77
Views
11
CrossRef citations to date
0
Altmetric
Review

Selectin inhibitors

&
Pages 305-317 | Published online: 02 Mar 2005

Bibliography

  • GALLATIN WM, WEISSMAN IL, BUTCHER EC: A cell-surface molecule involved in organ-specific homing of lymphocytes. Nature (1983) 304:30–34.
  • LEWINSOHN DM, BARGATZE RF, BUTCHER EC: Leukocyte-endothelial cell recognition: evidence of a common molecular mechanism shared by neutrophils, lymphocytes, and other leukocytes. Immunol. (1987) 138:4313–4321.
  • GENG JG, BEVILACQUA MP, MOORE KL et al.: Rapid neutrophil adhesion to activated endothelium mediated by GMP-140. Nature (1990) 343:757–760.
  • HATTORI R, HAMILTON KK, FUGATE RD, MCEVER RP, SIMS PJ: Stimulated secretion of endothelium von Willebrand factor is accompanied by rapid redistribution to the cell surface of the intracellular granule membrane protein GMP-140. j. Biol. Chem. (1989) 264:7768–7771.
  • BEVILACQUA MP, POBER JS, MENDRICK DL, COTRAN RS, GIMBRONE MA JR: Identification of an inducible endothelial-leukocyte adhesion molecule. Proc. Natl. Acad. Sci. USA (1987) 84:9238–9242.
  • SPRINGER TA: Traffic signals on endothelium for lymphocyte recirculation and leukocyte emigration. Ann. Rev Physiol. (1995) 57:827–872.
  • BUTCHER EC: Leukocyte-endothelial cell recognition: three (or more) steps to specificity and diversity. Cell (1991) 67:1033–1036.
  • JUNG U, NORMAN KE, RAMOS CL, SCHARFFETTER-KOCHANEK K, BEAUDET AL, LEY K: Transit time of leukocytes rolling through venules controls cytokine-induced inflammatory cell recruitment in vivo. " Clin. Invest. (1998) 102:1526–1533.
  • LEY K, BULLARD DC, ARBONES ML et al.: Sequential contribution of L- and P-selectin to leukocyte rolling in vivo. " Exp. Med. (1995) 181:669–675.
  • MAYADAS TN, JOHNSON RC, RAYBURN H, HYNES RO, WAGNER DD: Leukocyte rolling and extravasation are severly compromised in P-selectin deficient mice. Cell (1993) 74:541-554. BULLARD DC, KUNKEL EJ, KUBO H et al.: Infectious susceptibility and severe deficiency of leukocyte rolling and recruitment in E-selectin and P-selectin double mutant mice. J. Exp. Med. (1996) 183:2329–2336.
  • FRENETTE PS, MAYADAS TN, RAYBURN H, HYNES RO, WAGNER DD: Susceptibility to infection and altered hematopoiesis in mice deficient in both P- and E- selectins. Cell (1996) 84:563–574.
  • LABOW MA, NORTON CR, RUMBERGER JM et al.: Characterization of E-selectin-deficient mice: demonstration of overlapping function of the endothelial selectins. Immunity (1994) 1:709–720.
  • ARBONES ML, ORD DC, LEY K et at: Lymphocyte homing and leukocyte rolling and migration are impaired in L-selectin-deficient mice. Immunity (1994) 1:247–260.
  • FEIZI T: Carbohydrate-mediated recognition systems in innate immunity. Immunological Reviews (2000) 173:79–88.
  • HEMMERICH S, BERTOZZI CR, LEFFLER H, ROSEN SD: Identification of the sulfated monosaccharides of G1yCAM-1, an endothelial-derived ligand for L-selectin. Biochemistry (1994) 33:4820–4829.
  • GALUSTIAN C, CHILDS RA, STOLL M, ISHIDA H, KISO M, FEIZI T: Synergistic interactions of the two classes of ligand, sialyl-Lewis'fxfuco-oligosaccharides and short sulpho-motifs, with the P- and L-selectins: implications for therapeutic inhibitor designs. Immunology (2002) 105:350–359.
