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Abstract: Synthetic construction of a Lex determinant was accomplished via slightly modified Gabriel amine synthesis from three building blocks. Further transformations followed by polymerization of the Lex derivative gave a glycopolymer having trisaccharidic units as pendant-type epitopes. [Copyright &y& Elsevier]

Shiga toxin (Stx) is a major virulence factor in infection with Stx-producing Escherichia coli (STEC). We developed a series of linear polymers of acrylamide, each with a different density of trisaccharide of globotriaosylceramide (Gb3), which is a receptor for Stx, and identified Gb3 polymers with highly clustered trisaccharides as Stx adsorbents functioning in the gut. The Gb3 polymers specifically bound to both Stx1 and Stx2 with high affinity and markedly inhibited the cytotoxic activities of these toxins. Oral administration of the Gb3 polymers protected mice after administration of a fatal dose of E. coli O157:H7, even when the polymers were administered after the infection had been established. In these mice, the serum level of Stx was markedly reduced and fatal brain damage was substantially suppressed, which suggests that the Gb3 polymers entrap Stx in the gut and prevent its entrance into the circulation. These results indicate that the Gb3 polymers can be used as oral therapeutic agents that function in the gut against STEC infections. [ABSTRACT FROM AUTHOR]

Examines the therapeutic agent with oriented carbohydrates in treating infections caused by Shiga toxin-producing (Stx) Escherichia coli. Development of carbosilane dendrimers; Effects of Stx; Degradation of Stx by phagocytic macrophages in reticuloendothelial system.

[Display omitted] • One-pot reaction by means of Birch reduction followed by Williamson ether synthesis, for thiobenzylated CD and iodo-trehalose proceeded efficiently. • CD dimer linked through a trehalose moiety was synthesized. • Inclusion properties of the CD-dimer were carried out. • The CD-dimer is able to includes one TNS molecule. Synthetic assembly of two β-cyclodextrins (CDs) was efficiently accomplished using a 6,6′-di-iodotrehalose derivative as a unique linker by means of a one-pot reaction in liquid ammonia for Birch reduction and subsequent S N 2 replacement. The unique sulfide-linked CD dimer displayed a wider hydrophobic region due to the cavity of the CDs and a part of similar structure of a trehalose linker. An inclusion property of the CD dimer was tentatively examined using TNS (2-p-toluidinylnaphthalene-6-sulfonate) as a model guest compound. [ABSTRACT FROM AUTHOR]