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MedKoo Cat#: 540178 | Name: Gliotoxin
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Description:

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

Gliotoxin is a toxin found in Aspergillus. It induces apoptosis in cervical cancer cells and chondrosarcoma cells, suppresses the adaptive immune response in leukocytes, and inhibits the proteasome in Plasmodium falciparum.

Chemical Structure

Gliotoxin
Gliotoxin
CAS#67-99-2

Theoretical Analysis

MedKoo Cat#: 540178

Name: Gliotoxin

CAS#: 67-99-2

Chemical Formula: C13H14N2O4S2

Exact Mass: 326.0395

Molecular Weight: 326.39

Elemental Analysis: C, 47.84; H, 4.32; N, 8.58; O, 19.61; S, 19.65

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Aspergillin; Gliotoxin;
IUPAC/Chemical Name
(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,5a,6-tetrahydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
InChi Key
FIVPIPIDMRVLAY-RBJBARPLSA-N
InChi Code
InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
SMILES Code
CN1C([C@]23CC4=CC=C[C@@H]([C@H]4N2C([C@]1(SS3)CO)=O)O)=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
>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
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C20M11C10
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis.
In vitro activity:
Consistent with the literature, treatment with higher concentrations of GTX (gliotoxin) at 100 nM and 1 μM caused apoptosis and death of primary CD4+ and CD8+ T cells as well as B cells, natural killer (NK) cells, and monocytes, as shown by annexin V staining followed by flow cytometry (Figs. 2, D and E, and 3C and figs. S3B and S4, A to C). Reference: Sci Adv. 2020 Aug 12;6(33):eaba6617. https://pubmed.ncbi.nlm.nih.gov/32851167/
In vivo activity:
The effect of GTX (gliotoxin) in the CNS was evaluated in lumbar spinal cord samples, seven days after its third dose, in both normal and EAE mice. No inflammation or demyelination was observed in normal mice, as illustrated in Figure 3(A1,B1). However, GTX caused inflammation (Figure 3(A2)) and demyelination (Figure 3(B2)) in this group. As expected, a clear process of inflammation (Figure 3(A3)) and demyelination (Figure 3(B3)) was present in the EAE mice. GTX inoculation in EAE mice resulted in a much more pronounced cell infiltration in the meningeal compartment and cortex (Figure 3(A4)), and demyelination (Figure 3(B4)). Reference: Toxins (Basel). 2019 Jul 26;11(8):443. https://pubmed.ncbi.nlm.nih.gov/31357414/
Solvent mg/mL mM
Solubility
DMF 5.0 15.32
DMSO 5.0 15.32
DMSO:PBS (pH 7.2) (1:5) 0.5 1.53
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 326.39 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:
