Polyanionic drugs and viral oncogenesis: A novel approach to control infection, tumor-associated inflammation and angiogenesis

Molecules

Volumn 13, Issue 11, 2008, Pages 2758-2785

  Urbinati, Chiara ^a   Chiodelli, Paola ^a   Rusnati, Marco ^a  

^a UNIVERSITY OF BRESCIA   (Italy)

Author keywords

Angiogenesis; Cancer; Infectious diseases; Polyanionics

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; POLYANIONS; POLYMER;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; HUMAN; INFLAMMATION; METABOLISM; NEOVASCULARIZATION (PATHOLOGY); STRUCTURE ACTIVITY RELATION; VIROLOGY; VIRUS CELL TRANSFORMATION; VIRUS INFECTION;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL TRANSFORMATION, VIRAL; HUMANS; INFLAMMATION; NEOVASCULARIZATION, PATHOLOGIC; POLYMERS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR VIRUS INFECTIONS;

EID: 56349167518     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13112758     Document Type: Article

References (225)

1. Rusnati, M.; Tulipano, G.; Spillmann, D.; Tanghetti, E.; Oreste, P.; Zoppetti, G.; Giacca, M.; Presta, M. Multiple interactions of HIV-I Tat protein with size-defined heparin oligosaccharides. J. Biol. Chem. 1999, 274, 28198-28205.
2. Rusnati, M.; Presta, M. Interaction of angiogenic basic fibroblast growth factor with endothelial cell heparan sulfate proteoglycans. Biological implications in neovascularization. Int. J. Clin. Lab. Res. 1996, 26, 15-23.
3. Rusnati, M.; Urbinati, C.; Tanghetti, E.; Dell'Era, P.; Lortat-Jacob, H.; Presta, M. Cell membrane GM1 ganglioside is a functional coreceptor for fibroblast growth factor 2. Proc. Natl. Acad. Sci. USA 2002, 99, 4367-4372.
4. Poon, G. M.; Gariepy, J. Cell-surface proteoglycans as molecular portals for cationic peptide and polymer entry into cells. Biochem. Soc. Trans. 2007, 35, 788-793.
5. Olofsson, S.; Bergstrom, T. Glycoconjugate glycans as viral receptors. Ann. Med. 2005, 37, 154-172.
6. Wadstrom, T.; Ljungh, A. Glycosaminoglycan-binding microbial proteins in tissue adhesion and invasion: key events in microbial pathogenicity. J. Med. Microbiol. 1999, 48, 223-233.
7. Rusnati, M.; Urbinati, C.; Presta, M. Internalization of basic fibroblast growth factor (bFGF) in cultured endothelial cells: role of the low affinity heparin-like bFGF receptors. J. Cell Physiol. 1993, 154, 152-161.
8. Jones, L. S.; Yazzie, B.; Middaugh, C. R. Polyanions and the proteome. Mol. Cell Proteomics 2004, 3, 746-769.
9. Salamat-Miller, N.; Fang, J.; Seidel, C. W.; Assenov, Y.; Albrecht, M.; Middaugh, C. R. A network-based analysis of polyanion-binding proteins utilizing human protein arrays. J. Biol. Chem. 2007, 282, 10153-10163.
10. Doiron, A. L.; Kirkpatrick, A. P.; Rinker, K. D. TGF-beta and TNF-a affect cell surface proteoglycan and sialic acid expression on vascular endothelial cells. Biomed. Sci. Instrum. 2004, 40, 331-336.
11. Hippenmeyer, P. J.; Ruminski, P. G.; Rico, J. G.; Lu, H. S.; Griggs, D. W. Adenovirus inhibition by peptidomimetic integrin antagonists. Antiviral. Res. 2002, 55, 169-178.
12. Guerrero, C. A.; Mendez, E.; Zarate, S.; Isa, P.; Lopez, S.; Arias, C. F. Integrin alpha(v)beta(3) mediates rotavirus cell entry. Proc. Natl. Acad. Sci. USA 2000, 97, 14644-14649.
13. Schengrund, C. L. "Multivalent" saccharides: development of new approaches for inhibiting the effects of glycosphingolipids-binding pathogens. Biochem. Pharm. 2003, 65, 699-707.
14. Gullino, P. Prostaglandins and gangliosides of tumor microenvironment: their role in angiogenesis. Acta Oncol. 1995, 34, 439-441.
15. Chang, F.; Li, R.; Ladisch, S. Shedding of gangliosides by human medulloblastoma cells. Exp. Cell Res. 1991, 234, 341-346.
16. Kumar, C. C. Integrin alpha v beta 3 as a therapeutic target for blocking tumor-induced angiogenesis. Curr. Drug Targets 2003, 4, 123-131.
17. Munoz, E. M.; Linhardt, R. J. Heparin-binding domains in vascular biology. Arterioscler. Thromb. Vase. Biol. 2004, 24, 1549-1557.
18. Rusnati, M.; Presta, M. Extracellular angiogenic growth factor interactions: an angiogenesis interactome survey. Endothelium 2006, 13, 93-111.
19. Powell, A. K.; Yates, E. A.; Fernig, D. G.; Turnbull, J. E. Interactions of heparin/heparan sulfate with proteins: appraisal of structural factors and experimental approaches. Glycobiology 2004, 14, 17R-30R.
20. Rusnati, M.; Urbinati, C.; Presta, M. Glycomics and angiogenesis: biological implications and therapeutical exploiting. In: New Development in Therapeutic Glycomics; Delehedde, M., Lortat-Jacob, H., Eds; Research Signpost; Trivandum, India, 2006; pp. 33-77.
21. Petitou, M.; Casu, B.; Lindahl, U. 1976-1983, a critical period in the history of heparin: the discovery of the antithrombin binding site. Biochimie 2003, 85, 83-89.
22. Conrad, H. E. Heparin binding proteins; Academic Press: New York, USA, 1998.
23. Lindahl, U.; Lidholt, K.; Spillmann, D.; Kjellen, L. More to "heparin" than anticoagulation. Thromb. Res. 1994, 75, 1-32.
24. Casu, B.; Grazioli, G.; Razi, N.; Guerrini, M.; Naggi, A.; Torri, G.; Oreste, P.; Tursi, F.; Zoppetti, G.; Lindahl, U. Heparin-like compounds prepared by chemical modification of capsular polysaccharide from E. coli K5. Carbohydr. Res. 1994, 263, 271-284.
25. Volpi, N. Therapeutic applications of glycosaminoglycans. Curr. Med. Chem. 2006, 13, 1799-1810.
26. Rusnati, M.; Presta, M. Fibroblast growth factors/fibroblast growth factor receptors as targets for the development of anti-angiogenesis strategies. Curr. Pharm. Des. 2007, 13, 2025-2044.
27. Barrett, M. P.; Gilbert, I. H. Targeting of toxic compounds to the trypanosome's interior. Adv. Parasitol. 2006, 63, 125-183.
28. Abiose, A. Onchocercal eye disease and the impact of Mectizan treatment. Ann. Trop. Med. Parasitol. 1998, 92, Suppl. 1, S11-S22.
29. Rusnati, M.; Tulipano, G.; Urbinati, C.; Tanghetti, E.; Giuliani, R.; Giacca, M.; Ciomei, M.; Corallini, A.; Presta, M. The basic domain in HIV-1 Tat protein as a target for polysulfonated heparin-mimicking extracellular Tat antagonists. J. Biol. Chem. 1998, 273, 16027-16037.
30. Manetti, F.; Corelli, F.; Mongelli, N.; Borgia, A. L.; Botta, M. Research on anti-HIV-1 agents. Investigation on the CD4-Suradista binding mode through docking experiments. J. Comput. Aided Mol. Des. 2000, 14, 355-368.
31. Finch, P. W.; Yee, L. K.; Chu, M. Y.; Chen, T. M.; Lipsky, M. H.; Maciag, T.; Friedman, S.; Epstein, M. H.; Calabresi, P. Inhibition of growth factor mitogenicity and growth of tumor cell xenografts by a sulfonated distamycin A derivative. Pharmacology 1997, 55, 269-278.
