High-affinity ligands of siglec receptors and their therapeutic potentials

Current Medicinal Chemistry

Volumn 18, Issue 23, 2011, Pages 3537-3550

  Magesh, S ^a,d   Ando, H ^a,c   Tsubata, T ^b   Ishida, H ^a   Kiso, M ^a,c  

^a GIFU UNIVERSITY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d RUTGERS UNIVERSITY   (United States)

Author keywords

Carbohydrates; CD22; CD33; Glycoconjugates; High affinity ligands; Immune system; Immunoglobulin; Inhibitor design; MAG; Sialic acid; Sialoadhesin; Siglec

Indexed keywords

B LYMPHOCYTE RECEPTOR; CD169 ANTIGEN; CD170 ANTIGEN; CD22 ANTIBODY; CD22 ANTIGEN; CD33 ANTIGEN; CD34 ANTIGEN; CELL ANTIBODY; LECTIN; LYMPHOCYTE ANTIGEN; RECEPTOR; SIALIC ACID; SIALIC ACID BINDING IMMUNOGLOBULIN LIKE LECTIN; SIALIC ACID BINDING IMMUNOGLOBULIN LIKE LECTIN RECEPTOR; SIALOADHESIN; SIGLEC 4; UNCLASSIFIED DRUG;

ACUTE GRANULOCYTIC LEUKEMIA; ALLERGY; ALZHEIMER DISEASE; AMINO ACID SEQUENCE; ARTICLE; B CELL LYMPHOMA; B LYMPHOCYTE; BACTERIAL INFECTION; BASOPHIL; BINDING AFFINITY; CD8+ T LYMPHOCYTE; CORONARY ARTERY DISEASE; CRYSTAL STRUCTURE; DENDRITIC CELL; EOSINOPHIL; EOSINOPHILIA; HUMAN; HYDROPHOBICITY; IMMUNE SYSTEM; LIGAND BINDING; LUPUS ERYTHEMATOSUS; LYMPHOMA; MACROPHAGE; MAST CELL; MENINGOCOCCOSIS; MOLECULAR DOCKING; MONOCYTE; MULTIPLE SCLEROSIS; NATURAL KILLER CELL; NEISSERIA MENINGITIDIS; NEOPLASM; NEUTROPHIL; NONHODGKIN LYMPHOMA; NONHUMAN; OLIGODENDROGLIA; OSTEOPOROSIS; PARAPLEGIA; PROTEIN FUNCTION; PROTEIN STRUCTURE; PROTEIN TARGETING; RECEPTOR AFFINITY; RHEUMATOID ARTHRITIS; SCHWANN CELL; SJOEGREN SYNDROME; SYSTEMIC LUPUS ERYTHEMATOSUS; TROPHOBLAST; TRYPANOSOMA CRUZI; VIRUS INFECTION;

ANTIGENS, CD; ANTIGENS, CD22; ANTIGENS, DIFFERENTIATION, MYELOMONOCYTIC; GLYCOCONJUGATES; HUMANS; LECTINS; LIGANDS; MEMBRANE GLYCOPROTEINS; MYELIN-ASSOCIATED GLYCOPROTEIN; N-ACETYLNEURAMINIC ACID; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, IMMUNOLOGIC;

EID: 80051959474     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986711796642580     Document Type: Article

References (136)

1. Varki, A. Diversity in the sialic acids. Glycobiology, 1992, 2(1), 25-40.
2. Angata, T.; Varki, A. Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem. Rev., 2002, 102(2), 439-469. (Pubitemid 35381636)
3. Schauer, R. Sialic acids as regulators of molecular and cellular interactions. Curr. Opin. Struct. Biol., 2009, 19(5), 507-514.
4. Varki, A. Sialic acids as ligands in recognition phenomena. FASEB J., 1997, 11(4), 248-255. (Pubitemid 27118325)
5. Varki, A. Sialic acids in human health and disease. Trends Mol. Med., 2008, 14(8), 351-360.
6. Varki, N.M.; Varki, A. Diversity in cell surface sialic acid presentations: implications for biology and disease. Lab. Invest., 2007, 87(9), 851-857. (Pubitemid 47267816)
7. Angata, T. Molecular diversity and evolution of the Siglec family of cellsurface lectins. Mol. Divers., 2006, 10(4), 555-566. (Pubitemid 44885232)
8. Crocker, P.R. Siglecs: sialic-acid-binding immunoglobulin-like lectins in cell-cell interactions and signalling. Curr. Opin. Struct. Biol., 2002, 12(5), 609-615. (Pubitemid 35449068)
9. Varki, A.; Angata, T. Siglecs - the major subfamily of I-type lectins. Glycobiology, 2006, 16(1), 1R-27R. (Pubitemid 43009801)
10. Crocker, P.R., Siglecs in innate immunity. Curr. Opin. Pharmacol., 2005, 5(4), 431-437. (Pubitemid 40932048)
11. Crocker, P.R.; Paulson, J.C.; Varki, A. Siglecs and their roles in the immune system. Nat. Rev. Immunol., 2007, 7(4), 255-266. (Pubitemid 46480955)
12. Crocker, P.R.; Varki, A. Siglecs in the immune system. Immunology, 2001, 103(2), 137-145. (Pubitemid 32521342)
13. Crocker, P.R.; Varki, A. Siglecs, sialic acids and innate immunity. Trends Immunol., 2001, 22(6), 337-342. (Pubitemid 32675248)
14. Brinkman-Van der Linden, E.C.; Sjoberg, E.R.; Juneja, L.R.; Crocker, P.R.; Varki, N.; Varki, A. Loss of N-glycolylneuraminic acid in human evolution. Implications for sialic acid recognition by siglecs. J. Biol. Chem., 2000, 275(12), 8633-8640. (Pubitemid 30180213)
15. Varki, A. Colloquium paper: uniquely human evolution of sialic acid genetics and biology. Proc. Natl. Acad. Sci. U. S. A, 2010, 107 Suppl. 2, 8939-8946.
