1,4,5-Tridesoxy-1,4-imino-5-(4-me-thoxyphenyl)-D-xylo-pentitol-3-acetat

Bezeichnung:1,4,5-Tridesoxy-1,4-imino-5-(4-me-thoxyphenyl)-D-xylo-pentitol-3-acetat

CAS-Nr22862-76-6

Englisch Name:ANISOMYCIN

CBNumberCB5363672

SummenformelC14H19NO4

Molgewicht265.3

MOL-Datei22862-76-6.mol

Synonyma

1,4,5-Tridesoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol-3-acetat

1,4,5-Tridesoxy-1,4-imino-5-(4-me-thoxyphenyl)-D-xylo-pentitol-3-acetat

1,4,5-Tridesoxy-1,4-imino-5-(4-me-thoxyphenyl)-D-xylo-pentitol-3-acetat physikalisch-chemischer Eigenschaften

Schmelzpunkt	140-141 C
Siedepunkt	408.52°C (rough estimate)
alpha	D23 -30° (methanol)
Dichte	1.1356 (rough estimate)
Brechungsindex	1.5230 (estimate)
Flammpunkt	87℃
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	methanol: 20 mg/mL, clear, colorless to faintly yellow
pka	7.9(at 25℃)
Aggregatzustand	solid
Farbe	white
Wasserlöslichkeit	Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
maximale Wellenlänge (λmax)	283nm(EtOH)(lit.)
Merck	14,670
BRN	20705
Stabilität	Stable. Incompatible with strong oxidizing agents.
InChI	1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
InChIKey	YKJYKKNCCRKFSL-RDBSUJKOSA-N
SMILES	COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1

Sicherheit

Kennzeichnung gefährlicher	T,Xn
R-Sätze:	25-36/37/38-20/21/22
S-Sätze:	45-36-26
RIDADR	UN 3462 6.1/PG 3
WGK Germany	3
RTECS-Nr.	BZ9800000
F	3-10
HazardClass	6.1(b)
PackingGroup	III
HS Code	29419090
Speicherklasse	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral
Toxizität	LD50 orl-rat: 72 mg/kg ANTCAO 5,490,55

Gefahreninformationscode (GHS)

ANISOMYCIN Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Anisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable.
Chemische Eigenschaften
Crystalline
Verwenden
It is applied as an antiparasitic agent and antineoplastic agent. It acts as a protein synthesis inhibitor (blocks translation), potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. It also scts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK).
Verwenden
Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells.
Definition
ChEBI: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.
Biologische Aktivität
Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD).
Biochem/physiol Actions
Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.
Sicherheitsprofil
Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits toxic fumes ofNOx.
Lager
+4°C
Einzelnachweise
[1] C A HAZZALIN. Anisomycin selectively desensitizes signalling components involved in stress kinase activation and fos and jun induction.[J]. Molecular and Cellular Biology, 1998, 18 4: 1844-1854. DOI:10.1128/mcb.18.4.1844
[2] IMTIAZ A MAWJI. A chemical screen identifies anisomycin as an anoikis sensitizer that functions by decreasing FLIP protein synthesis.[J]. Cancer research, 2007, 67 17: 8307-8315. DOI:10.1158/0008-5472.can-07-1687

1,4,5-Tridesoxy-1,4-imino-5-(4-me-thoxyphenyl)-D-xylo-pentitol-3-acetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

22862-76-6, ANISOMYCIN Verwandte Suche:

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