  • BRUEHL RE, BERTOZZI CR, ROSEN SD: Minimal sulfated carbohydrates for recognition by L-selectin and the MECA-79 antibody. I Biol. Chem. (2000) 275:32642–32648.
  • SOMERS WS, TANG J, SHAW GD, CAMPHAUSEN RT: Insight into the molecular basis of leukocyte tethering and rolling revealed by structures of P- and E-selectin bound to sLex and PSGL-1. Cell (2000) 103:467–479.
  • GRAVES BJ, CROWTHER RL, CHANDRAM C et al.: Insight into E-selectin/ligand interaction from the crystal structure and mutagenesis of the lec/EGF domains. Nature (1994) 367:532–538.
  • LEFER DJ: Pharmacology of selectin inhibitors in ischemia/reperfusion states. Ann. Rev. Pharmacol. Toxicol. (2000) 40:283–294.
  • EBNET K, VESTWEBER D: Molecular mechanisms that control leukocyte extravasation:the selectins and the chemokines. Histochem. Cell Biol. (1999) 112:1–23.
  • KAILA N, THOMAS BE: Design and synthesis of sialyl Lewis' mimics as E- and P-selectin inhibitors. Medicinal Research Reviews (2002) 22:566–601.
  • BERTOZZI CR, KIESSLING LL: Chemical glycobiology. Science (2001) 291:2357–2364.
  • YUEN C-T, BEZOUSKA K, O'BRIEN J et al.: Sulfated blood group Lewis'. J. Biol. Chem. (1994) 269:1595–1598.
  • KOENIG A, JAIN R, VIG R, NORGARD-SUMNICHT KE, MATTA KL, VARKI A: Selectin inhibition: synthesis and evaluation of novel sialylated, sulfated and fucosylated oligosaccharides, including the major capping group of G1yCAM-1. Clycobiology (1997) 7:79–93.
  • MANNING DD, BERTOZZI CR, POHL NL, ROSEN SD, KIESSLING LL: Selectin-saccharide interactions: revealing structure-function relationships with chemical synthesis. Org. Chem. (1995) 60:6254–6255.
  • OHMOTO H, NAKAMURA K, INOUE T et al.: Studies on selectin blockers: structure-activity relationships of sialyl Lewis x analogs. Med. Chem. (1996) 39:1339–1343.
  • MANNING DD, BERTOZZI CR, ROSEN SD, KIESSLING LL: Tin-mediated phosphorylation: synthesis and selectin binding of a phospho Lewis a analog. Tetrahedron Lett (1996) 37:1953–1956.
  • MUSSER JH, RAO N, NASHED M et al.:Structure-activity studies based on the sialyl Lewis X epitope. Pharmacochem. Libt (1993) 20 (Trends in drug research ):33–40.
  • HANESSIAN S, HUYNH HK, REDDY GV et al.: Exploration of I3-turn scaffolding motifs as components of sialyl Lewis x mimetics and their relevance to P-selectin. Bioorg. Med. Chem. Lett. (1998) 8:2803–2808.
  • HANESSIAN S, REDDY GV, HUYNH HK, PAN J, PEDATELLA S: Design and synthesis of sialyl Le' mimetics based on carbocyclic scaffolds derived from ( -) quinic acid. Bioorg. Med. Chem. Lett. (1997) 7:2729–2734.
  • HUANG H, WONG C-H: Synthesis of biologically active sialyl Lewis x mimetics. J. Org. Chem. (1995) 60:3100–3106.
  • TOEPFER A, KRETZSCHMAR G, BARTNIK E: Synthesis of novel mimetics of the sialyl Lewis x determinant. Tetrahedron Lett. (1995) 36:9161–9164.
  • BAMFORD MJ, BIRD MI, GORE PM et a/.: Synthesis and biological activity of conformationally constrained sialyl Lewis x analogues with reduced carbohydrate character. Bioorg. Med. Chem. Lett. (1996) 6:239–244.
  • PAGAN JA, COOPER K: Synthesis of a galactose-fucose disaccharide mimic of sialyl Lewis x. Bioorg. Med. Chem. Lett. (1994) 4:2563–2566.
