Mechanism of action and efficacy of RX-111, a thieno[2,3-c]pyridine derivative and small molecule inhibitor of protein interaction with glycosaminoglycans (SMIGs), in delayed-type hypersensitivity, TNBS-induced colitis and experimental autoimmune encepha
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  • 作者:Nicholas Harris ; Juraj Koppel ; Ferenc Zsila ; Stefan Juhas…
  • 关键词:Small molecule drug ; Glycosaminoglycan ; Heparin binding protein ; Heparan sulfate ; Inflammation ; Autoimmune disease
  • 刊名:Inflammation Research
  • 出版年:2016
  • 出版时间:April 2016
  • 年:2016
  • 卷:65
  • 期:4
  • 页码:285-294
  • 全文大小:1,013 KB
  • 参考文献:1.Taylor KM, Irving PM. Optimization of conventional therapy in patients with IBD. Nat Rev Gastroenterol Hepatol. 2011;8:646–56.CrossRef PubMed
    2.Tabas I, Glass CK. Anti-inflammatory therapy in chronic disease: challenges and opportunities. Science. 2013;339(6116):166–72.CrossRef PubMed PubMedCentral
    3.Cahill RNP, et al. The effects of antigen on the migration of recirculating lymphocytes through single lymph nodes. J Exp Med. 1976;143:870–88.CrossRef PubMed
    4.Warnock RA, et al. Molecular mechanisms of lymphocyte homing to peripheral lymph nodes. J Exp Med. 1998;187:205–16.CrossRef PubMed PubMedCentral
    5.Danese S. Development of drugs to target interactions between leukocytes and endothelial cells and treatment algorithms for inflammatory bowel diseases. Gastroenterology. 2014;147:981–9.CrossRef PubMed
    6.Berger JR, Houff SA. Neurological infections: the year of PML and influenza. Lancet (Neurology). 2010;9:14–7.CrossRef
    7.Butcher EC, et al. Lymphocyte trafficking and regional immunity. Adv Immunol. 1999;72:209–53.CrossRef PubMed
    8.Mori N, et al. Anti-inflammatory drugs and endothelial cell adhesion molecule expression in murine vascular beds. Gut. 1999;44:186–95.CrossRef PubMed PubMedCentral
    9.Topilla-Salmi SK, et al. Endothelial L-selectin ligands in sinus mucosa during chronic maxillary rhinosinusitis. Am J Respir Crit Care Med. 2002;171:1350–7.CrossRef
    10.Harris N, et al. Small molecule inhibitors of protein interaction with glycosaminoglycans (SMIGs), a novel class of bioactive agents with anti-inflammatory properties. Biochim Biophys Acta. 2014;1840:245–54.CrossRef PubMed
    11.Lange-Asschenfeldt B, et al. Increased and prolonged inflammation and angiogenesis in delayed-type hypersensitivity reactions elicited in the skin of thrombospondin-2—deficient mice. Blood. 2002;99:538–45.CrossRef PubMed
    12.Reuter BK, et al. Exacerbation of inflammation-associated colonic injury in rat through inhibition of cyclooxygenase-2. J Clin Invest. 1996;98:2076–85.CrossRef PubMed PubMedCentral
    13.Archellos JJ, et al. Role of the leukocyte-adhesion molecule L-selectin in experimental autoimmune encephalomyelitis. J Neurol Sci. 1998;159:127–34.CrossRef
    14.Noravyan AS, et al. Synthesis of 2-and 4-substituted 5,6,7,8-tetrahydro-7-isopropylpyrido[4′,3′:4,5]thieno[2,3-d]pyrimidines. Pharm Chem J. 1980;14:111–3.