1. Stoszko M, Al-Hatmi AMS, Skriba A, Roling M, Ne E, Crespo R, Mueller YM, Najafzadeh MJ, Kang J, Ptackova R, LeMasters E, Biswas P, Bertoldi A, Kan TW, de Crignis E, Sulc M, Lebbink JHG, Rokx C, Verbon A, van Ijcken W, Katsikis PD, Palstra RJ, Havlicek V, de Hoog S, Mahmoudi T. Gliotoxin, identified from a screen of fungal metabolites, disrupts 7SK snRNP, releases P-TEFb, and reverses HIV-1 latency. Sci Adv. 2020 Aug 12;6(33):eaba6617. doi: 10.1126/sciadv.aba6617. PMID: 32851167; PMCID: PMC7423394. 2. Hubmann R, Schnabl S, Araghi M, Schmidl C, Rendeiro AF, Hilgarth M, Demirtas D, Ali F, Staber PB, Valent P, Zielinski C, Jäger U, Shehata M. Targeting Nuclear NOTCH2 by Gliotoxin Recovers a Tumor-Suppressor NOTCH3 Activity in CLL. Cells. 2020 Jun 18;9(6):1484. doi: 10.3390/cells9061484. PMID: 32570839; PMCID: PMC7348714. 3. Fraga-Silva TFC, Mimura LAN, Leite LCT, Borim PA, Ishikawa LLW, Venturini J, Arruda MSP, Sartori A. Gliotoxin Aggravates Experimental Autoimmune Encephalomyelitis by Triggering Neuroinflammation. Toxins (Basel). 2019 Jul 26;11(8):443. doi: 10.3390/toxins11080443. PMID: 31357414; PMCID: PMC6722733. 4. Hubmann R, Sieghart W, Schnabl S, Araghi M, Hilgarth M, Reiter M, Demirtas D, Valent P, Zielinski C, Jäger U, Shehata M. Gliotoxin Targets Nuclear NOTCH2 in Human Solid Tumor Derived Cell Lines In Vitro and Inhibits Melanoma Growth in Xenograft Mouse Model. Front Pharmacol. 2017 Jul 7;8:319. doi: 10.3389/fphar.2017.00319. PMID: 28736522; PMCID: PMC5500618.
In vitro protocol:
1. Stoszko M, Al-Hatmi AMS, Skriba A, Roling M, Ne E, Crespo R, Mueller YM, Najafzadeh MJ, Kang J, Ptackova R, LeMasters E, Biswas P, Bertoldi A, Kan TW, de Crignis E, Sulc M, Lebbink JHG, Rokx C, Verbon A, van Ijcken W, Katsikis PD, Palstra RJ, Havlicek V, de Hoog S, Mahmoudi T. Gliotoxin, identified from a screen of fungal metabolites, disrupts 7SK snRNP, releases P-TEFb, and reverses HIV-1 latency. Sci Adv. 2020 Aug 12;6(33):eaba6617. doi: 10.1126/sciadv.aba6617. PMID: 32851167; PMCID: PMC7423394. 2. Hubmann R, Schnabl S, Araghi M, Schmidl C, Rendeiro AF, Hilgarth M, Demirtas D, Ali F, Staber PB, Valent P, Zielinski C, Jäger U, Shehata M. Targeting Nuclear NOTCH2 by Gliotoxin Recovers a Tumor-Suppressor NOTCH3 Activity in CLL. Cells. 2020 Jun 18;9(6):1484. doi: 10.3390/cells9061484. PMID: 32570839; PMCID: PMC7348714.
In vivo protocol:
1. Fraga-Silva TFC, Mimura LAN, Leite LCT, Borim PA, Ishikawa LLW, Venturini J, Arruda MSP, Sartori A. Gliotoxin Aggravates Experimental Autoimmune Encephalomyelitis by Triggering Neuroinflammation. Toxins (Basel). 2019 Jul 26;11(8):443. doi: 10.3390/toxins11080443. PMID: 31357414; PMCID: PMC6722733. 2. Hubmann R, Sieghart W, Schnabl S, Araghi M, Hilgarth M, Reiter M, Demirtas D, Valent P, Zielinski C, Jäger U, Shehata M. Gliotoxin Targets Nuclear NOTCH2 in Human Solid Tumor Derived Cell Lines In Vitro and Inhibits Melanoma Growth in Xenograft Mouse Model. Front Pharmacol. 2017 Jul 7;8:319. doi: 10.3389/fphar.2017.00319. PMID: 28736522; PMCID: PMC5500618.