  • UCHIYAMA T, VASSILEV VP, KAJIMOTO T et al: Design and synthesis of sialyl Lewis x mimetics. j. Am. Chem. Soc.(1995) 117: 5395–5396.
  • HUANG H, WONG C-H: Synthesis of biologically active sialyl Lewis x mimetics. J. Org. Chem. (1995) 60:3100–3106.
  • UCHIYAMA T, WOLTERING TI, WONG W et al.: Design and synthesis of C-linked fucosides as inhibitors of E-selectin. Bioorg. Med. Chem. (1996) 4:1149–1165.
  • TOEPFER A, KRETZSCHMAR G: Piperidine carboxylic acid derivatives as sialyl Lewis x mimetics. Bioorg. Med. Chem. Lett. (1997) 7:1311–1316.
  • LIU A, DILLON K, CAMPBELL PM, COX DC, HURYN DM: Synthesis of E-selectin inhibitors: use of an aryl-cyclohexyl ether as a disaccharide scaffold. Tetrahedron Lett. (1996) 37:3785–3788.
  • BANTELLI R, ERNST B. Synthesis of sialyl Lewis x mimics: replacement of galactose by aromatic spacers. Tetrahedron Lett. (1997) 38:4059–4062
  • HANESSIAN S, PRABHANJAN H: Design and synthesis of glycomimetic prototypes-a model sialyl Lewis x ligand for E-selectin. Synlett. (1994) 868–870.
  • DEKANY G, WRIGHT K, WARD p, TOTH I: Synthesis of sialyl Lewis x analogues. Carbohydrate Chem. (1996) 15:383–398.
  • KAILA N, YU H-A, XIANG Y: Design and synthesis of novel sialyl Lewis x mimics. Tetrahedron Lett. (1995) 36:5503–5506.
  • BIRKBECK AA, LEY SV, PRODGER IC:Spiroketal glycomimetics: the synthesis of a conformationally restrained sialyl Lewis x mimic. Bioorg. Med. Chem. Lett. (1995) 5:2637–2642.
  • CAPPI MW, MOREE WJ, QIAO L, MARRON TG, WETZ-SCHMIDT G, WONG C-H: Synthsis of novel 6-amido-6-deoxy-L-galactose derivatives as sialyl Lewis x mimetics. Bioorg. Med. Chem. (1997) 5:283–296.
  • KOGAN TP, DUPRE B, KELLER KM et al.: Rational design and synthesis of small molecule, non-oligosaccharide selectin inhibitors: a-D-mannosepyranosyloxy biphenyl-substituted carboxylic acids. .1 Med. Chem. (1995) 38:4976–4984.
  • KOGAN TP, DUPRE B, BUI H et al.: Novelsynthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl) 4 (2 a D mannopyranosyloxy) phenyl] hexane (TBC12 69). J. Med. Chem. (1998) 41:1099–1111.
  • SAKAGAMI M, HORIE K, NAKAMOTO K, KAWAGUCHI T, HAMANA H: Sialyl Lewis x-polysaccharide conjugates: targeting inflammatory lesions. Bioorg. Med. Chem. Lett. (1998) 8:2783–2786.
  • SEARS P, WONG C-H: Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition. Angew Chem. hat Ed. (1999) 38:2300–2324.
  • THOMA G, PATTON IT, MAGNANI IL, ERNST B, OHRLEIN R, DUTHALER RO: Versatile functionalization of polylysine: synthesis, characterization and use of neoglycoconjugates. .1 Am. Chem. Soc. (1999) 12:5919–5929.
  • STAHN R, SCHAEFER H, KERNCHEN F, SCHREIBER J: Multivalent sialyl Lewis x ligands of definite structures as inhibitors of E-selectin mediated cell adhesion. Clycobiology (1998) 8:311–319.
  • ROY R: Syntheses and some applications of chemically defined multivalent glycoconjugates. Curt Opin. Struct. Biol. (1996) 6:692–702.
  • KIESSLING LL, POHL NL: Strength in numbers: non-natural polyvalent carbohydrate derivatives. Chem. Biol. (1996) 3:71–77.
  • MAMMEN M, CHOI S-K, WHITESIDES GM: Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew Chem. mt. Ed. (1998) 37:2754–2794.