    15.Jiao QC, et al. Investigation on the binding site in heparin by spectrophotometry. Talanta. 1989;48:1095–101.CrossRef
    16.Zsila F. Glycosaminoglycan and DNA binding induced intra- and intermolecular exciton coupling of the bis-4-aminoquinoline surfen. Chirality. 2015;27:605–12.CrossRef PubMed
    17.Desreumaux P, et al. Attenuation of colon inflammation through activators of the retinoid X receptor (RXR)/peroxisome proliferator-activated receptor γ (PPAR γ) heterodimer: a basis for new therapeutic strategies. J Exp Med. 2001;93:827–38.CrossRef
    18.Constantinescu CS, et al. Experimental autoimmune encephalomyelitis (EAE) as a model for multiple sclerosis (MS). Br J Pharmacol. 2011;164:1079–106.CrossRef PubMed PubMedCentral
    19.Spertini O, et al. Leukocyte adhesion molecule-1 (LAM-1, L-selectin) interacts with an inducible endothelial cell ligand to support leukocyte adhesion. J Immunol. 1991;147(8):2565–73.PubMed
    20.Kansas GS, et al. A role for the epidermal growth factor-like domain of P-selectin in ligand recognition and cell adhesion. J Cell Biol. 1994;124:609–18.CrossRef PubMed
    21.Luscinskas FW, et al. Cytokine-activated human endothelial monolayers support enhanced neutrophil transmigration via a mechanism involving both endothelial-leukocyte adhesion molecule-1 and intercellular adhesion molecule-1. J Immunol. 1991;146(5):1617–25.PubMed
    22.Kawashima H. Roles of sulfated glycans in lymphocyte homing. Biol Pharm Bull. 2006;29:2343–9.CrossRef PubMed
    23.Nelson RM, et al. Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation. Blood. 1993;82:3253–8.PubMed
    24.Xie X, et al. Inhibition of selectin-mediated cell adhesion and prevention of acute inflammation by non-anticoagulant sulfated saccharides. J Biol Chem. 2000;275:34818–25.CrossRef PubMed
    25.Hirakawa J, et al. Novel anti-carbohydrate antibodies reveal the cooperative function of sulfated N- and O-glycans in lymphocyte homing. J Biol Chem. 2010;285:40864–78.CrossRef PubMed PubMedCentral
    26.Prankerd RJ. Critical compilation of pK a values for pharmaceutical substances. In: Brittain HG, editor. Profiles of drug substances, excipients and related methodology, vol. 33; 2007.
    27.Butcher EC, Picker LJ. Lymphocyte homing and homeostasis. Science. 1996;272(5258):60–6.CrossRef PubMed
    28.von Andrian UH, Memple TR. Homing and cellular traffic in lymph nodes. Nat Rev Immunol. 2003;3:867–78.CrossRef
    29.Girard JP, et al. HEVs, lymphatics and homeostatic immune cell trafficking in lymph nodes. Nat Rev Immunol. 2012;12(11):762–73.CrossRef PubMed
    30.Sperandio M. Selectins and glycosyltransferases in leukocyte rolling in vivo. FEBS J. 2006;273:4377–89.CrossRef PubMed
    31.Rosen SD. Ligands for L-selectin: homing, inflammation, and beyond. Annu Rev Immunol. 2004;2004(22):129–56.CrossRef
    32.Finger EB. Adhesion through L-selectin requires a threshold hydrodynamic shear. Nature. 1996;379(6562):266–9.CrossRef PubMed
    33.Lawrence MB, Springer TA. Leukocytes roll on a selectin at physiologic flow rates: distinction from and prerequisite for adhesion through integrins. Cell. 1991;65:859–73.CrossRef PubMed
    34.Bao X, et al. Endothelial heparan sulfate controls chemokine presentation in recruitment of lymphocytes and dendritic cells to lymph nodes. Immunity. 2010;33(5):817–29.CrossRef PubMed PubMedCentral
    35.Tsuboi K, et al. Role of high endothelial venule-expressed heparan sulfate in chemokine presentation and lymphocyte homing. J Immunol. 2013;191(1):448–55.CrossRef PubMed PubMedCentral
    36.Kunkel EJ. The roles of L-selectin, β7 integrins and P-selectin in leukocyte rolling and adhesion in high endothelial venules of Peyer’s patches. J Immunol. 1998;161:2449–56.PubMed
