For research use only, not for therapeutic use.
Enniatin A1（Cat No.:R000360）is a cyclic hexadepsipeptide belonging to the enniatin family of mycotoxins produced by Fusarium species. It exhibits antimicrobial, antifungal, and anticancer properties, making it of interest in pharmaceutical research. Enniatin A1 acts as an ionophore, disrupting ion gradients across cellular membranes, which leads to its biological effects, including apoptosis in cancer cells. It has been studied for its potential as an anticancer agent, especially due to its ability to induce cell cycle arrest and apoptosis. Additionally, Enniatin A1 is valuable in research on natural products and mycotoxin toxicology.
| Catalog Number | R000360 |
| CAS Number | 4530-21-6 |
| Synonyms | cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl] |
| Molecular Formula | C35H61N3O9 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (3S,6R,9S,12R,15S,18R)-3,9-bis[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,15,18-tetra(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
| InChI | InChI=1S/C35H61N3O9/c1-16-22(11)25-34(43)46-27(19(5)6)30(39)36(13)24(18(3)4)33(42)45-28(20(7)8)31(40)37(14)26(23(12)17-2)35(44)47-29(21(9)10)32(41)38(25)15/h18-29H,16-17H2,1-15H3/t22-,23-,24-,25-,26-,27+,28+,29+/m0/s1 |
| InChIKey | OWUREPXBPJFMOK-CIRFPNLUSA-N |
| SMILES | CC[C@H](C)[C@H]1C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)[C@@H](C)CC)C)C(C)C)C(C)C)C)C(C)C |
| Reference | Ionophore antibiotics produced by the fungus Fusarium orthoceras var. enniatum and other Fusaria. Gaumann E. et al. , Experientia 1947, 3, 202.<br/><br/>/Sandwich/ complexation in cyclopeptides and its implications in membrane processes. Ivanov V.T. Ann. N. Y. Acad. Sci. 1975, 264, 221.<br/><br/>Interaction of cyclic peptides and depsipeptides with calmodulin. Mereish K.A. et al. , Pept. Res. 1990, 3, 233.<br/><br/>Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae. Hiraga K. et al. , Biochem. Biophys. Res. Commun. 2005, 328, 1119.<br/><br/>Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells. Dornetshuber R. et al. , Chem. Res. Toxicol. 2007, 20, 465.</span></p> |
