Marine compounds with therapeutic potential in gram-negative sepsis

Marine Drugs

Volumn 11, Issue 6, 2013, Pages 2216-2229

  Solov'eva, Tamara ^a   Davydova, Viktoria ^a   Krasikova, Inna ^a   Yermak, Irina ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Carrageenan; Chitosan; Endotoxin; Endotoxin antagonists; Lipid A; Sepsis

Indexed keywords

CARRAGEENAN; CD14 ANTIGEN; CHITOSAN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPID A; LIPOPOLYSACCHARIDE; MYELOID DIFFERENTIATION FACTOR 88; PROTEIN MD 2; TOLL LIKE RECEPTOR 4; TUMOR NECROSIS FACTOR ALPHA;

ALTEROMONAS; ANIMAL EXPERIMENT; ANIMAL MODEL; BINDING AFFINITY; BLASTOCHLORIS VIRIDIS; CHEMICAL STRUCTURE; CHRYSEOBACTERIUM; CONTROLLED STUDY; COVALENT BOND; ESCHERICHIA COLI; GENE EXPRESSION; GRAM NEGATIVE SEPSIS; HUMAN; IDIOMARINA; IMMUNOCOMPETENT CELL; IMMUNOMODULATION; IMMUNOSTIMULATION; LIPOPHILICITY; MARINOMONAS; MOUSE; NONHUMAN; PHYLOGENY; PROTEIN BINDING; PSEUDOALTEROMONAS; RED ALGA; REVIEW; SEPTIC SHOCK;

ANIMALIA; BACTERIA (MICROORGANISMS); CRUSTACEA; NEGIBACTERIA; RHODOPHYTA;

EID: 84879472868     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11062216     Document Type: Review

References (54)