32. Spillmann, D. Heparan sulfate: anchor for viral intruders? Biochimie 2001, 83, 811-817.
33. Barbouche, R.; Lortat-Jacob, H.; Jones, I. M.; Fenouillet, E. Glycosaminoglycans and protein disulfide isomerase-mediated reduction of HIV Env. Mol. Pharmacol. 2005, 67, 1111-1118.
34. Vives, R. R.; Imberty, A.; Sattentau, Q. J.; Lortat-Jacob, H. Heparan sulfate targets the HIV-1 envelope glycoprotein gp120 coreceptor binding site. J. Biol. Chem. 2005, 280, 21353-21357.
35. Harrop, H. A.; Rider, C. C. Heparin and its derivatives bind to HIV-1 recombinant envelope glycoproteins, rather than to recombinant HIV-1 receptor, CD4. Glycobiology 1998, 8, 131-137.
36. Crublet, E.; Andrieu, J. P.; Vives, R. R.; Lortat-Jacob, H. The HIV-1 envelope glycoprotein gp120 features four heparan sulfate binding domains, including the co-receptor binding site. J. Biol. Chem. 2008, 283, 15193-15200.
37. Shukla, D.; Liu, J.; Blaiklock, P.; Shworak, N. W.; Bai, X.; Esko, J. D.; Cohen, G. H.; Eisenberg, R. J.; Rosenberg, R. D.; Spear, P. G. A novel role for 3-O-sulfated heparan sulfate in herpes simplex virus 1 entry. Cell 1999, 99, 13-22.
38. Lederman, S.; Gulick, R.; Chess, L. Dextran sulfate and heparin interact with CD4 molecules to inhibit the binding of coat protein (gp120) of HIV. J. Immunol. 1989, 143, 1149-1154.
39. Ueki, M.; Watanabe, S.; Saitoh, T.; Nakashima, H.; Yamamoto, N.; Ogawara, H. Synthesis and chain length-anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine. Bioorg. Med. Chem. 2001, 9, 487-492.
40. Sydow, G.; Klocking, H. P. Effect of pentosan polysulfate (SP 54) on the reverse transcriptase activity of several retroviruses. Biomed. Biochim. Acta 1987, 46, 527-530.
41. Rideout, D.; Schinazi, R.; Pauza, C. D.; Lovelace, K.; Chiang, L. C.; Calogeropoulou, T.; McCarthy, M.; Elder, J. H. Derivatives of 4-amino-3,6-disulfonato-1,8-naphthalimide inhibit reverse transcriptase and suppress human and feline immunodeficiency virus expression in cultured cells. J. Cell. Biochem. 1993, 51, 446-457.
42. Witvrouw, M.; De Clercq, E. Sulfated polysaccharides extracted from sea algae as potential antiviral drugs. Gen. Pharmacol. 1997, 29, 497-511.
43. Moelling, K.; Schulze, T.; Diringer, H. Inhibition of human immunodeficiency virus type 1 RNase H by sulfated polyanions. J. Virol. 1989, 63, 5489-5491.
44. Rusnati, M.; Presta, M. HIV-1 Tat protein: a target for the development of anti-AIDS therapies. Drug Fut. 2002, 27, 481-493.
45. Dziarski, R. Synergistic enhancement of T cell responses and interleukin-1 receptor expression byinterleukin-1 and heparin or dextran sulfate. Cell Immunol. 1992, 145, 100-110.
46. Laudanna, C.; Constantin, G.; Baron, P.; Scarpini, E.; Scarlato, G.; Cabrini, G.; Dechecchi, C.; Rossi, F.; Cassatella, M. A.; Berton, G. Sulfatides trigger increase of cytosolic free calcium and enhanced expression of tumor necrosis factor-alpha and interleukin-8 mRNA in human neutrophils. Evidence for a role of L-selectin as a signaling molecule. J. Biol. Chem. 1994, 269, 4021-4026.
47. Nie, X.; Shi, B.; Ding, Y.; Tao, W. Preparation of a chemically sulfated polysaccharide derived from Grifóla frondosa and its potential biological activities. Int. J. Biol. Macromol. 2006, 39, 228-233.
48. Bae, S. Y.; Yim, J. H.; Lee, H. K.; Pyo, S. Activation of murine peritoneal macrophages by sulfated exopolysaccharide from marine microalga Gyrodinium impudicum (strain KG03): involvement of the NF-kappaB and JNK pathway. Int. Immunopharmacol. 2006, 6, 473-484.
49. Smith, S. A.; Kotwal, G. J. Virokines: novel immunomodulatory agents. Expert Opin. Biol. Ther. 2001, 1, 343-357.
50. Seet, B. T.; Barrett, J.; Robichaud, J.; Shilton, B.; Singh, R.; McFadden, G. Glycosaminoglycan binding properties of the myxoma virus CC-chemokine inhibitor, M-Tl. J. Biol. Chem. 2001, 276, 30504-30513.
51. Ruiz-Arguello, M. B.; Smith, V. P.; Campanella, G. S.; Baleux, F.; Arenzana-Seisdedos, F.; Luster, A. D.; Alcami, A. An ectromelia virus protein that interacts with chemokines through their glycosaminoglycan binding domain. J. Virol. 2008, 82, 917-926.
52. Tyagi, M.; Rusnati, M.; Presta, M.; Giacca, M. Internalization of HIV-1 tat requires cell surface heparan sulfate proteoglycans. J. Biol. Chem. 2001, 276, 3254-3261.
53. Rusnati, M.; Presta, M. HIV-1 Tat protein and endothelium: from protein/cell interaction to AIDS-associated pathologies. Angiogenesis 2002, 5, 141-151.
54. Nyberg, K.; Ekblad, M.; Bergstrom, T.; Freeman, C.; Parish, C. R.; Ferro, V.; Trybala, E. The low molecular weight heparan sulfate-mimetic, PI-88, inhibits cell-to-cell spread of herpes simplex virus. Antiviral Res. 2004, 63, 15-24.
55. Herold, B. C.; Gerber, S. I.; Belval, B. J.; Siston, A. M.; Shulman, N. Differences in the susceptibility of herpes simplex virus types 1 and 2 to modified heparin compounds suggest serotype differences in viral entry. J. Virol. 1996, 70, 3461-3469.
56. Mastromarino, P.; Seganti, L.; Petruzziello, R.; Gabrieli, R.; Divizia, M.; Pana, A.; Orsi, N. Influence of polyions on the early steps of enterovirus infection. 7. Chemother. 1991, 3, 203-208.
57. Sa-Carvalho, D.; Rieder, E.; Baxt, B.; Rodarte, R.; Tanuri, A.; Mason, P. W. Tissue culture adaption of foot-and-mouth disease virus selects viruses that bind to heparin and are attenuated in cattle. J. Virol. 1997, 71, 5115-5123.
58. Ying, C.; Van Pelt, J. F.; Van Lommel, A.; Van Ranst, M.; Leyssen, P.; De Clercq, E.; Neyts, J. Sulphated and sulphonated polymers inhibit the initial interaction of hepatitis B virus with hepatocytes. Antivir. Chem. Chemother. 2002, 13, 157-164.
59. Basu, A.; Kanda, T.; Beyene, A.; Saito, K.; Meyer, K.; Ray, R. Sulfated homologues of heparin inhibit hepatitis C virus entry into mammalian cells. J. Virol. 2007, 81, 3933-3941.
60. Lembo, D.; Donalisio, M.; Rusnati, M.; Bugatti, A.; Cornaglia, M.; Cappello, P.; Giovarelli, M.; Oreste, P.; Landolfo, S. Sulfated K5 Escherichia coli polysaccharide derivatives as wide range inhibitors of genital types of human papillomavirus. Antimicrob. Agents Chemother. 2008, 52, 1374-1381.
61. Zhang, Y.; Schols, D.; De Clercq, E. Selective activity of various antiviral compounds against HHV-7 infection. Antiviral. Res. 1999, 43, 23-35.
62. Birkmann, A.; Mahr, K.; Ensser, A.; Yaguboglu, S.; Titgemeyer, F.; Fleckenstein, B.; Neipel, F. Cell surface heparan sulfate is a receptor for human herpesvirus 8 and interacts with envelope glycoprotein K8.1. J. Virol. 2001, 75, 11583-11593.
63. Baba, M.; Snoeck, R.; Pauwels, R.; de Clercq, E. Sulfated polysaccharides are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, and human immunodeficiency virus. Antimicrob. Agents Chemother. 1988, 32, 1742-1745.
