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Minimal structural requirements of alkyl gamma-lactones capable of antagonizing the cocaine-induced motility decrease in planarians
We recently reported that the natural cyclic lactone, parthenolide, and related analogs prevent the expression of behavioral effects induced by cocaine in planarians and that parthenolide’s gamma-lactone ring is required for this effect. In the present work, we tested a series of alkyl gamma-lactones with varying chain length (1-8 carbons) to determine their ability to antagonize the planarian motility decrease induced by 200 muM cocaine. Alkyl lactones with up to a 4-carbon alkyl chain did not affect planarian motility or antagonized the cocaine-induced motility decrease; only the compound gamma-nonalactone (a gamma-lactone with a 5-carbon chain) was able to prevent the cocaine-induced behavioral patterns, while alkyl lactones with longer carbon chains failed to prevent the cocaine-induced effects. Thus, we conclude that the optimal structural features of this family of compounds to antagonize cocaine’s effect in this experimental system is a gamma-lactone ring with at a 5-carbon long functional group.
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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem