Ophiobolin A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563257

CAS#: 4611-05-6

Description: Ophiobolin A is an inhibitor of calmodulin action in calcium regulation.

Chemical Structure

img
Ophiobolin A
CAS# 4611-05-6
Instruction

Theoretical Analysis

MedKoo Cat#: 563257
Name: Ophiobolin A
CAS#: 4611-05-6
Chemical Formula: C25H36O4
Exact Mass: 400.26
Molecular Weight: 400.550
Elemental Analysis: C, 74.96; H, 9.06; O, 15.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Ophiobolin A; Ophiobolin-A; Cochliobolin A; NSC 114340; Cochliobolin-A; NSC114340; NSC-114340;

IUPAC/Chemical Name: 14,18-Epoxy-3-hydroxy-5-oxo-ophiobola-7,19-dien-25-al

InChi Key: MWYYLZRWWNBROW-HAHMYURFSA-N

InChi Code: InChI=1S/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-/t16-,18?,19-,21+,22+,23+,24+,25-/m0/s1

SMILES Code: C[C@@]([C@]1(C[C@]2(CC[C@]([C@@]2(C/C=C([C@@]31[H])/C=O)[H])(O4)[C@H](CC4/C=C(C)\C)C)C)[H])(O)CC3=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 400.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Olschewski DN, Hofschröer V, Nielsen N, Seidler DG, Schwab A, Stock C. The Angiotensin II Type 1 Receptor Antagonist Losartan Affects NHE1-Dependent Melanoma Cell Behavior. Cell Physiol Biochem. 2018;45(6):2560-2576. doi: 10.1159/000488274. Epub 2018 Mar 16. PubMed PMID: 29558744.

2: Kim IY, Kwon M, Choi MK, Lee D, Lee DM, Seo MJ, Choi KS. Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostasis. Oncotarget. 2017 Nov 20;8(63):106740-106752. doi: 10.18632/oncotarget.22537. eCollection 2017 Dec 5. PubMed PMID: 29290985; PubMed Central PMCID: PMC5739770.

3: Morrison R, Lodge T, Evidente A, Kiss R, Townley H. Ophiobolin A, a sesterpenoid fungal phytotoxin, displays different mechanisms of cell death in mammalian cells depending upon the cancer cell origin. Int J Oncol. 2017 Mar;50(3):773-786. doi: 10.3892/ijo.2017.3858. Epub 2017 Jan 19. PubMed PMID: 28112374; PubMed Central PMCID: PMC5358713.

4: Rodolfo C, Rocco M, Cattaneo L, Tartaglia M, Sassi M, Aducci P, Scaloni A, Camoni L, Marra M. Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells. PLoS One. 2016 Dec 9;11(12):e0167672. doi: 10.1371/journal.pone.0167672. eCollection 2016. PubMed PMID: 27936075; PubMed Central PMCID: PMC5147944.

5: Fanelli F, Reveglia P, Masi M, Mulè G, Zonno MC, Cimmino A, Vurro M, Evidente A. Influence of light on the biosynthesis of ophiobolin A by Bipolaris maydis. Nat Prod Res. 2017 Apr;31(8):909-917. doi: 10.1080/14786419.2016.1253084. Epub 2016 Nov 7. PubMed PMID: 27820961.

6: Wang S, Luo X, Yan R, Wang Q, Qi Q, Chi X, Zhang L, Yu Z, Cai B, Chen JL, Liu H. 3-Anhydro-6-hydroxy-ophiobolin A displays high in vitro and in vivo efficacy against influenza A virus infection. Protein Cell. 2016 Nov;7(11):839-843. PubMed PMID: 27743345; PubMed Central PMCID: PMC5084159.

7: Chidley C, Trauger SA, Birsoy K, O'Shea EK. The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine. Elife. 2016 Jul 12;5. pii: e14601. doi: 10.7554/eLife.14601. PubMed PMID: 27403889; PubMed Central PMCID: PMC4942256.

8: Pósa A, Szabó R, Szalai Z, Kupai K, Deim Z, Murlasits Z, Bencsik O, Szekeres A, Vágvölgyi C, Balogh L, Juhász B, Szilvássy Z, Varga C. The effect of acute ophiobolin A treatment on HO-mediated inflammatory processes. Hum Exp Toxicol. 2017 Jun;36(6):594-602. doi: 10.1177/0960327116658107. Epub 2016 Jul 10. PubMed PMID: 27402683.

9: Najumudeen AK, Jaiswal A, Lectez B, Oetken-Lindholm C, Guzmán C, Siljamäki E, Posada IM, Lacey E, Aittokallio T, Abankwa D. Cancer stem cell drugs target K-ras signaling in a stemness context. Oncogene. 2016 Oct 6;35(40):5248-5262. doi: 10.1038/onc.2016.59. Epub 2016 Mar 14. PubMed PMID: 26973241; PubMed Central PMCID: PMC5057041.