64. Zhu, Z.; Gershon, M. D.; Ambron, R.; Gabel, C.; Gershon, A. A. Infection of cells by varicella zoster virus: inhibition of viral entry by mannose-6-phosphate and heparin. Proc. Natl. Acad. Sci. USA 1995, 92, 3546-2550.
65. Jones, K. S.; Petrow-Sadowski, C.; Bertolette, D. C.; Huang, Y.; Ruscetti, F. W. Heparan sulfate proteoglycans mediate attachment and entry of human T-cell leukemia virus type 1 virions into CD4+ T cells. J. Virol. 2005, 79, 12692-12702.
66. Lopalco, L.; Ciccomascolo, F.; Lanza, P.; Zoppetti, G.; Caramazza, I.; Leoni, F.; Beretta, A.; Siccardi, A. G. Anti-HIV type 1 properties of chemically modified heparins with diminished anticoagulant activity. AIDS Res. Hum. Retroviruses 1994, 10, 787-793.
67. Lee, E.; Pavy, M.; Young, N.; Freeman, C.; Lobigs, M. Antiviral effect of the heparan sulfate mimetic, PI-88, against dengue and encephalitic flaviviruses. Antiviral. Res. 2006, 69, 31-38.
68. Andrei, G.; De Clercq, E. Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. Antiviral Res. 1990, 14, 287-299.
69. Hosoya, M.; Balzarini, J.; Shigeta, S.; De Clercq, E. Differential inhibitory effects of sulfated polysaccharides and polymers on the replication of various myxoviruses and retroviruses, depending on the composition of the target amino acid sequences of the viral envelope glycoproteins. Antimicrob. Agents Chemother. 1991, 35, 2515-2520.
70. Hallak, L. K.; Spillmann, D.; Collins, P. L.; Peeples, M. E. Glycosaminoglycan sulfation requirements for respiratory syncytial virus infection. J. Virol. 2000, 74, 10508-10513.
71. Konlee, M. Sulfated polysaccharides (chondroitin sulfate and carrageenan) plus glucosamine sulfate are potent inhibitors of HIV. Posit. Health News 1998, 4-7.
72. Buck, C. B.; Thompson, C. D.; Roberts, J. N.; Muller, M.; Lowy, D. R.; Schiller, J. T. Carrageenan is a potent inhibitor of papillomavirus infection. PLoS Pathog. 2006, 2, e69.
73. Talarico, L. B.; Damonte, E. B. Interference in dengue virus adsorption and uncoating by carrageenans. Virology 2007, 363, 473-485.
74. Girond, S.; Crance, J. M.; Van Cuyck-Gandre, H.; Renaudet, J.; Deloince, R. Antiviral activity of carrageenan on hepatitis A virus replication in cell culture. Res. Virol. 1991, 142, 261-270.
75. Briolant, S.; Garin, D.; Scaramozzino, N.; Jouan, A.; Crance, J. M. In vitro inhibition of Chikungunya and Semliki Forest viruses replication by antiviral compounds: synergistic effect of interferon-alpha and ribavirin combination. Antiviral Res. 2004, 61, 111-117.
76. Talarico, L. B.; Pujol, C. A.; Zibetti, R. G.; Faria, P. C.; Noseda, M. D.; Duarte, M. E.; Damonte, E. B. The antiviral activity of sulfated polysaccharides against dengue virus is dependent on virus serotype and host cell. Antiviral Res. 2005, 66, 103-110.
77. Malhotra, R.; Ward, M.; Bright, H.; Priest, R.; Foster, M. R.; Hurle, M.; Blair, E.; Bird, M. Isolation and characterisation of potential respiratory syncytial virus receptor(s) on epithelial cells. Microbes Infect. 2003, 5, 123-133.
78. Crance, J. M.; Gratier, D.; Guimet, J.; Jouan, A. Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds. Res. Virol. 1997, 148, 353-365.
79. Romanos, M. T.; Andrada-Serpa, M. J.; Mourao, P. A.; Yoneshigue-Valentin, Y.; Costa, S. S.; Pereira, M. S.; Miranda, M. M.; Goncalves, J. L.; Wigg, M. D. A sulphated fucan from the Laminaria abyssalis inhibits the human T cell lymphotropic virus type 1-induced syncytium formation in HeLa cells. Antivir. Chem. Chemother. 2002, 13, 219-221.
80. Flores, O.; Lee, G.; Kessler, J.; Miller, M.; Schlief, W.; Tomassini, J.; Hazuda, D. Host-cell positive transcription elongation factor b kinase activity is essential and limiting for HIV type 1 replication. Proc. Natl. Acad. Sci. USA 1999, 96, 7208-7213.
81. Cheshenko, N.; Keller, M. J.; MasCasullo, V.; Jarvis, G. A.; Cheng, H.; John, M.; Li, J. H.; Hogarty, K.; Anderson, R. A.; Waller, D. P.; Zaneveld, L. J.; Profy, A. T.; Klotman, M. E.; Herold, B. C. Candidate topical microbicides bind herpes simplex virus glycoprotein B and prevent viral entry and cell-to-cell spread. Antimicrob. Agents Chemother. 2004, 48, 2025-2036.
82. Christensen, N. D.; Reed, C. A.; Culp, T. D.; Hermonat, P. L.; Howett, M. K.; Anderson, R. A.; Zaneveld, L. J. Papillomavirus microbicidal activities of high-molecular-weight cellulose sulfate, dextran sulfate, and polystyrene sulfonate. Antimicrob. Agents Chemother. 2001, 45, 3427-3432.
83. El-Sadr, W. M.; Mayer, K. H.; Maslankowski, L.; Hoesley, C.; Justman, J.; Gai, F.; Mauck, C.; Absalon, J.; Morrow, K.; Masse, B.; Soto-Torres, L.; Kwiecien, A. Safety and acceptability of cellulose sulfate as a vaginal microbicide in HIV-infected women. Aids 2006, 20, 1109-1116.
84. Neyts, J.; Meerbach, A.; McKenna, P.; De Clercq, E. Use of the yellow fever virus vaccine strain 17D for the study of strategies for the treatment of yellow fever virus infections. Antiviral Res. 1996, 30, 125-132.
85. Mastromarino, P.; Petruzziello, R.; Macchia, S.; Rieti, S.; Nicoletti, R.; Orsi, N. Antiviral activity of natural and semisynthetic polysaccharides on the early steps of rubella virus infection. J. Antimicrob. Chemother. 1997, 39, 339-345.
86. Ida, H.; Kuráta, A.; Eguchi, K.; Yamashita, I.; Nakashima, M.; Sakai, M.; Kawabe, Y.; Nakamura, T.; Nagataki, S. Mechanism of inhibitory effect of dextran sulfate and heparin on human T-cell lymphotropic virus type I (HTLV-I)-induced syncytium formation in vitro: role of cell-to-cell contact. Antiviral Res. 1994, 23, 143-159.
87. Yang, D. W.; Ohta, Y.; Yamaguchi, S.; Tsukada, Y.; Haraguchi, Y.; Hoshino, H.; Amagai, H.; Kobayashi, I. Sulfated colominic acid: an antiviral agent that inhibits the human immunodeficiency virus type 1 in vitro. Antiviral Res. 1996, 31, 95-104.
88. Konishi, K.; Gu, Y.; Hatano, I.; Ushijima, H. Effect of sulfated colominic acid on enteric virus (rotavirus, poliovirus and coxsackievirus) infections in vitro. Jpn. J. Infect. Dis. 2000, 53, 62-66.
89. Gordon, M.; Deeks, S.; De Marzo, C.; Goodgame, J.; Guralnik, M.; Lang, W.; Mimura, T.; Pearce, D.; Kaneko, Y. Curdlan sulfate (CRDS) in a 21-day intravenous tolerance study in human immunodeficiency virus (HIV) and cytomegalovirus (CMV) infected patients: indication of anti-CMV activity with low toxicity. J. Med. 1997, 28, 108-128.
90. Vicenzi, E.; Gatti, A.; Ghezzi, S.; Oreste, P.; Zoppetti, G.; Poli, G. Broad spectrum inhibition of HIV-1 infection by sulfated K5 Escherichia coli polysaccharide derivatives. Aids 2003, 17, 177-181.