1. Cohen, J. The immunopathogenesis of sepsis. Nature 2002, 420, 885-891. (Pubitemid 36019643)
2. Van Amersfoort, E.S.; van Berkel, T.J.; Kuiper, J. Receptors, mediators, and mechanisms involved in bacterial sepsis and septic shock. Clin. Microbiol. Rev. 2003, 16, 379-414. (Pubitemid 36871313)
3. Hawkins, L.D.; Christ, W.J.; Rossignol, D.P. Inhibition of endotoxin response by synthetic TLR4 antagonists. Curr. Topics Med. Chem. 2004, 4, 1147-1171. (Pubitemid 38923439)
4. Rietschel, E.T.; Kirikae, T.; Schade, F.U.; Mamat, U.; Schmidt, G.; Loppnow, H.; Ulmer, A.J.; Zahinger, U.; Seydel, U.; Di Padova, F.; et al. Bacterial endotoxin: Molecular relationships of structure to activity and fuction. FASEB J. 1994, 8, 217-225.
5. Imoto, M.; Kusumoto, S.; Shiba, T.; Naoki, H.; Iwashita, T.; Rietschel, E.T.; Wollenweber, H.-W.; Galanos, C.; Luderitz, O. Chemical structure of Escherichia coli lipid A: Linkage site of acyl groups in the disaccharide backbone. Tetrahedron Lett . 1983, 24, 4017-4021.
6. Roppel, J.; Mayer, H.; Weckesser, J. Identification of a 2,3-diamino-2,3-dideoxyhexose in the lipid A component of lipopolysaccharides of Rhodopseudomonas viridis and Rhodopseudomonas palustris . Carbohydr. Res. 1975, 40, 31-40.
7. Qureshi, N.; Takayama, K.; Kurtz, R. Diphosphoryl lipid A obtained from nontoxic lipopolysaccharide of Rhodopseudomonas sphaeroides is on endotoxin antagonist in mice. Infect. Immun. 1991, 59, 441-444.
8. Bunnell, E.; Lynn, M.; Habet, K.; Neumann, A.; Perdomo, C.A.; Friedhoff, L.T.; Rogers, S.L.; Parrillo, J.E. A lipid A analog, E5531, blocks the endotoxin response in human volunteers with experimental endotoxemia. Crit. Care Med. 2000, 28, 2713-2720.
9. Ribi, E. Beneficial modification of the endotoxin molecule. J. Biol. Response Mod. 1984, 3, 1-9. (Pubitemid 14172083)
10. Sato, K.; Yung, Y.C.; Fukushima, A.; Saiki, I.; Takahashi, T.A.; Fujihara, M.; Tonooka, S.; Azuma, I. A novel synthetic lipid A analog with low endotoxicity, DT-5461, prevents lethal endotoxemia. Infect. Immun. 1995, 63, 2859-2866.
11. Raetz, C.R.H.; Reynolds, C.M.; Trent, M.S.; Bishop, R.E. Lipid A modification systems in Gram-negative bacteria. Annu. Rev. Biochem. 2007, 76, 295-329.
12. Zahringer, U.; Linder, B.; Rietschel, E.T. Molecular structure of lipid, the endotoxic center of bacterial lipopolysaccharides. Adv. Carbohydr. Chem. Biochem. 1994, 50, 211-276.
13. DiRienzo, J.M.; MacLeod, R.A. Composition of the fractions separated by polyacrylamide gel electrophoresis of the lipopolysaccharide of a marine bacterium. J. Bacteriol. 1978, 136, 158-167. (Pubitemid 9037965)
14. Moule, A.L.; Wilkinson, S.G. Composition of lipopolysaccharides grom Alteromonas putrefaciens (Shewanella putrefaciens). J. Gen. Microbiol. 1989, 135, 163-173.
15. Corsaro, M.M.; Piaz, F.D.; Lanzetta, R.; Parrilli, M. Lipid A structure of Pseudoalteromonas haloplanktis TAC 125: Use of electrospray ionization tandem mass spectrometry for the determination of fatty acid distribution. J. Mass Spectrom. 2002, 37, 481-488. (Pubitemid 34578390)
16. Krasikova, I.N.; Kapustina, N.V.; Svetashev, V.I.; Gorshkova, R.P.; Tomshich, S.V.; Nazarenko, E.L.; Komandrova, N.A.; Ivanova, E.P.; Gorshkova, N.M.; Romanenko, L.A.; et al. Chemical characterization of lipid A from some marine Proteobacteria. Biochemistry (Mosc.) 2001, 66, 1047-1054.
17. Krasikova, I.N.; Kapustina, N.V.; Isakov, V.V.; Gorshkova, N.M.; Solov'eva, T.F. Elucidation of structure of lipid A from the marine Gram-negative bacterium Pseudoalteromonas haloplanktis ATCC 14393T. Russ. J. Bioorg. Chem. 2004, 30, 367-373. (Pubitemid 39127808)
18. T. Chem. Nat. Compd. 2007, 43, 519-524.
19. T. Biochemistry (Mosc.) 2004, 69, C.407-C.412.
