene A4 hydrolase. Inhibits tumor cell proliferation.

brand name

Bestatin

General Description

Bestatin was found in the culture broth of Streptomyces olivoreticuli in 1976by Umezawa et al. in the course of screening specific enzyme inhibitors of microbial origin. It shows inhibitory activity against specific exopeptidases, e.g., aminopeptidase B and leucine aminopeptidase. However, it does not act against aminopeptidase A, carboxypeptidases A and B, or endopeptidases. Bestatin acts as a bioresponse modifier and shows antitumor activity via stimulation of immuno response in the host. In combination with cytotoxic anticancer drugs, it is now under clinical evaluation for use in cancer therapy.

Biological Activity

Aminopeptidase inhibitor (K i = 0.001-90 mM); inhibits enkephalin metabolism and leukotriene A 4 hydrolase. Inhibits tumor cell proliferation.

Safety Profile

Poison by intraperitoneal route.Moderately toxic by subcutaneous route. Experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx.

storage

Store at +4°C

Clinical claims and research

Bestatin (ubenimex) is a potent inhibitor of aminopeptidase N and aminopeptidase B, which was isolated from a culture filtrate of Streptomyces olivoreticuli during the search for specific inhibitors of enzymes present on the membrane of eukaryotic cells. Inhibitors of aminopeptidase activity are associated with macrophage activation and differentiation, and Bestatin has shown significant therapeutic effects in several clinical trials. In one multi-institutional study, patients with acute non-lymphocytic leukemia (ANLL) were randomized to receive either Bestatin or control orally after completion of induction and consolidation therapy, and concomitant with maintenance chemotherapy. Remission duration was prolonged in the Bestatin group, although this difference did not reach statistical significance. However, OS was prolonged in the Bestatin group. Recently, a confirmatory phase III trial in ANLL was reported that extended the observation to a significant prolongation of remission. Bestatin has also shown adjuvant activity when administered to acute leukemia and CML patients who did not develop graft-versus-host disease (GVHD) within 30 days following BMT. Bestatin-treated acute leukemia patients had an increased incidence of chronic low-grade GVHD compared with the control arm and a lower relapse rate. Recently, a phase III study of resected stage 1 squamous cell lung cancer patients treated orally with either Bestatin or placebo daily for 2 years revealed that 5-year cancer-free survival was significantly greater in the Bestatin group (71%) as compared to the placebo group (62%). OS was also significantly improved, as was cancer-free survival. Recent studies in patients with nonsmall cell lung cancer (NSCLCs) suggest that it also has anti-angiogenic activity.

Mode of action

Bestatin acts as an immunomodulator by activating macrophages and T lymphocytes.

References

1. umezawa h, aoyagi t, suda h, hamada m, takeuchi t, bestatin, an inhibitor of aminopeptidase b, produced by actinomycetes, j antibiot (tokyo). 1976 jan; 29(1):97-9.2. umezawa, h., aoyagi, t., suda, h., hamada, m., and takeuchi, t. 197615. antibiotics 29, 97.3. suda, h., takita, t., aoyagi, t., and umezawa, h. (1976) j. antibiotics 29, 100.4. nakamura, h., suda, h., takita, t., aoyagi, t., umezawa, h., and iitaka, y. (1976) j. antibiotics 29, 102.5. umezawa, s., tsuchiya, t., and tatsuta, k. (1966) bull. chem. sot. japan 39, 1235. 6. barlow, c. b., and gijthrie, r. d. (1967) j. chem. sot. (c) 1194. 7. bukhari, s. t. k., guthrie, r. d., scott, a. i., and wrixon, a. d. (1970) tetrahedron 26, 3653.8. suda et al. inhibition of aminopeptidase b and leucine aminopeptidase by bestatin and its stereoisomer, archives of biochemistry and biophysics, 77, 196-200 (1976)

