A series of N-acyloxy-pyridine-2-thione analogues (known as Barton’s ester or PTOC ester) were synthesized using four different starting carboxylic acids (adamantyl, cyclohexyl, 4-cyclohexylbutyryl and 2-ethylbutanoyl). These pyridine-2-thione-N-oxycarbonyl (PTOC) esters are able to produce carbon-centred radical species (from primary to tertiary) by photochemical activation using common tungsten lamps or sunlight as light sources. In this paper we report formation of inclusion complexes of these compounds in β-cyclodextrin by co-evaporation method. 2D-NMR spectra of complexes were taken in D2O and demonstrate in details the stereochemistry of PTOC-cyclodextrin adducts configuration. PTOC esters bearing different kind of moieties, led to a different inclusion complex capacity and a different interaction with the toroidal cavity. The complexes in situ irradiated have been able to inhibit matrix metalloproteinase (MMP) selectively and in a dose dependent way.
CYCLODEXTIN-CARRIED RADICALS INHIBIT EXPRESSION OF METALLOPROTEINASES IN VITRO
CASTAGNINO, ENZO;
2007
Abstract
A series of N-acyloxy-pyridine-2-thione analogues (known as Barton’s ester or PTOC ester) were synthesized using four different starting carboxylic acids (adamantyl, cyclohexyl, 4-cyclohexylbutyryl and 2-ethylbutanoyl). These pyridine-2-thione-N-oxycarbonyl (PTOC) esters are able to produce carbon-centred radical species (from primary to tertiary) by photochemical activation using common tungsten lamps or sunlight as light sources. In this paper we report formation of inclusion complexes of these compounds in β-cyclodextrin by co-evaporation method. 2D-NMR spectra of complexes were taken in D2O and demonstrate in details the stereochemistry of PTOC-cyclodextrin adducts configuration. PTOC esters bearing different kind of moieties, led to a different inclusion complex capacity and a different interaction with the toroidal cavity. The complexes in situ irradiated have been able to inhibit matrix metalloproteinase (MMP) selectively and in a dose dependent way.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
