OPHIOBOLIN A Struktur

OPHIOBOLIN A

Bezeichnung:OPHIOBOLIN A

CAS-Nr4611-05-6

Englisch Name:OPHIOBOLIN A

CBNumberCB2735485

SummenformelC25H36O4

Molgewicht400.55

MOL-Datei4611-05-6.mol

OPHIOBOLIN A physikalisch-chemischer Eigenschaften

Schmelzpunkt	182°C
Siedepunkt	443.19°C (rough estimate)
Dichte	1.0278 (rough estimate)
Brechungsindex	1.4460 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO (up to 10 mg/ml)
Aggregatzustand	White to off-white solid.
pka	13.84±0.70(Predicted)
Farbe	White
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22
S-Sätze:	36
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	RL1576000
HS Code	2932190090
Toxizität	mouse,LD50,intraperitoneal,21mg/kg (21mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 143, 1981.

Gefahreninformationscode (GHS)

OPHIOBOLIN A Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Ophiobolin A (4611-05-6) selectively inhibits the growth of cancer cells (IC50=0.4-4.3 μM) over normal cells (IC50=20.9 μM).1 Induces non-apoptotic cell death in glioblastoma cells and is active in an in vivo model.2 Covalently reacts with primary amines such as lysine side chains2 and phosphatidylethanolamine3 forming unique pyrrole adducts. Induces ER stress4, paraptosis4 and autophagy5.
Verwenden
Ophiobolin A is the dominant member of a class of phytotoxic metabolites produced by plant pathogenic fungi. Ophiobolin A acts by inhibiting calmodulin action in calcium regulation.
Definition
ChEBI: A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18.
Einzelnachweise
1) Bhatia et al. (2016), Anticancer activity of Ophiobolin A, isolated from the endophytic fungus Bipolaris setariae; Nat. Prod. Res., 30 1455 2) Dasari et al. (2015), Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure-activity relationship and unique pyrrolylation of primary amines; Bioorg. Med. Chem. Lett., 25 4544 3) Chidley et al. (2016), The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine; Elife., 5 e14601 4) Kim et al. (2017), Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostatis; Oncotarget, 8 106740 5) Rodolfo et al. (2016), Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells; PLoS One, 11 e0167672

OPHIOBOLIN A Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

4611-05-6, OPHIOBOLIN A Verwandte Suche:

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