Synthesis and biological evaluation of carbocyclic analogues of lipid X: New nonpolar antagonists of LPS induced TNF production

Drug Design and Discovery

Volumn 16, Issue 1, 1999, Pages 41-48

  Augy Dorey, Sophie ^a   Billington, David C ^b,d   Camara, José A ^a   Gero, Stephan D ^a   Sagnard, Isabelle ^a   Quiclet Sire, Beatrice ^a   Ghezzi, Daniel ^c  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

^c Inst Richerche F   (Italy)

^d ASTON UNIVERSITY   (United Kingdom)

Author keywords

Biological activity; Carbocyclic lipid X; Endotoxic shock; Lipid X; TNF

Indexed keywords

LIPID X; LIPOPOLYSACCHARIDE; TUMOR NECROSIS FACTOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; SEPTIC SHOCK;

ACIDS, CARBOCYCLIC; DRUG INTERACTIONS; GLYCOLIPIDS; HUMANS; LIPOPOLYSACCHARIDES; SHOCK, SEPTIC; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0032817418     PISSN: 10559612     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. W.J. Christ, O. Asano, A.L.C. Robidoux, M. Perez, Y.A Wang, G R. Dubuc, W.E. Gavin, L.D. Hawkins, P.D. Mcguinness, M.A. Mullarkey, M.D. Lewis, Y. Kishi, T. Kawata, J.R. Bristol, J.R. Rose, D.P. Rossignol, S. Kobayashi, L. Hishinuma, A. Kimura, N. Asakawa, K. Katayama and I. Yamatsu (1995). E5531. A pure endotoxin antagonist of high potency, Science, 268, 80-83.
2. O. Holst (1995). Endotoxin antagonists: possible candidates for the treatment of gram-negative sepsis, Angew. Chem. Int. Ed. Engl., 34, 2000-2002.
3. M. Nishijima and C.R.H. Raetz (1979). Membrane lipid biogenesis in Escherichia coli: identification of genetic loci for phosphatidylglycero phosphate synthetase and construction of mutants lacking phosphatidyl glycerol, J. Biol. Chem., 254, 7837-7844.
4. I.A. Macher (1987). A convenient synthesis of 2-deoxy-2-((R)-3-hydroxytetradecanamido)-3-O-((R)-3-hydroxytetra-decanoyl)- α-D-glucopyranose-1-phosphate (lipid X). Carbohydrate Res., 162, 79-84.
5. H. Aschauer, A. Grob, J. Hildebrandt, E. Schuetze and P. Stutz (1990). Highly purified lipid X is devoid of immunostimulatory activity. Isolation and characterization of immunostimulating contaminants in a batch of synthetic lipid X, J. Biol. Chem., 265, 9159-9164.
6. C Lam, J. Hildebrandt, E. Schutze, B. Rosenwirth, R. Proctor, E. Liehl and P. Stutz (1991). Immunostimulatory, but not antiendotoxin, activity of lipid-X is due to small amounts of contaminating N,O-acylated disaccharide-1-phosphate: in vitro and In vivo reevaluation of the biologicalactivity of synthetic lipid-X, Infect and Immun., 59, 2351-2358.
7. S. Augy-Dorey, P. Dalko, S.D. Géro, B. Quiclet-Sire, J Eustache and P. Stutz (1993). Synthesis of carbocyclic analogues of lipid X, Tetrahedron, 49, 7997-8006.
8. M. Miyamoto, M.L. Baker and M.D. Lewis (1992). Synthesis of the carbon pseudosugar analogue of lipid X, Tetrahedron Lett., 33, 3725-3728.
9. M. Inage, H Chaki, M. Imoto, T. Shimamoto, S. Kusomoto and T Shiba (1983). Synthetic approaches to lipid A: preparation of phosphorylated disaccharides containing (R)-3-hydroxyacyl and (R)-3-acyloxyacyl groups. Tetrahedron Lett., 24, 2011-2014.
10. M. Inage, H. Chaki, S. Kusumoto and T. Shiba (1981) Chemical synthesis of phosphorylated fundamental structure of lipid-A, Tetrahedron Lett, 22, 2281-2284.
11. T. Tanaka, S. Tamatsukuri and M. Ikehara (1986). New approach to the synthesis of deoxynucleoside-phosphoramidite derivatives. Tetrahedron Lett., 27, 199-202 and references therein.
12. P.K. Jadhav (1989). Asymmetric-synthesis of (3R)-alkanoyloxytetra decanoic acids: components of bacterial lipopolysaccharides, Tetrahedron Lett., 30, 4763- 4766.
13. M. Kiso, S. Tanaka, M. Fujita, Y. Fujishima, Y. Ogawa, H. Ishida and A. Hasegawa (1987). Synthesis of the optically active 4-O-phosphono-D-glucosamine derivatives related to the nonreducing sugar subunit of bacterial lipid A, Carbohydrate Res., 162, 127-140.