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Merck
CN

SML0188

Ikarugamycin

≥98% (HPLC), from Streptomyces sp.

别名:

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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关于此项目

经验公式(希尔记法):
C29H38N2O4
化学文摘社编号:
分子量:
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.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

存储类别

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

法规信息

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分析证书(COA)

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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
Ikarugamycin: A Natural Product Inhibitor of Clathrin-Mediated Endocytosis
Elkin SR, et al.
Traffic, 17(10), 1139-1149 (2016)
Pathogen-and host-directed antileishmanial effects mediated by polyhexanide (PHMB)
Firdessa R, et al.
PLoS Neglected Tropical Diseases, 9(10), e0004041-e0004041 (2015)
Elisabetta Onelli et al.
Journal of experimental botany, 59(11), 3051-3068 (2008-07-08)
Positively charged nanogold was used as a probe to trace the internalization of plasma membrane (PM) domains carrying negatively charged residues at an ultrastructural level. The probe revealed distinct endocytic pathways within tobacco protoplasts and allowed the morphology of the

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