[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin

Bestatin Struktur
58970-76-6
CAS-Nr.
58970-76-6
Bezeichnung:
[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin
Englisch Name:
Bestatin
Synonyma:
UBENIMEX;nk421;BENIMEX;BESTATIN;NSC 265489;Bestatin D10;Bestatin, >=99%;Ubenimex Ubenimex;UbeniMex(Bestatin);Bestatin, UbeniMex
CBNumber:
CB9324019
Summenformel:
C16H24N2O4
Molgewicht:
308.37
MOL-Datei:
58970-76-6.mol

[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin Eigenschaften

Schmelzpunkt:
245 °C (dec.)(lit.)
alpha 
D20 -15.5° (c = 1.0 in 1N HCl)
Siedepunkt:
448.76°C (rough estimate)
Dichte
1.0917 (rough estimate)
Brechungsindex
1.5800 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
Aqueous Acid (Slightly, Sonicated), DMSO (Slightly, Heated)
pka
8.1, 3.1(at 25℃)
Aggregatzustand
Powder
Farbe
White
Optische Aktivität
[α]20/D 11°, c = 1 in 1 M NaOH
Wasserlöslichkeit
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.
Merck 
13,9910
InChIKey
VGGGPCQERPFHOB-RDBSUJKOSA-N
CAS Datenbank
58970-76-6(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
S-Sätze: 22-24/25
WGK Germany  3
RTECS-Nr. OH2915000
HS Code  29242998
Toxizität LD50 in male, female mice, male, female rats (g/kg): 1.3, 1.9, 1.9, 2.1 s.c.; 0.19, 0.19, 0.90, 0.78 i.p.; >4.0, >4.0, >2.0, >2.0 orally (Sakakibara)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P271 Nur im Freien oder in gut belüfteten Räumen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P312 Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P403+P233 An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.

[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.

Beschreibung

Bestatin is an aminopeptidase inhibitor originally isolated from S. olivoreticuli. It inhibits aminopeptidase B (IC50 = 0.05 μg/ml), aminopeptidase N (IC50 = 16.9 μM), leucine aminopeptidase (IC50 = 0.01 μg/ml), and the aminopeptidase activity of leukotriene A4 (LTA4) hydrolase (Kapp = 172 nM). It is selective for these aminopeptidases over aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, and thermolysin. Bestatin inhibits the production of LTB4 in erythrocytes when used at a concentration of 70 μM. It increases the expression of Akt, inhibits proliferation, migration, and invasion, and induces autophagy and apoptosis in 5637 bladder cancer cells. Bestatin (5 and 15 mg/kg) decreases serum levels of LTB4 and reduces tumor growth in a patient-derived xenograft (PDX) mouse model of colorectal cancer.

Chemische Eigenschaften

white powder, soluble in methanol, ethanol, DMSO and other organic solvents, from Streptomyces olivoreticuli.

Verwenden

Ubenimex (also known as bestatin) is a competitive aminopeptidase B inhibitor with an IC50 of 100 mg/ml for K562 cells. Proliferation of all the cell lines except KG1 was inhibited by bestatin. P39/TSU, HL60 and U937 were highly sensitive, with 50% growth inhibitory concentration. It is useful in the treatment of non-lymphocytic leukemia. In other types of cancers ubenimex added to radiotherapy or chemotherapy following surgery significantly inmases survival time through immunopotentiation. It is being studied for use in the treatment of acute myelocytic leukemia.

Allgemeine Beschreibung

Bestatin was found in the culture broth of Streptomyces olivoreticuli in 1976by Umezawa et al. in the course of screening specific enzyme inhibitors of microbial origin. It shows inhibitory activity against specific exopeptidases, e.g., aminopeptidase B and leucine aminopeptidase. However, it does not act against aminopeptidase A, carboxypeptidases A and B, or endopeptidases. Bestatin acts as a bioresponse modifier and shows antitumor activity via stimulation of immuno response in the host. In combination with cytotoxic anticancer drugs, it is now under clinical evaluation for use in cancer therapy.

Biologische Aktivität

Aminopeptidase inhibitor (K i = 0.001-90 mM); inhibits enkephalin metabolism and leukotriene A 4 hydrolase. Inhibits tumor cell proliferation.

Sicherheitsprofil

Poison by intraperitoneal route.Moderately toxic by subcutaneous route. Experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx.

[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


[S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 389)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Chengdu Aslee Biopharmaceuticals, Inc.
28-85305008
CHINA 964 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21695 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
bruce@xrdchem.cn CHINA 566 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28180 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22968 58
BOC Sciences
+1-631-485-4226
inquiry@bocsci.com United States 19553 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 419 58

58970-76-6([S-(R*,S*)]-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucin)Verwandte Suche:


  • UbenaMix, Inobestin, NK 421
  • L-Leucine,N-[(2S,3R)-3-aMino-2-hydroxy-1-oxo-4-phenylbutyl]-
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine 97%
  • 3-(r)-amino-2-(s)-hydroxy-4-phenylbutanoyl-(s)-leucine
  • n-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-,(s-(r*,s*))-l-leucin
  • nk421
  • N-[(2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL]-L-LEUCINE
  • N-((2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCINE
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU
  • [(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-LEU-OH
  • [(2S, 3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE
  • BESTATIN
  • BENIMEX
  • L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, [S-(R*,S*)]-
  • L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]- (9CI)
  • NSC 265489
  • [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbuty1)-L-leucine
  • [S-(R*,S*)]-N-(3-amino-2-hydroxy-4-phenylbutyroyl)-L-leucine
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine,97%
  • UbeniMex(Bestatin)
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine, 97% 500MG
  • Bestatin, UbeniMex
  • (2R)-2-[(2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido]-4-Methylpentanoic acid
  • (S)-2-((2S,3R)-3-aMino-2-hydroxy-4-phenylbutanaMido)-4-Methylpentanoic acid
  • N-[(2S,3R)-3-AMino-2-hydroxy-4-phenylbutyryl]-L-leucine|(-)-N-[3(R)-AMino-2(S)-hydroxy-4-phenylbutyryl]-L-leucine
  • [S-(R*,S*)]-N-(3-Amino-2-hydroxy-1-oxo-4-phenylbutyl)-L-leucine
  • Bestatin, >=99%
  • N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine≥ 98% (HPLC)
  • Bestatin - CAS 58970-76-6 - Calbiochem
  • Bestatin free base
  • Bestatin-d5 (Ubenimex-d5)
  • Ubenimex Ubenimex
  • Bestatin USP/EP/BP
  • Bestatin D10
  • UBENIMEX
  • DIBUTYL CARBONATE 542-52-9
  • 58970-76-6
  • C16H24N2O4
  • CH32CHCH2CHNHCOCHOHCHNH2CH2C6H5CO2H
  • Leucine Derivatives
  • Peptide Synthesis
  • Specialty Synthesis
  • Unnatural Amino Acid Derivatives
  • ProteaseInhibitors
  • Ubenimex
  • Pepetides
  • Active Pharmaceutical Ingredients
  • peptides
  • Bestatin
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