In vivo protection provided by a synthetic new alpha-galactosyl ceramide analog against bacterial and viral infections in murine models

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 10, 2010, Pages 4129-4136

  Lin, Kun Hsien ^a,c   Liang, Jian Jong ^b   Huang, Wen I ^a   Lin Chu, Shao Ying ^a   Su, Ching Yao ^a,c   Lee, Yi Ling ^b   Jan, Jia Tsong ^a   Lin, Yi Ling ^a,b   Cheng, Yih Shyun E ^a   Wong, Chi Huey ^a,c  

^a GENOMICS RESEARCH CENTER   (Taiwan)

^b INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GALACTOSYLCERAMIDE; CD1D ANTIGEN; GLYCOLIPID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC PROPHYLAXIS; ANTIVIRAL ACTIVITY; ARTICLE; BACTERIAL INFECTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IN VIVO STUDY; MOUSE; NONHUMAN; PRIORITY JOURNAL; SPHINGOMONAS; TH1 CELL; VIRUS INFECTION;

ANIMALS; ANTI-BACTERIAL AGENTS; FEMALE; GALACTOSYLCERAMIDES; GRAM-NEGATIVE BACTERIAL INFECTIONS; MICE; MICE, INBRED BALB C; SPHINGOMONAS; STAPHYLOCOCCUS AUREUS;

EID: 77957348634     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00368-10     Document Type: Article

References (39)

