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Ikarugamycin 目录号 GC43892

Ikarugamycin is a macrocyclic antibiotic first isolated from Streptomyces sp.

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Sample solution is provided at 25 µL, 10mM.


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Chemical Properties

Cas No. 36531-78-9 SDF Download SDF
别名 N/A
化学名 (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
Canonical SMILES O=C(C1=C(O)[C@H](CCCN2)NC1=O)/C=C/[C@@H]3C[C@@]4([H])[C@@](C=C[C@]5([H])[C@]4([H])C[C@@H](C)[C@H]5CC)([H])[C@H]3C/C=C\C2=O
分子式 C29H38N2O4 分子量 478.6
溶解度 Soluble in DMSO,DMF, slightly in ethanol, methanol 储存条件 Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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Ikarugamycin is a macrocyclic antibiotic first isolated from Streptomyces sp. that demonstrates potent antiprotozoal activity.[1] It exhibits cytotoxic effects in cancer cell lines, inhibiting cell proliferation (IC50 = 221.3 nM in HL-60 cells) through genotoxicity and by inducing apoptosis and activation of caspases.[2] It also was shown to significantly inhibit oxidized low-density lipoprotein-induced accumulation of cholesteryl esters in macrophages at 1-4 μM.[3] Additionally, ikarugamycin is used to inhibit clathrin-coated pit-mediated endocytosis.[4]
[1]. Jomon, K., Kuroda, Y., Ajisaka, M., et al. A new antibiotic, ikarugamycin. J.Antibiot.(Tokyo) 25(5), 271-280 (1972).
[2]. Popescu, R., Heiss, E.H., Ferk, F., et al. Ikarugamycin induces DNA damage, intracellular calcium increase, p38 MAP kinase activation and apoptosis in HL-60 human promyelocytic leukemia cells. Mutation Research 709-710, 60-66 (2011).
[3]. Hasumi, K., Shinohara, C., Naganuma, S., et al. Inhibition of the uptake of oxidized low-density lipoprotein in macrophage J774 by the antibiotic ikarugamycin. European Journal of Biochemistry 205(2), 841-846 (1992).
[4]. Luo, T., Fredericksen, B.L., Hasumi, K., et al. Human immunodeficiency virus type 1 Nef-induced CD4 cell surface downregulation is inhibited by ikarugamycin. Journal of Virology 75(5), 2488-2492 (2001).