Panosialin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03746 |
| CAS | |
| Molecular Weight | 480.63 |
| Molecular Formula | C21H36O8S2 |
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Description
It is produced by the strain of Str. sp OH-5186. It can inhibit α,β-glucosidase and mannose glycosidase. It can inhibit the influenza virus and has weak anti-microbial effect.
Specification
| Synonyms | Panosialin I; 1,3-Benzenediol, 5-(13-methyltetradecyl)-, bis(hydrogen sulfate) |
| IUPAC Name | [3-(13-methyltetradecyl)-5-sulfooxyphenyl] hydrogen sulfate |
| Canonical SMILES | CC(C)CCCCCCCCCCCCC1=CC(=CC(=C1)OS(=O)(=O)O)OS(=O)(=O)O |
| InChI | InChI=1S/C21H36O8S2/c1-18(2)13-11-9-7-5-3-4-6-8-10-12-14-19-15-20(28-30(22,23)24)17-21(16-19)29-31(25,26)27/h15-18H,3-14H2,1-2H3,(H,22,23,24)(H,25,26,27) |
| InChI Key | NGWLEVXPPLCHNC-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Viruses |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Highly sensitive cell-based assay system to monitor the sialyl Lewis X biosynthesis mediated by alpha1-3 fucosyltransferase-VII
Masahiko Miyashiro, Sachiko Furuya, Kotomi Fujishige, Takahisa Sugita Biochem Biophys Res Commun. 2004 Nov 5;324(1):98-107. doi: 10.1016/j.bbrc.2004.09.025.
The sialyl Lewis X (sLe(x)) determinant on leukocytes serves as a ligand for selectin family cell adhesion molecules, and selectin-carbohydrate interaction is considered to play an important role in the process of leukocyte extravasation during inflammation. Among several alpha1-3 fucosyltransferases (FucTs), FucT-VII plays a critical role in the biosynthesis of sLe(x)-epitopes. Therefore, small molecules specifically designed to inhibit the FucT-VII enzyme may have potential as anti-inflammatory agents. Here, we have developed a versatile cell-based assay system to monitor sLe(x) biosynthesis using the GeneSwitch System. This system is a mifepristone (MFP)-inducible mammalian expression system, and human transfectant T lymphoblasts expressed the mRNA of FucT-VII and the sLe(x)-epitopes on the cell surface in a time-dependent manner in the presence of MFP, with very low background transcription. Furthermore, when the transfectants were treated with the FucT-VII inhibitor panosialin, sLe(x) expression on the induced cells was inhibited dose dependently without alteration at the mRNA level of FucT-VII. These results suggest that the FucT-VII may be a major regulator of the biosynthesis of the sLe(x)-epitopes on T lymphoblasts, and this cell-based assay may be utilized for a screening system of FucT-VII inhibitors.
2. Panosialins, inhibitors of enoyl-ACP reductase from Streptomyces sp. AN1761
Yun Ju Kwon, Mi-Jin Sohn, Taegwon Oh, Sang-Nae Cho, Chang-Jin Kim, Won-Gon Kim J Microbiol Biotechnol. 2013 Feb;23(2):184-8. doi: 10.4014/jmb.1209.09038.
In the continued search for inhibitors of enoyl-acyl carrier protein (ACP) reductase, we found that four acylbenzenediol sulfate metabolites from Streptomyces sp. AN1761 potently inhibited bacterial enoyl-ACP reductases of Staphylococcus aureus, Streptococcus pneumoniae, and Mycobacterium tuberculosis. Their structures were identified as panosialins A, B, wA, and wB by MS and NMR data. They showed stronger inhibition against S. aureus FabI and S. pneumoniae FabK with IC50 of 3-5 microM than M. tuberculosis InhA with IC50 of 9-12 microM. They also exhibited a stronger antibacterial spectrum on S. aureus and S. pneumoniae than M. tuberculosis. In addition, the higher inhibitory activity of panosialin wB than panosialin B on fatty acid biosynthesis was consistent with that on bacterial growth, suggesting that they could exert their antibacterial activity by inhibiting fatty acid synthesis.
3. Sulfotanone, a new alkyl sulfonic acid derivative from Streptomyces sp. IFM 11694 with TRAIL resistance-overcoming activity
Mohamed S Abdelfattah, Naoki Ishikawa, Utpal K Karmakar, Masami Ishibashi J Nat Med. 2016 Apr;70(2):266-70. doi: 10.1007/s11418-015-0951-3. Epub 2015 Nov 25.
One new alkyl sulfonic acid derivative, sulfotanone (1), and the known panosialin wA (2) were isolated from the methanolic extract of mycelium of Streptomyces sp. 11694. The structure of the new compound (1) was established by a combination of spectroscopic techniques, including HRESIMS, IR, 1D and 2D NMR measurements. Compound 1 (40 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistance in human gastric adenocarcinoma cell lines.
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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 ╳