91. Lederman, S.; Bergmann, J. E.; Cleary, A. M.; Yellin, M. J.; Fusco, P. J.; Chess, L. Sulfated polyester interactions with the CD4 molecule and with the third variable loop domain (v3) of gp120 are chemically distinct. AIDS Res. Hum. Retroviruses 1992, 8, 1599-1610.
92. Ishihara, C.; Yoshimatsu, K.; Tsuji, M.; Arikawa, J.; Saiki, I.; Tokura, S.; Azuma, I. Anti-viral activity of sulfated chitin derivatives against Friend murine leukaemia and herpes simplex type-1 viruses. Vaccine 1993, 11, 670-674.
93. Ueki, M.; Watanabe, S.; Ishii, Y.; Okunaka, O.; Uchino, K.; Saitoh, T.; Higashi, K.; Nakashima, H.; Yamamoto, N.; Ogawara, H. Synthesis and anti-HIV activity of nonatyrosine N- and 01-9-decasulfate. Bioorg. Med. Chem. 2001, 9, 477-486.
94. Schulze, A.; Gripon, P.; Urban, S. Hepatitis B virus infection initiates with a large surface protein-dependent binding to heparan sulfate proteoglycans. Hepatology 2007, 46, 1759-1768.
95. Garson, J. A.; Lubach, D.; Passas, J.; Whitby, K.; Grant, P. R. Suramin blocks hepatitis C binding to human hepatoma cells in vitro. J. Med. Virol. 1999, 57, 238-242.
96. Inoue, N.; Winter, J.; Lal, R. B.; Offermann, M. K.; Koyano, S. Characterization of entry mechanisms of human herpesvirus 8 by using an Rta-dependent reporter cell line. J. Virol. 2003, 77, 8147-8152.
97. Aguilar, J. S.; Rice, M.; Wagner, E. K. The polysulfonated compound suramin blocks adsorption and lateral difusion of herpes simplex virus type-1 in vero cells. Virology 1999, 258, 141-151.
98. Pesce, C. D.; Ciprani, F.; D'Onofrio, C.; Alvino, E.; Perno, C. F.; Bonmassar, E.; Calio, R. Low concentrations of suramin can reduce in vitro infection of human cord blood lymphocytes with HTLV-I during long-term culture. Antiviral Res. 1987, 8, 247-260.
99. Clanton, D. J.; Buckheit, R. W., Jr.; Terpening, S. J.; Kiser, R.; Mongelli, N.; Borgia, A. L.; Schultz, R.; Narayanan, V.; Bader, J. P.; Rice, W. G. Novel sulfonated and phosphonated analogs of distamycin which inhibit the replication of HIV. Antiviral Res. 1995, 27, 335-354.
100. Baba, M.; Konno, K.; Shigeta, S.; Wickramasinghe, A.; Mohan, P. Selective inhibition of human cytomegalovirus replication by naphthalenedisulfonic acid derivatives. Antiviral Res. 1993, 20, 223-233.
101. Dezube, B. J.; Dahl, T. A.; Wong, T. K.; Chapman, B.; Ono, M.; Yamaguchi, N.; Gillies, S. D.; Chen, L. B.; Crumpacker, C. S. A fusion inhibitor (FP-21399) for the treatment of human immunodeficiency virus infection: a phase I study. J. Infect. Dis. 2000, 182, 607-610.
102. Taylor, D. L.; Brennan, T. M.; Bridges, C. G.; Mullins, M. J.; Tyms, A. S.; Jackson, R.; Cardin, A. D. Potent inhibition of human immunodeficiency virus by MDL 101028, a novel sulphonic acid polymer. Antiviral Res. 1995, 28, 159-173.
103. Vzorov, A. N.; Bozja, J.; Dixon, D. W.; Marzilli, L. G.; Compans, R. W. Parameters of inhibition of HIV-1 infection by small anionic microbicides. Antiviral Res. 2007, 73, 60-68.
104. Arciola, C. R.; Bustanji, Y.; Conti, M.; Campoccia, D.; Baldassarri, L.; Samori, B.; Montanaro, L. Staphylococcus epidermidis-fibronectin binding and its inhibition by heparin. Biomaterials 2003, 24, 3013-3019.
105. Hess, D. J.; Henry-Stanley, M. J.; Erlandsen, S. L.; Wells, C. L. Heparan sulfate proteoglycans mediate Staphylococcus aureus interactions with intestinal epithelium. Med. Microbiol. Immunol. 2006, 195, 133-141.
106. Fallgren, C.; Andersson, A.; Ljungh, A. The role of glycosaminoglycan binding of staphylococci in attachment to eukaryotic host cells. Curr. Microbiol. 2001, 43, 57-63.
107. Henry-Stanley, M. J.; Hess, D. J.; Erickson, E. A.; Garni, R. M.; Wells, C. L. Role of heparan sulfate in interactions of Listeria monocytogenes with enterocytes. Med. Microbiol. Immunol. 2003, 192, 107-115.
108. Utt, M.; Wadstrom, T. Identification of heparan sulphate binding surface proteins of Helicobacter pylori: inhibition of heparan sulphate binding with sulphated carbohydrate polymers. J. Med. Microbiol. 1997, 46, 541-546.
109. Rosett, W.; Hodges, G. R. Antimicrobial activity of heparin. J. Clin. Microbiol. 1980, 11, 30-34.
110. Leong, J. M.; Morrissey, P. E.; Ortega-Barria, E.; Pereira, M. E.; Coburn, J. Hemagglutination and proteoglycan binding by the Lyme disease spirochete, Borrelia burgdorferi. Infect. Immun. 1995, 63, 874-883.
111. Herold, B. C.; Siston, A.; Bremer, J.; Kirkpatrick, R.; Wilbanks, G.; Fugedi, P.; Peto, C.; Cooper, M. Sulfated carbohydrate compounds prevent microbial adherence by sexually transmitted disease pathogens. Antimicrob. Agents Chemother.1991, 41, 2776-2780.
112. Menozzi, F. D.; Rouse, J. H.; Alavi, M.; Laude-Sharp, M.; Müller, J.; Bischoff, R.; Brennan, M. J.; Locht, C. Identification of a heparin-binding hemagglutinin present in mycobacteria. J. Exp. Med. 1996, 184, 993-1001.
113. Thomas, R.; Brooks, T. Common oligosaccharide moieties inhibit the adherence of typical and atypical respiratory pathogens. J. Med. Microbiol. 2004, 53, 833-840.
114. Thomas, R. J.; Brooks, T. J. Oligosaccharide receptor mimics inhibit Legionella pneumophila attachment to human respiratory epithelial cells. Microb. Pathog. 2004, 36, 83-92.
115. Bosetto, M. C.; Giorgio, S. Leishmania amazonensis: multiple receptor-ligand interactions are involved in amastigote infection of human dendritic cells. Exp. Parasitol. 2007, 116, 306-310.
116. Nishimura, K.; Shima, K.; Asakura, M.; Ohnishi, Y.; Yamasaki, S. Effects of heparin administration on Trypanosoma brucei gambiense infection in rats. 7. Parasitol. 2005, 91, 219-222.
117. Vogt, A. M.; Pettersson, F.; Moll, K.; Jonsson, C.; Normark, J.; Ribacke, U.; Egwang, T. G.; Ekre, H. P.; Spillmann, D.; Chen, Q.; Wahlgren, M. Release of sequestered malaria parasites upon injection of a glycosaminoglycan. PLoS Pathog. 2006, 2, e100.
118. Schwartz-Albiez, R.; Adams, Y.; von der Lieth, C. W.; Mischnick, P.; Andrews, K. T.; Kirschfink, M. Regioselectively modified sulfated cellulose as prospective drug for treatment of malaria tropica. Glycoconj. J. 2007, 24, 57-65.
119. Calvet, C. M.; Toma, L.; De Souza, F. R.; Meirelles Mde, N.; Pereira, M. C. Heparan sulfate proteoglycans mediate the invasion of cardiomyocytes by Trypanosoma cruzi. J. Eukaryot. Microbiol. 2003, 50, 97-103.
