[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL
Bestatin hydrochloride
CAS: 65391-42-6
Molecular Formula: C16H25ClN2O4
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL - Names and Identifiers
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL - Physico-chemical Properties
| Molecular Formula | C16H25ClN2O4 |
| Molar Mass | 344.83 |
| Melting Point | 216-218 °C |
| Water Solubility | Soluble in water (4 mg/ml, warm), DMSO (>25 mg/ml), methanol, acetic acid, dimethyl formamide, and 100% ethanol. |
| Solubility | H2O: 25 mg/mL, clear, colorless |
| Appearance | White to off-white powder. |
| Color | White |
| BRN | 4628066 |
| Storage Condition | 2-8°C |
| 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. |
| Physical and Chemical Properties | Bioactive Bestatin hydrochloride (Ubenimex hydrochloride) is a CD13 (Aminopeptidase N)/APN and leucotriene A4 hydrolase inhibitor commonly used in cancer research. |
| Use | Application can be used as a molecular tool for protein sequence determination, in the food industry is usually used in combination with protease, widely used in the production of spices and cheese, protein hydrolysate debittering, deep hydrolysis of proteins and preparation of polypeptides. |
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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 |
| FLUKA BRAND F CODES | 3-10 |
| HS Code | 29242995 |
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL - Uses and methods of synthesis
Overview
aminopeptidase, a class of proteolytic enzymes, it can be from the protein or polypeptide chain of the N-terminal from outside to inside one of the free amino acids to, so also known as exopendase, according to its role after the product is different, is divided into two categories, namely the production of amino acid alpha-aminoacylpeptidyl hydrolase (alpha-amino-acetyl-peptide hydroase) and dipeptidyl peptide hydrolase (dipeptidyl-peptide hydrolase), which generates dipeptides; Has good hydrolytic ability and debittering ability; Can be used as a molecular tool for protein sequence determination, in the food industry, it is usually used in combination with protease. It is widely used in the production of condiment and cheese, debittering of protein hydrolysate, deep hydrolysis of protein and preparation of polypeptide.
classification
The products after its action are different and can be divided into two categories: α-aminoacylpeptidyl hydrolase (α-amino-acyl-peptide hydroase) which produces amino acids and dipeptidyl peptide hydrolase (dipeptidyl-peptide hydrolase) to produce dipeptides.
It can be classified into leucine aminopeptidase, valine aminopeptidase, phenylalanine aminopeptidase, proline aminopeptidase and the like depending on the most reactive substrate.
preparation method
fermentation broth of Bacillus subtilis Zj016 was centrifuged at 4 ℃ for 10 min at 10 000 r/min, and the supernatant was clarified with 18% (NH4)2SO4; the supernatant was centrifuged and concentrated by ultrafiltration using an ultrafiltration membrane with a relative molecular mass of 50000. The concentrated solution was desalted by an ultrafiltration membrane with a relative molecular mass of 30 000, and ethanol was precipitated by 68% volume fraction; the precipitate was vacuum freeze-dried to give an aminopeptidase enzyme activity of 4.0 x 105U/ g.
pharmacological effects
The most significant role is to remove the bitter taste of protein hydrolysate, such as soy protein hydrolysate, the bitter taste of the peptide is proportional to the amount of hydrophobic amino acids at the N-terminal, exopeptidase can effectively remove these hydrophobic amino acids.
in vitro studies
Bestatin enhances ATRA-induced differentiation and inhibits ATRA-driven phosphorylation of p38 MAPK in ATRA-sensitive APL NB4 cells. Bestatin can not reverse the differentiation block in ATRA-resistant APL MR2 cells. CD13 ligation with anti-CD13 antibody WM-15 results in phosphorylation of p38 MAPK, reduces the inhibition of Bestatin on the phosphorylation of p38 MAPK and completely abolishes the enhancement of Bestatin on ATRA-inducing differentiation in NB4 cells. Bestatin (600 μM)-treated cells progress slower through the cell cycle due to decreased rate of cell growth and the frequency of cell division. Bestatin inhibits the frequency of mitosis and the inherent multinuclearity in D. discoideum and is not cytotoxic to D. discoideum cells at 0-600 μM. Bestatin inhibits aminopeptidase activity in lysates of PsaA-GFP- and GFP-expressing cells by 69.39% ± 10.5% and 39.93% ± 18.7% of control, respectively.
in vivo studies
Bestatin (20 μM) significantly reduces CD13 expression in diabetic mice and results a significant inhibition of MMP-9 specific gelationolytic band densities compared to diabetic vehicle-treated mice. Bestatin treatment significantly inhibits the expression of VEGF and heparanase in diabetic mice. Intravitreal bestatin treatment significantly downregulates the expression of both HIF-1α and VEGF in diabetic mice retinas. Furthermore the upregulated expression of heparanase in diabetic mice retinas is significantly inhibited by intravitreal bestatin treatment. Bestatin (10, 1, and 0.1mg/kg, I .p.) treatment before the antigen-potentiated humoral response to SRBC results in an increased number of splenocytes producing hemolytic anti-SRBC antibodies (PFC) and the 2-ME-resistant serum hemagglutinin titer (at a dose of 0.1 mg/kg). Bestatin (1 and 0.1 mg/kg) administered to mice five times on alternate days after cyclophosphamide injection does not change the suppressive effect of the drug regarding the number of PFC, and even causes the further decrease of the total anti-SRBC hemagglutinins at dose of 1 mg/kg on day 7 after antigen stimulation.
Last Update：2024-04-09 15:16:21
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Multiple SpecificationsSpot supply
Product Name: Bestatin hydrochloride Visit Supplier Webpage Request for quotationCAS: 65391-42-6
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: Bestatin hydrochloride Visit Supplier Webpage Request for quotationCAS: 65391-42-6
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Spot supply
Product Name: Bestatin hydrochloride Visit Supplier Webpage Request for quotationCAS: 65391-42-6
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
View History
[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL
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BENZIMIDAZOLONE YELLOS H4G
3-AMINO-3-(3-BROMOPHENYL)PROPANOIC ACID
METHYL-[2-(4-NITRO-PHENYL)-ETHYL]-AMINE
2,6-DIMETHOXYL-5-PYRIDINEBORONIC ACID
Oct-7-enyloxirane
DIGOXIN EP IMPURITY G (NEODIGOXIN)
SULFURIC ANHYDRIDE
Propanoic acid, 2-bromo-2-methyl-,2-[(2-bromo-2-methyl-1-oxo...
2-[(Aminoiminomethyl)thio]ethanesulfonic acid(14C)