SML0188
Ikarugamycin
≥98% (HPLC), from Streptomyces sp.
Synonym(s):
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)-, IKA, TU-6239 C3
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About This Item
Empirical Formula (Hill Notation):
C29H38N2O4
CAS Number:
Molecular Weight:
478.62
UNSPSC Code:
12352200
NACRES:
NA.77
biological source
Streptomyces sp.
Quality Level
Assay
≥98% (HPLC)
solubility
chloroform: 1 mg/mL (requires heating and sonication)
methanol: 1 mg/mL (requires heating and sonication)
DMSO: 5 mg/mL (requires heating and sonication)
antibiotic activity spectrum
Gram-positive bacteria
parasites
Mode of action
protein synthesis | interferes
storage temp.
−20°C
Application
Ikarugamycin has been used as an inhibitor of clathrin coated pit-mediated endocytosis in flow cytometry, as CME inhibitor to determine its suitability as a tool to study and distinguish endocytic pathways in mammalian cells and for endocytic inhibitor treatment in Hela cells.
Biochem/physiol Actions
Ikarugamycin (IKA) is an antibiotic. It acts as an important tool for probing routes of endocytic trafficking. It has the ability to prevent clathrin-mediated endocytosis (CME) in plant cells. IKA is also capable of changing Golgi morphology.
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, 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.
Features and Benefits
This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Vera Bandmann et al.
The Plant journal : for cell and molecular biology, 70(4), 578-584 (2012-01-04)
In eukaryotic cells, several pathways exist for the internalization of plasma membrane proteins and extracellular cargo molecules. These endocytic pathways can be divided into clathrin-dependent and clathrin-independent pathways. While clathrin-dependent pathways are known to be involved in a variety of
K Hasumi et al.
European journal of biochemistry, 205(2), 841-846 (1992-04-15)
The antiprotozoal antibiotic ikarugamycin was found to significantly inhibit oxidized low-density lipoprotein(LDL)-induced accumulation of cholesteryl ester in macrophage J774 at a concentration over 1-4 microM. Cholesteryl ester synthesis from [14C]oleate in the macrophages was similarly inhibited by the antibiotic, while
Chongxi Liu et al.
International journal of systematic and evolutionary microbiology, 63(Pt 10), 3579-3584 (2013-04-16)
A novel ikarugamycin-producing actinomycete, designated strain NEAU-Da3(T), was isolated from soybean root [Glycine max (L.) Merr.] and characterized using a polyphasic approach. 16S rRNA gene sequence similarity studies showed that strain NEAU-Da3(T) belonged to the genus Streptomyces, and was most
Visualizing the cellular route of entry of a cystine-knot peptide with Xfect transfection reagent by electron microscopy
Gao X, et al.
Scientific Reports, 9(1), 6907-6907 (2019)
Ikarugamycin: A Natural Product Inhibitor of Clathrin-Mediated Endocytosis
Elkin SR, et al.
Traffic, 17(10), 1139-1149 (2016)
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