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Ikarugamycin is an antibiotic initially produced by species of Streptomyces that exhibits antibacterial, anti-protozoal, and anticancer activities. Ikarugamycin prevents formation of the bacterial 70S ribosomal subunit, inhibiting protein translation. In vitro, ikarugamycin inhibits CCP-dependent phagocytosis, preventing PMA-induced downregulation of CD4. Additionally, ikarugamycin inhibits uptake of oxidized LDL, preventing accumulation of cholesterol ester in macrophages.
| Cas No. | 36531-78-9 |
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| Purity | ≥98% |
| Formula | C29H38N2O4 |
| Formula Wt. | 478.62 |
| 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 |
| Solubility | Soluble in chloroform 1 mg/mL, requires gentle heating and sonication; Soluble in methanol 1 mg/mL, requires gentle heating and sonication; Soluble in DMSO 5 mg/mL, requires gentle heating and sonication |
| Appearance | White Crystal Powder |
| Store Temp | -20°C |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Popescu R, Heiss EH, Ferk F, et al. Ikarugamycin induces DNA damage, intracellular calcium increase, p38 MAP kinase activation and apoptosis in HL-60 human promyelocytic leukemia cells. Mutat Res. 2011 May 10;709-710:60-6. PMID: 21392513.
Luo T, Fredericksen BL, Hasumi K, et al. Human immunodeficiency virus type 1 Nef-induced CD4 cell surface downregulation is inhibited by ikarugamycin. J Virol. 2001 Mar;75(5):2488-92. PMID: 11160755.
Hasumi K, Shinohara C, Naganuma S, et al. Inhibition of the uptake of oxidized low-density lipoprotein in macrophage J774 by the antibiotic ikarugamycin. Eur J Biochem. 1992 Apr 15;205(2):841-6. PMID: 1572375.
Jomon K, Kuroda Y, Ajisaka M, et al. A new antibiotic, ikarugamycin. J Antibiot (Tokyo). 1972 May;25(5):271-80. PMID: 4625358.