16. von Gunten, S.; Bochner, B.S. Basic and clinical immunology of Siglecs. Ann. N. Y. Acad. Sci, 2008, 1143, 61-82.
17. O'Reilly, M.K.; Paulson, J.C. Siglecs as targets for therapy in immune-cellmediated disease. Trends Pharmacol. Sci., 2009, 30(5), 240-248.
18. Polson, A.G.; Williams, M.; Gray, A.M.; Fuji, R.N.; Poon, K.A.; McBride, J.; Raab, H.; Januario, T.; Go, M.; Lau, J.; Yu, S.F.; Du, C.; Fuh, F.; Tan, C.; Wu, Y.; Liang, W.C.; Prabhu, S.; Stephan, J.P.; Hongo, J.A.; Dere, R.C.; Deng, R.; Cullen, M.; de Tute, R.; Bennett, F.; Rawstron, A.; Jack, A.; Ebens, A. Anti-CD22-MCC-DM1: an antibody-drug conjugate with a stable linker for the treatment of non-Hodgkin's lymphoma. Leukemia, 2010, 24(9), 1566-1573.
19. Stasi, R. Gemtuzumab ozogamicin: an anti-CD33 immunoconjugate for the treatment of acute myeloid leukaemia. Expert Opin. Biol. Ther., 2008, 8(4), 527-540. (Pubitemid 351570415)
20. Takeshita, A.; Yamakage, N.; Shinjo, K.; Ono, T.; Hirano, I.; Nakamura, S.; Shigeno, K.; Tobita, T.; Maekawa, M.; Kiyoi, H.; Naoe, T.; Ohnishi, K.; Sugimoto, Y.; Ohno, R. CMC-544 (inotuzumab ozogamicin), an anti-CD22 immuno-conjugate of calicheamicin, alters the levels of target molecules of malignant B-cells. Leukemia, 2009, 23(7), 1329-1336.
21. Wayne, A.S.; Kreitman, R.J.; Findley, H.W.; Lew, G.; Delbrook, C.; Steinberg, S.M.; Stetler-Stevenson, M.; Fitzgerald, D.J.; Pastan, I. Anti-CD22 immunotoxin RFB4(dsFv)-PE38 (BL22) for CD22-positive hematologic malignancies of childhood: preclinical studies and phase I clinical trial. Clin. Cancer Res., 2010, 16(6), 1894-1903.
22. Chen, W.C.; Completo, G.C.; Sigal, D.S.; Crocker, P.R.; Saven, A.; Paulson, J.C. In vivo targeting of B-cell lymphoma with glycan ligands of CD22. Blood, 2010, 115(23), 4778-4786.
23. Abdu-Allah, H.H.M.; Watanabe, K.; Hayashizaki, K.; Iwayama, Y.; Takematsu, H.; Kozutsumi, Y.; Tsubata, T.; Ishida, H.; Kiso, M. Synthesis of biotinylated sialoside to probe CD22-ligand interactions. Tet. Lett., 2009, 50(31), 4488-4491.
24. Blixt, O.; Collins, B.E.; van den Nieuwenhof, I.M.; Crocker, P.R.; Paulson, J.C. Sialoside specificity of the siglec family assessed using novel multivalent probes: identification of potent inhibitors of myelin-associated glycoprotein. J. Biol. Chem., 2003, 278(33), 31007-31019. (Pubitemid 36994614)
25. Chen, X.; Varki, A. Advances in the biology and chemistry of sialic acids. ACS Chem. Biol., 2010, 5(2), 163-176.
26. Chokhawala, H.A.; Huang, S.; Lau, K.; Yu, H.; Cheng, J.; Thon, V.; Hurtado-Ziola, N.; Guerrero, J.A.; Varki, A.; Chen, X. Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides. ACS Chem. Biol., 2008, 3(9), 567-576.
27. Collins, B.E.; Blixt, O.; Han, S.; Duong, B.; Li, H.; Nathan, J.K.; Bovin, N.; Paulson, J.C. High-affinity ligand probes of CD22 overcome the threshold set by cis ligands to allow for binding, endocytosis, and killing of B cells. J. Immunol., 2006, 177(5), 2994-3003. (Pubitemid 44277815)
28. Kelm, S.; Brossmer, R.; Isecke, R.; Gross, H.J.; Strenge, K.; Schauer, R. Functional groups of sialic acids involved in binding to siglecs (sialoadhesins) deduced from interactions with synthetic analogues. Eur. J. Biochem., 1998, 255(3), 663-672. (Pubitemid 28372301)
29. Kelm, S.; Gerlach, J.; Brossmer, R.; Danzer, C.P.; Nitschke, L. The ligand-binding domain of CD22 is needed for inhibition of the B cell receptor signal, as demonstrated by a novel human CD22-specific inhibitor compound. J. Exp. Med., 2002, 195(9), 1207-1213. (Pubitemid 34517147)
30. Kalovidouris, S.A.; Blixt, O.; Nelson, A.; Vidal, S.; Turnbull, W.B.; Paulson, J.C.; Stoddart, J.F. Chemically defined sialoside scaffolds for investigation of multivalent interactions with sialic acid binding proteins. J. Org. Chem., 2003, 68(22), 8485-8493. (Pubitemid 37336523)
31. Blixt, O.; Han, S.; Liao, L.; Zeng, Y.; Hoffmann, J.; Futakawa, S.; Paulson, J.C. Sialoside analogue arrays for rapid identification of high affinity siglec ligands. J. Am. Chem. Soc., 2008, 130(21), 6680-6681. (Pubitemid 351748384)
32. Mesch, S.; Moser, D.; Strasser, D.S.; Kelm, A.; Cutting, B.; Rossato, G.; Vedani, A.; Koliwer-Brandl, H.; Wittwer, M.; Rabbani, S.; Schwardt, O.; Kelm, S.; Ernst, B. Low molecular weight antagonists of the myelin-associated glycoprotein: synthesis, docking, and biological evaluation. J. Med. Chem., 2010, 53(4), 1597-1615.