1. Blauvelt, M. L., M. Khalili, W. Jaung, J. Paulsen, A. C. Anderson, S. B. Wilson, and A. R. Howell. 2008. Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation. Bioorg. Med. Chem. Lett. 18:6374-6376.
2. Brigl, M., P. van den Elzen, X. Chen, J. H. Meyers, D. Wu, C. H. Wong, F. Reddington, P. A. Illarianov, G. S. Besra, M. B. Brenner, and J. E. Gumperz. 2006. Conserved and heterogeneous lipid antigen specificities of CD1d-restricted NKT cell receptors. J. Immunol. 176:3625-3634.
3. Chang, Y. J., J. R. Huang, Y. C. Tsai, J. T. Hung, D. Wu, M. Fujio, C. H. Wong, and A. L. Yu. 2007. Potent immune-modulating and anticancer effects of NKT cell stimulatory glycolipids. Proc. Natl. Acad. Sci. U. S. A. 104:10299-10304.
4. Chen, L. K., Y. L. Lin, C. L. Liao, C. G. Lin, Y. L. Huang, C. T. Yeh, S. C. Lai, J. T. Jan, and C. Chin. 1996. Generation and characterization of organ-tropism mutants of Japanese encephalitis virus in vivo and in vitro. Virology 223:79-88.
5. Chiba, A., S. Oki, K. Miyamoto, H. Hashimoto, T. Yamamura, and S. Miyake. 2004. Suppression of collagen-induced arthritis by natural killer T cell activation with OCH, a sphingosine-truncated analog of alpha-galactosylceramide. Arthritis Rheum. 50:305-313.
6. Fan, G., Y. S. Pan, K. C. Lu, Y. P. Cheng, W. C. Lin, S. Lin, C. H. Lin, C. H. Wong, J. M. Fang, and C. C. Lin. 2005. Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes. Tetrahedron 61:1855-1862.
7. Franck, R. W., and M. Tsuji. 2006. Alpha-c-galactosylceramides: synthesis and immunology. Acc. Chem. Res. 39:692-701.
8. Fujio, M., D. Wu, R. Garcia-Navarro, D. D. Ho, M. Tsuji, and C. H. Wong. 2006. Structure-based discovery of glycolipids for CD1d-mediated NKT cell activation: tuning the adjuvant versus immunosuppression activity. J. Am. Chem. Soc. 128:9022-9023.
9. Godfrey, D. I., H. R. MacDonald, M. Kronenberg, M. J. Smyth, and L. Van Kaer. 2004. NKT cells: what's in a name? Nat. Rev. Immunol. 4:231-237.
10. Gonzalez-Aseguinolaza, G., L. Van Kaer, C. C. Bergmann, J. M. Wilson, J. Schmieg, M. Kronenberg, T. Nakayama, M. Taniguchi, Y. Koezuka, and M. Tsuji. 2002. Natural killer T cell ligand alpha-galactosylceramide enhances protective immunity induced by malaria vaccines. J. Exp. Med. 195:617-624.
11. Ho, L. P., L. Denney, K. Luhn, D. Teoh, C. Clelland, and A. J. McMichael. 2008. Activation of invariant NKT cells enhances the innate immune response and improves the disease course in influenza A virus infection. Eur. J. Immunol. 38:1913-1922.
12. Hung, L. C., C. C. Lin, S. K. Hung, B. C. Wu, M. D. Jan, S. H. Liou, and S. L. Fu. 2007. A synthetic analog of alpha-galactosylceramide induces macrophage activation via the TLR4-signaling pathways. Biochem. Pharmacol. 73:1957-1970.
13. Johnson, T. R., S. Hong, L. Van Kaer, Y. Koezuka, and B. S. Graham. 2002. NK T cells contribute to expansion of CD8(+) T cells and amplification of antiviral immune responses to respiratory syncytial virus. J. Virol. 76:4294-4303.
14. Kaieda, S., C. Tomi, S. Oki, T. Yamamura, and S. Miyake. 2007. Activation of invariant natural killer T cells by synthetic glycolipid ligands suppresses autoantibody-induced arthritis. Arthritis Rheum. 56:1836-1845. (Pubitemid 47110383)
15. Kakimi, K., L. G. Guidotti, Y. Koezuka, and F. V. Chisari. 2000. Natural killer T cell activation inhibits hepatitis B virus replication in vivo. J. Exp. Med. 192:921-930.
16. Kinjo, Y., D. Wu, G. Kim, G. W. Xing, M. A. Poles, D. D. Ho, M. Tsuji, K. Kawahara, C. H. Wong, and M. Kronenberg. 2005. Recognition of bacterial glycosphingolipids by natural killer T cells. Nature 434:520-525.
17. Kobayashi, E., K. Motoki, T. Uchida, H. Fukushima, and Y. Koezuka. 1995. KRN7000, a novel immunomodulator, and its antitumor activities. Oncol. Res. 7:529-534.
18. Koto, S., N. Morishima, K. Takenaka, K. Kanemitsu, N. Shimoura, M. Kase, S. Kojiro, T. Nakamura, T. Kawase, and S. Zen. 1989. 2-Methoxyethyl group for protection of reducing hydroxyl group of aldose. Bull. Chem. Soc. Jpn. 62:3549-3566.
19. Kuklin, N. A., G. D. Pancari, T. W. Tobery, L. Cope, J. Jackson, C. Gill, K. Overbye, K. P. Francis, J. Yu, D. Montgomery, A. S. Anderson, W. McClements, and K. U. Jansen. 2003. Real-time monitoring of bacterial infection in vivo: development of bioluminescent staphylococcal foreign-body and deep-thigh-wound mouse infection models. Antimicrob. Agents Chemother. 47:2740-2748.
