Ikarugamycin
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| Category | Antibiotics |
| Catalog number | BBF-01875 |
| CAS | 36531-78-9 |
| Molecular Weight | 478.62 |
| Molecular Formula | C29H38N2O4 |
| Purity | >99% by HPLC |
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Description
An unusual pentacyclic tetramic acid produced by streptomyces phaeochromogenes; potent activity against the protozoan, trichomonas vaginalis; demonstrates selective gram positive antibacterial activity, and anti-ulcer activity possibly via inhibition of H. Pylori; 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; a useful agent for studying the process of endocytosis.
Specification
| Synonyms | 14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione |
| Storage | -20°C |
| IUPAC Name | (1Z,3E,5S,7R,8R,10R,11R,12S,15R,16S,18Z,25S)-11-ethyl-2-hydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.07,15.08,12]octacosa-1,3,13,18-tetraene-20,27,28-trione |
| Canonical SMILES | CCC1C(CC2C1C=CC3C2CC4C3CC=CC(=O)NCCCC5C(=O)C(=C(C=C4)O)C(=O)N5)C |
| InChI | InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,32H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+,27-25-/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1 |
| InChI Key | GHXZHWYUSAWISC-KZRBWAKNSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Acicular Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; parasites |
| Boiling Point | 741.91°C at 760 mmHg |
| Melting Point | 252-255°C |
| Density | 1.2 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Biocatalytic Total Synthesis of Ikarugamycin
Janine Antosch, Tobias A M Gulder, Christian Greunke, Anna Glöckle Angew Chem Int Ed Engl . 2017 Apr 3;56(15):4351-4355. doi: 10.1002/anie.201611063.
Nature provides an inexhaustible diversity of small organic molecules with beautiful molecular architectures that have strong and selective inhibitory activities. However, this tremendous biomedical potential often remains inaccessible, as the structural complexity of natural products can render their synthetic preparation extremely challenging. This problem is addressable by harnessing the biocatalytic procedures evolved by nature. In this work, we present an enzymatic total synthesis of ikarugamycin. The use of an iterative PKS/NRPS machinery and two reductases has allowed the construction of 15 carbon-carbon and 2 carbon-nitrogen bonds in a biocatalytic one-pot reaction. By scaling-up this method we demonstrate the applicability of biocatalytic approaches for the ex vivo synthesis of complex natural products.
2. Heterologous reconstitution of ikarugamycin biosynthesis in E. coli
Janine Antosch, Françoise Schaefers, Tobias A M Gulder Angew Chem Int Ed Engl . 2014 Mar 10;53(11):3011-4. doi: 10.1002/anie.201310641.
Polycyclic tetramate macrolactams (PTMs) are a family of biomedically promising natural products with challenging molecular frameworks. Despite these interesting properties, so far only relatively little is known about the biosynthetic origin of PTMs, in particular concerning the mechanism by which their ring systems are formed. Herein we present the first insights into these processes by using the biosynthesis of ikarugamycin as an example. This has been facilitated by the first heterologous expression of a PTM biosynthetic gene cluster in Escherichia coli. With this approach it will not only become possible to mechanistically investigate already known PTM biosynthetic pathways in more detail in the future, but also to interrogate cryptic PTM biosynthetic pathways chemically and biochemically.
3. A potent endocytosis inhibitor Ikarugamycin up-regulates TNF production
Takehito Asakawa, Mamoru Watanabe, Michio Onizawa, Yuichi Hiraoka, Kiichiro Tsuchiya, Tomoaki Mochimaru, Hiromasa Ohira, Rie Hikichi, Shigeru Oshima, Ryuichi Okamoto, Takashi Nagaishi, Mai Murakami, Chiharu Sakuma, Ai Minamidate, Chikako Saito Biochem Biophys Rep . 2021 Jul 8;27:101065. doi: 10.1016/j.bbrep.2021.101065.
Ikarugamycin (IK) is an antibiotic which has been reported to have a variety of functions, such as inhibition of clathrin-mediated endocytosis (CME), anti-tumor effects and regulation of the immune system. Whether IK influences cytokine production is poorly understood. We have investigated the relationship between IK and production of tumor necrosis factor-α (TNF). TNF plays a pivotal role in pathogenesis of many diseases. Although the dynamics of soluble TNF (sTNF) has been widely explored so far, the functions of the membrane form of TNF (mTNF) have not been fully elucidated. We demonstrated that IK increases the amount of mTNF and prolongs the duration of TNF expression. This effect is unrelated to the shedding activity of disintegrin and metalloproteinase domain-containing protein 17 (ADAM 17). Our results revealed that there is a mechanism to terminate inflammation at the cellular level which IK dysregulates. Furthermore, IK can be a tool to study TNF signaling due to its effect of increasing mTNF expression.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