33. O'Reilly, M.K.; Collins, B.E.; Han, S.; Liao, L.; Rillahan, C.; Kitov, P.I.; Bundle, D.R.; Paulson, J.C. Bifunctional CD22 ligands use multimeric immunoglobulins as protein scaffolds in assembly of immune complexes on B cells. J. Am. Chem. Soc., 2008, 130(24), 7736-7745. (Pubitemid 351842137)
34. Zaccai, N.R.; Maenaka, K.; Maenaka, T.; Crocker, P.R.; Brossmer, R.; Kelm, S.; Jones, E.Y. Structure-guided design of sialic acid-based Siglec inhibitors and crystallographic analysis in complex with sialoadhesin. Structure, 2003, 11(5), 557-567. (Pubitemid 36579133)
35. Powell, L.D.; Varki, A. I-type lectins. J. Biol. Chem., 1995, 270(24), 14243-14246.
36. Angata, T.; Margulies, E.H.; Green, E.D.; Varki, A. Large-scale sequencing of the CD33-related Siglec gene cluster in five mammalian species reveals rapid evolution by multiple mechanisms. Proc. Natl. Acad. Sci. U. S. A, 2004, 101(36), 13251-13256. (Pubitemid 39209651)
37. Angata, T.; Varki, N.M.; Varki, A. A second uniquely human mutation affecting sialic acid biology. J. Biol. Chem., 2001, 276(43), 40282-40287.
38. Biesen, R.; Demir, C.; Barkhudarova, F.; Grun, J.R.; Steinbrich-Zollner, M.; Backhaus, M.; Haupl, T.; Rudwaleit, M.; Riemekasten, G.; Radbruch, A.; Hiepe, F.; Burmester, G.R.; Grutzkau, A. Sialic acid-binding Ig-like lectin 1 expression in inflammatory and resident monocytes is a potential biomarker for monitoring disease activity and success of therapy in systemic lupus erythematosus. Arthritis Rheum., 2008, 58(4), 1136-1145. (Pubitemid 351564017)
39. Hartnell, A.; Steel, J.; Turley, H.; Jones, M.; Jackson, D.G.; Crocker, P.R. Characterization of human sialoadhesin, a sialic acid binding receptor expressed by resident and inflammatory macrophage populations. Blood, 2001, 97(1), 288-296. (Pubitemid 32061272)
40. Kirchberger, S.; Majdic, O.; Steinberger, P.; Bluml, S.; Pfistershammer, K.; Zlabinger, G.; Deszcz, L.; Kuechler, E.; Knapp, W.; Stockl, J. Human rhinoviruses inhibit the accessory function of dendritic cells by inducing sialoadhesin and B7-H1 expression. J. Immunol., 2005, 175(2), 1145-1152. (Pubitemid 41095001)
41. Monteiro, V.G.; Lobato, C.S.; Silva, A.R.; Medina, D.V.; de Oliveira, M.A.; Seabra, S.H.; de Souza, W.; DaMatta, R.A. Increased association of Trypanosoma cruzi with sialoadhesin positive mice macrophages. Parasitol. Res., 2005, 97(5), 380-385. (Pubitemid 41551249)
42. Rempel, H.; Calosing, C.; Sun, B.; Pulliam, L. Sialoadhesin expressed on IFN-induced monocytes binds HIV-1 and enhances infectivity. PLoS One, 2008, 3(4), e1967.
43. Xiong, Y.S.; Zhou, Y.H.; Rong, G.H.; Wu, W.L.; Liang, Y.; Yang, Z.X.; Geng, H.L.; Zhong, R.Q. Siglec-1 on monocytes is a potential risk marker for monitoring disease severity in coronary artery disease. Clin. Biochem., 2009, 42(10-11), 1057-1063.
44. Kimura, N.; Ohmori, K.; Miyazaki, K.; Izawa, M.; Matsuzaki, Y.; Yasuda, Y.; Takematsu, H.; Kozutsumi, Y.; Moriyama, A.; Kannagi, R. Human B-lymphocytes express alpha2-6-sialylated 6-sulfo-N-acetyllactosamine serving as a preferred ligand for CD22/Siglec-2. J. Biol. Chem., 2007, 282(44), 32200-32207. (Pubitemid 350106438)
45. Leonard, J.P.; Goldenberg, D.M. Preclinical and clinical evaluation of epratuzumab (anti-CD22 IgG) in B-cell malignancies. Oncogene, 2007, 26(25), 3704-3713. (Pubitemid 46842705)
46. Nitschke, L. CD22 and Siglec-G: B-cell inhibitory receptors with distinct functions. Immunol. Rev., 2009, 230(1), 128-143.
47. Steinfeld, S.D.; Youinou, P. Epratuzumab (humanised anti-CD22 antibody) in autoimmune diseases. Expert Opin. Biol. Ther., 2006, 6(9), 943-949.