    37.Steeber DA, et al. Efficient lymphocyte migration across high endothelial venules of mouse Peyer’s patches requires overlapping expression of L-selectin and β7 integrin. J Immunol. 1998;161:6638–47.PubMed
    38.Rivera-Nieves J, et al. L-selectin, α4β1, and α4β7 integrins participate in CD4+ T cell recruitment to chronically inflamed small intestine. J Immunol. 2005;174:2343–52.CrossRef PubMed
    39.Belmiro CLR, et al. Biochemical and immunohistochemical analysis of glycosaminoglycans in inflamed and non-inflamed intestinal mucosa of patients with Crohn’s disease. Int J Colorectal Disord. 2005;20:295–304.CrossRef
    40.Feurer C, et al. Chronic relapsing allergic encephalomyelitis in the Lewis Rat. J Neuroimmunol. 1985;10:159–66.CrossRef PubMed
    41.Brocke S, et al. Antibodies to CD44 and integrin α4, but not L-selectin, prevent central nervous system inflammation and experimental encephalomyelitis by blocking secondary leukocyte recruitment. Proc Natl Acad Sci USA. 1999;96:6896–901.CrossRef PubMed PubMedCentral
    42.Steffen BJ, et al. lOAM-1, VCAM-1, and MAdCAM-1 are expressed on choroid plexus epithelium but not endothelium and mediate binding of lymphocytes in vitro. Am J Pathol. 1996;148:1819–38.PubMed PubMedCentral
    43.Wolburg K. Ultrastructural localization of adhesion molecules in the healthy and inflamed choroid plexus of the mouse. Cell Tissue Res. 1999;296(2):259–69.CrossRef PubMed
    44.Li O, et al. CD62L is required for the priming of encephalitogenic T cells but does not play a major role in the effector phase of experimental autoimmune encephalomyelitis. Scand J Immunol. 2006;64:117–24.CrossRef PubMed
    45.Mangano K, et al. Variable effects of cyclophosphamide in rodent models of experimental allergic encephalomyelitis. Clin Exp Immunol. 2009;159:159–68.CrossRef PubMed
    46.Donia M, et al. Specific and strain-independent effects of dexamethasone in the prevention and treatment of experimental autoimmune encephalomyelitis in rodents. Scand J Immunol. 2010;72:396–407.CrossRef PubMed
    47.Chen X, et al. Combined treatment with minocycline and prednisone attenuates experimental autoimmune encephalomyelitis in C57 BL/6 mice. J Neuroimmunol. 2009;210:22–9.CrossRef PubMed
    48.Shu YQ, et al. Combined therapy with methylprednisolone and ulinastatin in experimental autoimmune encephalomyelitis. Chin Med J. 2013;126(18):3439–45.PubMed
    49.Renkonnen J, et al. Glycosylation might provide endothelial zip codes for organ-specific leukocyte traffic into inflammatory sites. Am J Pathol. 2002;161:543–50.CrossRef
    50.Kobayashi M, et al. GlcNAc6ST-1-mediated decoration of MAdCAM-1 protein with L selectin ligand carbohydrates directs disease activity of ulcerative colitis. Inflamm Bowel Dis. 2004;15(5):697–706.CrossRef
    51.Bistrup A, et al. Detection of a sulfotransferase (HEC-GlcNAc6ST) in high endothelial venules of lymph nodes and in high endothelial venule-like vessels within ectopic lymphoid aggregates. Am J Pathol. 2004;164:1635–44.CrossRef PubMed PubMedCentral
    52.Pablos JL, et al. An HEV-restricted sulfotransferase is expressed in rheumatoid arthritis synovium and is induced by lymphotoxin-α/β and TNF-α in cultured endothelial cells. BMC Immunol. 2005;6:6.CrossRef PubMed PubMedCentral
    53.Suzawa K, et al. Preferential induction of peripheral lymph node addressin on high endothelial venule-like vessels in the active phase of ulcerative colitis. Am J Gastroenterol. 2007;102(7):1499–509.CrossRef PubMed
    54.Kansas GS. Selectins and their ligands: current concepts and controversies. Blood. 1966;88:3259–87.
