OPHIOBOLIN A

Product Name: OPHIOBOLIN A
CAS No.: 4611-05-6
Chemical Name: OPHIOBOLIN A
Synonyms: ophiobolin;cochliobolin;OPHIOBOLIN A;COCHLIOBOLIN A;Ophiobolin A >=95% (HPLC);Ophiobolin A (Cochliobolin A);Ophiobolin, Helminthosporium sp.;Cochliobolin A, Ophiobolin, Ophiobalin;ophiobolin A from helminthosporium sp.;18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
CBNumber: CB2735485
Molecular Formula: C25H36O4
Formula Weight: 400.55
MOL File: 4611-05-6.mol

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OPHIOBOLIN A Property

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.

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Safety

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.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1478
Product name: Ophiobolin A
Purity: ≥95% (HPLC)
Packaging: 100μG
Price: $91.6
Updated: 2023/01/07

Sigma-Aldrich

Product number: SML1478
Product name: Ophiobolin A
Purity: ≥95% (HPLC)
Packaging: 1MG
Price: $359
Updated: 2023/01/07

Cayman Chemical

Product number: 15381
Product name: Ophiobolin A
Purity: ≥95%
Packaging: 1mg
Price: $275
Updated: 2024/03/01

Cayman Chemical

Product number: 15381
Product name: Ophiobolin A
Purity: ≥95%
Packaging: 5mg
Price: $820
Updated: 2024/03/01

Usbiological

Product number: 207314
Product name: Ophiobolin A
Packaging: 100ug
Price: $312
Updated: 2021/12/16

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OPHIOBOLIN A Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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OPHIOBOLIN A Suppliers

China 28 Switzerland 2 United Kingdom 3 United States 12 Global 45

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Tel: 400-400-6206333 18521732826
Fax: 021-50323701
Email: market@aladdin-e.com
Country: China
ProdList: 25003
Advantage: 65

Shanghai EFE Biological Technology Co., Ltd.

Tel: 021-65675885 18964387627
Fax: 021-65675885
Email: info@efebio.com
Country: China
ProdList: 9806
Advantage: 58

Lynnchem

Tel: 86-(0)29-85992781 17792393971
Email: info@lynnchem.com
Country: China
ProdList: 4587
Advantage: 58

Novachemistry

Tel: 44-20819178-90 02081917890
Fax: (0)2080432064
Email: info@novachemistry.com
Country: United Kingdom
ProdList: 4381
Advantage: 58

Shenzhen Regent Biochemical Technology Co., Ltd.

Tel: 0755-0755-85201366 18938635012
Fax: 0755-85201366
Email: sales@regentsciences.com
Country: China
ProdList: 9357
Advantage: 58

Shenzhen Polymeri Biochemical Technology Co., Ltd.

Tel: +86-400-002-6226 +86-13028896684;
Email: sales@rrkchem.com
Country: China
ProdList: 56902
Advantage: 58

BOC Sciences

Tel: 16314854226; +16314854226
Email: inquiry@bocsci.com
Country: United States
ProdList: 19741
Advantage: 58

TargetMol Chemicals Inc.

Tel: +1-781-999-5354 +1-00000000000
Email: marketing@targetmol.com
Country: United States
ProdList: 32063
Advantage: 58

Shaanxi Dideu Medichem Co. Ltd

Tel: 029-81145920 13259709322
Fax: 029-88380327
Email: 1027@dideu.com
Country: China
ProdList: 10009
Advantage: 58

Meng Cheng Technology (Shanghai) Co., LTD

Tel: 400-820-6829
Email: sales@mitachieve.com
Country: China
ProdList: 8860
Advantage: 58

4611-05-6, OPHIOBOLIN ARelated Search:

(R)-(-)-1-OCTEN-3-OL, 99 Diacetone Alcohol 2-Isopropyl-5-methyl-2-hexenal 7-METHOXY-3,7-DIMETHYLOCTANAL ALLYLCYCLOPENTANE CYCLOOCTENE OPHIOBOLIN A 2,2-DIMETHYLTETRAHYDROFURAN 3-METHYLCYCLOOCTENE 1-METHYL-1-CYCLOOCTENE undec-1-en-3-ol 2-PROPYL-2-HEPTENAL OPHIOBOLIN H ophiobolin C 2,4-DIMETHYLCYCLOPENTANONE OPHIOBOLIN B Ophiobolin methoxy bromide ophiobolin M

18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14

cochliobolin

ophiobolin

COCHLIOBOLIN A

ophiobolin A from helminthosporium sp.

Ophiobolin, Helminthosporium sp.

(18R)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

(18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-diene-25-al

Cochliobolin A, Ophiobolin, Ophiobalin

OPHIOBOLIN A

Spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxo-, (2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-

Ophiobolin A >=95% (HPLC)

Ophiobolin A (Cochliobolin A)

4611-05-6

C25H36O4

Cell Signaling and Neuroscience

Calcium Antagonists

Cell Biology

BioChemical

Intracellular Calcium Signaling