20. Krasikova, I.N.; Kapustina, N.V.; Isakov, V.V.; Dmitrenok, A.S.; Dmitrenok, P.S.; Gorshkova, N.M.; Solov'eva, T.F. Detailed structure of lipid A from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119T. Eur. J. Biochem. 2004, 271, 2895-2904. (Pubitemid 38986926)
21. Vorobeva, E.V.; Dmitrenok, A.S.; Dmitrenok, P.S.; Isakov, V.V.; Krasikova, I.N.; Solov'eva, T.F. The structure of uncommon lipid A from the marine bacterium Marinomonas communis ATCC 27118T. Russ. J. Bioorg. Chem. 2005, 31, 362-371. (Pubitemid 41204456)
22. Vorobeva, E.V.; Krasikova, I.N.; Dmitrenok, A.S.; Dmitrenok, P.S.; Nedashkovskaya, O.I.; Solov'eva, T.F. An unusual lipid A from a marine bacterium Chryseobacterium scophtalmum CIP 104199T. Russ. J. Bioorg. Chem. 2006, 32, 485-491. (Pubitemid 44411687)
23. Beutler, B.; Milsark, I.W.; Cerami, A.C. Passive immunization against cachectin/tumor necrosis factor protects mice from lethal effect of endotoxin. Science 1985, 229, 869-871. (Pubitemid 16246587)
24. Vorobeva, E.V.; Krasikova, I.N.; Solov'eva, T.F. Influence of lipopolysaccharides and lipids A from some marine bacteria on spontaneous and Escherichia coli LPS-induced TNF-α release from peripheral human blood cells. Biochemistry (Mosc.) 2006, 71, 759-766. (Pubitemid 44092039)
25. Christ, W.J.; Asano, O.; Robidoux, A.L.C.; Perez, M.; Wang, Y.A.; Dubuc, G.R.; Gavin, W.E.; Hawkins, L.D.; Mcguinness, P.D.; Mullarkey, M.A.; et al. E5531, a pure endotoxin antagonist of high potency. Science 1995, 268, 80-83.
26. Kean, T.; Thanou, M. Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliv. Rev. 2010, 62, 3-11.
27. Nishimura, K.; Nishimura, S.; Nishi, N.; Saiki, I.; Tokura, S.; Azuma, I. Immunologic activity of chitin and its derivatives. Vaccine 1984, 2, 93-99.
28. Il'ina, A.V.; Varlamov, V.P. Chitosan-Based polyelectrolyte complexes: A review. Appl. Biochem. Microbiol. 2005, 41, 5-11. (Pubitemid 40363120)
29. Anspach, F.B. Endotoxin removal by affinity sorbents. J. Biochem. Biophys. Meth . 2001, 49, 665-681. (Pubitemid 33022580)
30. Kong, M.; Chen, X.G.; Xing, K.; Park, H.J. Antimicrobial properties of chitosan and mode of action: A state of the art review. Int. J. Food Microbiol . 2010, 144, 51-63.
31. Jurgens, G.; Muller, M.; Gardiel, P.; Koch, M.N.J.; Nakakubo, H.; Blume, A.; Brandenburg, K. Investigation into the interaction of recombinant human serum albumin with Re - Lipopolysaccharide and lipid A. J. Endotoxin Res. 2002, 8, 115-126. (Pubitemid 34546188)
32. Andersson, M.; Giorard, R.; Cazenave, P. Interaction of NK-lysine, a peptide produced by cytolytic lymphocytes, with endotoxin. Infect. Immun. 1999, 67, 201-205. (Pubitemid 29021649)
33. Davydova, V.N.; Naberezhnykh, G.A.; Yermak, I.M.; Gorbach, V.I.; Solov'eva, T.F. Determination of binding constants of lipopolysaccharides of different structure with chitosan. Biochemistry (Mosc.) 2006, 71, 332-339.
34. Yermak, I.M.; Davidova, V.N.; Gorbach, V.I.; Luk'yanov, P.A.; Solov'eva, T.F.; Ulmer, A.J.; Buwitt-Beckmann, U.; Rietschel, E.T.; Ovodov, Y.S. Forming and immunological properties of some lipopolysaccharide-chitosan complexes. Biochimie 2006, 88, 23-30. (Pubitemid 41668615)
35. Seydel, U.; Hawkins, L.; Schromm, A.B.; Heine, H.; Scheel, O.; Koch, M.H.; Brandenburg, K. The generalized endotoxic principle. Eur. J. Immunol. 2003, 33, 1586-1592. (Pubitemid 36790419)
36. Wilkinson, S.G. Bacterial lipopolysaccharides - Themes and variations. Prog. Lipid Res. 1996, 35, 283-343. (Pubitemid 27092445)
37. Naberezhnykh, G.A.; Gorbach, V.I.; Likhatskaya, G.N.; Davidova, V.N.; Solov'eva, T.F. Interaction of N -acylated chitosans with lipopolysaccharide. Biochemistry (Mosc.) 2008, 73, 432-441.