20. Liang, J. J., C. L. Liao, J. T. Liao, Y. L. Lee, and Y. L. Lin. 2009. A Japanese encephalitis virus vaccine candidate strain is attenuated by decreasing its interferon antagonistic ability. Vaccine 27:2746-2754.
21. Liang, P. H., M. Imamura, X. Li, D. Wu, M. Fujio, R. T. Guy, B. C. Wu, M. Tsuji, and C. H. Wong. 2008. Quantitative microarray analysis of intact glycolipid-CD1d interaction and correlation with cell-based cytokine production. J. Am. Chem. Soc. 130:12348-12354.
22. Minagawa, S., C. Ohyama, S. Hatakeyama, N. Tsuchiya, T. Kato, and T. Habuchi. 2005. Activation of natural killer T cells by alpha-galactosylceramide mediates clearance of bacteria in murine urinary tract infection. J. Urol. 173:2171-2174.
23. Morita, M., K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima. 1995. Structure-activity relationship of alpha-galactosylceramides against B16-bearing mice. J. Med. Chem. 38:2176-2187.
24. Natori, T., M. Morita, K. Akimoto, and Y. Koezuka. 1994. Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus. Tetrahedron 50:2771-2784. (Pubitemid 24095872)
25. Sireci, G., M. P. La Manna, D. Di Liberto, M. Lo Dico, M. Taniguchi, F. Dieli, and A. Salerno. 2008. Prophylaxis of lipopolysaccharide-induced shock by alpha-galactosylceramide. J. Leukoc. Biol. 84:550-560.
26. Sireci, G., M. P. La Manna, C. Di Sano, D. Di Liberto, S. A. Porcelli, M. Kronenberg, F. Dieli, and A. Salerno. 2007. Pivotal advance: alpha-galactosylceramide induces protection against lipopolysaccharide-induced shock. J. Leukoc. Biol. 81:607-622.
27. Su, C. Y., S. Y. Wang, J. J. Shie, K. S. Jeng, N. J. Temperton, J. M. Fang, C. H. Wong, and Y. S. Cheng. 2008. In vitro evaluation of neuraminidase inhibitors using the neuraminidase-dependent release assay of hemagglutinin- pseudotyped viruses. Antiviral Res. 79:199-205.
28. Taniguchi, M., M. Harada, S. Kojo, T. Nakayama, and H. Wakao. 2003. The regulatory role of Valpha14 NKT cells in innate and acquired immune response. Annu. Rev. Immunol. 21:483-513.
29. Thurnhofer, S., and W. Vetter. 2007. Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction. Tetrahedron 63:1140-1145. (Pubitemid 44958904)
30. Trappeniers, M., S. Goormans, K. Van Beneden, T. Decruy, B. Linclau, A. Al-Shamkhani, T. Elliott, C. Ottensmeier, J. M. Werner, D. Elewaut, and S. Van Calenbergh. 2008. Synthesis and in vitro evaluation of alpha-GalCer epimers. Chem. Med. Chem. 3:1061-1070.
31. Tupin, E., Y. Kinjo, and M. Kronenberg. 2007. The unique role of natural killer T cells in the response to microorganisms. Nat. Rev. Microbiol. 5:405-417.
32. van der Vliet, H. J., J. W. Molling, B. M. von Blomberg, N. Nishi, W. Kolgen, A. J. van den Eertwegh, H. M. Pinedo, G. Giaccone, and R. J. Scheper. 2004. The immunoregulatory role of CD1d-restricted natural killer T cells in disease. Clin. Immunol. 112:8-23.
33. van Dommelen, S. L., H. A. Tabarias, M. J. Smyth, and M. A. Degli-Esposti. 2003. Activation of natural killer (NK) T cells during murine cytomegalovirus infection enhances the antiviral response mediated by NK cells. J. Virol. 77:1877-1884.
34. Velmourougane, G., R. Raju, G. Bricard, J. S. Im, G. S. Besra, S. A. Porcelli, and A. R. Howell. 2009. Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH. Bioorg. Med. Chem. Lett. 19:3386-3388.
35. Wu, D., M. Fujio, and C. H. Wong. 2008. Glycolipids as immunostimulating agents. Bioorg. Med. Chem. 16:1073-1083.
36. Wu, D., D. M. Zajonc, M. Fujio, B. A. Sullivan, Y. Kinjo, M. Kronenberg, I. A. Wilson, and C. H. Wong. 2006. Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d. Proc. Natl. Acad. Sci. U. S. A. 103:3972-3977.
37. Wu, L., and L. Van Kaer. 2009. Natural killer T cells and autoimmune disease. Curr. Mol. Med. 9:4-14.
38. Wu, S. F., C. J. Lee, C. L. Liao, R. A. Dwek, N. Zitzmann, and Y. L. Lin. 2002. Antiviral effects of an iminosugar derivative on flavivirus infections. J. Virol. 76:3596-3604.
39. Yoshimoto, T., A. Bendelac, C. Watson, J. Hu-Li, and W. E. Paul. 1995. Role of NK1.1+ T cells in a TH2 response and in immunoglobulin E production. Science 270:1845-1847.