N-tetradecylcarbamyl lipopeptides as novel agonists for toll-like receptor 2

Journal of Medicinal Chemistry

Volumn 57, Issue 15, 2014, Pages 6873-6878

  Willems, Marian M J H P ^a   Zom, Gijs G ^b   Khan, Selina ^b   Meeuwenoord, Nico ^a   Melief, Cornelis J M ^b,c   Van Der Stelt, Mario ^a   Overkleeft, Herman S ^a   Codée, Jeroen D C ^a   Van Der Marel, Gijsbert A ^a   Ossendorp, Ferry ^b   Filippov, Dmitri V ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^c ISA Pharmaceuticals   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; HETERODIMER; LIPOPEPTIDE; N TETRADECYLCARBAMYL DERIVATIVE; TOLL LIKE RECEPTOR 2; TOLL LIKE RECEPTOR AGONIST; UNCLASSIFIED DRUG; CARBAMIC ACID DERIVATIVE; IMMUNOLOGICAL ADJUVANT; PAM(3)CSK(4) PEPTIDE; TOLL LIKE RECEPTOR 1;

AMINO TERMINAL SEQUENCE; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENDRITIC CELL; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; EVALUATION STUDY; HUMAN; HUMAN CELL; HYDROGEN BOND; IMMUNOSTIMULATION; IN VITRO STUDY; SOLID PHASE SYNTHESIS; AGONISTS; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; PHYSIOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ADJUVANTS, IMMUNOLOGIC; CARBAMATES; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DENDRITIC CELLS; HUMANS; LIPOPEPTIDES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TOLL-LIKE RECEPTOR 1; TOLL-LIKE RECEPTOR 2;

EID: 84906099879     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500722p     Document Type: Article

References (23)

