IUPAC/Chemical Name
(1aS,4R,4aS,8S,9R,11aR,12aS)-4,4a,8,9-tetrahydro-4-hydroxy-9-(2-hydroxy-3,4-dimethoxyphenyl)-12H-8,11a-(iminomethano)-1aH,7H-[1,2,4]dithiazepino[4,3-b]oxireno[e][1,2]benzoxazine-7,13-dione
InChi Key
VZUFPCHAVLFFAY-GGLVFAGASA-N
InChi Code
InChI=1S/C20H20N2O8S2/c1-27-10-5-3-8(13(24)14(10)28-2)15-12-17(25)22-20(32-31-15,18(26)21-12)7-19-11(29-19)6-4-9(23)16(19)30-22/h3-6,9,11-12,15-16,23-24H,7H2,1-2H3,(H,21,26)/t9-,11+,12-,15-,16+,19+,20-/m1/s1
SMILES Code
[H][C@@]([C@H](SS[C@]12C[C@]34O[C@H]3C=C[C@H]([C@]54[H])O)C6=CC=C(C(OC)=C6O)OC)(C(N2O5)=O)NC1=O
Purity
>70% (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
2934.99.9001
Biological target:
Gliovirin is an antibiotic active against Pythium ultimum.
In vitro activity:
Gliovirin inhibited inducible TNF-alpha promoter activity and synthesis in LPS/IFN-gamma-stimulated macrophages/monocytes and Jurkat T-cells, co-stimulated with 12-O-tetradecanoylphorbol-13-acetate (TPA)/ionomycin, in a dose-dependent manner, with IC(50) values ranging from 0.21 to 2.1 microM (0.1-1 microg/ml).
Reference: Biol Chem. 2007 Jun;388(6):627-37. https://pubmed.ncbi.nlm.nih.gov/17552910/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
480.51
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 |
Formulation protocol:
1. Rether J, Serwe A, Anke T, Erkel G. Inhibition of inducible tumor necrosis factor-alpha expression by the fungal epipolythiodiketopiperazine gliovirin. Biol Chem. 2007 Jun;388(6):627-37. doi: 10.1515/BC.2007.066. PMID: 17552910.
In vitro protocol:
1. Rether J, Serwe A, Anke T, Erkel G. Inhibition of inducible tumor necrosis factor-alpha expression by the fungal epipolythiodiketopiperazine gliovirin. Biol Chem. 2007 Jun;388(6):627-37. doi: 10.1515/BC.2007.066. PMID: 17552910.
1. Rether, J., Serwe, A., Anke, T., et al. Inhibition of inducible tumor necrosis factor-α expression by the fungal epipolythiodiketopiperazine gliovirin. Biol. Chem. 388(6), 627-637 (2007).
2. Howell, C.R., and Stipanovic, R.D. Gliovirin, a new antibiotic from Gliocladium virens, and its role in the biological control of Pythium ultimum. Can. J. Microbiol. 29(3), 321-324 (1983).
3. Iwatsuki, M., Otoguro, K., Ishiyama, A., et al. In vitro antitrypanosomal activity of 12 low-molecular-weight antibiotics and observations of structure/activity relationships. J. Antibiot. (Tokyo) 63(10), 619-622 (2010).
