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The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLA) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toxoid vaccines, certain MLA derivatives enhance the production of tetanus toxoid-specific antibodies in mice.

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Crown ether complexation solubilizes organic and inorganic salts in nonpolar media. Induction of crystallization from such solutions can result in crystallization of the free salt rather than the complex. This affords the opportunity to examine solvent effects on the crystallization of salts and other polar materials, leading to the modification of crystal shape and lattice. This approach, which we term complexation-mediated crystallization, has been applied to the crystallization of simple organic salts and to the formation of metal sulfides. The resulting crystal morphologies and structures are presented, as are the structures of an unusual potassium complex of 18-crown-6 and crown ether complexes of lead (11) acetate, hexaaquozinc(II), and aquo(trichloro)zinc(II).

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