BestatinA potent aminopeptidase inhibitor

Bestatin (CAS 58970-76-6)

Bestatin | CAS 58970-76-6 is rated 5.0 out of 5 by 2.
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Synonym: [(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-Leu
Application: A potent aminopeptidase inhibitor
CAS Number: 58970-76-6
Purity: >99%
Molecular Weight: 308.4
Molecular Formula: C16H24N2O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Bestatin is a potent aminopeptidase inhibitor. The compound has multiple physiological functions including the ability to act as an immunomodifier and enhance the proliferation of human bone marrow granulocyte-macrophage progenitor cells to form CFU-GM colonies. Research indicates that bestatin can indirectly act on monocytes by inhibiting Aminopeptidase B, which in turn inhibits the catabolism of tuftsin. Bestatin has also been shown to inhibit Leukotriene A4 hydrolase (LTA4H). This compound has been demonstrated to bind to cell surfaces and research indicates that it can directly stimulate lymphocytes through its fixation on the cell surface. The agent has been used in multiple leukemia studies.


References

1. Aoyagi, T. and Umezawa, H. 1981. Acta Biol. Med. Ger. 40: 1523-1529. PMID: 7044007
2. Inoue, T., et al. 1994. J. Clin. Endocrinol. Metab. 79: 171-175. PMID: 7913090
3. Lkhagvaa, B., et al. 2008. Cytokine. 44: 386-391. PMID: 19036603
4. Jia, M.R., et al. 2010. Front Neurosci. 4: 50. PMID: 20631848

Appearance :
Crystalline or powder
Physical State :
Solid
Solubility :
Soluble in water (<1 25), DMSO (2 mg/ml), methanol (5 mg/ml), 1eq. NaOH (50 mM), ethanol (<1 mg/ml at 25° C), acetic acid, aq. HCl, and alkaline solution. Insoluble in ethyl acetate, benzene, hexane, and chloroform.
Storage :
Desiccate at -20° C
Melting Point :
233-236° C
Boiling Point :
604.66° C at 760 mmHg (Predicted)
Density :
1.20 g/cm3 (Predicted)
Refractive Index :
n20D 1.56 (Predicted)
Optical Activity :
α20/D -11°, c = 1 in 1 M NaOH
IC50 :
Cytosol aminopeptidase: IC50 = 0.5 nM (bovine); Aminopeptidase N: IC50 = 5 nM (pig); Zinc aminopeptidase: IC50 = 0.28 µM (Plasmodium falciparum FcB1/Columbia); amino peptidase b: IC50 = 1-10 µM
Ki Data :
Leucine aminopeptidase: Ki= 0.6 nM (human); Aminopeptidase B: Ki= 14 nM (rat); Cystinyl aminopeptidase: Ki= 20 nM (rat); Zinc aminopeptidase: Ki= 0.19 µM (Plasmodium falciparum FcB1/Columbia)
pK Values :
pKa: 3.28 (Predicted), pKb: 6.87 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
OH2915000
PubChem CID :
72172
Merck Index :
14: 9842
MDL Number :
MFCD00083262
EC Number :
261-529-2
Beilstein Registry :
4704312
SMILES :
CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O

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Bestatin  Product Citations

See how others have used Bestatin. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 13 total

PMID: # 27760898  Mitsui, T.|Ishida, M.|Izawa, M.|Arita, J.| et al. 2017. Endocr. J. 64: 103-115.

PMID: # 26607765  Hamon, Y. et al. 2015. The FEBS journal.

PMID: # 21787835  Mitsui, T. et al. 2011. Mol. Cell. Endocrinol. 345: 68-78.

PMID: # 20631848  Jia, MR. et al. 2010. Front Neurosci. 4: -.

PMID: # 17088482  Skinner-Adams, TS. et al. 2007. Antimicrob. Agents Chemother. 51: 759-762.

PMID: # 12531805  O'Farrell, AM. et al. 2003. Blood. 101: 3597-3605.

PMID: # 8667199  Greene, DL. et al. 1996. J. Pharmacol. Exp. Ther. 277: 1366-1375.

PMID: # 8422382  Taylor, A. et al. 1993. Biochemistry. 32: 784-790.

PMID: # 6208315  Knoblich, A. et al. 1984. J. Gen. Virol. 65 ( Pt 10): 1675-1686.

PMID: # 6238401  Dunlap, BE. et al. 1984. Scand. J. Immunol. 20: 237-245.

Citations 1 to 10 of 13 total
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Rated 5 out of 5 by from Used as specific inhibitor of APN Used as specific inhibitor of APN - PMID 26607765
Date published: 2015-12-03
Rated 5 out of 5 by from Skinner Skinner-Adams, et. al. (PubMed ID 17088482) used Bestatin in their research to identify if the HIV protease inhibitors target digestive-vacoule plasmepsins. -SCBT Publication Review
Date published: 2015-05-02
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