Viriditoxin

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

MedKoo CAT#: 461858

CAS#: 35483-50-2

Description: Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin.


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Viriditoxin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461858
Name: Viriditoxin
CAS#: 35483-50-2
Chemical Formula: C34H30O14
Exact Mass: 662.1636
Molecular Weight: 662.6
Elemental Analysis: C, 61.63; H, 4.56; O, 33.80


Synonym: Viriditoxin; SC 28762; SC-28762; SC28762;

IUPAC/Chemical Name: dimethyl 2,2'-(9,9',10,10'-tetrahydroxy-7,7'-dimethoxy-1,1'-dioxo-3,3',4,4'-tetrahydro-1H,1'H-[8,8'-bibenzo[g]isochromene]-3,3'-diyl)diacetate

InChi Key: KPSSJZWNGXQOMD-UHFFFAOYSA-N

InChi Code: InChI=1S/C34H30O14/c1-43-19-9-15-5-13-7-17(11-21(35)45-3)47-33(41)25(13)29(37)23(15)31(39)27(19)28-20(44-2)10-16-6-14-8-18(12-22(36)46-4)48-34(42)26(14)30(38)24(16)32(28)40/h5-6,9-10,17-18,37-40H,7-8,11-12H2,1-4H3

SMILES Code: O=C(OC)CC(O1)CC2=CC3=CC(OC)=C(C4=C(OC)C=C5C=C(CC(CC(OC)=O)O6)C(C6=O)=C(O)C5=C4O)C(O)=C3C(O)=C2C1=O


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Kundu S, Kim TH, Yoon JH, Shin HS, Lee J, Jung JH, Kim HS. Viriditoxin regulates apoptosis and autophagy via mitotic catastrophe and microtubule formation in human prostate cancer cells. Int J Oncol. 2014 Dec;45(6):2331-40. doi: 10.3892/ijo.2014.2659. Epub 2014 Sep 17. PubMed PMID: 25231051.

2: Liu Y, Kurtán T, Yun Wang C, Han Lin W, Orfali R, Müller WE, Daletos G, Proksch P. Cladosporinone, a new viriditoxin derivative from the hypersaline lake derived fungus Cladosporium cladosporioides. J Antibiot (Tokyo). 2016 Sep;69(9):702-6. doi: 10.1038/ja.2016.11. Epub 2016 Feb 24. PubMed PMID: 26905758.

3: Grove CI, Shaw JT. Second-Generation Synthesis of (-)-Viriditoxin. Synthesis (Stuttg). 2012;2012(3):362-371. PubMed PMID: 23049144; PubMed Central PMCID: PMC3461596.

4: Park YS, Grove CI, González-López M, Urgaonkar S, Fettinger JC, Shaw JT. Synthesis of (-)-viriditoxin: a 6,6'-binaphthopyran-2-one that targets the bacterial cell division protein FtsZ. Angew Chem Int Ed Engl. 2011 Apr 11;50(16):3730-3. doi: 10.1002/anie.201007298. Epub 2011 Mar 16. PubMed PMID: 21413107; PubMed Central PMCID: PMC3325170.

5: Fabiano RJ, Tu AT. Purification and biochemical study of viriditoxin, tissue damaging toxin, from prairie rattlesnake venom. Biochemistry. 1981 Jan 6;20(1):21-7. PubMed PMID: 6781535.

6: Lillehoj EB, Milburn MS. Viriditoxin production by Aspergillus viridi-nutans and related species. Appl Microbiol. 1973 Aug;26(2):202-5. PubMed PMID: 4582816; PubMed Central PMCID: PMC379751.

7: Smyth JE, Butler NM, Keller PA. A twist of nature--the significance of atropisomers in biological systems. Nat Prod Rep. 2015 Nov;32(11):1562-83. doi: 10.1039/c4np00121d. Review. PubMed PMID: 26282828.

8: Hood RD, Hayes AW, Scammell JG. Effects of prenatal administration of citrinin and viriditoxin to mice. Food Cosmet Toxicol. 1976 Jun;14(3):175-8. PubMed PMID: 950209.

9: Wong DT, Hamill RL. Viriditoxin induces swelling and atpase by activation of calcium transport in liver mitochondria. Biochem Biophys Res Commun. 1976 Jul 12;71(1):332-8. PubMed PMID: 134706.

10: Wang J, Galgoci A, Kodali S, Herath KB, Jayasuriya H, Dorso K, Vicente F, González A, Cully D, Bramhill D, Singh S. Discovery of a small molecule that inhibits cell division by blocking FtsZ, a novel therapeutic target of antibiotics. J Biol Chem. 2003 Nov 7;278(45):44424-8. Epub 2003 Sep 2. PubMed PMID: 12952956.

11: Gutiérrez JM, Cerdas L. [Mechanism of action of myotoxins isolated from snake venoms]. Rev Biol Trop. 1984 Nov;32(2):213-22. Review. Spanish. PubMed PMID: 6400184.

12: Foss MH, Eun YJ, Grove CI, Pauw DA, Sorto NA, Rensvold JW, Pagliarini DJ, Shaw JT, Weibel DB. Inhibitors of bacterial tubulin target bacterial membranes in vivo.. Medchemcomm. 2013 Jan 1;4(1):112-119. Epub 2012 Jul 18. PubMed PMID: 23539337; PubMed Central PMCID: PMC3607388.

13: Samson RA, Houbraken J, Varga J, Frisvad JC. Polyphasic taxonomy of the heat resistant ascomycete genus Byssochlamys and its Paecilomyces anamorphs. Persoonia. 2009 Jun;22:14-27. doi: 10.3767/003158509X418925. Epub 2009 Feb 10. PubMed PMID: 20198134; PubMed Central PMCID: PMC2789542.

14: Noh TH, Sen L, Hong J, Lee JH, Moon HR, Jung JH. Antibacterial activities of viriditoxin congeners and synthetic analogues against fish pathogens. Bioorg Med Chem Lett. 2017 Nov 15;27(22):4970-4974. doi: 10.1016/j.bmcl.2017.10.015. Epub 2017 Oct 9. PubMed PMID: 29037949.

15: Hong SB, Shin HD, Hong J, Frisvad JC, Nielsen PV, Varga J, Samson RA. New taxa of Neosartorya and Aspergillus in Aspergillus section Fumigati. Antonie Van Leeuwenhoek. 2008 Jan-Feb;93(1-2):87-98. Epub 2007 Jul 4. PubMed PMID: 17610141; PubMed Central PMCID: PMC2140094.

16: Anderson DE, Kim MB, Moore JT, O'Brien TE, Sorto NA, Grove CI, Lackner LL, Ames JB, Shaw JT. Comparison of small molecule inhibitors of the bacterial cell division protein FtsZ and identification of a reliable cross-species inhibitor. ACS Chem Biol. 2012 Nov 16;7(11):1918-28. doi: 10.1021/cb300340j. Epub 2012 Oct 5. PubMed PMID: 22958099; PubMed Central PMCID: PMC3514448.

17: Talbot JJ, Houbraken J, Frisvad JC, Samson RA, Kidd SE, Pitt J, Lindsay S, Beatty JA, Barrs VR. Discovery of Aspergillus frankstonensis sp. nov. during environmental sampling for animal and human fungal pathogens. PLoS One. 2017 Aug 9;12(8):e0181660. doi: 10.1371/journal.pone.0181660. eCollection 2017. PubMed PMID: 28792943; PubMed Central PMCID: PMC5549889.