Synonym
Acetylgliotoxin; Gliotoxin acetate; Gliotoxin monoacetate
IUPAC/Chemical Name
10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 6-(acetyloxy)-2,3,5a,6-tetrahydro-3-(hydroxymethyl)-2-methyl-, (3R-(3alpha,5abeta,6beta,10aalpha))-
InChi Key
ANMNRGVATKMYOR-UOVKNHIHSA-N
InChi Code
InChI=1S/C15H16N2O5S2/c1-8(19)22-10-5-3-4-9-6-14-12(20)16(2)15(7-18,24-23-14)13(21)17(14)11(9)10/h3-5,10-11,18H,6-7H2,1-2H3/t10-,11-,14+,15+/m0/s1
SMILES Code
CN1C(=O)[C@]23CC4=CC=C[C@H](OC(=O)C)[C@H]4N2C(=O)[C@@]1(CO)SS3
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
368.42
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.
| 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 |
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.
