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Studies on Scavenger Receptor Inhibitors. Part 1: Synthesis and Structure-Activity Relationships of Novel Derivatives of Sulfatides

Studies on Scavenger Receptor Inhibitors. Part 1: Synthesis and Structure-Activity Relationships of Novel Derivatives of Sulfatides

Kazuya Yoshiizumi, Fumio Nakajima, Rika Dobashi, Noriyasu Nishimura, Shoji Ikeda

Bioorg Med Chem. 2002 Aug;10(8):2445-60.

PMID: 12057634

Abstract:

Scavenger receptors have been proven to be implicated in the formation of atherosclerotic lesions. A series of novel derivatives of sulfatides were synthesized, and their inhibitory activities against incorporation of DiI-acetyl-LDL into macrophages were evaluated in order to clarify the structure-activity relationships of sulfatides as a scavenger receptor inhibitor and find out novel inhibitors with synthetic easiness. The chemical modification of the substructures of sulfatides led to the establishment of the following structure-activity relationships; (1) the ceramide moiety can be replaced with another structure bearing two long chains, (2) the galactose moiety can be replaced with another structure or be deleted without a large decrease in the inhibitory activity, (3) the sulfate moiety was crucial, and it was the most preferable functional group for a potent inhibitory activity. The inhibitory activity of (S)-2-octadecanoylamino-2-tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) against incorporation of DiI-acetyl-LDL into macrophages was proven to be based on the inhibition against the binding of acetyl-LDL to the surface of macrophages. We discovered novel scavenger receptor inhibitors with synthetic easiness, such as (S)-2-octadecanoylamino-2-(tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) and 2-octadecanoylamino-1-(octadecanoylaminomethyl)ethyl sulfate sodium salt (13q).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP546747	Ethyl sulfate sodium salt		546-74-7	Price

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