| Identification | More | [Name]
BESTATIN HYDROCHLORIDE | [CAS]
65391-42-6 | [Synonyms]
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HYDROCHLORIDE
(AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCINE HYDROCHLORIDE
BESTATIN
BESTATIN HCL
BESTATIN HYDROCHLORIDE
N-[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE HYDROCHLORIDE
N-(3R-AMINO-2S-HYDROXY-1-OXO-4-PHENYLBUTYL)-L-LEUCINE, MONOHYDROCHLORIDE
N-(2S,3R-3-AMINO-2-HYDROXY-4-PHENYLBUTY-RYL)-L-LEUCINE HCL
Bestatin.HCI | [Molecular Formula]
C16H25ClN2O4 | [MDL Number]
MFCD00058004 | [Molecular Weight]
344.83 | [MOL File]
65391-42-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
216-218 °C | [storage temp. ]
−20°C
| [solubility ]
H2O: 25 mg/mL, clear, colorless
| [form ]
White to off-white powder. | [color ]
White | [Water Solubility ]
Soluble in water (4 mg/ml, warm), DMSO (>25 mg/ml), methanol, acetic acid, dimethyl formamide, and 100% ethanol. | [BRN ]
4628066 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO, distilled water, or ethanol may be stored at -20° for up to 1 month. | [InChIKey]
XGDFITZJGKUSDK-UDYGKFQRSA-N | [CAS DataBase Reference]
65391-42-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
3-10 | [HS Code ]
29242995 |
| Hazard Information | Back Directory | [Description]
Bestatin HCl (65391-42-6) inhibits leucine aminopeptidase and aminopeptidases B and N. Inhibits leukotriene A4 hydrolase. Displays immunostimulant activity via activation of macrophages and T lymphocytes. Displays antitumor activity. | [Uses]
Bestatin has been used as a protease inhibitor for the purification of his-tagged Tau protein. | [Uses]
Bestatin is an inhibitor of amino peptidases and a potent, irreversible inhibitor of LTA4 hydrolase. It inhibits the amino peptidase activity of LTA4 hydrolase with a Ki value of 201 nM. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation. It does not inhibit carboxypeptidases. | [Uses]
competitive aminopeptidase B inhibitor | [Definition]
ChEBI: Bestatin (hydrochloride) is a peptide. | [General Description]
Chemical structure: amino acid derivatives | [Biochem/physiol Actions]
A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation. | [in vivo]
in a mouse dorsal air sac assay, oral administration of bestatin (100-200 mg/kg/day) showed a significant inhibitory activity against the melanoma cell-induced angiogenesis. bestatin also inhibited the tube-like formation of human umbilical vein endothelial cells (huvecs). furthermore, after the orthotopic implantation of b16-bl6 melanoma cells into mice, bestatin administration (50-100 mg/kg/day, i.p) reduced the number of vessels oriented towards the established primary tumor mass on the dorsal side of mice [1]. | [storage]
Store at -20°C | [References]
1) Orning et al. (1991), Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes; J. Biol. Chem., 266 1375
2) Wang et al. (2010), The effect of different species aminopeptidase N structure on the activity screening of aminopeptidase N inhibitor; Biol. Pharm. Bull., 33 1658 |
|
|