For research use only. Not for therapeutic Use.
Ikarugamycin（Cat No.:R004984）is an antibiotic compound that exhibits inhibitory effects on clathrin-mediated endocytosis (CME). It interferes with the process of CME, which is responsible for the internalization of various molecules into cells through clathrin-coated vesicles. By inhibiting CME, ikarugamycin disrupts the normal cellular uptake and trafficking of substances. Its dual action as an antibiotic and CME inhibitor makes it a potentially valuable compound for understanding cellular processes and exploring therapeutic applications.
| Catalog Number | R004984 |
| CAS Number | 36531-78-9 |
| Synonyms | (2R,3R,7Z,14S,19E)-3-ethyl-2,3,3aS,5aR,5bS,6,10,11,12,13,14,15,20aS,21,21aR,21bR-hexadecahydro-22-hydroxy-2-methyl-14,17-metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione |
| Molecular Formula | C29H38N2O4 |
| Purity | ≥95% |
| Target | Antibiotic |
| Storage | -20°C |
| IUPAC Name | (1Z,3E,5S,7R,8R,10R,11R,12S,15R,16S,18Z,25S)-11-ethyl-2-hydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.07,15.08,12]octacosa-1,3,13,18-tetraene-20,27,28-trione |
| InChI | InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,32H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+,27-25-/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1 |
| InChIKey | GHXZHWYUSAWISC-KZRBWAKNSA-N |
| SMILES | CC[C@@H]1[C@@H](C[C@H]2[C@H]1C=C[C@H]3[C@@H]2C[C@@H]/4[C@@H]3C/C=C\C(=O)NCCC[C@H]5C(=O)/C(=C(\C=C4)/O)/C(=O)N5)C |
| Reference | A new antibiotic, ikarugamycin. Jomom K. et al. , J. Antibiot. 1972, 25, 271.<br/><br/>Inhibition of the uptake of oxidized low-density lipoprotein in macrophage J774 by the antibiotic ikarugamycin. Hasumi K. et al. , Eur. J. Biochem. 1992, 205, 841.<br/><br/>Human immunodeficiency virus type 1 Nef-induced CD4 cell surface downregulation is inhibited by ikarugamycin. Luo T. et al. , J. Virol. 2001, 75, 2488.<br/><br/>Distinct endocytic pathways identified in tobacco pollen tubes using charged nanogold. Moscatelli A. et al. , J. Cell Sci. 2007, 120, 3804.</span></p> |
