Immunomodulatory properties of novel nucleotide oligomerization domain 2 (Nod2) agonistic desmuramyldipeptides

Journal of Medicinal Chemistry

Volumn 55, Issue 14, 2012, Pages 6478-6488

  Jakopin, Žiga ^a   Gobec, Martina ^a   Mlinarič Raščan, Irena ^a   Sollner Dolenc, Marija ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE RECRUITMENT DOMAIN PROTEIN 15; IONOMYCIN; MURABUTIDE; MURAMYL DIPEPTIDE DERIVATIVE; PHORBOL 13 ACETATE 12 MYRISTATE;

ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNOMODULATION; PERIPHERAL BLOOD MONONUCLEAR CELL; PROTEIN EXPRESSION;

ACETYLMURAMYL-ALANYL-ISOGLUTAMINE; CYTOKINES; DIPEPTIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HEK293 CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMMUNOLOGIC FACTORS; LEUKOCYTES, MONONUCLEAR; NOD2 SIGNALING ADAPTOR PROTEIN; TIME FACTORS;

EID: 84864188529     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300503b     Document Type: Article

References (38)

1. Doyle, S. L.; O'Neill, L. A. J. Toll-like receptors: from the discovery of NFκB to new insights into transcriptional regulations in innate immunity Biochem. Pharmacol. 2006, 72, 1102-1113
2. Hood, J. D.; Warshakoon, H. J.; Kimbrell, M. R.; Shukla, N. M.; Malladi, S. S.; Wang, X.; David, S. A. Immunoprofiling toll-like receptor ligands: comparison of immunostimulatory and proinflammatory profiles in ex vivo human blood models Hum. Vaccines 2010, 6, 322-335
3. Gloire, G.; Legrand-Poels, S.; Piette, J. NF-κB activation by reactive oxygen species: fifteen years later Biochem. Pharmacol. 2006, 72, 1493-1505
4. Hui, C. K.; Lau, G. K. K. Advances in immunomodulating therapy of HBV infection Int. J. Med. Sci. 2005, 2, 24-29
5. Geddes, K.; Magalhães, J. G.; Girardin, S. E. Unleashing the therapeutic potential of NOD-like receptors Nat. Rev. Drug Discovery 2009, 8, 465-479
6. Fritz, J. H.; Ferrero, R. L.; Philpott, D. J.; Girardin, S. E. Nod-like proteins in immunity, inflammation and disease Nat. Immunol. 2006, 7, 1250-1257
7. Coulombe, F.; Divangahi, M.; Veyrier, F.; de Léséleuc, L.; Gleason, J. L.; Yang, Y.; Kelliher, M. A.; Pandey, A. K.; Sassetti, C. M.; Reed, M. B.; Behr, M. A. Increased NOD2-mediated recognition of N -glycolyl muramyl dipeptide J. Exp. Med. 2009, 206, 1709-1716
8. Lecat, A.; Piette, J.; Legrand-Poels, S. The protein Nod2: an innate receptor more complex than previously assumed Biochem. Pharmacol. 2010, 80, 2021-2031
9. Inohara, N.; Ogura, Y.; Chen, F. F.; Muto, A.; Nuñez, G. Human Nod1 confers responsiveness to bacterial lipopolysaccharides J. Biol. Chem. 2001, 276, 2551-2554
10. Shaw, M. H.; Kamada, N.; Warner, N.; Kim, Y. G.; Nuñez, G. The ever-expanding function of NOD2: autophagy, viral recognition, and T cell activation Trends Immunol. 2011, 32, 73-79
11. Windheim, M.; Lang, C.; Peggie, M.; Plater, L. A.; Cohen, P. Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide Biochem. J. 2007, 404, 179-190
12. Tada, H.; Aiba, S.; Shibata, K.; Ohteki, T.; Takada, H. Synergistic effect of Nod1 and Nod2 agonists with Toll-like receptor agonists on human dendritic cells to generate interleukin-12 and T helper type 1 cells Infect. Immun. 2005, 73, 7967-7976
