Ubenimex

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Ubenimex[1]
Ubenimex2DCSD.svg
Ubenimex3DanJ.gif
Names
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
58970-76-6
65391-42-6 (HCl)
ChEMBL ChEMBL29292 YesY
ChemSpider 65145
Jmol-3D images Image
PubChem 72172
UNII I0J33N5627 YesY
Properties
C16H24N2O4
Molar mass 308.38 g·mol−1
Melting point 245 °C (473 °F; 518 K) (decomposes)
Hazards
S-phrases S22 S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

Ubenimex (INN), also known by the brand name Bestatin, is a competitive protease inhibitor. It is an inhibitor of aminopeptidase B,[2] leukotriene A4 hydrolase,[3] and aminopeptidase N.[4] It is being studied for use in the treatment of acute myelocytic leukemia.[5] It is derived from Streptomyces olivoreticuli.[6]

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

References[edit]

  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. 
  6. ^ Bauvois, B; Dauzonne, D (January 2006). "Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: Chemistry, biological evaluations, and therapeutic prospects". Medicinal Research Reviews 26 (1): 88–130. doi:10.1002/med.20044. PMID 16216010. 

External links[edit]

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