Design and evaluation of ω-hydroxy fatty acids containing α-GalCer analogues for CD1d-mediated NKT cell activation

ACS Medicinal Chemistry Letters

Volumn 5, Issue 4, 2014, Pages 331-335

  Lim, Chaemin ^a   Kim, Jae Hyun ^a   Baek, Dong Jae ^a   Lee, Joo Youn ^a   Cho, Minjae ^a   Lee, Yoon Sook ^a   Kang, Chang Yuil ^a   Chung, Doo Hyun ^a   Cho, Won Jae ^b   Kim, Sanghee ^a  

^a Seoul National University   (South Korea)

^b Chonnam National University   (South Korea)

Author keywords

CD1d; drug design; hydrogen bonding interaction; NKT cell activator; Galactosylceramide

Indexed keywords

ALPHA GALACTOSYLCERAMIDE; CD1D ANTIGEN; FUNCTIONAL GROUP; GAMMA INTERFERON; HYDROXY FATTY ACID; INTERLEUKIN 2; INTERLEUKIN 4; OMEGA HYDROXY FATTY ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CYTOKINE PRODUCTION; CYTOKINE RELEASE; CYTOKINE RESPONSE; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HYDROGEN BOND; HYDROGENOLYSIS; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR MODEL; MOUSE; NATURAL KILLER T CELL; NONHUMAN; PRIORITY JOURNAL; T LYMPHOCYTE ACTIVATION;

EID: 84898025489     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400517b     Document Type: Article

References (30)