13. Park, J. H.; Kim, Y. G.; Shaw, M.; Kanneganti, T. D.; Fujimoto, Y.; Fukase, K.; Inohara, N.; Nuñez, G. Nod1/RICK and TLR signaling regulate chemokine and antimicrobial innate immune responses in mesothelial cells J. Immunol. 2007, 179, 514-521
14. Fritz, J. H.; Girardin, S. E.; Fitting, C.; Werts, C.; Mengin-Lecreulx, D.; Caroff, M.; Cavaillon, J. M.; Philpott, D. J.; Adib-Conguy, M. Synergistic stimulation of human monocytes and dendritic cells by Toll-like receptor 4 and Nod1- and Nod2-activating agonists Eur. J. Immunol. 2005, 35, 2459-2470
15. Cooper, A. M.; Mayer-Barber, K. D.; Sher, A. Role of innate cytokines in mycobacterial infection Mucosal Immunol. 2011, 4, 252-260
16. Mizgerd, J. P.; Spieker, M. R.; Doerschuk, C. M. Early response cytokines and innate immunity: essential roles for TNF receptor 1 and type I IL-1 receptor during Escherichia coli pneumonia in mice J. Immunol. 2001, 166, 4042-4048
17. Naumann, M. Nuclear factor-κB activation and innate immune response in microbial pathogen infection Biochem. Pharmacol. 2000, 60, 1109-1114
18. Koch, E.; Klaas, C. A.; Rüngeler, P.; Castro, V.; Mora, G.; Vichnewski, W.; Merfort, I. Inhibition of inflammatory cytokine production and lymphocyte proliferation by structurally different sesquiterpene lactones correlates with their effect on activation of NF-κB Biochem. Pharmacol. 2001, 62, 795-801
19. Ellouz, F.; Adam, A.; Ciorbaru, R.; Lederer, E. Minimal requirements for adjuvant activity of bacterial peptidoglycan derivatives Biochem. Biophys. Res. Commun. 1974, 59, 1317-1325
20. Inohara, N.; Ogura, Y.; Fontalba, A.; Gutierrez, O.; Pons, F.; Crespo, J.; Fukase, K.; Inamura, S.; Kusumoto, S.; Hashimoto, M.; Foster, S. J.; Moran, A. P.; Fernandez-Luna, J. L.; Nuñez, G. Host recognition of bacterial muramyl dipeptide mediated through NOD2 J. Biol. Chem. 2003, 278, 5509-5512
21. Girardin, S. E.; Boneca, I. G.; Viala, J.; Chamaillard, M.; Labigne, A.; Thomas, G.; Philpott, D. J.; Sansonetti, P. J. Nod2 is a general sensor of peptidoglycan through muramyl dipeptide (MDP) detection J. Biol. Chem. 2003, 278, 8869-8872
22. Bahr, G. M. Immune and Antiviral Effects of the Synthetic Immunomodulator Murabutide. In Vaccine Adjuvants: Immunological and Clinical Principles; Hackett, C. J.; Harn, D. A., Jr., Eds.; Humana Press: Totowa, NJ, 2006; pp 193-219.
23. Himes, R.; Lee, S.; McMenigall, K.; Russel-Jones, G. The influence of molecular adjuvants in the cutaneous response to antigen after topical vaccination Vaccine 2011, 29, 5393-5398
24. Vidal, V.; Dewulf, J.; Bahr, G. M. Enhanced maturation and functional capacity of monocyte-derived immature dendritic cells by the synthetic immunomodulator murabutide Immunology 2001, 103, 479-487
25. Vidal, V.; Castéran, N.; Riendeau, C. J.; Kornfeld, H.; Darcissac, E. C. A.; Capron, A.; Bahr, G. M. Macrophage stimulation with murabutide, an HIV-suppressive muramyl peptide derivative, selectively activates extracellular signal-regulated kinases 1 and 2, C/EBPβ and STAT1: role of CD14 and Toll-like receptors 2 and 4 Eur. J. Immunol. 2001, 31, 1962-1971
