Bestatin | 58970-76-6

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)

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 (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

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)

Bestatin synthesis

Synthesis of Bestatin from (2S,3R)-3-(((Benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid

Bestatin Preparation Products And Raw materials

Raw materials

(2S,3R)-3-(((Benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid

Preparation Products

Bestatin Suppliers

Global( 407)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	21634	55
Hubei XinRunde Chemical Co., Ltd.	+8615102730682	bruce@xrdchem.cn	CHINA	566	55
Shanghai Zheyan Biotech Co., Ltd.	18017610038	zheyansh@163.com	CHINA	3619	58
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29884	58
Biochempartner	0086-13720134139	candy@biochempartner.com	CHINA	965	58
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28172	58
Accela ChemBio Inc.	+1-858-6993322	info@accelachem.com	United States	17322	58
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22963	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58

Supplier	Advantage
Chengdu Aslee Biopharmaceuticals, Inc.	58
Henan Tianfu Chemical Co.,Ltd.	55
Hubei XinRunde Chemical Co., Ltd.	55
Shanghai Zheyan Biotech Co., Ltd.	58
career henan chemical co	58
Biochempartner	58
Hubei Jusheng Technology Co.,Ltd.	58
Accela ChemBio Inc.	58
Hubei xin bonus chemical co. LTD	58
BOC Sciences	58

View Lastest Price from Bestatin manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-19	Bestatin 58970-76-6	US $48.00-112.00 / mg		99.63%	10g	TargetMol Chemicals Inc.
2024-11-19	Bestatin 58970-76-6	US $48.00-112.00 / mg		99.63%	10g	TargetMol Chemicals Inc.
2024-10-25	Ubenimex 58970-76-6	US $0.00 / kg	1kg	0.99	500kg	Hebei Yanxi Chemical Co., Ltd.

Bestatin
58970-76-6
US $48.00-112.00 / mg
99.63%
TargetMol Chemicals Inc.

Bestatin
58970-76-6
US $48.00-112.00 / mg
99.63%
TargetMol Chemicals Inc.

Ubenimex
58970-76-6
US $0.00 / kg
0.99
Hebei Yanxi Chemical Co., Ltd.

Bestatin Spectrum

Bestatin(58970-76-6)¹HNMR Bestatin(58970-76-6)IR

58970-76-6(Bestatin)Related Search:

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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

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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 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