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Official Journal of the Japan Wood Research Society

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Sulfated glycofuranans as inhibitors of melanoma lung metastasis

Journal of Wood Science volume 48, pages 204–209 (2002)Cite this article

Abstract

Chemically synthesized (1 → 5)-β-d-glucofuranan, (1 → 5)-β-d-galactofuranan, (1 → 5)-β-d-xylofuranan, (1 → 5)-α-L-arabinofuranan, natural xylan, and curdlan were sulfated to investigate their inhibitory activities on B16-BL6 lung metastasis and anticoagulant activities. (1 → 5)-β-d-Glucofuranan sulfate, (1 → 5)-β-d-galactofuranan sulfate, xylan sulfate, and curdlan sulfate had binding abilities with B16-BL6 melanoma lysate. The inhibitory activities of sulfated polysaccharides on B16-BL6 lung metastasis selected by heparin binding assay were in the order (1 → 5)-β-d-galactofuranan sulfate > (1 → 5)--β-d-glucofuranan sulfate > xylan sulfate ≫ curdlan sulfate. Furthermore, (1 → 5)-β-d-galactofuranan sulfate, (1 → 5)-β-d-glucofuranan sulfate, and xylan sulfate had not only high inhibitory activity on B16-BL6 lung metastasis but also low anticoagulant activity. The correlation between chemical structure and biological activity is discussed.

References

  1. Hashi M, Takeshita T (1979) Antitumor effect of 4-O-methylglucuronoxylan on solid tumor in mice. Agric Biol Chem 43:951–959

    CAS  Google Scholar 

  2. Hashi M, Takeshita T (1979) Host-mediated antitumor effect of 4-O-methylglucuronoxylan. Agric Biol Chem 43:961–967

    CAS  Google Scholar 

  3. Nishimura SI, Kai H, Shinada K, Yoshida T, Tokura S, Kurita K, Nakashima H, Yamamoto N, Uryu T (1998) Regioselective syntheses of sulfated polysaccharides: specific anti-HIV-1 activity of novel chitin sulfates. Carbohydr Res 306:427–433

    Article  CAS  PubMed  Google Scholar 

  4. Hattori K, Yoshida T, Nakashima H, Premanathan M, Aragaki R, Mimura T, Kaneko Y, Yamamoto N, Uryu T (1998) Synthesis of sulfonated amino-polysaccharides having anti-HIV and blood anticoagulant activities. Carbohydr Res 312:1–8

    Article  CAS  PubMed  Google Scholar 

  5. Irimura T, Nakajima M, Nicolson GL (1986) Chemically modified heparins as inhibitors of heparan sulfate specific endo-β-glucuronidase (heparanase) of metastatic melanoma cells. Biochemistry 25:5322–5328

    Article  CAS  PubMed  Google Scholar 

  6. Vlodavsky I, Friedmann Y, Michael E, Aingorn H, Atzmon R, Ishan-Michaeli R, Bitan M, Pappo O, Peretz T, Michal I, Spector L, Pecker I (1999) Mammalian heparanase: gene cloning, expression and function in tumor progression and metastasis. Nat Med 5:793–802

    Article  CAS  PubMed  Google Scholar 

  7. Hulett MD, Freeman C, Hamdorf BJ, Baker RT, Harris M, Parish CR (1999) Cloning of mammalian heparanase, an important enzyme in tumor invasion and metastasis. Nat Med 5:803–809

    Article  CAS  PubMed  Google Scholar 

  8. Kussie PH, Hulmes JD, Ludwig DL, Patel S, Navarro EC, Seddon AP, Giorgio NA, Bohlen P (1999) Cloning and functional expression of a human heparanase gene. Biochem Biophys Res Commun 261:183–187

    Article  CAS  PubMed  Google Scholar 

  9. Toyoshima M, Nakajima M (1999) Human heparanase: purification, characterization, cloning, and expression. J Biol Chem 274:24153–24160

    Article  CAS  PubMed  Google Scholar 

  10. Nakajima M, Irimura T, Ferrante ND, Nicolson GL (1984) Metastatic melanoma cell heparanase. J Biol Chem 259:2283–2290

    CAS  PubMed  Google Scholar 

  11. Parish CR, Freeman C, Brown KJ, Francis DJ, Cowden WB (1999) Identification of sulfated oligosaccharide-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity. Cancer Res 59:3433–3441