  • GARDINER JM: The therapeutic potential of synthetic multivalent carbohydrates. Expert Opin. havestig. Drugs (1998) 7:405–410.
  • WANG R, WONG C-H: Synthesis of sialyl Lewis x mimetics: use of 0-a-Fucosyl-(1R, 2/0-2-aminocyclohexanol. Terahedron Lett. (1996) 37:5427–5430.
  • •This class of compounds are discussed in detail in reference 17.
  • LIN C-C, SHIMAZAKI M, HECK M-P et al.: Synthesis of sialyl Lewis x mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition.j Am. Chem. Soc.(1996) 118:6826–6840.
  • LIN C-C, KIMURA T, WU S-H, WEITZ-SCHMIDT G, WONG C-H: Liposome-like fucopeptides as sialyl Lewis x mimetics. Bioorg. Med. Chem. Lett. (1996) 6:2755–2760.
  • WU S-H, SHIMAZAKI M, LIN C-C et al: Synthesis of fucopeptides as sialyl Lewis x mimetics. Angew Chem. hat Ed. (1996) 35:88–90.
  • LAMPE TFJ, WETZ-SCHMIDT G, WONG C-H: Parallel synthesis of sialyl Lewis x mimetics on a solid phase: access to a library of fucopeptides. Angew Chem. mt. Ed.(1998) 37:1707–1711.
  • PARDELLA L: TBC-1269 Texas biotechnology corp. Anti-inflammatory immunomodulatory Invest. Drugs (1999) 1:56–60.
  • RADI ZA, CAVERLY JM, DIXON RA, BROGDEN KA, ACKERMANN MR: Effects of the synthetic selectin inhibitor TBC1269 on tissue damage during acute Mannheimia haemolytica-induced pneumonia in neonatal calves. Am. .1 Vet. Res.(2001) 62(1):17–22.316
  • SLEE DH, ROMANO S, YU Jet al.: Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with anti-inflammatory activity. Med. Chem. (2001) 44:2094–2107.
  • WANG L, BROWN JR, VARKI A, ESKO JD: Heparin's anti-inflammatory effects require glucosamine 6-0-sulfation and are mediated by blockade of L- and P-selectins. Clin. Invest. (2002) 110:127–136.
  • DEFREES SA, KOSCH W, WAY W et al.: Ligand recognition by E-selectin: synthesis, inhibitory activity and conformational analysis of bivalent sialyl Lewis x analogs. Am. Chem. Soc. (1995) 117:66–79.
  • MIYAUCHI H, YURI M, TANAKA M, KAWAMURA N, HAYASHI M: Synthesis and inhibitory effects of bivalent sialyl Lewis x analogs at preventing cell adhesion. Bioorganic Med. Chem. Lett. (1997) 7:989–992.
  • BLACK WAP, DEWAR ET, WOODNAD FN: Manufacture of algal chemicals, IV, laboratory scale isolation of fucoidin from brown marine algae. .1 Sci. Food Agric. (1952) 3:122–129.
  • FUKUDA MN, OHYAMA C, LOWITZ K et al.: A peptide mimic of E-selectin ligand inhibits sialyl Lewis x-dependent lung colonization of tumor cells. Cancer R. (2000) 60:450–456.
  • ALLPORT JR, DING HT, AGER A, STEEBER DA, TEDDER TF, LUSCINSKAS FW: L-selectin shedding does not regulate human neutrophil attachment, rolling, or transition across human vascular endothelium in vitro. (1997) 158:4365–4372.
  • INSUG 0, KIEBER-EMMONS T, OTVOS L, BLASZCZYK-THURIN M. Peptide mimicking sialyl Lewis x with anti-inflammatory activity. Biochem. Biophys. Res. Comm. (2000) 268:106–111.
  • NIEHRS C, HUTTNER WB, CARVALLO D, DEGRYSE EJ: Conversion of recombinant hirudin to the natural form by M vitro tyrosine sulfation. Differential substrate specificities of leech and bovine tyrosylprotein sulfotransferases. Biol. Chem. (1990) 265:9314–9318.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.