1. Morita, M.; Motoki, K.; Akimoto, K.; Natori, T.; Sakai, T.; Sawa, E.; Yamaji, K.; Koezuka, Y.; Kobayashi, E.; Fukushima, H. Structure-Activity Relationship of α-Galactosylceramides against B16-Bearing Mice J. Med. Chem. 1995, 38, 2176-2187
2. α14 NKT cells by Glycosylceramides Science 1997, 278, 1626-1629
3. Tupin, E.; Kinjo, Y.; Kronenberg, M. The Unique Role of Natural Killer T Cells in the Response to Microorganisms Nat. Rev. Microbiol. 2007, 5, 405-417
4. Balato, A.; Unutmaz, D.; Gaspari, A. A. Natural Killer T Cells: An Unconventional T-Cell Subset with Diverse Effector and Regulatory Functions J. Invest. Dermatol. 2009, 129, 1628-1642
5. Kronenberg, M. Toward An Understanding of NKT Cell Biology: Progress and Paradoxes Annu. Rev. Immunol. 2005, 23, 877-900
6. Tashiro, T. Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells Biosci. Biotechnol. Biochem. 2012, 76, 1055-1067
7. Banchet-Cadeddu, A.; Hénon, E.; Dauchez, M.; Renault, J.-H.; Monneaux, F.; Haudrechy, A. The Stimulating Adventure of KRN 7000 Org. Biomol. Chem. 2011, 9, 3080-3104
8. Mori, K.; Tashiro, T. Sphingolipids and Glycosphingolipids: Their Syntheses and Bioactivities Heterocycles 2011, 83, 951-1003
9. α14 NKT Cells in Innate and Acquired Immune Response Annu. Rev. Immnunol. 2003, 21, 483-513
10. Borg, N. A.; Wun, K. S.; Kjer-Nielsen, L.; Wilce, M. C. J.; Pellicci, D. G.; Koh, R.; Besra, G. S.; Bharadwaj, M.; Godfrey, D. I.; McCluskey, J.; Rossjohn, J. CD1d-Lipid-Antigen Recognition by the Semi-invariant NKT T-Cell Receptor Nature 2007, 448, 44-49
11. De Silva, A. D.; Park, J.-J.; Matsuki, N.; Stanic, A. K.; Brutkiewicz, R. R.; Medof, M. E.; Joyce, S. Lipid Protein Interactions: The Assembly of CD1d1 with Cellular Phospholipids Occurs in the Endoplasmic Reticulum J. Immunol. 2002, 168, 723-733
12. Bendelac, A.; Savage, P. B.; Teyton, L. The Biology of NKT Cells Annu. Rev. Immunol. 2007, 25, 297-336
13. Savage, P. B.; Teyton, L.; Bendelac, A. Glycolipids for Natural Killer T Cells Chem. Soc. Rev. 2006, 35, 771-779
14. Rissoan, M.-C.; Soumelis, V.; Kadowaki, N.; Grouard, G.; Briere, F.; de Waal Malefyt, R.; Liu, Y.-J. Reciprocal Control of T Helper Cell and Dendritic Cell Differentiation Science 1999, 283, 1183-1186
15. Godfrey, D. I.; Kronenberg, M. Going Both Ways: Immune Regulation via CD1d-Dependent NKT Cells J. Clin. Invest. 2004, 114, 1379-1388
16. Berkers, C. R.; Ovaa, H. Immunotherapeutic Potential for Ceramide-Based Activators of iNKT Cells Trends Pharmacol. Sci. 2005, 26, 252-257
17. Koch, M.; Stronge, V. S.; Shepherd, D.; Gadola, S. D.; Mathew, B.; Ritter, G.; Fersht, A. R.; Besra, G. S.; Schmidt, R. R.; Jones, E. Y.; Cerundolo, V. The Crystal Structure of Human CD1d with and without α-Galactosylceramide Nat. Immunol. 2005, 6, 819-826
18. Pellicci, D. G.; Patel, O.; Kjer-Nielsen, L.; Pang, S. S.; Sullivan, L. C.; Kyparissoudis, K.; Brooks, A. G.; Reid, H. H.; Gras, S.; Lucet, I. S.; Koh, R.; Smyth, M. J.; Mallevaey, T.; Matsuda, J. L.; Gapin, L.; McCluskey, J.; Godfrey, D. I.; Rossjohn, J. Differential Recognition of CD1d-α-Galactosyl Ceramide by the Vβ8.2 and Vβ7 Semi-Invariant NKT T Cell Receptors Immunity 2009, 31, 47-59
19. Patel, O.; Pellicci, D. G.; Uldrich, A. P.; Sullivan, L. C.; Bhati, M.; McKnight, M.; Richardson, S. K.; Howell, A. R.; Mallevaey, T.; Zhang, J.; Bedel, R.; Besra, G. S.; Brooks, A. G.; Kjer-Nielsen, L.; McCluskey, J.; Porcelli, S. A.; Gapin, L.; Rossjohn, J.; Godfrey, D. I. Vβ2 Natural Killer T Cell Antigen Receptor-Mediated Recognition of CD1d-Glycolipid Antigen Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 19007-19012
20. López-Sagaseta, J.; Kung, J. E.; Savage, P. B.; Gumperz, J.; Adams, E. J. The Molecular Basis for Recognition of CD1d/α- Galactosylceramide by a Human Non-Vα24 T Cell Receptor PLoS Biol. 2012, 10, e1001412
21. Giabbai, B.; Sidobre, S.; Max Crispin, M. D.; Sanchez-Ruìz, Y.; Bachi, A.; Kronenberg, M.; Wilson, I. A.; Degano, M. Crystal Structure of Mouse CD1d Bound to the Self Ligand Phosphatidylcholine: A Molecular Basis for NKT Cell Activation J. Immunol. 2005, 175, 977-984
22. Wu, D.; Fujio, M.; Wong, C.-H. Glycolipids as Immunostimulating Agents Bioorg. Med. Chem. 2008, 16, 1073-1083
23. Hydroxylated KRN7000 analogues with multiple hydroxyl groups on the phytosphingosine main chain and/or amide side chain of α-GalCer were recently reported; see Shiozaki, M.; Tashiro, T.; Koshino, H.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Synthesis and Biological Activity of Hydroxylated Analogues of KRN7000 (α-Galactosylceramide) Carbohydr. Res. 2013, 370, 46-66
24. Schiefner, A.; Fujio, M.; Wu, D.; Wong, C.-H.; Wilson, I. A. Structural Evaluation of Potent NKT Cell Agonists: Implications for Design of Novel Stimulatory Ligands J. Mol. Biol. 2009, 394, 71-82
25. Du, W.; Gervay-Hague, J. Efficient Synthesis of α-Galactosyl Ceramide Analogues Using Glycosyl Iodide Donors Org. Lett. 2005, 7, 2063-2065
26. Prigozy, T. I.; Naidenki, O.; Qasba, P.; Elewaut, D.; Brossay, L.; Khurana, A.; Natori, T.; Koezuka, Y.; Kulkarni, A.; Kronenberg, M. Glycolipid Antigen Processing for Presentation by CD1d Molecules Science 2001, 291, 664-667
27. + Regulartory T Cells? Eur. J. Immunol. 2005, 35, 1193-1200
28. East, J. E.; Kennedy, A. J.; Webb, T. J. Raising the Roof: The Preferential Pharmacological Stimulation of Th1 and Th2 Responses Mediated by NKT Cells Med. Res. Rev. 2014, 34, 45-76
29. Fujio, M.; Wu, D.; Garcia-Navarro, R.; Ho, D. D.; Tsuji, M.; Wong, C.-H. Structure-Based Discovery of Glycolipids for CD1d-Mediated NKT Cell Activation: Tuning the Adjuvant versus Immunosuppression Activity J. Am. Chem. Soc. 2006, 128, 9022-9023
30. Goff, R. D.; Gao, Y.; Mattner, J.; Zhou, D.; Yin, N.; Cantu, C., III; Teyton, L.; Bendelac, A.; Savage, P. B. Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells J. Am. Chem. Soc. 2004, 126, 13602-13603