| Identification | Back Directory | [Name]
IKARUGAMYCIN | [CAS]
36531-78-9 | [Synonyms]
TU-6239 C3
IKARUGAMYCIN
WSUGGLXIPUHOSG-XSYQVIBFSA-N
14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione
3-Ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-, (2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-
14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione, 3-ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-, (2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)- | [Molecular Formula]
C29H38N2O4 | [MDL Number]
MFCD01722005 | [MOL File]
36531-78-9.mol | [Molecular Weight]
478.62 |
| Chemical Properties | Back Directory | [Boiling point ]
741.9±60.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
chloroform: soluble1mg/mL (requires heating and sonication) | [form ]
White to off-white crystalline solid. | [pka]
4.50±1.00(Predicted) | [color ]
White to light yellow |
| Hazard Information | Back Directory | [Description]
Ikarugamycin is a macrocyclic antibiotic first isolated from Streptomyces sp. that demonstrates potent antiprotozoal activity. 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. It also was shown to significantly inhibit oxidized low-density lipoprotein-induced accumulation of cholesteryl esters in macrophages at 1-4 μM. Additionally, ikarugamycin is used to inhibit clathrin-coated pit-mediated endocytosis. | [Uses]
Ikarugamycin is an unusual pentacyclic tetramic acid produced by Streptomyces phaeochromogenes, with potent activity against the protozoan, Trichomonas vaginalis, reported in 1972. Ikarugamycin also demonstrates selective Gram positive antibacterial activity, and anti-ucler activity possibly via inhibition of H. pylori. In addition, ikarugamycin inhibits the uptake of oxidized low-density lipoprotein in mouse macrophages, blocks PMA and Nef-mediated cell surface CD4 down-regulation, and inhibits clathrin-coated pit-mediated endocytosis. Importantly, ikarugamycin is emerging as a useful agent for studying the process of endocytosis. | [Definition]
ChEBI: A polyketide macrolactam containing a tetramic acid (2,4-pyrrolidine-2,4-dione) ring system. It is isolated from Streptomyces as an antibitoic with antiprotozoal and cytotoxic activities. | [Biochem/physiol Actions]
Ikarugamycin, an unusual pentacyclic tetramic acid produced by Streptomyces sp., has a potent activity against the protozoan Trichomonas vaginalis with IC50 of 0.3-1.25 μg/mL. Ikarugamycin also demonstrates selective Gram positive antibacterial activity and exhibits anti-ulcer activity possibly through inhibition of Helicobacter. Ikarugamycin-induced inhibition of cholesteryl-ester accumulation reduced uptake of oxidized low-density lipoprotein (LDL) in mouse macrophages J774. Moreover, Ikarugamycin inhibits Nef-induced degradation of CD4 on Human Immunodeficiency Virus type 1 (HIV) infected T cells, thus increasing its half-life and possibly restoring some normal functions lost in the infected cells. Ikarugamycin inhibition of clathrin-coated pit-mediated endocytosis indicates it as a useful agent for studying the process of endocytosis. Ikarugamycin inhibit HL-60 cell proliferation through genotoxicity and apoptosis induction and to activated caspase by induction of intracellular rise in calcium levels and activation of p38 MAP kinase. | [storage]
Store at -20°C |
|
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Sigma-Aldrich
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Novachemistry
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Energy Chemical
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