48. Li, M.; Shibata, A.; Li, C.; Braun, P.E.; McKerracher, L.; Roder, J.; Kater, S.B.; David, S. Myelin-associated glycoprotein inhibits neurite/axon growth and causes growth cone collapse. J. Neurosci. Res., 1996, 46(4), 404-414. (Pubitemid 26414567)
49. Quarles, R.H. Myelin-associated glycoprotein (MAG): past, present and beyond. J. Neurochem., 2007, 100(6), 1431-1448. (Pubitemid 46376206)
50. Vyas, A.A.; Blixt, O.; Paulson, J.C.; Schnaar, R.L. Potent glycan inhibitors of myelin-associated glycoprotein enhance axon outgrowth in vitro. J. Biol. Chem., 2005, 280(16), 16305-16310. (Pubitemid 40616758)
51. Yang, L.J.; Schnaar, R.L. Axon regeneration inhibitors. Neurol. Res., 2008, 30(10), 1047-1052.
52. Angata, T.; Tabuchi, Y.; Nakamura, K.; Nakamura, M. Siglec-15: an immune system Siglec conserved throughout vertebrate evolution. Glycobiology, 2007, 17(8), 838-846. (Pubitemid 47241821)
53. Hiruma, Y.T.; Tsuda, E. Antibody Targeting osteroclast-related protein Siglec-15. U.S. Patent Application 08/19/2010, August 10, 2010.
54. Brinkman-Van der Linden, E.C.; Angata, T.; Reynolds, S.A.; Powell, L.D.; Hedrick, S.M.; Varki, A. CD33/Siglec-3 binding specificity, expression pattern, and consequences of gene deletion in mice. Mol. Cell. Biol., 2003, 23(12), 4199-4206. (Pubitemid 36666423)
55. Freeman, S.D.; Kelm, S.; Barber, E.K.; Crocker, P.R. Characterization of CD33 as a new member of the sialoadhesin family of cellular interaction molecules. Blood, 1995, 85(8), 2005-2012.
56. Linenberger, M.L. CD33-directed therapy with gemtuzumab ozogamicin in acute myeloid leukemia: progress in understanding cytotoxicity and potential mechanisms of drug resistance. Leukemia, 2005, 19(2), 176-182. (Pubitemid 40220577)
57. Peiper, S.C.; Ashmun, R.A.; Look, A.T. Molecular cloning, expression, and chromosomal localization of a human gene encoding the CD33 myeloid differentiation antigen. Blood, 1988, 72(1), 314-321.
58. Connolly, N.P.; Jones, M.; Watt, S.M. Human Siglec-5: tissue distribution, novel isoforms and domain specificities for sialic acid-dependent ligand interactions. Br. J. Haematol., 2002, 119(1), 221-238. (Pubitemid 35176524)
59. Cornish, A.L.; Freeman, S.; Forbes, G.; Ni, J.; Zhang, M.; Cepeda, M.; Gentz, R.; Augustus, M.; Carter, K.C.; Crocker, P.R. Characterization of siglec-5, a novel glycoprotein expressed on myeloid cells related to CD33. Blood, 1998, 92(6), 2123-2132. (Pubitemid 28446703)
60. Gunnarsson, P.; Levander, L.; Pahlsson, P.; Grenegard, M. The acute-phase protein alpha 1-acid glycoprotein (AGP) induces rises in cytosolic Ca2+ in neutrophil granulocytes via sialic acid binding immunoglobulin-like lectins (siglecs). FASEB J., 2007, 21(14), 4059-4069. (Pubitemid 350232362)
61. Jones, C.; Virji, M.; Crocker, P.R. Recognition of sialylated meningococcal lipopolysaccharide by siglecs expressed on myeloid cells leads to enhanced bacterial uptake. Mol. Microbiol., 2003, 49(5), 1213-1225. (Pubitemid 37153492)
62. Brinkman-Van der Linden, E.C.; Hurtado-Ziola, N.; Hayakawa, T.; Wiggleton, L.; Benirschke, K.; Varki, A.; Varki, N. Human-specific expression of Siglec-6 in the placenta. Glycobiology, 2007, 17(9), 922-931. (Pubitemid 47423882)
63. Patel, N.; Brinkman-Van der Linden, E.C.; Altmann, S.W.; Gish, K.; Balasubramanian, S.; Timans, J.C.; Peterson, D.; Bell, M.P.; Bazan, J.F.; Varki, A.; Kastelein, R.A. OB-BP1/Siglec-6. a leptin- and sialic acid-binding protein of the immunoglobulin superfamily. J. Biol. Chem., 1999, 274(32), 22729-22738.
64. Wang, S.N.; Hu, G.; Yao, Z. Diagnosis and treatment of Siglec-6 associated diseases. U.S. Patent 10/481529, February 13, 2008.
65. Angata, T.; Varki, A. Siglec-7: a sialic acid-binding lectin of the immunoglobulin superfamily. Glycobiology, 2000, 10(4), 431-438. (Pubitemid 30184614)
66. Avril, T.; Wagner, E.R.; Willison, H.J.; Crocker, P.R. Sialic acid-binding immunoglobulin-like lectin 7 mediates selective recognition of sialylated glycans expressed on Campylobacter jejuni lipooligosaccharides. Infect. Immun., 2006, 74(7), 4133-4141. (Pubitemid 43993346)
67. Falco, M.; Biassoni, R.; Bottino, C.; Vitale, M.; Sivori, S.; Augugliaro, R.; Moretta, L.; Moretta, A. Identification and molecular cloning of p75/AIRM1, a novel member of the sialoadhesin family that functions as an inhibitory receptor in human natural killer cells. J. Exp. Med., 1999, 190(6), 793-802.