1: Owens RA, O'Keeffe G, Smith EB, Dolan SK, Hammel S, Sheridan KJ, Fitzpatrick DA, Keane TM, Jones GW, Doyle S. Interplay between Gliotoxin Resistance, Secretion, and the Methyl/Methionine Cycle in Aspergillus fumigatus. Eukaryot Cell. 2015 Sep;14(9):941-57. doi: 10.1128/EC.00055-15. Epub 2015 Jul 6. PubMed PMID: 26150413; PubMed Central PMCID: PMC4551589. 2: Dolan SK, O'Keeffe G, Jones GW, Doyle S. Resistance is not futile: gliotoxin biosynthesis, functionality and utility. Trends Microbiol. 2015 Jul;23(7):419-28. doi: 10.1016/j.tim.2015.02.005. Epub 2015 Mar 10. Review. PubMed PMID: 25766143. 3: Vargas WA, Mukherjee PK, Laughlin D, Wiest A, Moran-Diez ME, Kenerley CM. Role of gliotoxin in the symbiotic and pathogenic interactions of Trichoderma virens. Microbiology. 2014 Oct;160(Pt 10):2319-30. doi: 10.1099/mic.0.079210-0. Epub 2014 Jul 31. PubMed PMID: 25082950. 4: Dolan SK, Owens RA, O'Keeffe G, Hammel S, Fitzpatrick DA, Jones GW, Doyle S. Regulation of nonribosomal peptide synthesis: bis-thiomethylation attenuates gliotoxin biosynthesis in Aspergillus fumigatus. Chem Biol. 2014 Aug 14;21(8):999-1012. doi: 10.1016/j.chembiol.2014.07.006. PubMed PMID: 25126990. 5: O'Keeffe G, Hammel S, Owens RA, Keane TM, Fitzpatrick DA, Jones GW, Doyle S. RNA-seq reveals the pan-transcriptomic impact of attenuating the gliotoxin self-protection mechanism in Aspergillus fumigatus. BMC Genomics. 2014 Oct 14;15:894. doi: 10.1186/1471-2164-15-894. PubMed PMID: 25311525; PubMed Central PMCID: PMC4209032. 6: Jia X, Chen F, Pan W, Yu R, Tian S, Han G, Fang H, Wang S, Zhao J, Li X, Zheng D, Tao S, Liao W, Han X, Han L. Gliotoxin promotes Aspergillus fumigatus internalization into type II human pneumocyte A549 cells by inducing host phospholipase D activation. Microbes Infect. 2014 Jun;16(6):491-501. doi: 10.1016/j.micinf.2014.03.001. Epub 2014 Mar 14. PubMed PMID: 24637030. 7: Svahn KS, Göransson U, Chryssanthou E, Olsen B, Sjölin J, Strömstedt AA. Induction of gliotoxin secretion in Aspergillus fumigatus by bacteria-associated molecules. PLoS One. 2014 Apr 4;9(4):e93685. doi: 10.1371/journal.pone.0093685. eCollection 2014. PubMed PMID: 24705440; PubMed Central PMCID: PMC3976306. 8: Wang DN, Toyotome T, Muraosa Y, Watanabe A, Wuren T, Bunsupa S, Aoyagi K, Yamazaki M, Takino M, Kamei K. GliA in Aspergillus fumigatus is required for its tolerance to gliotoxin and affects the amount of extracellular and intracellular gliotoxin. Med Mycol. 2014 Jul;52(5):506-18. doi: 10.1093/mmy/myu007. Epub 2014 May 20. PubMed PMID: 24847038. 9: Scharf DH, Habel A, Heinekamp T, Brakhage AA, Hertweck C. Opposed effects of enzymatic gliotoxin N- and S-methylations. J Am Chem Soc. 2014 Aug 20;136(33):11674-9. doi: 10.1021/ja5033106. Epub 2014 Aug 7. PubMed PMID: 25062268. 10: Nguyen VT, Lee JS, Qian ZJ, Li YX, Kim KN, Heo SJ, Jeon YJ, Park WS, Choi IW, Je JY, Jung WK. Gliotoxin isolated from marine fungus Aspergillus sp. induces apoptosis of human cervical cancer and chondrosarcoma cells. Mar Drugs. 2013 Dec 24;12(1):69-87. doi: 10.3390/md12010069. PubMed PMID: 24368570; PubMed Central PMCID: PMC3917261. 