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The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.

Abstract：

:To overcome the chemical and metabolic instability of the secondary fatty acyl residues in the AGP class of lipid A mimetics, the secondary ether lipid analogs of the potent TLR4 agonist CRX-527 (2) and TLR4 antagonist CRX-526 (3) were synthesized and evaluated along with their ester counterparts for agonist/antagonist activity in both in vitro and in vivo models. Like CRX-527, the secondary ether lipid 4 showed potent agonist activity in both murine and human models. Ether lipid 5, on the other hand, showed potent TLR4 antagonist activity similar to CRX-526 in human cell assays, but did not display any antagonist activity in murine models and, in fact, was weakly agonistic. Glycolipids 2, 4, and 5 were synthesized via a new highly convergent method utilizing a common advanced intermediate strategy. A new method for preparing (R)-3-alkyloxytetradecanoic acids, a key component of ether lipids 4 and 5, is also described.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Bazin HG,Murray TJ,Bowen WS,Mozaffarian A,Fling SP,Bess LS,Livesay MT,Arnold JS,Johnson CL,Ryter KT,Cluff CW,Evans JT,Johnson DA

doi

10.1016/j.bmcl.2008.09.060

subject

Has Abstract

pub_date

2008-10-15 00:00:00

pages

5350-4

issue

20

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)01131-1

journal_volume

18

pub_type

杂志文章

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