68. Nicoll, G.; Ni, J.; Liu, D.; Klenerman, P.; Munday, J.; Dubock, S.; Mattei, M.G.; Crocker, P.R. Identification and characterization of a novel siglec, siglec-7, expressed by human natural killer cells and monocytes. J. Biol. Chem., 1999, 274(48), 34089-34095. (Pubitemid 129511743)
69. Yamaji, T.; Teranishi, T.; Alphey, M.S.; Crocker, P.R.; Hashimoto, Y. A small region of the natural killer cell receptor, Siglec-7, is responsible for its preferred binding to alpha 2,8-disialyl and branched alpha 2,6-sialyl residues. A comparison with Siglec-9. J. Biol. Chem., 2002, 277(8), 6324-6332. (Pubitemid 34968425)
70. Bochner, B.S. Siglec-8 on human eosinophils and mast cells, and Siglec-F on murine eosinophils, are functionally related inhibitory receptors. Clin. Exp. Allergy, 2009, 39(3), 317-324.
71. Bochner, B.S.; Alvarez, R.A.; Mehta, P.; Bovin, N.V.; Blixt, O.; White, J.R.; Schnaar, R.L. Glycan array screening reveals a candidate ligand for Siglec-8. J. Biol. Chem., 2005, 280(6), 4307-4312. (Pubitemid 40288598)
72. Floyd, H.; Ni, J.; Cornish, A.L.; Zeng, Z.; Liu, D.; Carter, K.C.; Steel, J.; Crocker, P.R. Siglec-8. A novel eosinophil-specific member of the immunoglobulin superfamily. J. Biol. Chem., 2000, 275(2), 861-866. (Pubitemid 30051127)
73. Nutku, E.; Aizawa, H.; Hudson, S.A.; Bochner, B.S. Ligation of Siglec-8: a selective mechanism for induction of human eosinophil apoptosis. Blood, 2003, 101(12), 5014-5020. (Pubitemid 36857767)
74. von Gunten, S.; Vogel, M.; Schaub, A.; Stadler, B.M.; Miescher, S.; Crocker, P.R.; Simon, H.U. Intravenous immunoglobulin preparations contain anti-Siglec-8 autoantibodies. J. Allergy Clin. Immunol, 2007, 119(4), 1005-1011. (Pubitemid 46527831)
75. Angata, T.; Varki, A. Cloning, characterization, and phylogenetic analysis of siglec-9, a new member of the CD33-related group of siglecs. Evidence for co-evolution with sialic acid synthesis pathways. J. Biol. Chem., 2000, 275(29), 22127-22135. (Pubitemid 30621793)
76. Belisle, J.A.; Horibata, S.; Jennifer, G.A.; Petrie, S.; Kapur, A.; Andre, S.; Gabius, H.J.; Rancourt, C.; Connor, J.; Paulson, J.C.; Patankar, M.S. Identification of Siglec-9 as the receptor for MUC16 on human NK cells, B cells, and monocytes. Mol. Cancer, 2010, 9, 118.
77. Biedermann, B.; Gil, D.; Bowen, D.T.; Crocker, PR. Analysis of the CD33-related siglec family reveals that Siglec-9 is an endocytic receptor expressed on subsets of acute myeloid leukemia cells and absent from normal hematopoietic progenitors. Leuk. Res., 2007, 31(2), 211-220. (Pubitemid 44854197)
78. Carlin, A.F.; Uchiyama, S.; Chang, Y.C.; Lewis, A.L.; Nizet, V.; Varki, A. Molecular mimicry of host sialylated glycans allows a bacterial pathogen to engage neutrophil Siglec-9 and dampen the innate immune response. Blood, 2009, 113(14), 3333-3336.
79. von Gunten, S.; Yousefi, S.; Seitz, M.; Jakob, S.M.; Schaffner, T.; Seger, R.; Takala, J.; Villiger, P.M.; Simon, H.U. Siglec-9 transduces apoptotic and nonapoptotic death signals into neutrophils depending on the proinflammatory cytokine environment. Blood, 2005, 106(4), 1423-1431. (Pubitemid 41129611)
80. Zhang, J.Q.; Nicoll, G.; Jones, C.; Crocker, PR. Siglec-9, a novel sialic acid binding member of the immunoglobulin superfamily expressed broadly on human blood leukocytes. J. Biol. Chem, 2000, 275(29), 22121-22126. (Pubitemid 30621792)
81. Kivi, E.; Elima, K.; Aalto, K.; Nymalm, Y.; Auvinen, K.; Koivunen, E.; Otto, D.M.; Crocker, PR.; Salminen, T.A.; Salmi, M.; Jalkanen, S. Human Siglec-10 can bind to vascular adhesion protein-1 and serves as its substrate. Blood, 2009, 114(26), 5385-5392.
82. Li, N; Zhang, W.; Wan, T.; Zhang, J.; Chen, T.; Yu, Y; Wang, J.; Cao, X. Cloning and characterization of Siglec-10, a novel sialic acid binding member of the Ig superfamily, from human dendritic cells. J. Biol. Chem., 2001, 276(30), 28106-28112.
