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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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IKARUGAMYCIN Suppliers

Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9806
Advantage
58
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58
Shanghai Hongye Biotechnology Co. Ltd
Tel
400-9205774
Email
sales@glpbio.cn
Country
China
ProdList
6777
Advantage
58
Shenzhen Polymeri Biochemical Technology Co., Ltd.
Tel
+86-400-002-6226 +86-13028896684;
Email
sales@rrkchem.com
Country
China
ProdList
57412
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
AFINE CHEMICALS LIMITED
Tel
+86-0571-85134551
Fax
008657185134895
Email
sales@afinechem.com
Country
China
ProdList
15352
Advantage
58

36531-78-9, IKARUGAMYCINRelated Search:


  • 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