Ascofuranone

Chembox new
Name = Ascofuranone
ImageFile = Ascofuranone.png ImageSize = 200px
ImageName = Chemical structure of Ascofuranone
IUPACName = 3-Chloro-5- [(2E,6E)-7-(5,5-dimethyl-4-oxotetrahydro-2-furanyl)-3-methyl-2,6-octadien-1-yl] -4,6-dihydroxy-2-methylbenzaldehyde
OtherNames = Ascofuranon
Section1 = Chembox Identifiers
SMILES = Oc2c(C=O)c(C)c(Cl)c(O)c2CC=C(/C)CCC=C(/C) [C@@H] 1CC(=O)C(C)(C)O1
CASNo =
Section2 = Chembox Properties
Formual = C₂₃H₂₉ClO₅
MolarMass = 420.926 g mol^-1
MeltingPt =
Density =

Ascofuranone is an antibiotic produced by the fungus Ascochyta visiae that inhibits the "Trypanosoma brucei" alternative oxidase and is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness. [cite journal |author=Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A |title=An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei |journal=Mol. Biochem. Parasitol. |volume=84 |issue=2 |pages=271–80 |year=1997 |pmid=9084049 |doi=10.1016/S0166-6851(96)02797-1] The compound is effective both in vitro cell culture and in infections in mice.cite journal |author=Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N |title=The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice |journal=Parasitol. Int. |volume=52 |issue=2 |pages=155–64 |year=2003 |pmid=12798927 |doi=10.1016/S1383-5769(03)00012-6]

Ascofuranone has also been reported to have anti-tumor activity, [cite journal |author=Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G |title=Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes |journal=J. Antibiot. |volume=41 |issue=7 |pages=959–65 |year=1988 |pmid=3417568] and modulate the immune system. [cite journal |author=Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G |title=In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system |journal=Cancer Res. |volume=46 |issue=3 |pages=1073–8 |year=1986 |pmid=3080231]

References