    55.Watson SR. Glycoprotein ligands for L-selectin. In: Vestweber D, editor. The selectins. Amsterdam: Harwood Academic Publishers; 1997. p. 179–93.
    56.Homeister JW, et al. The α(1,3) fucosyltransferases FucT-IV and FucT-VII exert collaborative control over selectin-dependent leukocyte recruitment and lymphocyte homing. Immunity. 2001;15:115–26.CrossRef PubMed
    57.Kawashima H, et al. N-acetylglucosamine-6-O-sulfotransferases 1 and 2 cooperatively control lymphocyte homing through L-selectin ligand biosynthesis in high endothelial venules. Nat Immunol. 2005;6(11):1096–104.CrossRef PubMed
    58.Uchimura K, et al. A major class of L-selectin ligands is eliminated in mice deficient in two sulfotransferases expressed in high endothelial venules. Nat Immunol. 2005;6(11):1105–13.CrossRef PubMed
    59.Mitoma J, et al. Critical functions of N-glycans in L-selectin-mediated lymphocyte homing and recruitment. Nat Immunol. 2007;8(4):409–18.CrossRef PubMed
    60.Cardin AD, Weintraub HJR. Molecular modeling of protein–proteoglycan interactions. Arteriosclerosis. 1989;9:21–32.CrossRef PubMed
    61.Zhao W, et al. Binding affinities of vascular endothelial growth factor (VEGF) for heparin-derived oligosaccharides. Biosci Rep. 2012;32:71–81.CrossRef PubMed PubMedCentral
  • 作者单位:Nicholas Harris (1) (2)
    Juraj Koppel (3)
    Ferenc Zsila (4)
    Stefan Juhas (3) (8)
    Gabriela Il’kova (3) (7)
    Faina Yurgenzon Kogan (1)
    Orly Lahmy (1)
    Gizi Wildbaum (5)
    Nathan Karin (5)
    Regina Zhuk (1)
    Paul Gregor (1) (6)

    1. Rimonyx Pharmaceuticals Ltd., Rabin Science Park, 70400, Ness-Ziona, Israel
    2. Ephraim Katzir Department of Biotechnology Engineering, ORT Braude Academic College of Engineering, 21982, Karmiel, Israel
    3. Institute of Animal Physiology, Slovak Academy of Sciences, 04001, Kosice, Slovakia
    4. Biomolecular Self-Assembly Group, Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Budapest, Hungary
    8. Institute of Animal Physiology and Genetics of the ASCR, v. v. i., Rumburská 89, 277 21, Liběchov, Czech Republic
    7. GYN-FIV a.s., Záhradnícka 42, 821 085, Bratislava, Slovakia
    5. Department of Immunology, Rappaport Institute, Rappaport Faculty of Medicine, Technion, Haifa, Israel
    6. GISMO Therapeutics Inc., A253 ASTECC-UK, Lexington, KY, 40506, USA
  • 刊物类别:Biomedical and Life Sciences
  • 刊物主题:Biomedicine
    Immunology
    Pharmacology and Toxicology
    Allergology
    Dermatology
    Neurology
    Rheumatology
  • 出版者:Birkh盲user Basel
  • ISSN:1420-908X
文摘
Objective and design Elucidate the mechanism of action of the small molecule inhibitor of protein binding to glycosaminoglycans, RX-111 and assay its anti-inflammatory activity in animal models of inflammatory disease.

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