Immunobiological activities of a chemically synthesized lipid A of Porphyromonas gingivalis.

A synthetic lipid A of Porphyromonas gingivalis strain 381 (compound PG-381), which is similar to its natural lipid A, demonstrated no or very low endotoxic activities as compared to Escherichia coli-type synthetic lipid A (compound 506). On the other hand, compound PG-381 had stronger hemagglutinating activities on rabbit erythrocytes than compound 506. Compound PG-381 also induced mitogenic responses in spleen cells from lipopolysaccharide (LPS)-hyporesponsive C3H/HeJ mice, as well as LPS-responsive C3H/HeN mice. The addition of polymyxin B resulted in the inhibition of mitogenic activities, however, compound 506 did not show these capacities. Additionally, compound PG-381 showed a lower level of activity in inducing cytokine production in peritoneal macrophages and gingival fibroblasts from C3H/HeN mice, but not C3H/HeJ mice, in comparison to compound 506. Thus, this study demonstrates that the chemical synthesis of lipid A, mimicking the natural lipid A portion of LPS from P. gingivalis, confirms its low endotoxic potency and immunobiological activity.

[1]  T. Ogawa,et al.  Prevention of endotoxin-induced lethality in mice by calmodulin kinase activator. , 2000, FEMS immunology and medical microbiology.

[2]  K. Tanamoto.  Induction of Lethal Shock and Tolerance by Porphyromonas gingivalis Lipopolysaccharide ind-Galactosamine-Sensitized C3H/HeJ Mice , 1999, Infection and Immunity.

[3]  T. Kirikae,et al.  Lipopolysaccharides (LPS) of Oral Black-Pigmented Bacteria Induce Tumor Necrosis Factor Production by LPS-Refractory C3H/HeJ Macrophages in a Way Different from That of Salmonella LPS , 1999, Infection and Immunity.

[4]  S. Goyert,et al.  Lipopolysaccharide structure influences the macrophage response via CD14-independent and CD14-dependent pathways. , 1999, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[5]  K. Tanamoto,et al.  The lipid A moiety of Porphyromonas gingivalis lipopolysaccharide specifically mediates the activation of C3H/HeJ mice. , 1997, Journal of immunology.

[6]  A. Kinoshita,et al.  Antagonistic effect of synthetic peptides corresponding to the binding regions within fimbrial subunit protein from Porphyromonas gingivalis to human gingival fibroblasts. , 1997, Vaccine.

[7]  T. Ogawa,et al.  Stimulation of splenocytes in C3H/HeJ mice with Porphyromonas gingivalis lipid A in comparison with enterobacterial lipid A. , 1996, Immunobiology.

[8]  T. Ogawa,et al.  Immunopharmacological activities of the nontoxic monophosphoryl lipid A of Porphyromonas gingivalis. , 1996, Vaccine.

[9]  C. Manthey,et al.  Elimination of trace endotoxin protein from rough chemotype LPS , 1994 .

[10]  T. Ogawa.  Immunobiological properties of chemically defined lipid A from lipopolysaccharide of Porphyromonas (Bacteroides) gingivalis. , 1994, European journal of biochemistry.

[11]  T. Ogawa.  Chemical structure of lipid A from porphyromonas (bacteroides) gingivalis lipopolysaccharide , 1993, FEBS letters.

[12]  N. Skaug,et al.  Stimulation of B lymphocytes by lipopolysaccharides from anaerobic bacteria. , 1993, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[13]  M. Tamura,et al.  Lipopolysaccharides of Bacteroides intermedius (Prevotella intermedia) and Bacteroides (Porphyromonas) gingivalis Induce Interleukin-8 Gene Expression in Human Gingival Fibroblast Cultures , 1993, Infection and immunity.

[14]  S. Nagaoka,et al.  Lipopolysaccharides of Bacteroides intermedius (Prevotella intermedia) and Bacteroides (Porphyromonas) gingivalis induce interleukin-8 gene expression in human gingival fibroblast cultures , 1992 .

