Structural requirement for the agonist activity of the TLR2 ligand Pam2Cys

Amino Acids

Volumn 39, Issue 2, 2010, Pages 471-480

  Zeng, Weiguang ^a   Eriksson, Emily ^a   Chua, Brendon ^a   Grollo, Lara ^a   Jackson, David C ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Lipopeptide; Peptide; Structure activity relationship; TLR2; Vaccine

Indexed keywords

3 (1,2 DIHYDROXYPROPYL) PROPIONIC ACID; [2,3 BIS (PALMITOYLOXY)PROPYL]CYSTEINE; LIPOPEPTIDE; N (1,2 DIHYDROXYPROPYL) SUCCINIC ACID; TOLL LIKE RECEPTOR 2; UNCLASSIFIED DRUG; LIGAND; S-(2,3-BIS(PALMITOYLOXY)PROPYL)CYSTEINE;

ARTICLE; CD4+ T LYMPHOCYTE; CD8+ T LYMPHOCYTE; CELLULAR IMMUNITY; CHEMICAL BOND; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; HUMORAL IMMUNITY; IMMUNOGENICITY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; UPREGULATION; AGONISTS; CHEMISTRY;

LIGANDS; LIPOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TOLL-LIKE RECEPTOR 2;

EID: 80051704868     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-009-0463-0     Document Type: Article

References (37)

