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

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:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11571/746219
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 5
  • ???jsp.display-item.citation.isi??? 5
social impact