10: Lee D, Kim IY, Saha S, Choi KS. Paraptosis in the anti-cancer arsenal of natural products. Pharmacol Ther. 2016 Jun;162:120-33. doi: 10.1016/j.pharmthera.2016.01.003. Epub 2016 Jan 21. Review. PubMed PMID: 26802901.

11: Dasari R, Masi M, Lisy R, Ferdérin M, English LR, Cimmino A, Mathieu V, Brenner AJ, Kuhn JG, Whitten ST, Evidente A, Kiss R, Kornienko A. 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. 2015 Oct 15;25(20):4544-8. doi: 10.1016/j.bmcl.2015.08.066. Epub 2015 Aug 24. PubMed PMID: 26341136; PubMed Central PMCID: PMC4592837.

12: Bhatia DR, Dhar P, Mutalik V, Deshmukh SK, Verekar SA, Desai DC, Kshirsagar R, Thiagarajan P, Agarwal V. Anticancer activity of Ophiobolin A, isolated from the endophytic fungus Bipolaris setariae. Nat Prod Res. 2016 Jun;30(12):1455-8. doi: 10.1080/14786419.2015.1062760. Epub 2015 Jul 27. PubMed PMID: 26212208.

13: Zainudin NA, Condon B, De Bruyne L, Van Poucke C, Bi Q, Li W, Höfte M, Turgeon BG. Virulence, Host-Selective Toxin Production, and Development of Three Cochliobolus Phytopathogens Lacking the Sfp-Type 4'-Phosphopantetheinyl Transferase Ppt1. Mol Plant Microbe Interact. 2015 Oct;28(10):1130-41. doi: 10.1094/MPMI-03-15-0068-R. Epub 2015 Oct 5. PubMed PMID: 26168137.

14: Locato V, Uzal EN, Cimini S, Zonno MC, Evidente A, Micera A, Foyer CH, De Gara L. Low concentrations of the toxin ophiobolin A lead to an arrest of the cell cycle and alter the intracellular partitioning of glutathione between the nuclei and cytoplasm. J Exp Bot. 2015 May;66(10):2991-3000. doi: 10.1093/jxb/erv110. Epub 2015 Apr 18. PubMed PMID: 25890975.

15: Xue D, Wang Q, Chen Z, Cai L, Bao L, Qi Q, Liu L, Wang X, Jin H, Wang J, Wu H, Liu H, Chen Q. 3-Anhydro-6-hydroxy-ophiobolin A, a fungal sesterterpene from Bipolaris oryzae induced autophagy and promoted the degradation of α-synuclein in PC12 cells. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1464-70. doi: 10.1016/j.bmcl.2015.02.030. Epub 2015 Feb 21. PubMed PMID: 25748161.

16: Bencsik O, Papp T, Berta M, Zana A, Forgó P, Dombi G, Andersson MA, Salkinoja-Salonen M, Vágvölgyi C, Szekeres A. Ophiobolin A from Bipolaris oryzae perturbs motility and membrane integrities of porcine sperm and induces cell death on mammalian somatic cell lines. Toxins (Basel). 2014 Sep 23;6(9):2857-71. doi: 10.3390/toxins6092857. PubMed PMID: 25251540; PubMed Central PMCID: PMC4179164.

17: Morrison R, Gardiner C, Evidente A, Kiss R, Townley H. Incorporation of ophiobolin a into novel chemoembolization particles for cancer cell treatment. Pharm Res. 2014 Oct;31(10):2904-17. doi: 10.1007/s11095-014-1386-3. Epub 2014 May 3. PubMed PMID: 24792832.

18: Linxweiler M, Schorr S, Schäuble N, Jung M, Linxweiler J, Langer F, Schäfers HJ, Cavalié A, Zimmermann R, Greiner M. Targeting cell migration and the endoplasmic reticulum stress response with calmodulin antagonists: a clinically tested small molecule phenocopy of SEC62 gene silencing in human tumor cells. BMC Cancer. 2013 Dec 5;13:574. doi: 10.1186/1471-2407-13-574. PubMed PMID: 24304694; PubMed Central PMCID: PMC3878975.

19: Li K, Wang C, Yin G, Gao S. Construction of the basic skeleton of ophiobolin A and variecolin. Org Biomol Chem. 2013 Nov 21;11(43):7550-8. doi: 10.1039/c3ob41693c. PubMed PMID: 24096306.

20: Costa-Pessoa JM, Figueiredo CF, Thieme K, Oliveira-Souza M. The regulation of NHE₁ and NHE₃ activity by angiotensin II is mediated by the activation of the angiotensin II type I receptor/phospholipase C/calcium/calmodulin pathway in distal nephron cells. Eur J Pharmacol. 2013 Dec 5;721(1-3):322-31. doi: 10.1016/j.ejphar.2013.08.043. Epub 2013 Sep 25. PubMed PMID: 24076179.