Ubenimex

From Wikipedia, the free encyclopedia
Ubenimex[1]
IUPAC name

(2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid

Other names

Bestatin; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine

Identifiers
CAS number 58970-76-6, 
65391-42-6 (HCl)
PubChem 72172
ChEMBL CHEMBL29292 YesY
Jmol-3D images {{#if:CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O|Image 1
Properties
Molecular formula C16H24N2O4
Molar mass 308.37 g mol−1
Melting point 245 °C (dec.)
Hazards
S-phrases S22 S24/25
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ubenimex (INN), also known as bestatin, is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B,[2] leukotriene A4 hydrolase,[3] aminopeptidase N.[4] It is being studied for use in the treatment of acute myelocytic leukemia.[5]

Crystal structure of Bestatin.
Crystal structure of bestatin in the binding pocket of leukotriene A4 hydrolase. Rendered from PDB 1HS6.


References

  1. ↑ N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine at Sigma-Aldrich
  2. ↑ Umezawa,H., Aoyagi,T., Suda,H., Hamada,M. & Takeuchi,T. (1976). Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes. (29). pp. 97–99. 
  3. ↑ Muskardin,D.T., Voelkel,N.F. & Fitzpatrick,F.A. (1994). Modulation of pulmonary leukotriene formation and perfusion pressure by bestatin, an inhibitor of leukotriene A4 hydrolase. (48). pp. 131–137. 
  4. ↑ K Sekine, H Fujii and F Abe (1999). Induction of apoptosis by bestatin (ubenimex) in human leukemic cell lines 13 (5). pp. 729–734. 
  5. ↑ Hirayama, Y; Sakamaki, S; Takayanagi, N; Tsuji, Y; Sagawa, T; Chiba, H; Matsunaga, T; Niitsu, Y (2003). "Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival". Gan to kagaku ryoho. Cancer & chemotherapy 30 (8): 1113–8. PMID 12938265. 

External links

  • The MEROPS online database for peptidases and their inhibitors: Bestatin


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