83. Munday, J.; Kerr, S.; Ni, J.; Cornish, A.L.; Zhang, J.Q.; Nicoll, G.; Floyd, H.; Mattei, M.G.; Moore, P.; Liu, D.; Crocker, PR. Identification, characterization and leucocyte expression of Siglec-10, a novel human sialic acid-binding receptor. Biochem. J., 2001, 355(Pt 2), 489-497. (Pubitemid 32397810)
84. Whitney, G.; Wang, S.; Chang, H.; Cheng, K.Y; Lu, P.; Zhou, X.D.; Yang, W.P; McKinnon, M.; Longphre, M. A new siglec family member, siglec-10, is expressed in cells of the immune system and has signaling properties similar to CD33. Eur. J. Biochem., 2001, 268(23), 6083-6096. (Pubitemid 33132029)
85. Angata, T.; Kerr, S.C.; Greaves, D.R.; Varki, N.M.; Crocker, PR.; Varki, A. Cloning and characterization of human Siglec-11. A recently evolved signaling molecule that can interact with SHP-1 and SHP-2 and is expressed by tissue macrophages, including brain microglia. J. Biol. Chem., 2002, 277(27), 24466-24474. (Pubitemid 34951971)
86. Linnartz, B.; Wang, Y; Neumann, H. Microglial immunoreceptor tyrosine-based activation and inhibition motif signaling in neuro inflammation. Int. J. Alzheimers Dis., 2010, 2010, 7 pages.
87. Salminen, A.; Kaarniranta, K. Siglec receptors and hiding plaques in Alzheimer's disease. J. MolMed, 2009, 87(7), 697-701.
88. Wang, Y; Neumann, H. Alleviation of neurotoxicity by microglial human Siglec-11. J. Neurosci., 2010, 30(9), 3482-3488.
89. Angata, T.; Hayakawa, T.; Yamanaka, M.; Varki, A.; Nakamura, M. Discovery of Siglec-14, a novel sialic acid receptor undergoing concerted evolution with Siglec-5 in primates. FASEB J., 2006, 20(12), 1964-1973. (Pubitemid 44953896)
90. Yamanaka, M.; Kato, Y; Angata, T.; Narimatsu, H. Deletion polymorphism of SIGLEC14 and its functional implications. Glycobiology, 2009, 19(8), 841-846.
91. Cao, H.; Crocker, PR. Evolution of CD33-related siglecs: regulating host immune functions and escaping pathogen exploitation? Immunology, 2011, 132(1), 18-26.
92. Cao, H.; Lakner, U.; de Bono, B.; Traherne, J.A.; Trowsdale, J.; Barrow, A.D. SIGLEC16 encodes a DAP12-associated receptor expressed in macrophages that evolved from its inhibitory counterpart SIGLEC11 and has functional and non-functional alleles in humans. Eur. J. Immunol, 2008, 38(8), 2303-2315.
93. Lee, R.T.; Lee, YC. Affinity enhancement by multivalent lectin-carbohydrate interaction. Glycoconj. J., 2000, 17(7-9), 543-551. (Pubitemid 32480343)
94. Rudiger, H.; Siebert, H.C.; Solis, D.; Jimenez-Barbero, J.; Romero, A.; von der Lieth, C. W.; Diaz-Marino, T.; Gabius, H.J. Medicinal chemistry based on the sugar code: fundamentals of lectinology and experimental strategies with lectins as targets. Curr. Med. Chem., 2000, 7(4), 389-416. (Pubitemid 30396433)
95. Simanek, E.E.; McGarvey, G.J.; Jablonowski, J.A.; Wong, C.-H. Selectin-Carbohydrate Interactions: From Natural Ligands to Designed Mimics. Chem. Rev., 1998, 98(2), 833-862. (Pubitemid 128631443)
96. Bi, S.; Baum, L.G. Sialic acids in T cell development and function. Biochim. Biophys. Acta, 2009, 1790(12), 1599-1610.
97. Hedlund, M.; Tangvoranuntakul, P.; Takematsu, H.; Long, J.M.; Housley, G.D.; Kozutsumi, Y.; Suzuki, A.; Wynshaw-Boris, A.; Ryan, A.F.; Gallo, R.L.; Varki, N.; Varki, A. N-glycolylneuraminic acid deficiency in mice: implications for human biology and evolution. Mol. Cell. Biol., 2007, 27(12), 4340-4346. (Pubitemid 46906558)
98. Varki, N.M.; Strobert, E.; Dick Jr, E.J.; Benirschke, K.; Varki, A. Biomedical Differences Between Human and Nonhuman Hominids: Potential Roles for Uniquely Human Aspects of Sialic Acid Biology. Annu. Rev. Pathol., 2010.