11: Pena GA, Monge MP, González Pereyra ML, Dalcero AM, Rosa CA, Chiacchiera SM, Cavaglieri LR. Gliotoxin production by Aspergillus fumigatus strains from animal environment. Micro-analytical sample treatment combined with a LC-MS/MS method for gliotoxin determination. Mycotoxin Res. 2015 Aug;31(3):145-50. doi: 10.1007/s12550-015-0225-7. Epub 2015 May 16. PubMed PMID: 25982450. 12: Amatov T, Jahn U. Gliotoxin: nature's way of making the epidithio bridge. Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3312-4. doi: 10.1002/anie.201310982. Epub 2014 Feb 24. PubMed PMID: 24615992. 13: Sakamoto H, Egashira S, Saito N, Kirisako T, Miller S, Sasaki Y, Matsumoto T, Shimonishi M, Komatsu T, Terai T, Ueno T, Hanaoka K, Kojima H, Okabe T, Wakatsuki S, Iwai K, Nagano T. Gliotoxin suppresses NF-κB activation by selectively inhibiting linear ubiquitin chain assembly complex (LUBAC). ACS Chem Biol. 2015 Mar 20;10(3):675-81. doi: 10.1021/cb500653y. Epub 2014 Dec 17. PubMed PMID: 25494483. 14: Schlam D, Canton J, Carreño M, Kopinski H, Freeman SA, Grinstein S, Fairn GD. Gliotoxin Suppresses Macrophage Immune Function by Subverting Phosphatidylinositol 3,4,5-Trisphosphate Homeostasis. MBio. 2016 Apr 5;7(2):e02242. doi: 10.1128/mBio.02242-15. PubMed PMID: 27048806; PubMed Central PMCID: PMC4817266. 15: Scharf DH, Brakhage AA, Mukherjee PK. Gliotoxin--bane or boon? Environ Microbiol. 2016 Apr;18(4):1096-109. doi: 10.1111/1462-2920.13080. Epub 2015 Dec 21. Review. PubMed PMID: 26443473. 16: Chang SL, Chiang YM, Yeh HH, Wu TK, Wang CC. Reconstitution of the early steps of gliotoxin biosynthesis in Aspergillus nidulans reveals the role of the monooxygenase GliC. Bioorg Med Chem Lett. 2013 Apr 1;23(7):2155-7. doi: 10.1016/j.bmcl.2013.01.099. Epub 2013 Feb 4. PubMed PMID: 23434416; PubMed Central PMCID: PMC3640825. 17: Duell ER, Glaser M, Le Chapelain C, Antes I, Groll M, Huber EM. Sequential Inactivation of Gliotoxin by the S-Methyltransferase TmtA. ACS Chem Biol. 2016 Apr 15;11(4):1082-9. doi: 10.1021/acschembio.5b00905. Epub 2016 Feb 9. PubMed PMID: 26808594. 18: Anisha C, Radhakrishnan EK. Gliotoxin-producing endophytic Acremonium sp. from Zingiber officinale found antagonistic to soft rot pathogen Pythium myriotylum. Appl Biochem Biotechnol. 2015 Apr;175(7):3458-67. doi: 10.1007/s12010-015-1517-2. Epub 2015 Feb 10. PubMed PMID: 25820297. 19: Bhatnagar I, Kim SK. Gliotoxin from Aspergillus fumigatus reverses epithelial to mesenchymal transition: implications in renal fibrosis. Int J Med Microbiol. 2015 Jan;305(1):11-9. doi: 10.1016/j.ijmm.2014.09.005. Epub 2014 Oct 7. PubMed PMID: 25455839. 20: Chen J, Wang C, Lan W, Huang C, Lin M, Wang Z, Liang W, Iwamoto A, Yang X, Liu H. Gliotoxin Inhibits Proliferation and Induces Apoptosis in Colorectal Cancer Cells. Mar Drugs. 2015 Oct 2;13(10):6259-73. doi: 10.3390/md13106259. PubMed PMID: 26445050; PubMed Central PMCID: PMC4626688.