CAS Number58970-76-6
SynonymsBESTATIN; BENIMEX; Bestatin,UbeniMex; 2-(3-Amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid; nk421; MFCD00083262; N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucine; EINECS 261-529-2
Molecular FormulaC16H24N2O4
Molecular Weight308.37
Purity>99 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point604.7±55.0 °C at 760 mmHg
Melting Point245 °C (dec.)(lit.)
Appearancecrystalline solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 58970-76-6 |
| Catalog No. | 2A-9012882 |
| Chinese Name | 乌苯美司 |
| Synonyms | BESTATIN; BENIMEX; Bestatin,UbeniMex; 2-(3-Amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid; nk421; MFCD00083262; N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucine; EINECS 261-529-2 |
| Molecular Formula | C16H24N2O4 |
| Molecular Weight | 308.37 |
| Purity | >99 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 604.7±55.0 °C at 760 mmHg |
| Melting Point | 245 °C (dec.)(lit.) |
| Appearance | crystalline solid |
| Water Solubility | Water solubility: Practically insoluble; soluble i |
| Storage Condition | 2-8℃ |
| Application | Bestatin is a natural, broad-spectrum, competitive aminopeptidase inhibitor. |
| MDL Number | MFCD00083262 |
| SMILES | [N+H3][C@@H]([C@H](O)C(=O)N[C@H](CC(C)C)C(=O)[O-])Cc1ccccc1 |
| InChI | 1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13-,14+/m1/s1 |
| InChI Key | VGGGPCQERPFHOB-MCIONIFRSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/12882_1_58970_76_6.pdf |
| Bioactivity | Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Aminopeptidase Research Areas >> Cancer In Vitro 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[2]. 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[4]. In Vivo 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[1]. 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[3]. Kinase Assay Cells are harvested, washed, and lysed in NP-40 lysis buffer (50 mM Tris-HCl [pH 7.5], 150 mM NaCl, 0.5% NP-40). Total cell protein is quantified using the Bradford assay and 1-mg/mL protein aliquots are made. Ten microliters of total cell protein is mixed with 290 μL of substrate solution (0.1 mg/mL dithiothreitol [DTT], 0.1 mg/mL albumin, and 1 mM alanine-β-naphthylamide). Fluorometric measurements (340 nm excitation, 400 nm emission) are made after 15 and 30 min. The slope of the line between the 15- and 30-min measurements is used to represent aminopeptidase activity. Total cell protein is preincubated with bestatin, amastatin, puromycin, EDTA, and/or ZnCl2 for 20 min before the fluorometric aminopeptidase assay. Cell Assay Growing cells (1×106 to 2×106 cells/mL) are diluted to 1.0×103 cells/mL and transferred (3 mL) into a well in a 12-well multiwell plate (2.5-cm diameter/well). Cells are treated with 0, 10, 50, 100, 300, or 600 μM Bestatin and allowed to grow at 21°C shaking at 180 rpm for 48 h. A hemocytometer is used to measure cell density after 0, 24, and 48 h. Animal Admin Bestatin is dissolved in PBS. The agent (doses of 10, 1, and 0.1 mg/kg) is injected i.p. to non-cyclophosphamide-treated mice, 5 or 10 times at 24-h intervals before SRBC immunization. The mice are immunized 24 h after the last dose of bestatin. Pharmacological immunosuppression is induced by a single intraperitoneal injection of cyclophosphamide administered at a dose of 350 mg/kg, 12 days before SRBC immunization. Bestatin at the doses of 1 and 0.1 mg/kg is injected to cyclophosphamide-immunosuppressed mice i.p. five times at 48-h intervals or 10 times at 24-h intervals before SRBC immunization. The first dose of bestatin is administered 24 h after cyclophosphamide, while the last dose of the drug is injected 24h before SRBC immunization. References [1]. Hossain A, et al. Protective effects of bestatin in the retina of streptozotocin-induced diabetic mice. Exp Eye Res. 2016 Aug;149:100-6 [2]. Qian X, et al. Inhibition of p38 MAPK Phosphorylation Is Critical for Bestatin to Enhance ATRA-Induced Cell Differentiation in Acute Promyelocytic Leukemia NB4 Cells. Am J Ther. 2016 May-Jun;23(3):e680-9. [3]. Lis M, et al. The effects of bestatin on humoral response to sheep erythrocytes in non-treated and cyclophosphamide-immunocompromised mice. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):133-8 [4]. Poloz Y, et al. Bestatin inhibits cell growth, cell division, and spore cell differentiation in Dictyostelium discoideum. Eukaryot Cell. 2012 Apr;11(4):545-57 Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 604.7±55.0 °C at 760 mmHg Melting Point 245 °C (dec.)(lit.) Molecular Formula C16H24N2O4 Molecular Weight 308.373 Flash Point 319.5±31.5 °C Exact Mass 308.173615 PSA 112.65000 LogP 2.64 Vapour Pressure 0.0±1.8 mmHg at 25°C Index of Refraction 1.557 InChIKey VGGGPCQERPFHOB-RDBSUJKOSA-N SMILES CC(C)CC(NC(=O)C(O)C(N)Cc1ccccc1)C(=O)O |
| Use of | Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor. Properties Articles26 Name Ubenimex Synonym More Synonyms Ubenimex Biological Activity Description Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Aminopeptidase Research Areas >> Cancer References [1]. Hossain A, et al. Protective effects of bestatin in the retina of streptozotocin-induced diabetic mice. Exp Eye Res. 2016 Aug;149:100-6 [3]. Lis M, et al. The effects of bestatin on humoral response to sheep erythrocytes in non-treated and cyclophosphamide-immunocompromised mice. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):133-8 [4]. Poloz Y, et al. Bestatin inhibits cell growth, cell division, and spore cell differentiation in Dictyostelium discoideum. Eukaryot Cell. 2012 Apr;11(4):545-57 Chemical & Physical Properties Molecular Formula C16H24N2O4 Exact Mass 308.173615 PSA 112.65000 Index of Refraction 1.557 InChIKey VGGGPCQERPFHOB-RDBSUJKOSA-N |
| Transport Info | Product name: Purity: 99.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: No dangerous goods IMDG Code: No dangerous goods International Air Transport Dangerous Regulations: No dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special precautions for users No data available The company is not responsible for any damage caused by any operation or contact with the above products. For more terms of use, see invoice or package The reverse side of the mounting strip. |
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