26. Kikelj, D.; Pečar, S.; Kotnik, V.; Štalc, A.; Wraber-Herzog, B.; Simčič, S.; Ihan, A.; Klamfer, L.; Povšič, L.; Grahek, R.; Suhadolc, E.; Hočevar, M.; Hönig, H.; Rogi-Kohlenprath, R. N -{ trans -[[2′(Acetylamino) cyclohexyl]oxy]acetyl}- l -alanyl- d -glutamic acid: a novel immunologically active carbocyclic muramyl dipeptide analogue J. Med. Chem. 1998, 41, 530-539
27. Dzierzbicka, K.; Kołodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridine/acridone derivatives J. Med. Chem. 2003, 46, 183-189
28. Dzierzbicka, K.; Kołodziejczyk, A. M.; Wysocka-Skrzela, B.; Myśliwski, A.; Sosnowska, D. Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramylpeptides with acridine/acridone derivatives J. Med. Chem. 2001, 44, 3606-3615
29. Jakopin, Ž.; Corsini, E.; Gobec, M.; Mlinarič- Raščan, I.; Sollner Dolenc, M. Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs Eur. J. Med. Chem. 2011, 46, 3762-3777
30. Smrdel, P.; Grabnar, I.; Locatelli, I.; Černe, M.; Andrenšek, S.; Kovačič, N.; Kristl, A.; Bogataj, M.; Urleb, U.; Mrhar, A. Physicochemical and preclinical pharmacokinetic and toxicological evaluation of LK-423, a new phthalimido-desmuramyl-dipeptide derivative with immunomodulating activity Drug Dev. Ind. Pharm. 2009, 35, 1293-1304
31. Zhao, N.; Ma, Y.; Zhang, S.; Fang, X.; Liang, Z.; Liu, G. New muramyl dipeptide (MDP) mimics without the carbohydrate moiety as potential adjuvant candidates for a therapeutic hepatitis B vaccine (HBV) Bioorg. Med. Chem. Lett. 2011, 21, 4292-4295
32. Goodchild, A.; Nopper, N.; Craddock, A.; Law, T.; King, A.; Fanning, G.; Rivory, L.; Passioura, T. Primary leukocyte screens for innate agonists J. Biomol. Screening 2009, 14, 723-730
33. Baran, J.; Kowalczyk, D.; Oz̃óg, M.; Zembala, M. Three-color flow cytometry detection of intracellular cytokines in peripheral blood mononuclear cells: comparative analysis of phorbol myristate acetate-ionomycin and phytohemagglutinin stimulation Clin. Diagn. Lab. Immunol. 2001, 8, 303-313
34. Rostaing, L.; Tkaczuk, J.; Durand, M.; Peres, C.; Durand, D.; de Préval, C.; Ohayon, E.; Abbal, M. Kinetics of intracytoplasmic Th1 and Th2 cytokine production assessed by flow cytometry following in vitro activation of peripheral blood mononuclear cells Cytometry 1999, 35, 318-328
35. Prussin, C. Cytokine flow cytometry: understanding cytokine biology at the single-cell level J. Clin. Immunol. 1997, 17, 195-204
36. Ismair, M. G.; Vavricka, S. R.; Kullak-Ublick, G. A.; Fried, M.; Mengin-Lecreulx, D.; Girardin, S. E. hPepT1 selectively transports muramyl dipeptide but not Nod1-activating muramyl peptides Can. J. Physiol. Pharmacol. 2006, 84, 1313-1319
37. Charrier, L.; Merlin, D. The oligopeptide transporter hPepT1: gateway to the innate immune response Lab. Invest. 2006, 86, 538-546
38. Jakopin, Ž.; Dolenc, M. S. Microwave-assisted preparation of N-alkylated saccharins and their reactions with potassium t-butoxide Synth. Commun. 2010, 40, 2464-2474