99. Alphey, M.S.; Attrill, H.; Crocker, P.R.; van Aalten, D.M. High resolution crystal structures of Siglec-7. Insights into ligand specificity in the Siglec family. J. Biol. Chem., 2003, 278(5), 3372-3377. (Pubitemid 36801252)
100. Attrill, H.; Imamura, A.; Sharma, R.S.; Kiso, M.; Crocker, P.R.; van Aalten, D.M. Siglec-7 undergoes a major conformational change when complexed with the alpha(2,8)-disialylganglioside GT1b. J. Biol. Chem., 2006, 281(43), 32774-32783. (Pubitemid 46036833)
101. Avril, T.; North, S.J.; Haslam, S.M.; Willison, H.J.; Crocker, P.R. Probing the cis interactions of the inhibitory receptor Siglec-7 with alpha2,8-disialylated ligands on natural killer cells and other leukocytes using glycan-specific antibodies and by analysis of alpha2,8-sialyltransferase gene expression. J. Leukoc. Biol., 2006, 80(4), 787-796. (Pubitemid 44835897)
102. May, A.P.; Robinson, R.C.; Vinson, M.; Crocker, P.R.; Jones, E.Y. Crystal structure of the N-terminal domain of sialoadhesin in complex with 3' sialyllactose at 1.85 A resolution. Mol. Cell, 1998, 1(5), 719-728. (Pubitemid 128379249)
103. Zaccai, N.R.; May, A.P.; Robinson, R.C.; Burtnick, L.D.; Crocker, P.R.; Brossmer, R.; Kelm, S.; Jones, E.Y. Crystallographic and in silico analysis of the sialoside-binding characteristics of the Siglec sialoadhesin. J. Mol. Biol., 2007, 365(5), 1469-1479. (Pubitemid 46061426)
104. Zhuravleva, M.A.; Trandem, K.; Sun, P.D. Structural implications of Siglec-5-mediated sialoglycan recognition. J. Mol. Biol., 2008, 375(2), 437-447. (Pubitemid 350192476)
105. Thompson, J.D.; Higgins, D.G.; Gibson, T.J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res., 1994, 22(22), 4673-4680. (Pubitemid 24354800)
106. Attrill, H.; Takazawa, H.; Witt, S.; Kelm, S.; Isecke, R.; Brossmer, R.; Ando, T.; Ishida, H.; Kiso, M.; Crocker, P.R.; van Aalten, D.M. The structure of siglec-7 in complex with sialosides: leads for rational structure-based inhibitor design. Biochem. J., 2006, 397(2), 271-278. (Pubitemid 44076896)
107. Crocker, P.R.; Redelinghuys, P. Siglecs as positive and negative regulators of the immune system. Biochem. Soc. Trans., 2008, 36(Pt 6), 1467-1471.
108. Wu, C.; Rauch, U.; Korpos, E.; Song, J.; Loser, K.; Crocker, P.R.; Sorokin, L.M. Sialoadhesin-positive macrophages bind regulatory T cells, negatively controlling their expansion and autoimmune disease progression. J. Immunol., 2009, 182(10), 6508-6516.
109. Cao, Z.; Gao, Y.; Deng, K.; Williams, G.; Doherty, P.; Walsh, F.S. Receptors for myelin inhibitors: Structures and therapeutic opportunities. Mol. Cell. Neurosci., 2010, 43(1), 1-14.
110. Bernstein, I.D. CD33 as a target for selective ablation of acute myeloid leukemia. Clin. Lymphoma, 2002, 2 Suppl. 1, S9-11.
111. Vitale, C.; Romagnani, C.; Puccetti, A.; Olive, D.; Costello, R.; Chiossone, L.; Pitto, A.; Bacigalupo, A.; Moretta, L.; Mingari, M.C. Surface expression and function of p75/AIRM-1 or CD33 in acute myeloid leukemias: engagement of CD33 induces apoptosis of leukemic cells. Proc. Natl. Acad. Sci. U. S. A, 2001, 98(10), 5764-5769. (Pubitemid 32435716)
112. Yokoi, H.; Myers, A.; Matsumoto, K.; Crocker, P.R.; Saito, H.; Bochner, B.S. Alteration and acquisition of Siglecs during in vitro maturation of CD34+ progenitors into human mast cells. Allergy, 2006, 61(6), 769-776. (Pubitemid 43801413)
113. Crocker, P.R.; Gordon, S. Properties and distribution of a lectin-like hemagglutinin differentially expressed by murine stromal tissue macrophages. J. Exp. Med., 1986, 164(6), 1862-1875. (Pubitemid 17217969)
114. Crocker, P.R.; Mucklow, S.; Bouckson, V.; McWilliam, A.; Willis, A.C.; Gordon, S.; Milon, G.; Kelm, S.; Bradfield, P. Sialoadhesin, a macrophage sialic acid binding receptor for haemopoietic cells with 17 immunoglobulin-like domains. EMBO J., 1994, 13(19), 4490-4503. (Pubitemid 24310199)
115. Heikema, A.P.; Bergman, M.P.; Richards, H.; Crocker, P.R.; Gilbert, M.; Samsom, J.N.; van Wamel, W.J.; Endtz, H.P.; van Belkum, A. Characterization of the specific interaction between sialoadhesin and sialylated Campylobacter jejuni lipooligosaccharides. Infect. Immun., 2010, 78(7), 3237-3246.
116. Crocker, P.R.; Hartnell, A.; Munday, J.; Nath, D. The potential role of sialoadhesin as a macrophage recognition molecule in health and disease. Glycoconj. J., 1997, 14(5), 601-609. (Pubitemid 27353204)
117. Kelm, S.; Pelz, A.; Schauer, R.; Filbin, M.T.; Tang, S.; de Bellard, M.E.; Schnaar, R.L.; Mahoney, J.A.; Hartnell, A.; Bradfield, P.; et al. Sialoadhesin, myelin-associated glycoprotein and CD22 define a new family of sialic acid-dependent adhesion molecules of the immunoglobulin superfamily. Curr. Biol., 1994, 4(11), 965-972. (Pubitemid 124001032)
118. Walker, J.A.; Smith, K.G. CD22: an inhibitory enigma. Immunology, 2008, 123(3), 314-325. (Pubitemid 351192818)
119. Onodera, T.; Poe, J.C.; Tedder, T.F.; Tsubata, T. CD22 regulates time course of both B cell division and antibody response. J. Immunol., 2008, 180(2), 907-913.
120. Razi, N.; Varki, A. Masking and unmasking of the sialic acid-binding lectin activity of CD22 (Siglec-2) on B lymphocytes. Proc. Natl. Acad. Sci. U.S.A, 1998, 95(13), 7469-7474. (Pubitemid 28293276)
121. Schwardt, O.; Gathje, H.; Vedani, A.; Mesch, S.; Gao, G.P.; Spreafico, M.; von Orelli, J.; Kelm, S.; Ernst, B. Examination of the biological role of the alpha(2->6)-linked sialic acid in gangliosides binding to the myelin-associated glycoprotein (MAG). J. Med. Chem., 2009, 52(4), 989-1004.
