Design of a minimized cyclic tetrapeptide that neutralizes bacterial endotoxins

Journal of Peptide Science

Volumn 12, Issue 7, 2006, Pages 491-496

  Mora, Puig ^a   Mas Moruno, Carlos ^b   Tamboredo, Silvia ^a   Cruz, Luis J ^b   Pérez Payá, Enrique ^a,c   Albericio, Fernando ^b  

^a CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c INSTITUTO DE BIOMEDICINA DE VALENCIA   (Spain)

Author keywords

Disulfide bridge formation; Endotoxin; LALF; Lipid A; Molecular recognition; Peptide mapping; Peptides; Sepsis; Septic shock; Solid phase

Indexed keywords

BACTERIUM LIPOPOLYSACCHARIDE; ENDOTOXIN; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 03; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 04; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 05; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 06; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 07; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 08; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 09; LIMULUS LIPOPOLYSACCHARIDE FACTOR ANTIBODY 14C; LIPOPOLYSACCHARIDE BINDING PROTEIN; PROTEIN ANTIBODY; SCAFFOLD PROTEIN; TETRAPEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING COMPETITION; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; MOLECULAR RECOGNITION; NONHUMAN; PEPTIDE ANALYSIS; PEPTIDE MAPPING; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN MODIFICATION; RECEPTOR BINDING; RESIDUE ANALYSIS; SEPTIC SHOCK; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; BACTERIAL TOXINS; DRUG DESIGN; ENDOTOXINS; HUMANS; LIMULUS TEST; LIPOPOLYSACCHARIDES; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDE MAPPING; PEPTIDES, CYCLIC; SHOCK, SEPTIC;

BACTERIA (MICROORGANISMS);

EID: 33745936909     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.755     Document Type: Article

References (22)

1. Silverman H, Owen MJ. Bactericidal Endotoxin in Human Disease. XOMA: Berkeley, CA, USA, 1998; 1-28.
2. Riedemann NC, Guo RF, Ward PA. Novel strategies for the treatment of sepsis. Nat. Med. 2003; 9: 517-524.
3. Rietschel ET, Brade H, Holst O, Brade L, Muller-Loennies S, Mamat U, Zahringer U, Beckmann F, Seydel U, Brandenburg K, Ulmer AJ, Mattern T, Heine H, Schletter J, Loppnow H, Schonbeck U, Flad HD, Hauschildt S, Schade UF, Di Padova F, Kusumoto S, Schumann RR. Bacterial endotoxin: chemical constitution, biological recognition, host response, and immunological detoxification. Curr. Top. Microbiol. Immunol. 1996; 216: 39-81.
4. Hailman E, Lichenstein HS, Wurfel MM, Miller DS, Johnson DA, Kelley M, Busse LA, Zukowski MM, Wright SD. Lipopolysaccharide (LPS)-binding protein accelerates the binding of LPS to CD14. J. Exp. Med. 1994; 179: 269-277.
5. Schumann RR, Rietschel ET, Loppnow H. The role of CD14 and lipopolysaccharide-binding protein (LBP) in the activation of the different cell types by endotoxin. Med. Microbiol. Immunol. (Berl.) 1994; 183: 270-297.
6. Anderson KV. Toll signaling pathways in the innate immune response. Curr. Opin. Immunol. 2000; 12: 13-19.
7. Fischer CJ, Slotman GJ, Opal SM. Initial evaluation of human recombinant interleukin-1 receptor antagonist (IL-1ra) in the treatment of patients with sepsis syndrome: preliminary results from a phase III multicenter trials. Crit. Care Med. 1993; 4: 85.
8. Abraham E, Anzueto A, Gutierrez G. Double-blind randomised controlled trials of monoclonal antibody to human tumor necrosis factor in treatment of septic shock. Lancet 1998; 351: 929-933.
9. Hoess A, Watson S, Siber GR, Liddington R. Crystal structure of an endotoxin-neutralizing protein from the horseshoe crab, Limules anti-LPS factor, at 1.5 A resolution. EMBO J. 1993; 12: 3351-3356.
10. Ried C, Wahl C, Miethke T, Wellnhofer G, Landgraf C, Schneider-Mergener J, Hoess A. High affinity endotoxin-binding and neutralizing peptides based on the crystal structure of recombinant limulus anti-lipopolysaccharide factor. J. Biol. Chem. 1996; 271: 28120-28127.
11. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test detection of free terminal amino group in the solid-phase synthesis of peptides. Anal. Biochem. 1969; 34: 595.
12. Madder A, Farcy N, Hosten NGC, De Muynck H, De Clercq PJ, Barry J, Davis AP. A novel sensitive colorimetric assay for visual detection of solid-phase bound amines. Eur. J. Org. Chem. 1999; 11: 2787-2791.
13. Walker JM, Series Editor. Methods in Molecular Biology™. Peptide Analysis Protocols, Vol. 36. Dunn BM, Pennington MW. 1994.
14. Tam JP, Wu CR, Liu W, Zhang JW. Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications. J. Am. Chem. Soc. 1991; 113: 6657-6662.
15. Ellman GL. Tissue sulfhydryl group. Arch. Biochem. Biophys. 1959; 82: 70-77.
16. U.S Department of Health and Human Services, P.H.S., Food and Drug Administration. Guideline on Validation of the Limulus Amebocyte Lysate test as an End-Product Endotoxin test for Human and Animal Parental Drugs, Biological Products and Medical Services, Rockville, MD 20857, 1987.
17. Young NS, Levin J, Prendergast RA. An invertebrate coagulation system activated by endotoxin: evidence for enzymatic mechanism. J. Clin. Invest. 1972; 51(7): 1790-1797.
18. Tsubery H, Ofek I, Cohen S, Fridkin M. Structure-function studies of polymyxin B nonapeptide: implications to sensitization of gram-negative bacteria. J. Med. Chem. 2000; 43: 3085-3092.
19. Battafaraono RJ, Battafaraono RJ, Dahlberg PS, Ratz CA, Johnston JW, Gray BH, Haseman JR, Mayo KH, Dunn DL. Peptide derivatives of three distinct lipopolysaccharide binding proteins inhibit lipopolysaccharide-induced tumor necrosis factor-alpha secretion in vitro. Surgery 1995; 118: 318-324.
20. Schumann RR, Lamping N, Hoess A. Interchangeable endotoxin-binding domains in proteins with opposite lipopolysaccharide-dependent activities. J. Immunol. 1997; 159: 5599-5605.
21. Beamer LJ, Carroll SF, Eisenberg D. The BPI/LBP family of proteins: a structural analysis of conserved regions. Protein Sci. 1998; 7(4): 906-914.
22. Pristovsek P, Feher K, Szilagyi L, Kidric J. Structure of a synthetic fragment of the LALF protein when bound to lipopolysaccharide. J. Med. Chem. 2005; 48: 1666-1670.