IKARUGAMYCIN

ChemicalBook > CAS DataBase List > IKARUGAMYCIN

Product Name: IKARUGAMYCIN
CAS No.: 36531-78-9
Chemical Name: IKARUGAMYCIN
Synonyms: TU-6239 C3;turbinomycin;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)-
CBNumber: CB2754262
Molecular Formula: C29H38N2O4
Formula Weight: 478.62
MOL File: 36531-78-9.mol

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IKARUGAMYCIN Property

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

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 45
RIDADR: UN 2811 6.1 / PGIII
WGK Germany: 3
HS Code: 29419000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger
Hazard statements: H301Toxic if swalloed
Precautionary statements: P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 15386
Product name: Ikarugamycin
Purity: ≥99%
Packaging: 500μg
Price: $179
Updated: 2024/03/01

Cayman Chemical

Product number: 15386
Product name: Ikarugamycin
Purity: ≥99%
Packaging: 2.5mg
Price: $804
Updated: 2024/03/01

Usbiological

Product number: I2300-20
Product name: Ikarugamycin
Packaging: 500ug
Price: $426
Updated: 2021/12/16

TRC

Product number: I942005
Product name: Ikarugamycin
Packaging: 500μg
Price: $675
Updated: 2021/12/16

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IKARUGAMYCIN Chemical Properties,Usage,Production

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.

Uses

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.

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.

IKARUGAMYCIN Preparation Products And Raw materials

Raw materials

Preparation Products

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36531-78-9, IKARUGAMYCINRelated Search:

Azithromycin CYCLODODECENE 3-acetyltetramic acid IKARUGAMYCIN

TU-6239 C3

IKARUGAMYCIN

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)-

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)-

turbinomycin

36531-78-9

C29H4N2O4

C29H38N2O4

Antibiotic