Fumagillin
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MedKoo CAT#: 317134

CAS#: 23110-15-8

Description: Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism Aspergillus fumigatus. Fumagillin has been used in the treatment of microsporidiosis. It is also an amebicide. Fumagillin can block blood vessel formation by binding to an enzyme methionine aminopeptidase and for this reason, the compound, together with semisynthetic derivatives, are investigated as an angiogenesis inhibitor in the treatment of cancer.


Chemical Structure

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Fumagillin
CAS# 23110-15-8

Theoretical Analysis

MedKoo Cat#: 317134
Name: Fumagillin
CAS#: 23110-15-8
Chemical Formula: C26H34O7
Exact Mass: 458.23045
Molecular Weight: 458.55
Elemental Analysis: C, 68.10; H, 7.47; O, 24.42

Price and Availability

Size Price Availability Quantity
100.0mg USD 2650.0 2 Weeks
200.0mg USD 3650.0 2 Weeks
500.0mg USD 4250.0 2 Weeks
1.0g USD 4950.0 2 Weeks
2.0g USD 7950.0 2 Weeks
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Synonym: NSC9168; NSC 9168; NSC-9168; Fumidil B; Fumagillin, trade name: Fumagilina; Fugillin; Fumidil.

IUPAC/Chemical Name: (2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid

InChi Key: NGGMYCMLYOUNGM-IJIYPQOHSA-N

InChi Code: InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20?,23-,24-,25+,26+/m1/s1

SMILES Code: O=C(O)/C=C/C=C/C=C/C=C/C(O[C@H](CC1)[C@@H](OC)[C@H]([C@@]2(C)OC2C/C=C(C)\C)[C@]31CO3)=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, not in water

Shelf Life: >2 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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 458.55 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

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1: Kanno T, Uehara T, Osawa M, Fukumoto H, Mine S, Ueda K, Hasegawa H, Katano H. Fumagillin, a potent angiogenesis inhibitor, induces Kaposi sarcoma-associated herpesvirus replication in primary effusion lymphoma cells. Biochem Biophys Res Commun. 2015 Aug 7;463(4):1267-72. doi: 10.1016/j.bbrc.2015.06.100. Epub 2015 Jun 18. PubMed PMID: 26093300.

2: van den Heever JP, Thompson TS, Curtis JM, Pernal SF. Stability of dicyclohexylamine and fumagillin in honey. Food Chem. 2015 Jul 15;179:152-8. doi: 10.1016/j.foodchem.2015.01.111. Epub 2015 Jan 31. PubMed PMID: 25722149.

3: Zhang R, Pan D, Cai X, Yang X, Senpan A, Allen JS, Lanza GM, Wang LV. alphaVbeta3-targeted copper nanoparticles incorporating an Sn 2 lipase-labile fumagillin prodrug for photoacoustic neovascular imaging and treatment. Theranostics. 2015 Jan 1;5(2):124-33. doi: 10.7150/thno.10014. eCollection 2015. PubMed PMID: 25553103; PubMed Central PMCID: PMC4278999.

4: Zhou HF, Yan H, Hu Y, Springer LE, Yang X, Wickline SA, Pan D, Lanza GM, Pham CT. Fumagillin prodrug nanotherapy suppresses macrophage inflammatory response via endothelial nitric oxide. ACS Nano. 2014 Jul 22;8(7):7305-17. doi: 10.1021/nn502372n. Epub 2014 Jun 24. PubMed PMID: 24941020; PubMed Central PMCID: PMC4108210.

5: Blanchet E, Vansteelandt M, Le Bot R, Egorov M, Guitton Y, Pouchus YF, Grovel O. Synthesis and antiproliferative activity of ligerin and new fumagillin analogs against osteosarcoma. Eur J Med Chem. 2014 May 22;79:244-50. doi: 10.1016/j.ejmech.2014.04.012. Epub 2014 Apr 5. PubMed PMID: 24742383.

6: van den Heever JP, Thompson TS, Curtis JM, Ibrahim A, Pernal SF. Fumagillin: an overview of recent scientific advances and their significance for apiculture. J Agric Food Chem. 2014 Apr 2;62(13):2728-37. doi: 10.1021/jf4055374. Epub 2014 Mar 21. Review. PubMed PMID: 24621007.

7: Lin HC, Tsunematsu Y, Dhingra S, Xu W, Fukutomi M, Chooi YH, Cane DE, Calvo AM, Watanabe K, Tang Y. Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. J Am Chem Soc. 2014 Mar 19;136(11):4426-36. doi: 10.1021/ja500881e. Epub 2014 Mar 11. PubMed PMID: 24568283; PubMed Central PMCID: PMC3985917.

8: Desoubeaux G, Maakaroun-Vermesse Z, Lier C, Bailly E, Morio F, Labarthe F, Bernard L, Chandenier J. Successful treatment with fumagillin of the first pediatric case of digestive microsporidiosis in a liver-kidney transplant. Transpl Infect Dis. 2013 Dec;15(6):E250-9. doi: 10.1111/tid.12158. Epub 2013 Oct 23. PubMed PMID: 24298986.