120. Carruthers, V. B.; Hakansson, S.; Giddings, O. K.; Sibley, L. D. Toxoplasma gondii uses sulfated proteoglycans for substrate and host cell attachment. Infect. Immun. 2000, 68, 4005-4011.
121. Weiland, M. E.; Palm, J. E.; Griffiths, W. J.; McCaffery, J. M.; Svard, S. G. Characterisation of alpha-1 giardin: an immunodominant Giardia lamblia annexin with glycosaminoglycan-binding activity. Int. J. Parasitol. 2003, 33, 1341-1351.
122. Gysin, J.; Pouvelle, B.; Fievet, N.; Scherf, A.; Lepolard, C. Ex vivo desequestration of Plasmodium falciparum-infected erythrocytes from human placenta by chondroitin sulfate A. Infect. Immun. 1999, 67, 6596-6602.
123. Adams, Y.; Smith, S. L.; Schwartz-Albiez, R.; Andrews, K. T. Carrageenans inhibit the in vitro growth of Plasmodium falciparum and cytoadhesion to CD36. Parasitol. Res. 2005, 97, 290-294.
124. Herron, M. J.; Ericson, M. E.; Kurtti, T. J.; Munderloh, U. G. The interactions of Anaplasma phagocytophilum, endothelial cells, and human neutrophils. Ann. N. Y. Acad. Sci. 2005, 1063, 374-382.
125. Shibata, H.; KimuraTakagi, I.; Nagaoka, M.; Hashimoto, S.; Sawada, H.; Ueyama, S.; Yokokura, T. Inhibitory effect of Cladosiphon fucoidan on the adhesion of Helicobacter pylori to human gastric cells. J. Nutr. Sci. Vitaminol. (Tokyo) 1999, 45, 325-336.
126. Maruyama, H.; Tanaka, M.; Hashimoto, M.; Inoue, M.; Sasahara, T. The suppressive effect of Mekabu fucoidan on an attachment of Cryptosporidium parvum oocysts to the intestinal epithelial cells in neonatal mice. Life Sci. 2007, 80, 775-781.
127. Ortega-Barria, E.; Boothroyd, J. C. A Toxoplasma lectin-like activity specific for sulfated polysaccharides is involved in host cell infection. J. Biol. Chem. 1999, 274, 1267-1276.
128. Simões, J. A.; Citron, D. M.; Aroutcheva, A.; Anderson, R. A., Jr.; Chany, C. J., 2nd; Waller, D. P.; Faro, S.; Zaneveld, L. J. Two novel vaginal microbicides (polystyrene sulfonate and cellulose sulfate) inhibit Gardnerella vaginalis and anaerobes commonly associated with bacterial vaginosis. Antimicrob. Agents Chemother. 2002, 46, 2692-2695.
129. Adams, Y.; Freeman, C.; Schwartz-Albiez, R.; Ferro, V.; Parish, C. R.; Andrews, K. T. Inhibition of Plasmodium falciparum growth in vitro and adhesion to chondroitin-4-sulfate by the heparan sulfate mimetic PI-88 and other sulfated oligosaccharides. Antimicrob. Agents Chemother. 2006, 50, 2850-2852.
130. Fleck, S. L.; Birdsall, B.; Babon, J.; Dluzewski, A. R.; Martin, S. R.; Morgan, W. D.; Angov, E.; Kettleborough, C. A.; Feeney, J.; Blackman, M. J.; Holder, A. A. Suramin and suramin analogues inhibit merozoite surface protein-1 secondary processing and erythrocyte invasion by the malaria parasite Plasmodium falciparum. J. Biol. Chem. 2003, 278, 47670-47677.
131. Bisaggio, D. F.; Adade, C. M.; Souto-Padron, T. In vitro effects of suramin on Trypanosoma cruzi. Int. J. Antimicrob. Agents 2008, 31, 282-286.
132. Herold, B. C.; Bourne, N.; Marcellino, D.; Kirkpatrick, R.; Strauss, D. M.; Zaneveld, L. J.; Waller, D. P.; Anderson, R. A.; Chany, C. J.; Barham, B. J.; Stanberry, L. R.; Cooper, M. D. Poly(sodium 4-styrene sulfonate): an effective candidate topical antimicrobial for the prevention of sexually transmitted diseases. J. Infect. Dis. 2000, 181, 770-773.
133. Rueda, R. The role of dietary gangliosides on immunity and the prevention of infection. Br. J. Nutr. 2007, 98 Suppl. 1, S68-73.
134. Schwartsmann, G.; Sprinz, E.; Kalakun, L.; Yamagushi, N.; Sander, E.; Grivicich, I.; Koya, R.; Mans, D. R. Phase II study of pentosan polysulfate (PPS) in patients with AIDS-related Kaposi's sarcoma. Tumori 1996, 82, 360-363.
135. Mueller, N. Overview: viral agents and cancer. Environ. Health Perspect. 1995, 103 Suppl. 8, 259-261.
136. Castelli, R.; Porro, F.; Tarsia, P. The heparins and cancer: review of clinical trials and biological properties. Vase. Med. 2004, 9, 205-213.
137. Manero, F.; Ljubic-Thibal, V.; Moulin, M.; Goutagny, N.; Yvin, J. C.; Arrigo, A. P. Stimulation of Fas agonistic antibody-mediated apoptosis by heparin-like agents suppresses Hsp27 but not Bc1-2 protective activity. Cell Stress Chaperones 2004, 9, 150-166.
138. Aisa, Y.; Miyakawa, Y.; Nakazato, T.; Shibata, H.; Saito, K.; Ikeda, Y.; Kizaki, M. Fucoidan induces apoptosis of human HS-sultan cells accompanied by activation of caspase-3 and down-regulation of ERK pathways. Am. J. Hematol. 2005, 78, 7-14.
139. Parish, C. R.; Coombe, D. R.; Jakobsen, K. B.; Bennett, F. A.; Underwood, P. A. Evidence that sulphated polysaccharides inhibit tumour metastasis by blocking tumour-cell-derived heparanases. Int. J. Cancer 1987, 40, 511-518.
140. Isnard, N.; Robert, L.; Renard, G. Effect of sulfated GAGs on the expression and activation of MMP-2 and MMP-9 in corneal and dermal expiant cultures. Cell Biol. Int. 2003, 27, 779-784.
141. Aggarwal, B. B.; Shishodia, S.; Sandur, S. K.; Pandey, M. K.; Sethi, G. Inflammation and cancer: how hot is the link? Biochem. Pharmacol. 2006, 72, 1605-1621.
142. Carmeliet, P.; Jain, R. K. Angiogenesis in cancer and other diseases. Nature 2000, 407, 249-257.
143. Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat. Med. 1995, 1, 27-31.
144. Rusnati, M.; Tanghetti, E.; Urbinati, C.; Tulipano, G.; Marchesini, S.; Ziehe, M.; Presta, M. Interaction of fibroblast growth factor-2 (FGF-2) with free gangliosides: biochemical characterization and biological consequences in endothelial cell cultures. Mol. Biol. Cell 1999, 10, 313-327.
145. Mukherjee, P.; Faber, A. C.; Shelton, L. M.; Baek, R. C.; Chiles, T. C.; Seyfried, T. N. Ganglioside GM3 suppresses the pro-angiogenic effects of vascular endothelial growth factor and ganglioside GD1A. J. Lipid Res. 2008, in press.
146. Takahashi, H.; Ebihara, S.; Okazaki, T.; Asada, M.; Sasaki, H.; Yamaya, M. A comparison of the effects of unfractionated heparin, dalteparin and danaparoid on vascular endothelial growth factor-induced tumour angiogenesis and heparanase activity. Br. J. Pharmacol. 2005, 146, 333-343.
147. Ashikari-Hada, S.; Habuchi, H.; Kariya, Y.; Kimata, K. Heparin regulates vascular endothelial growth factor 165-dependent mitogenic activity, tube formation, and its receptor phosphorylation of human endothelial cells. Comparison of the effects of heparin and modified heparins. J. Biol. Chem. 2005, 280, 31508-31515.
148. Pisano, C.; Aulicino, C.; Vesci, L.; Casu, B.; Naggi, A.; Torri, G.; Ribatti, D.; Belleri, M.; Rusnati, M.; Presta, M. Undersulfated, low-molecular-weight glycol-split heparin as an antiangiogenic VEGF antagonist. Glycobiology 2005, 15, 1C-6C.
