Dehydrophenylahistin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00799 |
| CAS | |
| Molecular Weight | 348.40 |
| Molecular Formula | C20H20N4O2 |
Online Inquiry
Description
Dehydrophenylahistin are two dehydrogenated products produced by the enzymatic conversion of the fungal metabolite (-)-phenylhistidine [(-)-phenylahistin] through the cell-free extract of Streptomyces albulus KO23. It can inhibit the first lysis of sea urchin embryos.
Specification
| IUPAC Name | (3E,6E)-3-benzylidene-6-[[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene]piperazine-2,5-dione |
| Canonical SMILES | CC(C)(C=C)C1=C(N=CN1)C=C2C(=O)NC(=CC3=CC=CC=C3)C(=O)N2 |
| InChI | InChI=1S/C20H20N4O2/c1-4-20(2,3)17-14(21-12-22-17)11-16-19(26)23-15(18(25)24-16)10-13-8-6-5-7-9-13/h4-12H,1H2,2-3H3,(H,21,22)(H,23,26)(H,24,25)/b15-10+,16-11+ |
| InChI Key | AANRCAZDPPXTKN-RWPWKDLBSA-N |
Reference Reading
1. A novel potent cell cycle inhibitor dehydrophenylahistin--enzymatic synthesis and inhibitory activity toward sea urchin embryo
Hiroshi Kanzaki, Satohiro Yanagisawa, Kaneo Kanoh, Teruhiko Nitoda J Antibiot (Tokyo). 2002 Dec;55(12):1042-7. doi: 10.7164/antibiotics.55.1042.
A novel dehydrogenated cyclic dipeptide named as dehydrophenylahistin (deltaPLH) was effectively prepared from a fungal metabolite (-)-phenylahistin by the enzymatic conversion catalyzed by the cell-free extract of Streptomyces albulus KO-23, an albonoursin-producing actinomycete. deltaPLH exhibited more than 1,000 times as high potent inhibitory activity toward the first cleavage of sea urchin embryos as (-)-phenylahisitn which has been reported to be a cell cycle inhibitor and more than 10,000 as high as albonoursin, indicating that deltaPLH is a promising leading compound for anticancer drugs.
2. Enzymatic synthesis of dehydro cyclo(His-Phe)s, analogs of the potent cell cycle inhibitor, dehydrophenylahistin, and their inhibitory activities toward cell division
Hiroshi Kanzaki, Satohiro Yanagisawa, Teruhiko Nitoda Biosci Biotechnol Biochem. 2004 Nov;68(11):2341-5. doi: 10.1271/bbb.68.2341.
Cyclo(His-Phe) was effectively converted to its dehydro derivatives by the enzyme of Streptomyces albulus KO-23, an albonoursin-producing actinomycete. Two types of dehydro derivatives were isolated from the reaction mixture and identified as cyclo(DeltaHis-DeltaPhe) and cyclo(His-DeltaPhe). This is the first report on cyclo(His-DeltaPhe) and the enzymatic preparation of both compounds. Cyclo(DeltaHis-DeltaPhe), a tetradehydro cyclic dipeptide, exhibited a minimum inhibitory concentration of 0.78 mumol/ml inhibitory activity toward the first cleavage of sea urchin embryos, in contrast to cyclo(His-DeltaPhe) that had no activity. The finding that the isoprenylated derivative of cyclo(DeltaHis-DeltaPhe), dehydrophyenylahistin, had 2,000 times higher activity than cyclo(DeltaHis-DeltaPhe) indicates that an isoprenyl group attached to an imidazole ring of the compound was essential for the inhibitory activity.
Recommended Products
| BBF-02614 | Nystatin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
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 ╳
