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Merck
CN

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
NACRES:
NA.77
UNSPSC Code:
12352200
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biological source

Streptomyces sp.

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

Quality Level

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.

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Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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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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)
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
Rebuma Firdessa et al.
PLoS neglected tropical diseases, 9(10), e0004041-e0004041 (2015-10-03)
Cutaneous leishmaniasis (CL) is a neglected tropical disease caused by protozoan parasites of the genus Leishmania. CL causes enormous suffering in many countries worldwide. There is no licensed vaccine against CL, and the chemotherapy options show limited efficacy and high
Alessandra Moscatelli et al.
Journal of cell science, 120(Pt 21), 3804-3819 (2007-10-18)
In an attempt to dissect endocytosis in Nicotiana tabacum L. pollen tubes, two different probes--positively or negatively charged nanogold--were employed. The destiny of internalized plasma membrane domains, carrying negatively or positively charged residues, was followed at the ultrastructural level and
T Luo et al.
Journal of virology, 75(5), 2488-2492 (2001-02-13)
One well-characterized in vitro function of Nef is its ability to remove CD4, the human immunodeficiency virus (HIV) receptor, from the cell surface. Nef accomplishes this by accelerating the internalization and degradation of CD4. Current models propose that Nef promotes

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