Bestatin Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Bestatin Suppliers

Australia 1 Belgium 2 Brazil 1 Canada 2 China 311 China Hong Kong 1 Europe 1 Germany 5 India 8 Japan 5 Switzerland 5 Ukraine 1 United Kingdom 15 United States 49 Global 407
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
ApexBio Technology LLC
Tel
+1-832-696-8203
Fax
+1-832-641-3177
Email
info@apexbt.com
Country
United States
ProdList
477
Advantage
60
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
ALB Technology Limited
Tel
702-983-3769
Fax
702-983-3769
Email
sales@albtechnology.com
Country
United States
ProdList
2993
Advantage
55
Alabiotech Inc.
Tel
001-619-354-5251
Fax
001-855-855-6087
Email
sales@alabiotech-e.com
Country
United States
ProdList
972
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
Alfa Chemistry
Tel
Fax
1-516-927-0118
Email
Info@alfa-chemistry.com
Country
United States
ProdList
24072
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Accela ChemBio Inc.
Tel
+1-858-6993322
Fax
(+1)-858-876-1948
Email
info@accelachem.com
Country
United States
ProdList
17322
Advantage
58
BOC Sciences
Tel
+1-631-485-4226
Fax
1-631-614-7828
Email
inquiry@bocsci.com
Country
United States
ProdList
19553
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
Alfa Chemistry
Tel
--
Fax
--
Email
info@Alfa-Chemistry.com
Country
United States
ProdList
6814
Advantage
0
CarboMer, Inc.
Tel
--
Fax
--
Email
sales@carbomer.com
Country
United States
ProdList
4026
Advantage
67
AppliChem, LLC
Tel
--
Fax
--
Email
sales@applichem.com
Country
United States
ProdList
169
Advantage
50
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
OChem Incorporation
Tel
--
Fax
--
Email
sales@ocheminc.com
Country
United States
ProdList
6501
Advantage
60
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
HBCChem Inc.
Tel
--
Fax
--
Email
sales@hbcchem-inc.com
Country
United States
ProdList
4569
Advantage
30
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
Chem-Impex International, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6730
Advantage
64
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
ChemPacific Corporation
Tel
--
Fax
--
Email
sales@chempacific.com
Country
United States
ProdList
6891
Advantage
51
SynPep Corporation
Tel
--
Fax
--
Email
sales@synpep.com
Country
United States
ProdList
1943
Advantage
51
AMRESCO Inc.
Tel
--
Fax
--
Email
info@amresco-inc.com
Country
United States
ProdList
760
Advantage
73
Acros Organics USA
Tel
--
Fax
--
Email
eveleth@fisherchem.com
Country
United States
ProdList
3846
Advantage
81
BIOMOL INTERNATIONAL, LP
Tel
--
Fax
--
Email
info@biomol.com
Country
United States
ProdList
1499
Advantage
77
EMD Biosciences, Inc.
Tel
--
Fax
--
Email
technical@calbiochem.com
Country
United States
ProdList
6529
Advantage
66
INDOFINE Chemical Company, Inc.
Tel
--
Fax
--
Email
chemical@indofinechemical.com
Country
United States
ProdList
6176
Advantage
69
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
Crescent Chemical Co., Inc.
Tel
--
Fax
--
Email
sales@creschem.com
Country
United States
ProdList
4597
Advantage
68
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
More
Less

View Lastest Price from Bestatin manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Ubenimex 58970-76-6
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
500kg
Release date
2023-10-08
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
Ubenimex 58970-76-6
Price
US $46.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1 ton
Release date
2021-12-13
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
Ubenimex 58970-76-6
Price
US $12.39/KG
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
2tons
Release date
2021-12-27

58970-76-6, BestatinRelated Search:

Tris(hydroxymethyl)aminomethane N-CARBOBENZOXY-DL-LEUCINE ALTRENOGEST 6-Aminocaproic acid mecysteine CHLOROPHOSPHONAZO III Glycine L-tert-Leucine N-(2-HYDROXYETHYL)LACTAMIDE BESTATIN HYDROCHLORIDE H-BETA-ALA-LEU-OH H-BETA-ALA-ALA-OH (-)-N-[(2S, 3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE METHYL ESTER THREO-(2RS)-3-ACETYLAMINO-2-HYDROXY-4-OXO-4-PHENYLBUTYRIC ACID [UBENIMEX INTERMEDIATE] Bestatin AMINO ACIDS Ubenimex,AntitumorDrug H-BETA-ALA-DL-LEU-OH

  • UBENIMEX
  • UbenaMix, Inobestin, NK 421
  • L-Leucine,N-[(2S,3R)-3-aMino-2-hydroxy-1-oxo-4-phenylbutyl]-
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine 97%
  • 3-(r)-amino-2-(s)-hydroxy-4-phenylbutanoyl-(s)-leucine
  • n-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-,(s-(r*,s*))-l-leucin
  • nk421
  • Bestatin - CAS 58970-76-6 - Calbiochem
  • Bestatin free base
  • Bestatin-d5 (Ubenimex-d5)
  • N-[(2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL]-L-LEUCINE
  • N-((2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCINE
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU-OH
  • [(2S, 3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE
  • BESTATIN
  • BENIMEX
  • L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, [S-(R*,S*)]-
  • L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]- (9CI)
  • NSC 265489
  • [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbuty1)-L-leucine
  • [S-(R*,S*)]-N-(3-amino-2-hydroxy-4-phenylbutyroyl)-L-leucine
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine,97%
  • UbeniMex(Bestatin)
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine, 97% 500MG
  • Bestatin, UbeniMex
  • (2R)-2-[(2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido]-4-Methylpentanoic acid
  • (S)-2-((2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido)-4-Methylpentanoic acid
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine|(-)-N-[3(R)-AMino-2(S)-hydroxy-4-phenylbutyryl]-L-leucine
  • [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbutyl)-L-leucine
  • Bestatin, >=99%
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine≥ 98% (HPLC)
  • Ubenimex Ubenimex
  • Bestatin USP/EP/BP
  • Bestatin D10
  • DIBUTYL CARBONATE 542-52-9
  • Bestatin Impurity
  • 58970-76-6
  • C16H24N2O4
  • CH32CHCH2CHNHCOCHOHCHNH2CH2C6H5CO2H
  • Leucine Derivatives
  • Peptide Synthesis
  • Specialty Synthesis
  • Unnatural Amino Acid Derivatives
  • ProteaseInhibitors
  • Ubenimex
  • Pepetides
  • Active Pharmaceutical Ingredients
  • peptides
  • Bestatin
  • API