Basic information
- CAS
58970-76-6- Standard SMILES
CC(C)CC(NC(=O)C(O)C(N)Cc1ccccc1)C(=O)O- InChIKey
VGGGPCQERPFHOB-UHFFFAOYSA-N- Molecular formula
- C16H24N2O4
- Average molar mass
- 308.37 g/mol
- Monoisotopic mass
- 308.17360725
Overview
[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine is a peptide.
Names & identifiers
- Preferred name
- N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucine
- IUPAC
- 2-[(3-amino-2-hydroxy-4-phenylbutanoyl)amino]-4-methylpentanoic acid
- English name
- Bestatin
- Molecular formula
- C16H24N2O4
- Molecular weight
- 308.37
Names & synonyms
DTXSID50860737N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucineRefChem:1091138DTXCID40197084Bestatin;Ubenimex(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-LeuBestatin (Ubenimex)SCHEMBL8191715CHEMBL1161364WLN: 1Y1&1YVQMVYQYZ1R(2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acidCHEBI:182899
Show more names
UBENIMEXnk421BENIMEXBESTATINNSC 265489Bestatin D10Bestatin, >=99%Ubenimex UbenimexBestatin ImpurityBestatin free base
HMS3370B12HMS3394A03HMS3748C21HMS5079O16L-Leucine, [S-(R*,S*)]-s1591SBB0660732-[(3-amino-2-hydroxy-4-phenyl-butanoyl)amino]-4-methyl-pentanoic acid
Database identifiers
- CAS
58970-76-6
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 367
Physicochemical properties
- Melting point
- 245 °C · 245 °C (dec.)(lit.)
- alpha
- 20 · D20 -15.5° (c = 1.0 in 1N HCl)
- Boiling point
- 448.76 °C · 448.76°C (rough estimate)
- Density
- 1.0917 · 1.0917 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Aqueous Acid (Slightly, Sonicated), DMSO (Slightly, Heated)
- form
- Powder
- pka
- 8.1 · 8.1, 3.1(at 25℃)
- color
- White
- optical activity
- 20 · [α]20/D 11°, c = 1 in 1 M NaOH
- Water Solubility
- 1 · 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 · 13,9910
- Major Application
- peptide synthesis
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 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)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c
Chemistry & industry
Applications
DescriptionBestatin 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.
UsesUbenimex (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.
UsesBestatin 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.
General DescriptionBestatin 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.
Upstream & downstream products
Related reactions
0 records
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Compound notes
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