38. Davydova, V.N.; Yermak, I.M.; Gorbach, V.I.; Krasikova, I.N.; Solov'eva, T.F. Interaction of bacterial endotoxins with chitosan. Effect of endotoxin structure, chitosan molecular mass, and ionic strength of the solution on the formation of the complex. Biochemistry (Mosc.) 2000, 65, 1082-1090.
39. David, S.A.; Silverstein, R.; Amura, C.R.; Kielian, T.; Morrison, D.C. Lipopolyamines: Novel antiendotoxin compounds that reduce mortality in experimental sepsis caused by Gram-negative bacteria. Antimicrob. Agents Chemother. 1999, 43, 912-919. (Pubitemid 29165757)
40. Millera, K.A.; Kumarb, E.V.K.S.; Wooda, S.J.; Cromera, J.R.; Dattab, A.; David, S.A. Lipopolysaccharide sequestrants: Structural correlates of activity and toxicity in novel acylhomospermines. J. Med. Chem. 2005; 48, 2589-2599. (Pubitemid 40516448)
41. Naberezhnykh, G.A.; Gorbach, V.I.; Likhatskaya, G.N.; Bratskaya, S.Yu.; Solov'eva, T.F. Interaction of N-acylated and N-alkylated chitosans included in liposomes with lipopolysaccharide of Gram-negative bacteria. Biochemistry (Mosc.) 2013, 78, 301-308.
42. Roth, R.I. Hemoglobin enhances the binding of bacterial endotoxin to human endothelial cells. Thromb. Haemost. 1996, 76, 258-262. (Pubitemid 26285262)
43. Tapping, R.I.; Akashi, S.; Miyake, K.; Godowski, P.J.; Tobias, P.S. Toll-like receptor 4, but not Toll-like receptor 2, is a signaling receptor for Escherichia and Salmonella lipopolysaccharides. J. Immunol. 2000, 165, 5780-5787.
44. Otterlei, M.; Varum, K.M.; Ryan, L.; Espevik, T. Characterization of binding and TNF-α-inducing ability of chitosans on monocytes: The involvement of CD 14. Vaccine 1994, 12, 825-832.
45. Russell, J.A. Management of sepsis. N. Engl. J. Med. 2006, 355, 1699-1713. (Pubitemid 44583960)
46. Yermak, I.M.; Khotimchenko, Y.S. Chemical Properties, Biological Activities and Applications of Carrageenan from Red Algae. In Recent Advances in Marine Biotechnology; Fingerman, M., Nagabhushanam, R., Eds.; Science Publisher Inc.: New York, NY, USA, 2003; Volume 3, pp. 207-255.
47. Döcke, W.D.; Randow, F.; Styrhe, U.; Krausch, D.; Asadullah, K.; Reinke, P.; Volk, H.-D.; Kox, W. Monocyte deactivation in septic patients: Restoration by INF-γ treatment. Nat. Med. 1997, 3, 678-681.
48. Ivanushko, L.A.; Solov'eva, T.F.; Zaporozhets, T.S.; Lukyanov, P.A.; Gorbach, V.I.; Besednova, N.N. Comparative study of immunomodulating properties of chitosan and its derivatives. Med. Immunol. (Russ.) 2007, 9, 397-404.
49. Yermak, I.M.; Barabanova, A.O.; Aminin, D.L.; Davydova, V.N.; Sokolova, E.V.; Solov'eva, T.F.; Kim, Y.H.; Shin, K.S. Effects of structural peculiarities of carrageenans on their immunomodulatory and anticoagulant activities. Carbohydr. Polym. 2012, 87, 713-720.
50. Polyakova, A.M.; Astrina, O.S.; Bakhtina, Yu.A.; Maleev, V.V.; Barabanova, A.O.; Yermak, I.M. Possibility of correction of functional state of human trombocytes with natural polysaccharides in patients with alimentary toxic infections and in experimental endotoxinamia. Infektsionnye Bolezn. (Russ.) 2005, 3, 44-46.
51. Yermak, I.M.; Barabanova, A.O.; Kukarskikh, T.A.; Solovyova, T.F.; Bogdanovich, R.N.; Polyakova, A.M.; Astrina, O.S.; Maleev, V.V. Natural polysaccharide carrageenan inhibits toxic effect of Gram-negative bacterial endotoxins. Bull. Exp. Biol. Med. 2006, 141, 191-193.
52. Ivanushko, L.A.; Soloviova, T.F; Zaporozhets, T.S.; Somova, L.M.; Gorbatch, V.I. Antibacterial and antitoxic properties of chitosan and its derivatives. Pac. Med. J. (Russ.) 2009, 3, 82-85.
53. Khasina, E.I.; Sgrebneva, M.N.; Yermak, I.M.; Maleev, V.V. Effect of carrageenan on the non-specific resistance of mice with LPS-induced endotoxemia. J. Microbiol. Epidemiol. Immunol. (Russ.) 2007, 2, 57-60.
54. Khasina, E.I.; Sgrebneva, M.N.; Yermak, I.M; Gorbach, V.I. Chitosan and unspecific resistance. Bull. FEB RAS (Russ.) 2005, 1, 62-71.