4611-05-6

Basic information

• Product Name: OPHIOBOLIN A
• Synonyms: 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
• CAS NO: 4611-05-6
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.55
• Mol File: 4611-05-6.mol

Chemical Properties

• Melting Point: 182°C
• Boiling Point: 443.19°C (rough estimate)
• Flash Point: 177.8°C
• Appearance: /
• Density: 1.0278 (rough estimate)
• Vapor Pressure: 6.91E-14mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 10 mg/ml)
• PKA: 13.84±0.70(Predicted)
• 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.
• CAS DataBase Reference: OPHIOBOLIN A(CAS DataBase Reference)
• NIST Chemistry Reference: OPHIOBOLIN A(4611-05-6)
• EPA Substance Registry System: OPHIOBOLIN A(4611-05-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: RL1576000
• Hazardous Substances Data: 4611-05-6(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Ophiobolin A is used as an anticancer agent for its selective toxicity towards cancer cells compared to normal cells. It has demonstrated activity in an in vivo model and has the potential to induce non-apoptotic cell death in glioblastoma cells.
Used in Pharmaceutical Research:
Ophiobolin A is used as a research tool in the development of new cancer therapies due to its unique mechanism of action, which involves inhibiting calmodulin action in calcium regulation. Its ability to covalently react with primary amines and induce various cellular stress responses makes it a valuable compound for studying cancer cell biology and developing targeted treatments.
Used in Drug Delivery Systems:
Similar to gallotannin, Ophiobolin A could potentially be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes. These systems could involve the use of organic or metallic nanoparticles as carriers, aiming to enhance the delivery and efficacy of Ophiobolin A against cancer cells.

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

InChI:InChI=1/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-

Upstream product

• 1344673-75-1 2-[(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-formyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl pivalate 
• 1344673-84-2 2-[(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-hydroxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl pivalate 
• 1344673-73-9 (1R,2S,3S,4S)-4-(benzyloxy)-2-{[(2R,4S,5S,6R,7R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,7-dimethyl-6-prop-2-en-1-yl-1-oxaspiro[4.4]non-7-yl]methyl}-3-[1-(hydroxymethyl)ethenyl]-1-methylcyclopentanol 
• 1344673-83-1 2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate 
• 1344673-81-9 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol 
• 1344673-80-8 1-{(1R,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-tert-butyldiphenylsilyloxy-3-methyl-3-trimethylsilyloxycyclopentyl}ethanone 
• 1344673-95-5 1-((1R,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-tert-butyldiphenylsilyloxy-3-hydroxy-3-methylcyclopentyl)ethanone 
• 1344673-79-5 (1R,2S,3S,4S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-4-tert-butyldiphenylsilyloxy-3-hydroxymethyl-1-methylcyclopentanol 

Relevant articles and documents

Enantioselective total synthesis of (+)-ophiobolin A

The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the

Convergent total synthesis of (+)-ophiobolin A

At long last: The enantioselective total synthesis of the title compound, which was isolated in 1958, proceeds by a convergent approach. The assembly of the C,D-ring fragment and the A-ring fragment of the core structure is achieved by employing a Reforma