Пеницилловая кислота

Описание

Gram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.

Химические свойства

white to light beige crystals or powder

Использование

Gram negative bacteria utilize N-acylated homoserine lactones to coordinate expression of virulence in response to the density of the surrounding bacterial population in a process termed quorum sensing. By interfering with this communication and thereby disrupting virulence expression, quorum sensing inhibitors are emerging as an alternative to the conventional ways of fighting bacterial infections. Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. At 80 μM, penicillic acid inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. It has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.

Профиль безопасности

Poison by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Методы очистки

The lactone (furanone, anhydrous) hydrolyses to the acid (3-methoxy-4-oxo-hexa-2,5-dienoic acid, hydrate). It crystallises from water as the monohydrate (acid), or from pet ether as the anhydrous (lactone) compound. The free acid is in equilibrium with the lactone. UV: max 221nm ( 12,500) in 0.02M KOH; 228nm ( 11,500) in 0.02M HCl [Raphael J Chem Soc 1508 1948]. [Beilstein 3 II 519, 3 III 1467.] It is a possible antineoplastic.