[15]  T. Ogawa,et al.  Immunobiological activities of synthetic peptide segments of fimbrial protein from Porphyromonas gingivalis. , 1991, Biochemical and biophysical research communications.

[16]  M. Caron,et al.  Structure-Function Relationships , 1991 .

[17]  T. Ogawa,et al.  Lipopolysaccharides of oral anaerobes associated with chronic inflammation: chemical and immunomodulating properties. , 1990, International reviews of immunology.

[18]  A. Weintraub,et al.  Structural characterization of the lipid A component of Bacteroides fragilis strain NCTC 9343 lipopolysaccharide. , 1989, European journal of biochemistry.

[19]  Takashi Matsumoto,et al.  An improved procedure for metallocene-promoted glycosidation. Enhanced reactivity by employing 1:2-ratio of Cp2HfCl2-AgClO4 , 1989 .

[20]  I. Olsen,et al.  Fatty acids and sugars in lipoplysaccharides from Bacteroides intermedius. Bacteroides gingivalis and Bacteroides loescheii. , 1988, Oral microbiology and immunology.

[21]  M. Listgarten,et al.  Bacteroides gingivalis, Bacteroides intermedius and Actinobacillus actinomycetemcomitans in human periodontal diseases. , 1988, Journal of clinical periodontology.

[22]  T. Kato,et al.  Hemagglutinating activity of lipopolysaccharides from subgingival plaque bacteria , 1987, Infection and immunity.

[23]  H. Okamura,et al.  Low endotoxic activities of synthetic Salmonella-type lipid A with an additional acyloxyacyl group on the 2-amino group of beta (1-6) glucosamine disaccharide 1,4'-bisphosphate , 1986, Infection and immunity.

[24]  T. Kirikae,et al.  Hemagglutination Induced by Lipopolysaccharides and Lipid A , 1986, Microbiology and immunology.

[25]  S. Kusumoto,et al.  Total synthesis of escherichia coli lipid A , 1985 .

[26]  T. Ogawa,et al.  Immunopharmacological activities of a synthetic counterpart of a biosynthetic lipid A precursor molecule and of its analogs , 1985, Infection and immunity.

[27]  E. Rietschel,et al.  Chemical structure of Escherichia coli lipid A , 1985 .

[28]  M. Hayashi,et al.  Glycosylation using glucopyranosyl fluorides and silicon-based catalysts. Solvent dependency of the stereoselection , 1984 .

[29]  S. Kusumoto,et al.  Total Synthesis of Lipid A, Active Principle of Bacterial Endotoxin , 1984 .

[30]  S. Kusumoto,et al.  Synthetic approach to lipid A: Preparation of phosphorylated disaccharides containing (R)-3-hydroxyacyl and (R)-3-acyloxyacyl groups , 1983 .

[31]  K. Joiner,et al.  Lipopolysaccharides from Bacteroides fragilis are mitogenic for spleen cells from endotoxin responder and nonresponder mice , 1982, Infection and immunity.

[32]  W. Reutter,et al.  Galactosamine-induced sensitization to the lethal effects of endotoxin. , 1979, Proceedings of the National Academy of Sciences of the United States of America.

[33]  D. Morrison,et al.  Binding of polymyxin B to the lipid A portion of bacterial lipopolysaccharides. , 1976, Immunochemistry.

[34]  Schoffstall.  Cyclopropylmethyl dihydrogen phosphate. Preparation and use in the phosphorylation of nucleosides. , 1975, The Journal of organic chemistry.

[35]  J. Dittmer,et al.  A SIMPLE, SPECIFIC SPRAY FOR THE DETECTION OF PHOSPHOLIPIDS ON THIN-LAYER CHROMATOGRAMS. , 1964, Journal of lipid research.

[36]  H. Dörfel,et al.  Die quantitative Bestimmung reduzierender Zucker auf Papierchromatogrammen , 1954 .