Investigations into neuroprotectivity, stability, and water solubility of 7-O-cinnamoylsilibinin, its hemisuccinate and dehydro derivatives.

Abstract:

:Derivatives of the recently described potent neuroprotective 7-O-cinnamoylsilibinin ester were prepared: its hemisuccinate to improve water solubility and the dehydrosilibinin ester that was shown to form in assay media to investigate its role in overall neuroprotective effects. 7-O-Cinnamoyl-2,3-dehydrosilibinin is less neuroprotective than 7-O-cinnamoylsilibinin in a murine hippocampal cell line (HT-22) and we conclude that the dehydrosilibinin derivatives are not the actual carriers of neuroprotective properties, at least in the assay applied. Solubility of the test compounds was determined in shake-flask experiments and the ester's solubility was greatly improved by introduction of a hemisuccinate at the 23-position of silibinin. Time-stability curves in assay media were recorded. The hemisuccinate ester did not act as a prodrug to release 7-O-cinnamoylsilibinin but is the second ester bond to be cleaved. Nevertheless, it still exhibits significant neuroprotection. Therefore, its greatly increased solubility might effectively counterbalance lower in vitro neuroprotection.

journal_name

Arch Pharm (Weinheim)

journal_title

Archiv der Pharmazie

authors

Schramm S,Gunesch S,Lang F,Saedtler M,Meinel L,Högger P,Decker M

doi

10.1002/ardp.201800206

subject

Has Abstract

pub_date

2018-11-01 00:00:00

pages

e1800206

issue

11

eissn

0365-6233

issn

1521-4184

journal_volume

351

pub_type

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