1. Alphs HH, Gambhira R, Karanam B, Roberts JN, Jagu S, Schiller JT, Zeng W, Jackson DC, Roden RB (2008) Protection against heterologous human papillomavirus challenge by a synthetic lipopeptide vaccine containing a broadly cross-neutralizing epitope of L2. Proc Natl Acad Sci USA 105:5850-5855
2. Batzloff MR, Hartas J, Zeng W, Jackson DC, Good MF (2006) Intranasal vaccination with a lipopeptide containing a conformationally constrained conserved minimal peptide, a universal T cell epitope, and a self-adjuvanting lipid protects mice from group A streptococcus challenge and reduces throat colonization. J Infect Dis 194:325-330
3. Baz A, Buttigieg K, Zeng W, Rizkalla M, Jackson DC, Groves P, Kelso A (2008) Branched and linear lipopeptide vaccines have different effects on primary CD4+ and CD8+ T-cell activation but induce similar tumor-protective memory CD8+ T-cell responses. Vaccine 26:2570-2579
4. Belz G, Smith C, Bharadwaj M, Rice A, Jackson D (2004) DCs as targets for vaccine design. Cytotherapy 6:88-98
5. Borges E, Wiesmuller KH, Jung G, Walden P (1994) Efficacy of synthetic vaccines in the induction of cytotoxic T lymphocytes. Comparison of the costimulating support provided by helper T cells and lipoamino acid. J Immunol Methods 173:253-263
6. Buwitt-Beckmann U, Heine H, Wiesmuller KH, Jung G, Brock R, Akira S, Ulmer AJ (2005a) Toll-like receptor 6-independent signaling by diacylated lipopeptides. Eur J Immunol 35:282-289
7. Buwitt-Beckmann U, Heine H, Wiesmuller KH, Jung G, Brock R, Ulmer AJ (2005b) Lipopeptide structure determines TLR2 dependent cell activation level. Febs J 272:6354-6364
8. Buwitt-Beckmann U, Heine H, Wiesmuller KH, Jung G, Brock R, Akira S, Ulmer AJ (2006) TLR1-and TLR6-independent recognition of bacterial lipopeptides. J Biol Chem 281:9049-9057
9. Chua BY, Zeng W, Lau YF, Jackson DC (2007) Comparison of lipopeptide-based immunocontraceptive vaccines containing different lipid groups. Vaccine 25:92-101
10. Day EB, Zeng W, Doherty PC, Jackson DC, Kedzierska K, Turner SJ (2007) The context of epitope presentation can influence functional quality of recalled influenza A virus-specific memory CD8+ T cells. J Immunol 179:2187-2194
11. Deliyannis G, Kedzierska K, Lau YF, Zeng W, Turner SJ, Jackson DC, Brown LE (2006) Intranasal lipopeptide primes lungresident memory CD8+ T cells for long-term pulmonary protection against influenza. Eur J Immunol 36:770-778
12. Heine H, Lien E (2003) Toll-like receptors and their function in innate and adaptive immunity. Int Arch Allergy Immunol 130:180-192
13. Jackson DC, Fitzmaurice C, Sheppard RC, McMurray J, Brown LE (1995) Antigenic and immunogenic properties of synthetic peptide-based T-cell determinant polymers. Biomed Pept Proteins Nucleic Acids 1:171-176
14. Jackson DC, Lau YF, Le T, Suhrbier A, Deliyannis G, Cheers C, Smith C, Zeng W, Brown LE (2004) A totally synthetic vaccine of generic structure that targets Toll-like receptor 2 on dendritic cells and promotes antibody or cytotoxic T cell responses. Proc Natl Acad Sci USA 101:15440-15445
15. Jin MS, Lee JO (2008a) Structures of the toll-like receptor family and its ligand complexes. Immunity 29:182-191
16. Jin MS, Lee JO (2008b) Structures of TLR-ligand complexes. Curr Opin Immunol 20:414-419
17. Jin MS, Kim SE, Heo JY, Lee ME, Kim HM, Paik SG, Lee H, Lee JO (2007) Crystal structure of the TLR1-TLR2 heterodimer induced by binding of a tri-acylated lipopeptide. Cell 130:1071-1082
18. Jung G, Bessler WG (1995) Lipopeptides as adjuvant and intergratd adjuvanticity. In: Zegers ND, Boersma WJA, Claassen E (eds) Immunological recognition of peptides in medicine and biology. CRC Press, Boca Raton, pp 159-168
19. Kumagai Y, Takeuchi O, Akira S (2008) Pathogen recognition by innate receptors. J Infect Chemother 14:86-92
20. Lau YF, Deliyannis G, Zeng W, Mansell A, Jackson DC, Brown LE (2006) Lipid-containing mimetics of natural triggers of innate immunity as CTL-inducing influenza vaccines. Int Immunol 18:1801-1813
21. Lehner MD, Morath S, Michelsen KS, Schumann RR, Hartung T (2001) Induction of cross-tolerance by lipopolysaccharide and highly purified lipoteichoic acid via different Toll-like receptors independent of paracrine mediators. J Immunol 166:5161-5167
22. Metzger J, Jung G, Bessler WG, Hoffmann P, Strecker M, Lieberknecht A, Schmidt U (1991) Lipopeptides containing 2-(palmitoylamino)-6, 7-bis (palmitoyloxy) heptanoic acid: synthesis, stereospecific stimulation of B-lymphocytes and macrophages, and adjuvanticity in vivo and in vitro. J Med Chem 34:1969-1974
23. Metzger JW, Beck-Sickinger AG, Loleit M, Eckert M, Bessler WG, Jung G (1995) Synthetic S-(2, 3-dihydroxypropyl)-cysteinyl peptides derived from the N-terminus of the cytochrome subunit of the photoreaction centre of Rhodopseudomonas viridis enhance murine splenocyte proliferation. J Pept Sci 1:184-190
24. Muhlradt PF, Kiess M, Meyer H, Sussmuth R, Jung G (1997) Isolation, structure elucidation, and synthesis of a macrophage stimulatory lipopeptide from Mycoplasma fermentans acting at picomolar concentration. J Exp Med 185:1951-1958
25. Muhlradt PF, Kiess M, Meyer H, Sussmuth R, Jung G (1998) Structure and specific activity of macrophage-stimulating lipopeptides from Mycoplasma hyorhinis. Infect Immun 66:4804-4810
26. Sandor F, Latz E, Re F, Mandell L, Repik G, Golenbock DT, Espevik T, Kurt-Jones EA, Finberg RW (2003) Importance of extra-and intracellular domains of TLR1 and TLR2 in NFkappa B signaling. J Cell Biol 162:1099-1110
27. Schromm AB, Howe J, Ulmer AJ, Wiesmuller KH, Seyberth T, Jung G, Rossle M, Koch MH, Gutsmann T, Brandenburg K (2007) Physicochemical and biological analysis of synthetic bacterial lipopeptides: validity of the concept of endotoxic conformation. J Biol Chem 282:11030-11037
28. Schwandner R, Dziarski R, Wesche H, Rothe M, Kirschning CJ (1999) Peptidoglycan-and lipoteichoic acid-induced cell activation is mediated by toll-like receptor 2. J Biol Chem 274:17406-17409
29. Seyberth T, Voss S, Brock R, Wiesmuller KH, Jung G (2006) Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure-activity relationships. J Med Chem 49:1754-1765
30. Spohn R, Buwitt-Beckmann U, Brock R, Jung G, Ulmer AJ, Wiesmuller KH (2004) Synthetic lipopeptide adjuvants and Toll-like receptor 2-structure-activity relationships. Vaccine 22:2494-2499
31. Takeda K, Takeuchi O, Akira S (2002) Recognition of lipopeptides by Toll-like receptors. J Endotoxin Res 8:459-463
32. Takeuchi O, Kaufmann A, Grote K, Kawai T, Hoshino K, Morr M, Muhlradt PF, Akira S (2000) Cutting edge: preferentially the R-stereoisomer of the mycoplasmal lipopeptide macrophage activating lipopeptide-2 activates immune cells through a toll-like receptor 2-and MyD88-dependent signaling pathway. J Immunol 164:554-557
33. Vitiello A, Ishioka G, Grey HM, Rose R, Farness P, LaFond R, Yuan L, Chisari FV, Furze J, Bartholomeuz R et al (1995) Development of a lipopeptide-based therapeutic vaccine to treat chronic HBV infection. I. Induction of a primary cytotoxic T lymphocyte response in humans. J Clin Invest 95:341-349
34. Winzler C, Rovere P, Rescigno M, Granucci F, Penna G, Adorini L, Zimmermann VS, Davoust J, Ricciardi-Castagnoli P (1997) Maturation stages of mouse dendritic cells in growth factor dependent long-term cultures. J Exp Med 185:317-328
35. Zeng W, Ghosh S, Lau YF, Brown LE, Jackson DC (2002) Highly immunogenic and totally synthetic lipopeptides as self-adjuvanting immunocontraceptive vaccines. J Immunol 169:4905-4912
36. Zeng W, Gauci S, Ghosh S, Walker J, Jackson DC (2005) Characterisation of the antibody response to a totally synthetic immunocontraceptive peptide vaccine based on LHRH. Vaccine 23:4427-4435
37. Zeng W, Pagnon J, Jackson DC (2007) The C-terminal pentapeptide of LHRH is a dominant B cell epitope with antigenic and biological function. Mol Immunol 44:3724-3731