9: Zhou GC, Liu F, Wan J, Wang J, Wang D, Wei P, Ouyang P. Design, synthesis and evaluation of a cellular stable and detectable biotinylated fumagillin probe and investigation of cell permeability of fumagillin and its analogs to endothelial and cancer cells. Eur J Med Chem. 2013;70:631-9. doi: 10.1016/j.ejmech.2013.10.033. Epub 2013 Oct 25. PubMed PMID: 24211639.

10: Godron A, Accoceberry I, Couret A, Llanas B, Harambat J. Intestinal microsporidiosis due to Enterocytozoon bieneusi in a pediatric kidney transplant recipient successfully treated with fumagillin. Transplantation. 2013 Oct 27;96(8):e66-7. doi: 10.1097/TP.0b013e3182a902e7. PubMed PMID: 24132119.

11: Dhingra S, Lind AL, Lin HC, Tang Y, Rokas A, Calvo AM. The fumagillin gene cluster, an example of hundreds of genes under veA control in Aspergillus fumigatus. PLoS One. 2013 Oct 7;8(10):e77147. doi: 10.1371/journal.pone.0077147. eCollection 2013. PubMed PMID: 24116213; PubMed Central PMCID: PMC3792039.

12: Maggi M, Negri P, Plischuk S, Szawarski N, De Piano F, De Feudis L, Eguaras M, Audisio C. Effects of the organic acids produced by a lactic acid bacterium in Apis mellifera colony development, Nosema ceranae control and fumagillin efficiency. Vet Microbiol. 2013 Dec 27;167(3-4):474-83. doi: 10.1016/j.vetmic.2013.07.030. Epub 2013 Aug 9. PubMed PMID: 23978352.

13: Arico-Muendel CC, Blanchette H, Benjamin DR, Caiazzo TM, Centrella PA, DeLorey J, Doyle EG, Johnson SR, Labenski MT, Morgan BA, O'Donovan G, Sarjeant AA, Skinner S, Thompson CD, Griffin ST, Westlin W, White KF. Orally active fumagillin analogues: transformations of a reactive warhead in the gastric environment. ACS Med Chem Lett. 2013 Feb 22;4(4):381-6. doi: 10.1021/ml3003633. eCollection 2013 Apr 11. PubMed PMID: 24900682; PubMed Central PMCID: PMC4027436.

14: Huang WF, Solter LF, Yau PM, Imai BS. Nosema ceranae escapes fumagillin control in honey bees. PLoS Pathog. 2013 Mar;9(3):e1003185. doi: 10.1371/journal.ppat.1003185. Epub 2013 Mar 7. PubMed PMID: 23505365; PubMed Central PMCID: PMC3591333.

15: Lin HC, Chooi YH, Dhingra S, Xu W, Calvo AM, Tang Y. The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene. J Am Chem Soc. 2013 Mar 27;135(12):4616-9. doi: 10.1021/ja312503y. Epub 2013 Mar 19. PubMed PMID: 23488861; PubMed Central PMCID: PMC3652892.

16: Zbidah M, Lupescu A, Jilani K, Lang F. Stimulation of suicidal erythrocyte death by fumagillin. Basic Clin Pharmacol Toxicol. 2013 May;112(5):346-51. doi: 10.1111/bcpt.12033. Epub 2012 Dec 6. PubMed PMID: 23121865.

17: Audemard A, Le Bellec ML, Carluer L, Dargère S, Verdon R, Castrale C, Lobbedez T, Hurault de Ligny B. Fumagillin-induced aseptic meningoencephalitis in a kidney transplant recipient with microsporidiosis. Transpl Infect Dis. 2012 Dec;14(6):E147-9. doi: 10.1111/tid.12010. Epub 2012 Oct 2. PubMed PMID: 23025483.

18: Zhou HF, Yan H, Senpan A, Wickline SA, Pan D, Lanza GM, Pham CT. Suppression of inflammation in a mouse model of rheumatoid arthritis using targeted lipase-labile fumagillin prodrug nanoparticles. Biomaterials. 2012 Nov;33(33):8632-40. doi: 10.1016/j.biomaterials.2012.08.005. Epub 2012 Aug 24. PubMed PMID: 22922023; PubMed Central PMCID: PMC3583210.

19: Musser FR, Knighten KS, Self SR. Impact of Nosema (Microsporidia) infection and fumagillin treatment on Lygus lineolaris (Hemiptera: Miridae). J Invertebr Pathol. 2012 Oct;111(2):101-5. doi: 10.1016/j.jip.2012.07.001. Epub 2012 Jul 20. PubMed PMID: 22820067.

20: Pan D, Sanyal N, Schmieder AH, Senpan A, Kim B, Yang X, Hu G, Allen JS, Gross RW, Wickline SA, Lanza GM. Antiangiogenic nanotherapy with lipase-labile Sn-2 fumagillin prodrug. Nanomedicine (Lond). 2012 Oct;7(10):1507-19. doi: 10.2217/nnm.12.27. Epub 2012 Jun 18. PubMed PMID: 22709347; PubMed Central PMCID: PMC3498609.

Fumagillin

10.0mg / Not available