149. Norrby, K. 2.5 kDa and 5.0 kDa heparin fragments specifically inhibit microvessel sprouting and network formation in VEGF165-mediated mammalian angiogenesis. Int. J. Exp. Pathol. 2000, 81, 191-198.
150. Nikitovic, D.; Assouti, M.; Sifaki, M.; Katonis, P.; Krasagakis, K.; Karamanos, N. K.; Tzanakakis, G. N. Chondroitin sulfate and heparan sulfate-containing proteoglycans are both partners and targets of basic fibroblast growth factor-mediated proliferation in human metastatic melanoma cell lines. Int. J. Biochem. Cell Biol. 2008, 40, 72-83.
151. Casu, B.; Guerrini, M.; Naggi, A.; Perez, M.; Torri, G.; Ribatti, D.; Carminati, P.; Giannini, G.; Penco, S.; Pisano, C.; Belleri, M.; Rusnati, M.; Presta, M. Short heparin sequences spaced by glycol-split uronate residues are antagonists of fibroblast growth factor 2 and angiogenesis inhibitors. Biochemistry 2002, 41, 10519-10528.
152. Casu, B.; Guerrini, M.; Guglieri, S.; Naggi, A.; Perez, M.; Torri, G.; Cassinelli, G.; Ribatti, D.; Carminati, P.; Giannini, G.; Penco, S.; Pisano, C.; Belleri, M.; Rusnati, M.; Presta, M. Undersulfated and glycol-split heparins endowed with antiangiogenic activity. J. Med. Chem. 2004, 47, 838-848.
153. Abe, W.; Ikejima, K.; Lang, T.; Okumura, K.; Enomoto, N.; Kitamura, T.; Takei, Y.; Sato, N. Low molecular weight heparin prevents hepatic fibrogenesis caused by carbon tetrachloride in the rat. J. Hepatol. 2007, 46, 286-294.
154. Cheng, J. J.; Huang, N. K.; Chang, T. T.; Wang, D. L.; Lu, M. K. Study for anti-angiogenic activities of polysaccharides isolated from Antrodia cinnamomea in endothelial cells. Life Sci. 2005, 76, 3029-3042.
155. Sakiyama, R.; Fukuta, K.; Matsumoto, K.; Furukawa, M.; Takahashi, Y.; Nakamura, T. Stimulation of hepatocyte growth factor production by heparin-derived oligosaccharides. J. Biochem. (Tokyo) 2007, 141, 653-660.
156. Rusnati, M.; Coltrini, D.; Oreste, P.; Zoppetti, G.; Albini, A.; Noonan, D.; d'Adda di Fagagna, F.; Giacca, M.; Presta, M. Interaction of HIV-1 Tat protein with heparin. Role of the backbone structure, sulfation, and size. J. Biol. Chem. 1997, 272, 11313-11320.
157. Albini, A.; Benelli, R.; Presta, M.; Rusnati, M.; Ziehe, M.; Rubartelli, A.; Paglialunga, G.; Bussolino, F.; Noonan, D. HIV-tat protein is a heparin-binding angiogenic growth factor. Oncogene 1996, 12, 289-297.
158. Zou, P.; Zou, K.; Muramatsu, H.; Ichihara-Tanaka, K.; Habuchi, O.; Ohtake, S.; Ikematsu, S.; Sakuma, S.; Muramatsu, T. Glycosaminoglycan structures required for strong binding to midkine, a heparin-binding growth factor. Glycobiology 2003, 13, 35-42.
159. Soncin, F.; Strydom, D. J.; Shapiro, R. Interaction of heparin with human angiogenin. J. Biol. Chem. 1997, 272, 9818-9824.
160. Xu, Y.; Liu, Y. J.; Yu, Q. Angiopoietin-3 is tethered on the cell surface via heparan sulfate proteoglycans. J. Biol. Chem. 2004, 279, 41179-41188.
161. Deepa, S. S.; Umehara, Y.; Higashiyama, S.; Itoh, N.; Sugahara, K. Specific molecular interactions of oversulfated chondroitin sulfate E with various heparin-binding growth factors. Implications as a physiological binding partner in the brain and other tissues. J. Biol. Chem. 2002, 277, 43707-43716.
162. Fthenou, E.; Zafiropoulos, A.; Katonis, P.; Tsatsakis, A.; Karamanos, N. K.; Tzanakakis, G. N. Chondroitin sulfate prevents platelet derived growth factor-mediated phosphorylation of PDGF-Rbeta in normal human fibroblasts severely impairing mitogenic responses. J. Cell Biochem. 2008, 103,1866-1876.
163. Kawada, A.; Hiura, N.; Tajima, S.; Takahara, H. Alginate oligosaccharides stimulate VEGF-mediated growth and migration of human endothelial cells. Arch. Dermatol. Res. 1999, 291, 542-547.
164. Hoffman, R.; Burns, W. W., 3rd; Paper, D. H. Selective inhibition of cell proliferation and DNA synthesis by the polysulphated carbohydrate 1-carrageenan. Cancer Chemother. Pharmacol. 1995, 36, 325-334.
165. Hoffman, R.; Sykes, D. Inhibition of binding of basic fibroblast growth factor to low and high affinity receptors by carrageenans. Biochem. Pharmacol. 1993, 45, 2348-2351.
166. Koyanagi, S.; Tanigawa, N.; Nakagawa, H.; Soeda, S.; Shimeno, H. Oversulfation of fucoidan enhances its anti-angiogenic and antitumor activities. Biochem. Pharmacol. 2003, 65, 173-179.
167. Giraux, J. L.; Matou, S.; Bros, A.; Tapon-Bretaudiere, J.; Letourneur, D.; Fischer, A. M. Modulation of human endothelial cell proliferation and migration by fucoidan and heparin. Eur. J. Cell Biol. 1998, 77, 352-359.
168. Dias, P. F.; Siqueira, J. M., Jr.; Vendruscolo, L. F.; de Jesus Neiva, T.; Gagliardi, A. R.; Maraschin, M.; Ribeiro-do-Valle, R. M. Antiangiogenic and antitumoral properties of a polysaccharide isolated from the seaweed Sargassum stenophyllum. Cancer Chemother. Pharmacol. 2005, 56, 436-446.
169. Catlow, K. R.; Deakin, J. A.; Wei, Z.; Delehedde, M.; Fernig, D. G.; Gherardi, E.; Gallagher, J. T.; Pavao, M. S.; Lyon, M. Interactions of hepatocyte growth factor / scatter factor with various glycosaminoglycans reveal an important interplay between the presence of iduronate and sulfate density. J. Biol. Chem. 2008, 283, 5235-5248.
170. Miao, H. Q.; Ishai-Michaeli, R.; Peretz, T.; Vlodavsky, I. Laminarin sulfate mimics the effects of heparin on smooth muscle cell proliferation and basic fibroblast growth factor-receptor binding and mitogenic activity. J. Cell. Physiol. 1995, 164, 482-490.
171. Wang, L.; Geng, M.; Li, J.; Guan, H.; Ding, J. Studies of marine sulfated polymannuroguluronate on endothelial cell proliferation and endothelial immunity and related mechanisms. J. Pharmacol. Sci. 2003, 92, 367-373.
172. Lu, C. X.; Li, J.; Sun, Y. X.; Qi, X.; Wang, Q. J.; Xin, X. L.; Geng, M. Y. Sulfated polymannuroguluronate, a novel anti-AIDS drug candidate, inhibits HIV-1 Tat-induced angiogenesis in Kaposi's sarcoma cells. Biochem. Pharmacol. 2007, 74, 1330-1339.
173. Kobayashi, T.; Honke, K.; Miyazaki, T.; Matsumoto, K.; Nakamura, T.; Ishizuka, I.; Makita, A. Hepatocyte growth factor specifically binds to sulfoglycolipids. J. Biol. Chem. 1994, 269, 9817-9821.
174. Kurosawa, N.; Kadomatsu, K.; Ikematsu, S.; Sakuma, S.; Kimura, T.; Muramatsu, T. Midkine binds specifically to sulfatide the role of sulfatide in cell attachment to midkine-coated surfaces. Eur. J. Biochem. 2000, 267, 344-351.
