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

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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)

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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)

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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.

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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

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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 (K_app = 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

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Bestatin Suppliers

Australia 1 Belgium 2 Brazil 1 Canada 2 China 299 China Hong Kong 1 Europe 1 Germany 5 India 8 Japan 5 Switzerland 5 Ukraine 1 United Kingdom 15 United States 47 Global 393

LGM Pharma

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MedChemexpress LLC

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HBCChem, Inc.

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TargetMol Chemicals Inc.

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BOC Sciences

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Protheragen-ING

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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