{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T01:51:49Z","timestamp":1789869109630,"version":"4.0.1"},"reference-count":25,"publisher":"Oxford University Press (OUP)","issue":"3","license":[{"start":{"date-parts":[[2007,3,5]],"date-time":"2007-03-05T00:00:00Z","timestamp":1173052800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2007,3,15]]},"abstract":"<jats:title>Summary<\/jats:title><jats:p>Porphyromonas gingivalis is a Gram-negative anaerobic oral black-pigmented bacterium closely associated with chronic periodontitis. Lipopolysaccharide (LPS) derived from P. gingivalis is shown to be unusual because the LPS contains a greater number of lipid A species, such as tri-, tetra-, and\/or penta-acylated lipid As. In this study, a lipid A possessing penta-fatty acyl chains derived from P. gingivalis strain 381 (compound PG-381\u20135FA) was synthesized, and examined for its immunobiological activities, compared with a tri-acylated lipid A (compound PG-381\u20133FA) synthesized previously. Compound PG-381-5FA, similar to compound PG-381-3FA, demonstrated weaker activity in a Limulus test as compared with Escherichia coli-type synthetic lipid A (compound 506). Compound PG-381-5FA, followed by compound PG-381-3FA, induced KC, interleukin-6, and tumour necrosis factor-\u03b1 production in peritoneal macrophages from LPS-responsive C3H\/HeN mice, but not in those from LPS-hyporesponsive C3H\/HeJ mice. Furthermore, compound PG-381-5FA, as well as compound PG-381-3FA, activated nuclear factor-\u03baB via Toll-like receptor (TLR)4\/mD-2, but not TLR2, in a manner similar to compound 506, and worked as an antagonist for compound 506-induced cell activation. In the case of human peripheral blood mononuclear cells, compound PG-381-5FA showed much stronger IL-6-inducing activity than compound PG-381-3FA. The present results demonstrate that the chemical synthesis of a penta-acylated lipid A, mimicking the natural lipid A portion of LPS from P. gingivalis, is attributable to immune cell activation through TLR4, similar to that of compound 506.<\/jats:p>","DOI":"10.1111\/j.1365-2249.2007.03346.x","type":"journal-article","created":{"date-parts":[[2010,8,12]],"date-time":"2010-08-12T14:11:24Z","timestamp":1281622284000},"page":"529-536","source":"Crossref","is-referenced-by-count":52,"title":["Toll-like receptor 4-dependent recognition of structurally different forms of chemically synthesized lipid As of<i>Porphyromonas gingivalis<\/i>"],"prefix":"10.1093","volume":"148","author":[{"given":"N","family":"Sawada","sequence":"first","affiliation":[{"name":"Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"T","family":"Ogawa","sequence":"additional","affiliation":[{"name":"Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Y","family":"Asai","sequence":"additional","affiliation":[{"name":"Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Y","family":"Makimura","sequence":"additional","affiliation":[{"name":"Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"A","family":"Sugiyama","sequence":"additional","affiliation":[{"name":"Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2007,3,5]]},"reference":[{"key":"2022010414515931800_b1","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1128\/iai.49.1.225-237.1985","article-title":"Synthetic lipid A with endotoxic and related biological activities comparable to those of a natural lipid A from an Escherichia coli re-mutant","volume":"49","author":"Kotani","year":"1985","journal-title":"Infect Immun"},{"key":"2022010414515931800_b2","doi-asserted-by":"crossref","first-page":"872","DOI":"10.1128\/iai.52.3.872-884.1986","article-title":"Low endotoxic activities of synthetic Salmonella-type lipid A with an additional acyloxyacyl group on the 2-amino group of \u03b2 (1\u20136) glucosamine disaccharide 1,4\u2032-bisphosphate","volume":"52","author":"Kotani","year":"1986","journal-title":"Infect Immun"},{"key":"2022010414515931800_b3","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1111\/j.1600-051X.1988.tb00999.x","article-title":"Bacteroides gingivalis. 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