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Bestatin

CAS No.
58970-76-6
Chemical Name:
Bestatin
Synonyms
UBENIMEX;nk421;BENIMEX;BESTATIN;NSC 265489;Bestatin D10;Bestatin, >=99%;Ubenimex Ubenimex;UbeniMex(Bestatin);Bestatin, UbeniMex
CBNumber:
CB9324019
Molecular Formula:
C16H24N2O4
Molecular Weight:
308.37
MDL Number:
MFCD00083262
MOL File:
58970-76-6.mol
Last updated:2024-03-16 16:45:53

Bestatin Properties

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)
FDA UNII I0J33N5627

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c
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)
NFPA 704
0
2 0

Bestatin price More Price(58)

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

Bestatin Chemical Properties,Uses,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

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.

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.

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

Mode of action

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

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.

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)

59969-65-2
58970-76-6
Synthesis of Bestatin from (2S,3R)-3-(((Benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid

Bestatin Preparation Products And Raw materials

Global( 390)Suppliers
Supplier Tel Email Country ProdList Advantage
Chengdu Aslee Biopharmaceuticals, Inc.
28-85305008 CHINA 964 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682 bruce@xrdchem.cn CHINA 566 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Biochempartner
0086-13720134139 candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597 sales04@yibaibiotech.com CHINA 419 58

View Lastest Price from Bestatin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ubenimex pictures 2023-10-09 Ubenimex
58970-76-6
US $0.00 / kg 1kg 0.99 500kg Hebei Yanxi Chemical Co., Ltd.
Cordycepin pictures 2022-04-22 Cordycepin
73-03-0
US $0.00-0.00 / kg 0.1KG Assay>98% 200kgs Chengdu Hepu Pharmaceutical Technology Co. , Ltd
Ubenimex pictures 2022-02-25 Ubenimex
58970-76-6
US $46.00 / KG 1KG 99% 1 ton Hong Kong Tiansheng New Material Trading Co., Ltd
  • Ubenimex pictures
  • Ubenimex
    58970-76-6
  • US $0.00 / kg
  • 0.99
  • Hebei Yanxi Chemical Co., Ltd.
  • Cordycepin pictures
  • Cordycepin
    73-03-0
  • US $0.00-0.00 / kg
  • Assay>98%
  • Chengdu Hepu Pharmaceutical Technology Co. , Ltd
  • Ubenimex pictures
  • Ubenimex
    58970-76-6
  • US $46.00 / KG
  • 99%
  • Hong Kong Tiansheng New Material Trading Co., Ltd
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 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) Bestatin - CAS 58970-76-6 - Calbiochem Bestatin free base Bestatin-d5 (Ubenimex-d5) Ubenimex Ubenimex Bestatin USP/EP/BP Bestatin D10 UBENIMEX DIBUTYL CARBONATE 542-52-9 58970-76-6 C16H24N2O4 CH32CHCH2CHNHCOCHOHCHNH2CH2C6H5CO2H Leucine Derivatives Peptide Synthesis Specialty Synthesis Unnatural Amino Acid Derivatives ProteaseInhibitors Ubenimex Pepetides Active Pharmaceutical Ingredients peptides Bestatin