175. Letourneur, D.; Machy, D.; Pelle, A.; Marcon-Bachari, E.; D'Angelo, G.; Vogel, M.; Chaubet, F.; Michel, J. B. Heparin and non-heparin-like dextrans differentially modulate endothelial cell proliferation: in vitro evaluation with soluble and crosslinked polysaccharide matrices. J. Biomed. Mater. Res. 2002, 60, 94-100.
176. Hamma-Kourbali, Y.; Vassy, R.; Starzec, A.; Le Meuth-Metzinger, V.; Oudar, O.; Bagheri-Yarmand, R.; Perret, G.; Crepin, M. Vascular endothelial growth factor 165 (VEGF(165)) activities are inhibited by carboxymethyl benzylamide dextran that competes for heparin binding to VEGF(165) and VEGF(165).KDR Complexes. J. Biol. Chem. 2001, 276, 39748-39754.
177. Borawski, J.; Dubowski, M.; Pawlak, K.; Mysliwiec, M. Sulodexide induces hepatocyte growth factor release in humans. Eur. J. Pharmacol. 2007, 558, 167-171.
178. Matou, S.; Colliec-Jouault, S.; Galy-Fauroux, I.; Ratiskol, J.; Sinquin, C.; Guezennec, J.; Fischer, A. M.; Helley, D. Effect of an oversulfated exopolysaccharide on angiogenesis induced by fibroblast growth factor-2 or vascular endothelial growth factor in vitro. Biochem. Pharmacol. 2005, 69, 751-759.
179. Ishihara, M.; Ono, K.; Ishikawa, K.; Hattori, H.; Saito, Y.; Yura, H.; Akaike, T.; Ozeki, Y.; Tanaka, S.; Mochizuki, H.; Kurita, A. Enhanced ability of heparin-carrying polystyrene (HCPS) to bind to heparin-binding growth factors and to inhibit growth factor-induced endothelial cell growth. J. Biochem. (Tokyo) 2000, 127, 797-803.
180. de Paz, J. L.; Noti, C.; Bohm, F.; Werner, S.; Seeberger, P. H. Potentiation of fibroblast growth factor activity by synthetic heparin oligosaccharide glycodendrimers. Chem. Biol. 2007, 14, 879-887.
181. Kim, S. H.; Kiick, K. L. Heparin-mimetic sulfated peptides with modulated affinities for heparin-binding peptides and growth factors. Peptides 2007, 28, 2125-2136.
182. Benelli, U.; Bocci, G.; Danesi, R.; Lepri, A.; Bernardini, N.; Bianchi, F.; Lupetti, M.; Dolfi, A.; Campagni, A.; Agen, C.; Nardi, M.; Del Tacca, M. The heparan sulfate suleparoide inhibits rat corneal angiogenesis and in vitro neovascularization. Exp. Eye Res. 1998, 67, 133-142.
183. Leali, D.; Belleri, M.; Urbinati, C.; Coltrini, D.; Oreste, P.; Zoppetti, G.; Ribatti, D.; Rusnati, M.; Presta, M. Fibroblast growth factor-2 antagonist activity and angiostatic capacity of sulfated Escherichia coli K5 polysaccharide derivatives. J. Biol. Chem. 2001, 276, 37900-37908.
184. Presta, M.; Oreste, P.; Zoppetti, G.; Belleri, M.; Tanghetti, E.; Leali, D.; Urbinati, C.; Bugatti, A.; Ronca, R.; Nicoli, S.; Moroni, E.; Stabile, H.; Camozzi, M.; Hernandez, G. A.; Mitola, S.; Dell'Era, P.; Rusnati, M.; Ribatti, D. Antiangiogenic activity of semisynthetic biotechnological heparins: low-molecular-weight-sulfated Escherichia coli K5 polysaccharide derivatives as fibroblast growth factor antagonists. Arterioscler. Thromb. Vasc. Biol. 2005, 25, 71-76.
185. Urbinati, C.; Bugatti, A.; Oreste, P.; Zoppetti, G.; Waltenberger, J.; Mitola, S.; Ribatti, D.; Presta, M.; Rusnati, M. Chemically sulfated Escherichia coli K5 polysaccharide derivatives as extracellular HIV-1 Tat protein antagonists. FEBS Lett. 2004, 568, 171-177.
186. Joyce, J. A.; Freeman, C.; Meyer-Morse, N.; Parish, C. R.; Hanahan, D. A functional heparan sulfate mimetic implicates both heparanase and heparan sulfate in tumor angiogenesis and invasion in a mouse model of multistage cancer. Oncogene 2005, 24, 4037-4051.
187. Ferro, V.; Dredge, K.; Liu, L.; Hammond, E.; Bytheway, I.; Li, C.; Johnstone, K.; Karoli, T.; Davis, K.; Copeman, E.; Gautam, A. PI-88 and novel heparan sulfate mimetics inhibit angiogenesis. Semin. Thromb. Hemost. 2007, 33, 557-568.
188. Rouet, V.; Hamma-Kourbali, Y.; Petit, E.; Panagopoulou, P.; Katsoris, P.; Barritault, D.; Caruelle, J. P.; Courty, J. A synthetic glycosaminoglycan mimetic binds vascular endothelial growth factor and modulates angiogenesis. J. Biol. Chem. 2005, 280, 32792-32800.
189. Rouet, V.; Meddahi-Pelle, A.; Miao, H. Q.; Vlodavsky, I.; Caruelle, J. P.; Barritault, D. Heparin-like synthetic polymers, named RGTAs, mimic biological effects of heparin in vitro. J. Biomed. Mater. Res. A 2006, 78, 792-797.
190. Fannon, M.; Forsten-Williams, K.; Nugent, M. A.; Gregory, K. J.; Chu, C. L.; Goerges-Wildt, A. L.; Panigrahy, D.; Kaipainen, A.; Barnes, C.; Lapp, C.; Shing, Y. Sucrose octasulfate regulates fibroblast growth factor-2 binding, transport, and activity: Potential for regulation of tumor growth. J. Cell Physiol. 2008, 215, 434-441.
191. Kasbauer, C. W.; Paper, D. H.; Franz, G. Sulfated beta-(1→4)- galacto-oligosaccharides and their effect on angiogenesis. Carbohydr. Res. 2001, 330, 427-430.
192. Zugmaier, G.; Lippman, M. E.; Wellstein, A. Inhibition by pentosan polysulfate (PPS) of heparin-binding growth factors released from tumor cells and blockage by PPS of tumor growth in animals. J. Natl. Cancer Inst. 1992, 84, 1716-1724.
193. Rusnati, M.; Urbinati, C.; Caputo, A.; Possati, L.; Lortat-Jacob, H.; Giacca, M.; Ribatti, D.; Presta, M. Pentosan polysulfate as an inhibitor of extracellular HIV-1 Tat. J. Biol. Chem. 2001, 276, 22420-22425.
194. Sakairi, N.; Kuzuhara, H.; Okamoto, T.; Yajima, M. Synthesis and biological evaluation of 2-amino-2-deoxy- and 6-amino-6-deoxy-cyclomaltoheptaose polysulfates as synergists for angiogenesis inhibition. Bioorg. Med. Chem. 1996, 4, 2187-2192.
195. Watson, K.; Gooderham, N. J.; Davies, D. S.; Edwards, R. J. Interaction of the transactivating protein HIV-1 tat with sulphated polysaccharides. Biochem. Pharmacol. 1999, 57, 775-783.
196. Waltenberger, J.; Mayr, U.; Frank, H.; Hombach, V. Suramin is a potent inhibitor of vascular endothelial growth factor. A contribution to the molecular basis of its antiangiogenic action. J. Mol. Cell Cardiol. 1996, 28, 1523-1529.
197. Schilling-Schon, A.; Pleyer, U.; Hartmann, C.; Rieck, P. W. The role of endogenous growth factors to support corneal endothelial migration after wounding in vitro. Exp. Eye Res. 2000, 71, 583-589.
198. Rusnati, M.; Dell'Era, P.; Urbinati, C.; Tanghetti, E.; Massardi, M. L.; Nagamine, Y.; Monti, E.; Presta, M. A distinct basic fibroblast growth factor (FGF-2)/FGF receptor interaction distinguishes urokinase-type plasminogen activator induction from mitogenicity in endothelial cells. Mol. Biol. Cell. 1996, 7, 369-381.
