Gelastatin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-01482 |
| CAS | |
| Molecular Weight | 248.27 |
| Molecular Formula | C14H16O4 |
| Purity | ≥98% |
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Description
It is produced by the strain of Westerdykella multispora F50733. It can inhibit the activity of leucinase A and the IC50 of leucinase A is 0.63 μmol/L.
Specification
| Synonyms | (all-E)-5-(2,4-Hexadienylidene)-5,6-dihydro-2-oxo-2H-pyran-3-propanoic acid |
| Storage | RT. |
| IUPAC Name | 3-[(5E)-5-[(2E,4E)-hexa-2,4-dienylidene]-2-oxopyran-3-yl]propanoic acid |
| Canonical SMILES | CC=CC=CC=C1COC(=O)C(=C1)CCC(=O)O |
| InChI | InChI=1S/C14H16O4/c1-2-3-4-5-6-11-9-12(7-8-13(15)16)14(17)18-10-11/h2-6,9H,7-8,10H2,1H3,(H,15,16)/b3-2+,5-4+,11-6+ |
| InChI Key | ACFXHMLFZGREFW-JCESNKCLSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Gelastatins and their hydroxamates as dual functional inhibitors for TNF-alpha converting enzyme and matrix metalloproteinases: synthesis, biological evaluation, and mechanism studies
Song-Kyu Park, Sang Bae Han, Kiho Lee, Ho Jae Lee, Yung Hee Kho, Hyokon Chun, Yongseok Choi, Jae Young Yang, Yeo Dae Yoon, Chang-Woo Lee, Hwan Mook Kim, Hyun-Moo Choi, Hyun Seop Tae, Hee-Yoon Lee, Ky-Youb Nam, Gyoonhee Han Biochem Biophys Res Commun. 2006 Mar 10;341(2):627-34. doi: 10.1016/j.bbrc.2005.12.219. Epub 2006 Jan 17.
The hydroxamic acid analogues (2) of the natural product gelastatins (1) were prepared by 1 step conversion reaction. The synthetic analogues (2) showed potent enzymatic inhibitory activities against MMP-2, MMP-9, and TACE IC50's of 6, 23, and 28 nM, respectively. In addition, 2 were able to inhibit TNF-alpha production effectively in mice as well as in a macrophage cell line, RAW 264.7. The protective effect of 2 also was examined on LPS-induced acute septic shock model. The mechanism of TNF-alpha inhibition was examined by RT-PCR and Western blot analyses. The relation of TACE and alpha-secretase was examined using cellular alpha-secretase assays on IMR-32 and SH-SY5Y cell lines. The docking mode of 2 with the catalytic domain of TACE was illustrated to analyze the binding mode for the further analogue design.
2. Synthesis of arylidene-substituted gelastatin analogues and their screening for MMP-2 inhibitory activity
Eun Jin Kim, Soo Y Ko Bioorg Med Chem. 2005 Jun 2;13(12):4103-12. doi: 10.1016/j.bmc.2005.03.037. Epub 2005 Apr 25.
A series of arylidene-substituted gelastatin analogues were synthesized in a divergent manner. Each analogue was obtained as a mixture of isomers. Calculation methods were devised to deduce the MMP-2 inhibitory activity of each isomer from the activity of an isomeric mixture and its composition. This protocol is suitable for rapidly generating a variety of arylidene-substituted gelastatin analogues and screening them for highly active inhibitors.
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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 ╳
