title: 2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight.
abstract: In order to investigate the effect of the fixation of the orientations of the two long chains, three types of novel derivatives of scavenger receptor inhibitor 1 were synthesized, and their biological activities were evaluated. Among the novel derivatives, 2,4-bis(octadecanoylamino)benzenesulfonic acid sodium salt (4d) showed the most potent inhibitory activity against the incorporation of 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate-labeled acetyl-LDL (DiI-acetyl-LDL) into macrophages. 2,5-Bis(octadecanoylamino)benzenesulfonic acid sodium salt (4c), a regioisomer of 4d, did not exhibit as potent an inhibitory activity as 4d, meaning that the substitution pattern of two long chains on the benzene ring must be important. Compound 4d exhibited 10 times more potent inhibitory activity against the binding of 125I-labeled acetyl-LDL to the surface of macrophages than compound 1.
authors.affiliation: R & D Laboratories, Nippon Organon K.K., 1-5-90, Tomobuchi-cho, Miyakojima-ku, Osaka 534-0016, Japan. zumikazu@kd6.so-net.ne.jp
authors.forename: Kazuya
authors.initials: K
authors.lastname: Yoshiizumi
authors.forename: Fumio
authors.initials: F
authors.lastname: Nakajima
authors.forename: Rika
authors.initials: R
authors.lastname: Dobashi
authors.forename: Noriyasu
authors.initials: N
authors.lastname: Nishimura
authors.forename: Shoji
authors.initials: S
authors.lastname: Ikeda
mesh_terms: D000818:Animals; D001161:Arteriosclerosis / Q000188:drug therapy; D001557:Benzenesulfonates / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008077:Lipoproteins, LDL / Q000378:metabolism; D008264:Macrophages / Q000378:metabolism; D008970:Molecular Weight; D011485:Protein Binding / Q000187:drug effects; D011971:Receptors, Immunologic / Q000037:antagonists & inhibitors*; D051116:Receptors, Scavenger; D013329:Structure-Activity Relationship
chemical_list: D001557:Benzenesulfonates; D008077:Lipoproteins, LDL; D011971:Receptors, Immunologic; D051116:Receptors, Scavenger; C032365:benzenesulfonic acid