    CAS  PubMed  Google Scholar 

  12. Villanueva GB, Nakajima M, Nicolson GL (1988) Heparin derivatives as inhibitors of heparanase from metastatic melanoma cells. Ann NY Acad Sci 556:496–498

    Article  Google Scholar 

  13. Nakajima M, Irimura T, Nicolson G (1988) Heparanases and tumor metastasis. J Cell Biochem 36:157–167

    Article  CAS  PubMed  Google Scholar 

  14. Nishigaki F, Miyayasu K. Tsujimoto S, Manda T, Shimomura K (1995) Potentiation of the toxicity of tumor necrosis factor by tumors in mice. Circ Shock 44:77–83

    Google Scholar 

  15. Kamitakahara H, Nakatsubo F, Murakami K (1994) Ring-opening polymerization of 1,4-anhydro-α-d-glucopyranose derivatives having acyl groups and synthesis of (1 → 5)-β-d-glucofuranan. Macromolecules 27:5937–5942

    Article  CAS  Google Scholar 

  16. Tsujihata S, Nakatsubo F (1996) Synthesis of stereoregular (1 → 5)-β-d-galactofuranan by ring-opening polymerization of intramolecular orthoester. In: Abstracts of XVIIIth Japanese Carbohydrate Symposium, pp 57–58

  17. Hori M, Nakatsubo F (1998) Ring-opening polymerization of 1,4-anhydro-3-O-benzyl-2-O-acetyl-α-d-xylopyranose and synthesis of stereoregular (1 → 5)-β-D-xylofuranan. Macromolecules 31:7195–7198

    Article  CAS  Google Scholar 

  18. Hori M, Nakatsubo F (2000) Ring-opening polymerization of 3-O-benzyl-β-L-arabinofuranose 1,2,5-orthopivalate and synthesis of stereoregular (1 → 5)-a-L-arabinofuranan. Macromolecules 33:1148–1151

    Article  CAS  Google Scholar 

  19. Aspinall GO, Carpenter RC (1984) Structural investigations on the non-starchy polysaccharides of oat bran. Carbohydr Polym 4:271–282

    Article  CAS  Google Scholar 

  20. Saiki I, Murata J, Nakajima M, Tokura S, Azuma I (1990) Inhibition by sulfated chitin derivatives of invasion through extracellular matrix and enzymatic degradation by metastatic melanoma cells. Cancer Res 50:3631–3637

    CAS  PubMed  Google Scholar 

  21. Larm O, Larsson K, Scholander E, Andersson LO. Holmer E, Söderström G (1979) The preparation of a heparin analogue from alginic acid. Carbohydr Res 73:332–336

    Article  CAS  Google Scholar 

  22. Heinze T, Rahn K (1999) New polymers from cellulose sulphonates. J Pulp Pap Sci 25:136–140

    CAS  Google Scholar 

  23. Baumann H, Faust V (2001) Concepts for improved regioselective placement ofO-sulfo,N-sulfo,N-acetyl, andN-carboxymethyl groups in chitosan derivatives. Carbohydr Res 331:43–57

    Article  CAS  PubMed  Google Scholar 

  24. Hatanaka K, Yoshida T, Miyahata S, Sato T, Ono F, Uryu T, Kuzuhara H (1987) Synthesis of new heparinoids with high anticoagulant activity. J Med Chem 30:810–814

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, 606-8502, Kyoto, Japan

    Hiroshi Kamitakahara, Yuji Mikawa, Michiko Hori, Shigetomo Tsujihata & Fumiaki Nakatsubo

  2. Medicinal Biological Research Laboratories, Fujisawa Pharmaceutical Co., 532-8514, Osaka, Japan

    Fusako Nishigaki

  3. Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., 300-2698, Ibaraki, Japan

    Takashi Fujii

Authors
  1. Hiroshi Kamitakahara
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  2. Fusako Nishigaki
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  3. Yuji Mikawa
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  4. Michiko Hori
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  5. Shigetomo Tsujihata
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  6. Takashi Fujii
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  7. Fumiaki Nakatsubo
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Correspondence to Hiroshi Kamitakahara.

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Kamitakahara, H., Nishigaki, F., Mikawa, Y. et al. Sulfated glycofuranans as inhibitors of melanoma lung metastasis. J Wood Sci 48, 204–209 (2002). https://doi.org/10.1007/BF00771368

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