An aminopeptidase inhibitor
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Alternative(s)
70520Bestatin (hydrochloride)
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Bestatin

Item No. 21217

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-L-leucine
CAS Number
58970-76-6
Synonyms
  • NK 421
  • NSC 265489
Molecular Formula
C16H24N2O4
Formula Weight
308.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 0.16 mg/mL
SMILES
CC(C)C[C@@H](C(O)=O)N([H])C([C@@H](O)[C@H](N)CC1=CC=CC=C1)=O
InChi Code
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-YIOYIWSBSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Bestatin is an aminopeptidase inhibitor originally isolated from S. olivoreticuli.1 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).1,2,3 It is selective for these aminopeptidases over aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, and thermolysin.1 Bestatin inhibits the production of LTB4 (Item No. 20110) in erythrocytes when used at a concentration of 70 µM.3 It increases the expression of Akt, inhibits proliferation, migration, and invasion, and induces autophagy and apoptosis in 5637 bladder cancer cells.4 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.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Umezawa, H., Ayoagi, T., Suda, H., et al. Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes. J. Antibiot. (Tokyo) 29(1), 97-99 (1976).

    2. Melzig, M.F., and Bormann, H. Betulinic acid inhibits aminopeptidase N activity. Planta Med. 64(7), 655-657 (1998).

    3. Örning, L., Krivi, G., and Fitzpatrick, F.A. Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes. The Journal of Biological Chemisty 266(3), 1375-1378 (1991).

    4. Wang, X., Liu, Y., Liu, W., et al. Ubenimex, an APN inhibitor, could serve as an anti‑tumor drug in RT112 and 5637 cells by operating in an Akt‑associated manner. Mol. Med. Rep. 17(3), 4531-4539 (2018).

    5. Zhao, S., Yao, K., Li, D., et al. Inhibition of LTA4H by bestatin in human and mouse colorectal cancer. EBioMedicine 44, 361-374 (2019).