199. Sola, F.; Farao, M.; Ciomei, M.; Pastori, A.; Mongelli, N.; Grandi, M. FCE 27266, a sulfonic distamycin derivative, inhibits experimental and spontaneous lung and liver metastasis. Invasion Metastasis 1995, 15, 222-231.
200. Sola, F.; Gualandris, A.; Belleri, M.; Giuliani, R.; Coltrini, D.; Bastaki, M.; Molinari-Tosatti, M. P.; Bonardi, F.; Vecchi, A.; Fioretti, F.; Giavazzi, R.; Ciomei, M.; Grandi, M.; Mantovani, A.; Presta, M. Endothelial cells overexpressing basic fibroblast growth factor (FGF-2) induce vascular tumors in immunodeficient mice. Angiogenesis 1997, 1, 102-116.
201. Corallini, A.; Berti, M.; Rusnati, M.; Campioni, D.; Ciomei, M.; Sola, F.; Calza, N.; Zauli, G.; Presta, M.; Barbanti-Brodano, G.; Caputo, A. Characterization of the effects of two polysulfonated distamycin A derivatives, PNU145156E and PNU153429, on HIV type 1 Tat protein. AIDS Res. Hum. Retroviruses 1998, 14, 1561-1571.
202. Liekens, S.; Leali, D.; Neyts, J.; Esnouf, R.; Rusnati, M.; Dell'Era, P.; Maudgal, P. C.; De Clercq, E.; Presta, M. Modulation of fibroblast growth factor-2 receptor binding, signaling, and mitogenic activity by heparin-mimicking polysulfonated compounds. Mol. Pharmacol. 1999, 56, 204-213.
203. Bugatti, A.; Urbinati, C.; Ravelli, C.; De Clercq, E.; Liekens, S.; Rusnati, M. Heparin-mimicking sulfonic acid polymers as multitarget inhibitors of human immunodeficiency virus type 1 Tat and gp120 proteins. Antimicrob. Agents Chemother. 2007, 51, 2337-2345.
204. Terabayashi, T.; Morita, M.; Ueno, M.; Nakamura, T.; Urashima, T. Inhibition of influenza-virus-induced cytopathy by sialylglycoconjugates. Carbohydr. Res. 2006, 341, 2246-2253.
205. Kreuger, J.; Spillmann, D.; Li, J. P.; Lindahl, U. Interactions between heparan sulfate and proteins: the concept of specificity. J. Cell Biol. 2006, 174, 323-327.
206. Baba, M.; Schols, D.; De Clercq, E.; Pauwels, R.; Nagy, M.; Gyorgyi-Edelenyi, J.; Low, M.; Gorog, S. Novel sulfated polymers as highly potent and selective inhibitors of human immunodeficiency virus replication and giant cell formation. Antimicrob. Agents Chemother. 1990, 34, 134-138.
207. Schols, D.; Pauwels, R.; Desmyter, J.; De Clercq, E. Dextran sulfate and other polyanionic antiHIV compounds specifically interact with the viral gp120 glycoprotein expressed by T-cells persistently infected with HIV-1. Virology 1990, 175, 556-561.
208. Baba, M.; Schols, D.; Pauwels, R.; Nakashima, H.; De Clercq, E. Sulfated polysaccharides as potent inhibitors of HIV-induced syncytium formation: a new strategy towards AIDS chemotherapy. J. Acquir. Immune Defic. Syndr. 1990, 3, 493-499.
209. Mahoney, C. W.; Azzi, A.; Huang, K. P. Effects of suramin, an anti-human immunodeficiency virus reverse transcriptase agent, on protein kinase C. Differential activation and inhibition of protein kinase C isozymes. J. Biol. Chem. 1990, 265, 5424-5428.
210. Yahi, N.; Sabatier, J. M.; Nickel, P.; Mabrouk, K.; Gonzalez-Scarano, F.; Fantini, J. Suramin inhibits binding of the V3 region of HIV-1 envelope glycoprotein gp120 to galactosylceramide, the receptor for HIV-1 gp120 on human colon epithelial cells. J. Biol. Chem. 1994, 269, 24349-24353.
211. Witvrouw, M.; Fikkert, V.; Pluymers, W.; Matthews, B.; Mardel, K.; Schols, D.; Raff, J.; Debyser, Z.; De Clercq, E.; Holan, G.; Pannecouque, C. Polyanionic (i.e., polysulfonate) dendrimers can inhibit the replication of human immunodeficiency virus by interfering with both virus adsorption and later steps (reverse transcriptase/integrase) in the virus replicative cycle. Mol Pharmacol. 2000, 58, 1100-1108.
212. Tan, G. T.; Wickramasinghe, A.; Verma, S.; Hughes, S. H.; Pezzuto, J. M.; Baba, M.; Mohan, P. Sulfonic acid polymers are potent inhibitors of HIV-1 induced cytopathogenicity and the reverse transcriptases of both HIV-1 and HIV-2. Biochim. Biophys. Acta 1993, 1181, 183-188.
213. Noonan, D.; Albini, A. From the outside in: extracellular activities of HIV Tat. Adv. Pharmacol. 2000, 48, 229-250.
214. Eggert, A.; Ikegaki, N.; Kwiatkowski, J.; Zhao, H.; Brodeur, G. M.; Himelstein, B. P. High-level expression of angiogenic factors is associated with advanced tumor stage in human neuroblastomas. Clin. Cancer Res. 2000, 6, 1900-1908.
215. Hammache, D.; Pieroni, G.; Yahi, N.; Delezay, O.; Koch, N.; Lafont, H.; Tamalet, C.; Fantini, J. Specific interaction of HIV-1 and HIV-2 surface envelope glycoproteins with monolayers of galactosylceramide and ganglioside GM3. J. Biol. Chem. 1998, 273, 7967-7971.
216. Brown, G.; Rixon, H. W.; Sugrue, R. J. Respiratory syncytial virus assembly occurs in GM1-rich regions of the host-cell membrane and alters the cellular distribution of tyrosine phosphorylated caveolin-1. J. Gen. Virol. 2002, 83, 1841-1850.
217. Low, J. A.; Magnuson, B.; Tsai, B.; Imperiale, M. J. Identification of gangliosides CD1b and GT1b as receptors for BK virus. J. Virol. 2006, 80, 1361-1366.
218. Seeberger, P. H. Automated carbohydrate synthesis to drive chemical glycomics. Chem. Commun. (Camb) 2003, 1115-1121.
219. Feizi, T.; Fazio, F.; Chai, W.; Wong, C. H. Carbohydrate microarrays - a new set of technologies at the frontiers of glycomics. Curr. Opin. Struct. Biol. 2003, 13, 637-645.
220. Ashikari-Hada, S.; Habuchi, H.; Kariya, Y.; Itoh, N.; Reddi, A. H.; Kimata, K. Characterization of growth factor-binding structures in heparin/heparan sulfate using an octasaccharide library. J. Biol. Chem. 2004, 279, 12346-12354.
221. Freeman, C.; Liu, L.; Banwell, M. G.; Brown, K. J.; Bezos, A.; Ferro, V.; Parish, C. R. Use of sulfated linked cyclitols as heparan sulfate mimetics to probe the heparin/heparan sulfate binding specificity of proteins. J. Biol. Chem. 2005, 280, 8842-8849.
222. Rusnati, M.; Oreste, P.; Zoppetti, G.; Presta, M. Biotechnological engineering of heparin/heparan sulphate: a novel area of multi-target drug discovery. Curr. Pharm. Des. 2005, 11, 2489-2499.
223. Lubineau, A.; Lortat-Jacob, H.; Gavard, O.; Sarrazin, S.; Bonnaffe, D. Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-gamma in the nanomolar range. Chemistry 2004, 10, 4265-4282.
224. Krieger, E.; Geretti, E.; Brandner, B.; Goger, B.; Wells, T. N.; Kungl, A. J. A structural and dynamic model for the interaction of interleukin-8 and glycosaminoglycans: support from isothermal fluorescence titrations. Proteins 2004, 54, 768-775.
225. Raj, P. A.; Marcus, E.; Rein, R. Conformational requirements of suramin to target angiogenic growth factors. Angiogenesis 1998, 2, 183-199.