EI-1941-1
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02813 |
| CAS | 189828-31-7 |
| Molecular Weight | 240.25 |
| Molecular Formula | C12H16O5 |
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Description
It is originally isolated from Farrowia sp. E-1941. EI-1941-1 inhibited recombinant human ICE with an IC50 of 0.086 μmol/L. It also inhibits elastase and cathepsin.
Specification
| Synonyms | 2,3-Dihydroxy-5-propyl-1a,5,6,7a-tetrahydro-2H-oxireno[g]isochromen-7(3H)-one |
| IUPAC Name | (1aS,2R,5R,7aS)-2,3-dihydroxy-5-propyl-1a,2,3,5,6,7a-hexahydrooxireno[2,3-g]isochromen-7-one |
| Canonical SMILES | CCCC1CC2=C(C(C3C(C2=O)O3)O)C(O1)O |
| InChI | InChI=1S/C12H16O5/c1-2-3-5-4-6-7(12(15)16-5)9(14)11-10(17-11)8(6)13/h5,9-12,14-15H,2-4H2,1H3/t5-,9-,10-,11+,12?/m1/s1 |
| InChI Key | DJMYUSHSKVTQAD-ARRRXNATSA-N |
Properties
| Boiling Point | 510.8±50.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. EI-1941-1 and -2, novel interleukin-1 beta converting enzyme inhibitors Produced by Farrowia sp. E-1941. II. Taxonomy of producing strain, fermentation, isolation, physico-chemical properties, and biological properties
Fumito Koizumi, Hiroki Ishiguro, Katsuhiko Ando, Hidemasa Kondo, Mayumi Yoshida, Yuzuru Matsuda, Satoshi Nakanishi J Antibiot (Tokyo). 2003 Jul;56(7):603-9. doi: 10.7164/antibiotics.56.603.
EI-1941-1 and -2, novel interleukin-1 beta converting enzyme (ICE) inhibitors, were isolated from the culture broths of Farrowia sp. E-1941. EI-1941-1 and -2 selectively inhibited the human recombinant ICE activity with IC50 values of 0.086 and 0.006 microM, respectively. Taxonomy and fermentation of the producing strain and isolation, physico-chemical properties, structure elucidation, and biological properties of EI-1941-1 and -2 are described.
2. Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1beta converting enzyme, and biological properties of their derivatives
Mitsuru Shoji, Takao Uno, Hideaki Kakeya, Rie Onose, Isamu Shiina, Hiroyuki Osada, Yujiro Hayashi J Org Chem. 2005 Nov 25;70(24):9905-15. doi: 10.1021/jo0516436.
[reaction: see text] The first asymmetric total synthesis of EI-1941-1, -2, and -3, inhibitors of the interleukin-1beta converting enzyme (ICE), has been accomplished, starting from a chiral epoxy iodoquinone 11, a key intermediate in our total synthesis of epoxyquinols A and B. Despite a failure to synthesize the inhibitors by our postulated biosynthetic route, we were able to diastereoselectively synthesize them via an intramolecular carboxypalladation with the key steps being a 6-endo cyclization mode followed by beta-hydride elimination. The investigation of the biological properties of EI-1941-1, -2, and -3 and their derivatives disclosed them to be potent and effective ICE inhibitors with less cytotoxicity than EI-1941-1 and -2 in a cultured cell system.
3. EI-1941-1 and -2, novel interleukin-1beta converting enzyme inhibitors produced by Farrowia sp. E-1941. I. Biochemical characterization of EI-1941-1 and -2
Fumito Koizumi, Yuzuru Matsuda, Satoshi Nakanishi J Antibiot (Tokyo). 2003 May;56(5):464-9. doi: 10.7164/antibiotics.56.464.
EI-1941-1 and -2 isolated from the culture broths of Farrowia sp. selectively inhibited the human recombinant ICE activity with IC50 values of 0.086 and 0.006 microM, respectively, without inhibiting elastase and cathepsin B. EI-1941-1 and -2 also inhibited mature interleukin-1beta secretion from THP-1 cells induced by LPS with IC50 values of 5.0 and 10.3 microM, respectively. Biochemical characterizations of EI-1941-1 and -2 are described in this article.
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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 ╳
