IKARUGAMYCIN
- CAS No.
- 36531-78-9
- Chemical Name:
- IKARUGAMYCIN
- Synonyms
- TU-6239 C3;IKARUGAMYCIN;turbinomycin;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
- Molecular Weight:
- 478.62
- MDL Number:
- MFCD01722005
- MOL File:
- 36531-78-9.mol
- MSDS File:
- SDS
| 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) |
| EWG's Food Scores | 1 |
IKARUGAMYCIN price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 15386 | Ikarugamycin ≥99% | 36531-78-9 | 500μg | $179 | 2024-03-01 | Buy |
| Cayman Chemical | 15386 | Ikarugamycin ≥99% | 36531-78-9 | 2.5mg | $804 | 2024-03-01 | Buy |
| Usbiological | I2300-20 | Ikarugamycin | 36531-78-9 | 500ug | $426 | 2021-12-16 | Buy |
| TRC | I942005 | Ikarugamycin | 36531-78-9 | 500μg | $675 | 2021-12-16 | Buy |
IKARUGAMYCIN Chemical Properties,Uses,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-
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.
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.
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| AFINE CHEMICALS LIMITED | 0571-85134551 18958018566; | info@afinechem.com | China | 15377 | 58 |
| BOC Sciences | 16314854226; +16314854226 | inquiry@bocsci.com | United States | 19743 | 58 |
| Shaanxi Cuikang Pharmaceutical Technology Co., Ltd | +86-19164747840 +86-13119157289 | 13119157289@163.com | China | 2971 | 58 |
| Aladdin Scientific | +1-833-552-7181 | sales@aladdinsci.com | United States | 52927 | 58 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4428 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51471 | 80 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9709 | 58 |
| Lynnchem | 86-(0)29-85992781 17792393971 | info@lynnchem.com | China | 4587 | 58 |
| Novachemistry | 44-20819178-90 02081917890 | info@novachemistry.com | United Kingdom | 4381 | 58 |