Relationship between the lipophilicity of gallic acid n-alquil esters' derivatives and both myeloperoxidase activity and HOCl scavenging.

Abstract:

:The gallic acid and several n-alkyl gallates, with the same number of hydroxyl substituents, varying only in the side carbonic chain length, with respective lipophilicity defined through the C log P, were studied. It evidenced the structure-activity relationship of the myeloperoxidase activity inhibition and the hypochlorous acid scavenger property, as well as its low toxicity in rat hepatic tissue. The gallates with C log P below 3.0 (compounds 2-7) were more active against the enzyme activity, what means that the addition of 1-6 carbons (C log P between 0.92 and 2.92) at the side chain increased approximately 50% the gallic acid effect. However, a relationship between the HOCl scavenging capability and the lipophilicity was not observed. With these results it is possible to suggest that the gallates protect the HOCl targets through two mechanisms: inhibiting its production by the enzyme and scavenging the reactive specie.

journal_name

Bioorg Med Chem

authors

Rosso R,Vieira TO,Leal PC,Nunes RJ,Yunes RA,Creczynski-Pasa TB

doi

10.1016/j.bmc.2006.05.038

subject

Has Abstract

pub_date

2006-09-15 00:00:00

pages

6409-13

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00413-5

journal_volume

14

pub_type

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