1. Braun, V. Covalent lipoprotein from outer membrane of Escherichia coli Biochim. Biophys. Acta 1975, 415, 335-377
2. Bessler, W.; Resch, K.; Hancock, E.; Hantke, K. Induction of lymphocyte-proliferation and membrane changes by lipopeptide derivatives of lipoprotein from outer membrane of Escherichia coli Z. Immunitatsforsch. Immunobiol. 1977, 153, 11-22
3. Bessler, W. G.; Cox, M.; Lex, A.; Suhr, B.; Wiesmuller, K. H.; Jung, G. Synthetic lipopeptide analogs of bacterial lipoprotein are potent polyclonal activators for murine B lymphocytes J. Immunol. 1985, 135, 1900-1905
4. Metzger, J.; Wiesmuller, K. H.; Schaude, R.; Bessler, W. G.; Jung, G. Synthesis of novel immunologically active tripalmitoyl-S-glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations Int. J. Pept. Protein Res. 1991, 37, 46-57
5. Metzger, J.; Jung, G.; Bessler, W. G.; Hoffmann, P.; Strecker, M.; Lieberknecht, A.; Schmidt, U. 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. 1991, 34, 1969-1974
6. Bessler, W. G.; Johnson, R. B.; Wiesmuller, K.; Jung, G. B-Lymphocyte mitogenicity in vitro of a synthetic lipopeptide fragment derived from bacterial lipoprotein Hoppe-Seyler's Z. Physiol. Chem. 1982, 363, 767-770
7. Lex, A.; Wiesmuller, K. H.; Jung, G.; Bessler, W. G. A synthetic analog of Escherichia coli lipoprotein, tripalmitoyl pentapeptide, constitutes a potent immune adjuvant J. Immunol. 1986, 137, 2676-2681
8. Spohn, R.; Buwitt-Beckmann, U.; Brock, R.; Jung, G.; Ulmer, A. J.; Wiesmuller, K. H. Synthetic lipopeptide adjuvants and Toll-like receptor 2-structure-activity relationships Vaccine 2004, 22, 2494-2499
9. Reitermann, A.; Metzger, J.; Wiesmuller, K. H.; Jung, G.; Bessler, W. G. Lipopeptide derivatives of bacterial lipoprotein constitute potent immune adjuvants combined with or covalently coupled to antigen or hapten Biol. Chem. Hoppe-Seyler 1989, 370, 343-352
10. Hioe, C. E.; Qiu, H.; Chend, P. D.; Bian, Z.; Li, M. L.; Li, J.; Singh, M.; Kuebler, P.; McGee, P.; O'Hagan, D.; Zamb, T.; Koff, W.; Allsopp, C.; Wang, C. Y.; Nixon, D. F. Comparison of adjuvant formulations for cytotoxic T cell induction using synthetic peptides Vaccine 1996, 14, 412-418
11. 4 Eur. J. Biochem. 1999, 264, 369-373
12. Jin, M. S.; Kim, S. E.; Heo, J. Y.; Lee, M. E.; Kim, H. M.; Paik, S. G.; Lee, H.; Lee, J. O. Crystal structure of the TLR1-TLR2 heterodimer induced by binding of a tri-acylated lipopeptide Cell 2007, 130, 1071-1082
13. Jin, M. S.; Lee, J. O. Structures of the toll-like receptor family and its ligand complexes Immunity 2008, 29, 182-191
14. Kang, J. Y.; Nan, X.; Jin, M. S.; Youn, S. J.; Ryu, Y. H.; Mah, S.; Han, S. H.; Lee, H.; Paik, S. G.; Lee, J. O. Recognition of lipopeptide patterns by Toll-like receptor 2-Toll-like receptor 6 heterodimer Immunity 2009, 31, 873-884
15. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF chimera-a visualization system for exploratory research and analysis J. Comput. Chem. 2004, 25, 1605-1612
16. Zom, G. G. P.; Khan, S.; Filippov, D. V.; Ossendorp, F. TLR ligand-peptide conjugate vaccines: toward clinical application Adv. Immunol. 2012, 114, 177-201
17. + T-cells Mol. Immunol. 2009, 46, 1084-1091
18. Khan, S.; Bijker, M. S.; Weterings, J. J.; Tanke, H. J.; Adema, G. J.; van Hall, T.; Drijfhout, J. W.; Melief, C. J. M.; Overkleeft, H. S.; van der Marel, G. A.; Filippov, D. V.; van der Burg, S. H.; Ossendorp, F. Distinct uptake mechanisms but similar intracellular processing of two different Toll-like receptor ligand-peptide conjugates in dendritic cells J. Biol. Chem. 2007, 282, 21145-21159
19. Weterings, J. J.; Khan, S.; van der Heden, G. J.; Drijfhout, J. W.; Melief, C. J. M.; Overkleeft, H. S.; van der Burg, O. H.; Ossendorp, F.; van der Marel, G. A.; Filippov, D. V. Synthesis of 2-alkoxy-8-hydroxyadenylpeptides: towards synthetic epitope-based vaccines Bioorg. Med. Chem. Lett. 2006, 16, 3258-3261
20. Moyle, P. M.; Toth, I. Modern subunit vaccines: development, components, and research opportunities ChemMedChem 2013, 8, 360-376
21. Lu, W.; Apostol, I.; Qasim, M. A.; Warne, N.; Wynn, R.; Zhang, W. L.; Anderson, S.; Chiang, Y. W.; Ogin, E.; Rothberg, I.; Ryan, K.; Laskowski, M., Jr. Binding of amino acid side-chains to S-1 cavities of serine proteinases J. Mol. Biol. 1997, 266, 441-461
22. Wu, W.; Li, R.; Malladi, S. S.; Warshakoon, H. J.; Kimbrell, M. R.; Amolins, M. W.; Ukani, R.; Datta, A.; David, S. A. Structure-activity relationships in Toll-like receptor-2 agonistic diacylthioglycerol lipopeptides J. Med. Chem. 2010, 53, 3198-3213
23. Winzler, C.; Rovere, P.; Rescigno, M.; Granucci, F.; Penna, G.; Adorini, L.; Zimmermann, V. S.; Davoust, J.; Ricciardi-Castagnoli, P. Maturation stages of mouse dendritic cells in growth factor-dependent long-term cultures J. Exp. Med. 1997, 185, 317-328