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B8385

Sigma-Aldrich

Bestatin hydrochloride

powder, ≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C16H24N2O4 · HCl
Numéro CAS:
65391-42-6
Poids moléculaire :
344.83
Numéro Beilstein :
4628066
Numéro MDL:
MFCD00058004
Code UNSPSC :
12352202
ID de substance PubChem :
24278278
Nomenclature NACRES :
NA.77

product name

Bestatin hydrochloride, ≥98% (HPLC)

Source biologique

synthetic (organic)

Pureté

≥98% (HPLC)

Forme

powder

Pf

216 °C

Solubilité

water: 25 mg/mL, clear to very slightly hazy, colorless

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

O=C(N[C@@H](CC(C)C)C(O)=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1.Cl[H]

InChI

1S/C16H24N2O4.ClH/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);1H/t12-,13+,14+;/m1./s1

Clé InChI

XGDFITZJGKUSDK-UDYGKFQRSA-N

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Description générale

Chemical structure: amino acid derivatives

Actions biochimiques/physiologiques

A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.

Notes préparatoires

Solubility testing in water at 25 mg/ml yields a clear solution. Stock solutions at 1 mM are expected to be stable at least one month stored at -20 °C.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

Tina S Skinner-Adams et al.
Journal of medicinal chemistry, 50(24), 6024-6031 (2007-10-27)
Previous studies have pinpointed the M17 leucyl aminopeptidase of Plasmodium falciparum (PfLAP) as a target for the development of new antimalarials. This metallo-exopeptidase functions in the terminal stages of hemoglobin digestion and is inhibited by bestatin, a natural analog of
A Taylor
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 7(2), 290-298 (1993-02-01)
Aminopeptidases catalyze the cleavage of amino acids from the amino terminus of protein or peptide substrates. They are widely distributed throughout the animal and plant kingdoms and are found in many subcellular organelles, in cytoplasm, and as membrane components. Several
Hye Cheong Koo et al.
International journal of molecular sciences, 22(8) (2021-05-01)
It has been shown previously that a novel tetrapeptide, Arg-Leu-Tyr-Glu (RLYE), derived from human plasminogen inhibits vascular endothelial growth factor (VEGF)-induced angiogenesis, suppresses choroidal neovascularization in mice by an inhibition of VEGF receptor-2 (VEGFR-2) specific signaling pathway. In this study
Michael B Harbut et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(34), E526-E534 (2011-08-17)
Malaria causes worldwide morbidity and mortality, and while chemotherapy remains an excellent means of malaria control, drug-resistant parasites necessitate the discovery of new antimalarials. Peptidases are a promising class of drug targets and perform several important roles during the Plasmodium
Yekaterina Poloz et al.
Eukaryotic cell, 11(4), 545-557 (2012-02-22)
Bestatin methyl ester (BME) is an inhibitor of Zn(2+)-binding aminopeptidases that inhibits cell proliferation and induces apoptosis in normal and cancer cells. We have used Dictyostelium as a model organism to study the effects of BME. Only two Zn(2+)-binding aminopeptidases
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