122. Kelm, S.L.; Brossmer, R. Siglec inhibitors. U.S. Patent Application 10/481529, September 9, 2004.
123. Abdu-Allah, H.H.; Tamanaka, T.; Yu, J.; Zhuoyuan, L.; Sadagopan, M.; Adachi, T.; Tsubata, T.; Kelm, S.; Ishida, H.; Kiso, M. Design, synthesis, and structure-affinity relationships of novel series of sialosides as CD22-specific inhibitors. J. Med. Chem., 2008, 51(21), 6665-6681.
124. Abdu-Allah, H.H.; Watanabe, K.; Hayashizaki, K.; Takaku, C.; Tamanaka, T.; Takematsu, H.; Kozutsumi, Y.; Tsubata, T.; Ishida, H.; Kiso, M. Potent small molecule mouse CD22-inhibitors: exploring the interaction of the residue at C-2 of sialic acid scaffold. Bioorg. Med. Chem. Lett, 2009, 19(19), 5573-5575.
125. Abdu-Allah, H.H.; Watanabe, K.; Complete, G.C.; Sadagopan, M.; Hayashizaki, K.; Takaku, C.; Tamanaka, T.; Takematsu, H.; Kozutsumi, Y.; Paulson, J.C.; Tsubata, T.; Ando, H.; Ishida, H.; Kiso, M. CD22-antagonists with nanomolar potency: the synergistic effect of hydrophobic groups at C-2 and C-9 of sialic acid scaffold. Bioorg. Med. Chem., 2011, 19(6), 1966-1971.
126. Schnaar, R.L. Brain gangliosides in axon-myelin stability and axon regeneration. FEBS Lett., 2010, 584(9), 1741-1747.
127. Schnaar, R.L.; Collins, B.E.; Wright, L.P.; Kiso, M.; Tropak, M.B.; Roder, J.C.; Crocker, P.R. Myelin-associated glycoprotein binding to gangliosides. Structural specificity and functional implications. Ann. N. Y. Acad. Sci., 1998, 845, 92-105.
128. Vyas, A.A.; Patel, H.V.; Fromholt, S.E.; Heffer-Lauc, M.; Vyas, K.A.; Dang, J.; Schachner, M.; Schnaar, R.L. Gangliosides are functional nerve cell ligands for myelin-associated glycoprotein (MAG), an inhibitor of nerve regeneration. Proc. Natl. Acad. Sci. U.S.A, 2002, 99(12), 8412-8417. (Pubitemid 34651066)
129. Yang, L.J.; Zeller, C.B.; Shaper, N.L.; Kiso, M.; Hasegawa, A.; Shapiro, R.E.; Schnaar, R.L. Gangliosides are neuronal ligands for myelin-associated glycoprotein. Proc. Natl. Acad. Sci. U.S.A, 1996, 93(2), 814-818. (Pubitemid 26041175)
130. Bhunia, A.; Jayalakshmi, V.; Benie, A.J.; Schuster, O.; Kelm, S.; Rama Krishna, N.; Peters, T. Saturation transfer difference NMR and computational modeling of a sialoadhesin-sialyl lactose complex. Carbohydr. Res., 2004, 339(2), 259-267. (Pubitemid 38041132)
131. Shin, S.Y.; Gathje, H.; Schwardt, O.; Gao, G.P.; Ernst, B.; Kelm, S.; Meyer, B. Binding epitopes of gangliosides to their neuronal receptor, myelin-associated glycoprotein, from saturation transfer difference NMR. Chembiochem, 2008, 9(18), 2946-2949.
132. Schwizer, D.; Gathje, H.; Kelm, S.; Porro, M.; Schwardt, O.; Ernst, B. Antagonists of the myelin-associated glycoprotein: a new class of tetrasaccharide mimics. Bioorg. Med. Chem., 2006, 14(14), 4944-4957. (Pubitemid 43767120)
133. Gao, G.; Smiesko, M.; Schwardt, O.; Gathje, H.; Kelm, S.; Vedani, A.; Ernst, B. Mimetics of the tri- and tetrasaccharide epitope of GQ1balpha as myelin-associated glycoprotein (MAG) ligands. Bioorg. Med. Chem., 2007, 15(23), 7459-7469. (Pubitemid 47539135)
134. Shelke, S.V.; Gao, G.P.; Mesch, S.; Gathje, H.; Kelm, S.; Schwardt, O.; Ernst, B. Synthesis of sialic acid derivatives as ligands for the myelin-associated glycoprotein (MAG). Bioorg. Med. Chem., 2007, 15(14), 4951-4965. (Pubitemid 46836828)
135. Mesch, S.; Lemme, K.; Koliwer-Brandl, H.; Strasser, D.S.; Schwardt, O.; Kelm, S.; Ernst, B. Kinetic and thermodynamic properties of MAG antagonists. Carbohydr. Res., 2010, 345(10), 1348-1359.
136. Schwardt, O.; Koliwer-Brandl, H.; Zimmerli, R.; Mesch, S.; Rossato, G.; Spreafico, M.; Vedani, A.; Kelm, S.; Ernst, B. Design, synthesis, biological evaluation, and modeling of a non-carbohydrate antagonist of the myelin-associated glycoprotein. Bioorg. Med. Chem., 2010, 18(20), 7239-7251.