OPHIOBOLIN A Chemical Properties

Melting point:

182°C

Boiling point:

443.19°C (rough estimate)

Density 

1.0278 (rough estimate)

refractive index 

1.4460 (estimate)

storage temp. 

2-8°C

solubility 

Soluble in DMSO (up to 10 mg/ml)

form 

White to off-white solid.

pka

13.84±0.70(Predicted)

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

RL1576000

HS Code 

2932190090

Toxicity

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.

OPHIOBOLIN A Usage And Synthesis

Description

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.

Uses

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.

References

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(4611-05-6)Related Product Information

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