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58970-76-6 60660-75-5
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58970-76-6

58970-76-6 structure
58970-76-6 structure
  • Name: Ubenimex
  • Chemical Name: Ubenimex
  • CAS Number: 58970-76-6
  • Molecular Formula: C16H24N2O4
  • Molecular Weight: 308.373
  • Catalog: Biochemical Biological response modifier
  • Create Date: 2018-08-30 11:52:21
  • Modify Date: 2024-01-02 18:24:22
  • Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor.
Name Ubenimex
Synonyms BESTATIN
BENIMEX
Bestatin,UbeniMex
2-(3-Amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid
Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-
nk421
MFCD00083262
N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucine
EINECS 261-529-2
Description Bestatin is a natural, broad-spectrum, and competitive aminopeptidase inhibitor.
Related Catalog
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
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

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OH2915000
CHEMICAL NAME :
L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, (S-(R*,S*))-
CAS REGISTRY NUMBER :
58970-76-6
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C16-H24-N2-O4
MOLECULAR WEIGHT :
308.42
WISWESSER LINE NOTATION :
1Y1&1YVQMVYQYZ1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
780 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1900 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
63700 mg/kg/91D-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - proteinuria
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,401,1984 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1250 mg/kg
SEX/DURATION :
female 16-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
HMMRA2 Hormone and Metabolic Research. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1969- Volume(issue)/page/year: 21,366,1989
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS OH2915000

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title: CAS No. 58970-76-6 | Chemsrc address: https://www.chemsrc.com/en/baike/894785.html

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