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Ubenimex

From Wikipedia, the free encyclopedia
"Bestatin" redirects here. For other uses, seeBestatin (disambiguation).
Ubenimex[1]
Names
IUPAC name
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
Systematic IUPAC name
(2S)-2-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
Other names
Bestatin;N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.055.917Edit this at Wikidata
EC Number
  • 261-529-2
KEGG
UNII
  • 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
    Key: VGGGPCQERPFHOB-RDBSUJKOSA-N
  • CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
Properties
C16H24N2O4
Molar mass308.378 g·mol−1
Melting point245 °C (473 °F; 518 K) (decomposes)
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315,H319,H335
P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Ubenimex (INN), also known more commonly asbestatin, is a competitive, reversibleprotease inhibitor. It is aninhibitor ofarginyl aminopeptidase (aminopeptidase B),[3]leukotriene A4 hydrolase (azinc metalloprotease that displays bothepoxide hydrolase andaminopeptidase activities),[4]alanyl aminopeptidase (aminopeptidase M/N),[5]leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase),[6][7] andmembrane dipeptidase (leukotriene D4 hydrolase). It is being studied for use in the treatment ofacute myelocytic leukemia[8] andlymphedema.[9]It is derived fromStreptomyces olivoreticuli.[10] Ubenimex has been found to inhibit the enzymatic degradation ofoxytocin,vasopressin,enkephalins, and various otherpeptides and compounds.[citation needed]

Crystal structure of ubenimex
Crystal structure of ubenimex in the binding pocket of leukotriene A4 hydrolase. Rendered from PDB1HS6.

See also

[edit]

References

[edit]
  1. ^N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine atSigma-Aldrich
  2. ^"Ubenimex".pubchem.ncbi.nlm.nih.gov. Retrieved12 December 2021.
  3. ^Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. (1976)."Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes".The Journal of Antibiotics.29 (29):97–99.doi:10.7164/antibiotics.29.97.PMID 931798.
  4. ^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".Biochemical Pharmacology.48 (48):131–137.doi:10.1016/0006-2952(94)90232-1.PMID 8043014.
  5. ^K Sekine; H Fujii; F Abe (1999)."Induction of apoptosis by Bestatin (ubenimex) in human leukemic cell lines".Leukemia.13 (5):729–734.doi:10.1038/sj.leu.2401388.PMID 10374877.
  6. ^Nakanishi Y, Nomura S, Okada M, Ito T, Katsumata Y, Kikkawa F, Hattori A, Tsujimoto M, Mizutani S (2000). "Immunoaffinity purification and characterization of native placental leucine aminopeptidase/oxytocinase from human placenta".Placenta.21 (7):628–34.doi:10.1053/plac.2000.0564.PMID 10985965.
  7. ^Naruki M, Mizutani S, Goto K, Tsujimoto M, Nakazato H, Itakura A, Mizuno K, Kurauchi O, Kikkawa F, Tomoda Y (1996). "Oxytocin is hydrolyzed by an enzyme in human placenta that is identical to the oxytocinase of pregnancy serum".Peptides.17 (2):257–61.doi:10.1016/0196-9781(95)02124-8.PMID 8801531.S2CID 28486489.
  8. ^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.
  9. ^Tian, W; Rockson, S; Jiang, X; Kim, J; Begaye, A; Shuffle, EM; Tu, AB; Cribb, M; Nepiyushchikh, Z; Feroze, AH; Zamanian, RT; Dhillon, RT; Voelkel, NF; Peters-Golden, M; Kitajewski, J; Dixon, JB; Nicolls, MR (2017)."Leukotriene B4 antagonism ameliorates experimental lymphedema".Science Translational Medicine.9 (389) eaal3920.doi:10.1126/scitranslmed.aal3920.PMID 28490670.
  10. ^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.PMC 7168514.PMID 16216010.

External links

[edit]
Receptor
(ligands)
BLTTooltip Leukotriene B4 receptor
BLT1Tooltip Leukotriene B4 receptor 1
BLT2Tooltip Leukotriene B4 receptor 2
CysLTTooltip Cysteinyl leukotriene receptor
CysLT1Tooltip Cysteinyl leukotriene receptor 1
CysLT2Tooltip Cysteinyl leukotriene receptor 2
CysLTETooltip Cysteinyl leukotriene receptor E
Enzyme
(inhibitors)
5-LOXTooltip Arachidonate 5-lipoxygenase
12-LOXTooltip Arachidonate 12-lipoxygenase
15-LOXTooltip Arachidonate 15-lipoxygenase
LTA4HTooltip Leukotriene A4 hydrolase
LTB4HTooltip Leukotriene B4 ω-hydroxylase
LTC4STooltip Leukotriene C4 synthase
LTC4HTooltip Leukotriene C4 hydrolase
LTD4Tooltip Leukotriene D4 hydrolase
Others
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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