Tunicamycin

TUNICAMYCIN Struktur
11089-65-9
CAS-Nr.
11089-65-9
Bezeichnung:
Tunicamycin
Englisch Name:
TUNICAMYCIN
Synonyma:
isamycin;Nsc177382;Aids010655;TUNICAMYCIN;Aids-010655;TunicaMycin coMplex;Tunicamycin Mixture;TUNICAMYCIN USP/EP/BP;InSolution? Tunicamycin,;Tunicamycin (n= 8,9,10,11)
CBNumber:
CB4211576
Summenformel:
C37H60N4O16
Molgewicht:
816.89
MOL-Datei:
11089-65-9.mol

Tunicamycin Eigenschaften

Schmelzpunkt:
234-235℃ (decomposition)
alpha 
D20 +52° (c = 0.5 in pyridine)
Flammpunkt:
87℃
storage temp. 
2-8°C
Löslichkeit
Soluble in methanol, ethanol, DMSO, or DMF
Aggregatzustand
White to off-white solid
Farbe
White
Sensitive 
Moisture & Light Sensitive
BRN 
6888090
Stabilität:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey
YJQCOFNZVFGCAF-WPTOCQRYSA-N
EPA chemische Informationen
Tunicamycin (11089-65-9)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T+,T
R-Sätze: 28
S-Sätze: 28-37/39-45
RIDADR  UN 3462 6.1/PG 2
WGK Germany  3
RTECS-Nr. YO7980200
8-10-18-21
HazardClass  6.1(a)
PackingGroup  II
HS Code  29419090
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H300 Lebensgefahr bei Verschlucken. Akute Toxizität oral Kategorie 2 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Tunicamycin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R28:Sehr giftig beim Verschlucken.

S-Sätze Betriebsanweisung:

S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

Beschreibung

Tunicamycin mixture is a mixture of tunicamycins with variable trans-2,3-unsaturated branched chain fatty acid (BFCA) chain lengths. Tunicamycins are anti-microbial agents that are active against Gram-positive bacteria, fungi, and viruses. They inhibit the N-acetylhexosamine (HexNAc) phosphotransferase family of enzymes in bacteria and prevent peptidoglycan biosynthesis. In eukaryotes, they inhibit N-acetylglucosamine (GlcNAc) phosphotransferase (GPT), preventing the first step in N-linked glycosylation and inducing the unfolded protein response and cell death. The cellular toxicity of tunicamycins is linked to the trans-2,3-unsaturated BCFA, and saturated BCFA-containing tunicamycin derivatives, such as TunR1 and TunR2 , have reduced toxicity. Tunicamycins impair glycosylation of the receptor tyrosine kinases EGFR, HER2, HER3, and IGF-1R, which prevents their translocation out of the endoplasmic reticulum and Golgi apparatus and reduces their protein levels and activity. Tunicamycin sensitizes EGFR inhibitor-resistant U251 glioma and Bx/PC-3 pancreatic adenocarcinoma cells to irradiation.

Chemische Eigenschaften

White solid

Verwenden

The tunicamycins are a family of lipophilic nucleosides with fatty acids conjugated to an aminoglycoside group. The complex comprises analogues, tunicamycins I to X. This composition is typical of other products less precisely described as tunicamycins A to D. The tunicamycins act by blocking the formation of N-glycoside linkages to proteins via inhibition of formation of dolichol monophosphate from N-acetylglucosamine-1-phosphate. Tunicamycin blocks the synthesis of all N-linked glycoproteins (N-glycans) and causes cell cycle arrest in G1 phase. Tunicamycins are broadly active against prokaryotes, eukaryotes and viruses.

Definition

ChEBI: A mixture of antiviral nucleoside antibiotics produced by Streptomyces lysosuperificus. It contains at least 10 homologues comprising uracil, N-acetylglucosamine, an 11-carbon aminodialdose called tunicamine, and a fatty aci linked to the amino group of the tunicamine. The homologues vary in the composition of the fatty acid moiety.

Allgemeine Beschreibung

Tunicamycin was first isolated from Streptomyces lysosuperificus based on its antiviral activity. It contains N-acetylglucosamine and inhibits glycoprotein biosynthesis, including virus membrane glycoproteins.

läuterung methode

The components of this nucleotide antibiotic from Streptomyces sp. are purified by recrystallising 3 times from hot glass-distilled MeOH, and the white crystals are dissolved in 25% aqueous MeOH and separated on a Partisil ODS-10_ column (9.4 x 25 cm) [Magnum-9 Whatman] using a 260nm detector. The column is eluted with MeOH/H2O mixture adjusted to 1:4 (v/v) then to 2:4 (v/v). The individual components are recovered and lyophilised. Ten components have been isolated, and all were active (to varying extents) depending on the lengths of the aliphatic side-chains. The mixture has UV max at 205 and 260nm (A 1cm 230 and 110). It is stable in H2O at neutral pH but unstable in acidic solution. It inhibits protein glycosylation. [Mahoney & Duskin J Biol Chem 254 6572 1979, Elnein Trends Biochem Sci 6 219 1981, Takatsuki J Antibiot 24 215 1971.] Uracil, uridine and uridine nucleotides. These are resolved by ion-exchange chromatography with AG1 (Cl form). [Lindsay et al. Anal Biochem 24 506 1968.]

Tunicamycin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Tunicamycin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 193)Lieferanten
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Shaanxi Dideu Medichem Co. Ltd
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1026@dideu.com China 7724 58

11089-65-9(Tunicamycin)Verwandte Suche:


  • Aids010655
  • Aids-010655
  • Nsc177382
  • TunicaMycin froM StreptoMyces lysosuperficus
  • TunicaMycin coMplex
  • InSolution? Tunicamycin,
  • TUNICAMYCIN, STREPTOMYCES IYSOSUPERFICUS
  • TUNICAMYCIN, STREPTOMYCES LYSOSUPERFICUS
  • TUNICAMYCIN
  • tunicamycin from A streptomyces species
  • tunicamycin from streptomyces lysosuperificus
  • Tunicamycin Streptomyces sp.
  • TUNICAMYCIN FROM STREPTOMYCES LYSOSUPERFIUS NOV. SP.
  • Tunicamycin from Streptomyces chartreusis
  • tunicamycin from streptomyces sp.
  • Tunicamycin (n= 8,9,10,11)
  • InSolution Tunicamycin, Streptomyces lysosuperficus - CAS 11089-65-9 - Calbiochem
  • TUNICAMYCIN USP/EP/BP
  • Tunicamycin Mixture
  • N-linked,DNA,UDP-HexNAc,inhibit,anti-cancer,Inhibitor,ATF6,synthesis,Influenza Virus,invasion,XBP-1,Bacterial,Fungal,glycoprotein,Tunicamycin,Antibiotic
  • isamycin
  • 11089-65-9
  • C25H38N4O16
  • C39H64N4O16tunicamycinCn10
  • BioChemical
  • Antibiotics T-Z
  • Antibiotics
  • Antibiotics A to Z
  • NucleosidesMore...Close...
  • antibiotic
  • Antibacterial
  • Antibiotics
  • Antibiotics A to
  • Antibiotics by Application
  • Antibiotics T-ZAntibiotics
  • AntifungalAntibiotics
  • Antineoplastic and Immunosuppressive AntibioticsAntibiotics
  • AntiviralAntibiotics
  • Chemical Structure Class
  • Interferes with Protein SynthesisSpectrum of Activity
  • L - ZAntibiotics
  • Mechanism of Action
  • Spectrum of Activity
  • Signalling
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