In a process associated with ageing and neurodegeneration, radical peroxidation of docosahexaenoic acid (DHA) in neurons affords a multitude of prostaglandin-like neuroprostanes in a non-regioselective and non-stereoselective manner. In this paper, the synthesis of racemic 17-A4 -NeuroP and 14-A4 -NeuroP validated a general approach to several regioisomeric cyclopentenone A4 - and J4 -NeuroPs needed for bio- logical tests. In preliminary experiments 17-A4 -NeuroP, in analogy with 14-A4 -NeuroP, readily adducted GSH free thiol, suggesting a similar mechanism of action for biological activity.
Biology and chemistry of neuroprostanes. First total synthesis of 17-A4-NeuroP: Validation of a convergent strategy to a number of cyclopentenone neuroprostanes
PORTA, ALESSIO;PASI, MAURIZIO ANGELO;BRUNOLDI, ENRICO;ZANONI, GIUSEPPE;VIDARI, GIOVANNI
2013-01-01
Abstract
In a process associated with ageing and neurodegeneration, radical peroxidation of docosahexaenoic acid (DHA) in neurons affords a multitude of prostaglandin-like neuroprostanes in a non-regioselective and non-stereoselective manner. In this paper, the synthesis of racemic 17-A4 -NeuroP and 14-A4 -NeuroP validated a general approach to several regioisomeric cyclopentenone A4 - and J4 -NeuroPs needed for bio- logical tests. In preliminary experiments 17-A4 -NeuroP, in analogy with 14-A4 -NeuroP, readily adducted GSH free thiol, suggesting a similar mechanism of action for biological activity.File in questo prodotto:
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