Anti-HIV activity of sulfonated arabinofuranan and xylofuranan

Carbohydrate Polymers

Volumn 44, Issue 2, 2001, Pages 141-150

  Yoshida, T ^a   Kang, B W ^a   Hattori, K ^a   Mimura, T ^b   Kaneko, Y ^b   Nakashima, H ^c   Premanathan, M ^c   Aragaki, R ^c   Yamamoto, N ^d   Uryu, T ^e  

^a HOKKAIDO UNIVERSITY   (Japan)

^b AJINOMOTO CO INC   (Japan)

^c KAGOSHIMA UNIVERSITY   (Japan)

^d TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^e TEIKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; MOLECULAR WEIGHT; MONOMERS; PHOSPHORUS COMPOUNDS; RING OPENING POLYMERIZATION; SULFONATION;

ARABINOFURANAN; BLOOD ANTICOAGULANT ACTIVITY; XYLOFURANAN; XYLOPYRANAN;

POLYSACCHARIDES;

EID: 16744368402     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0144-8617(00)00210-1     Document Type: Article

References (33)

1. Boeckel C.A.A., Petitou M. The unique antithrombin III domain of heparin: A lead to new synthetic antithrombotics. Angewandte Chemie International Edition in English. 32:1993;1671-1690.
2. Broder S. AIDS modern concepts and therapeutic challenges. 1987;Marcel Dekker, New York.
3. Choi Y.S., Yoshida T., Mimura T., Kaneko Y., Nakashima H., Yamamoto N., Uryu T. Synthesis of sulfated octadecyl ribo-oligosaccharides with potent anti-AIDS virus activity by ring-opening polymerization of a 1,4-anhydro-ribose derivative. Carbohydrate Research. 282:1996;113-123.
4. Choi Y.S., Kang B.W., Lu R., Osawa M., Hattori K., Yoshida T., Mimura T., Kaneko Y., Nakashima H., Yamamoto N., Uryu T. Synthesis of sulfated deoxy-ribofuranans having selective anti-AIDS virus activity by ring-opening polymerization of 1,4-anhydro ribose derivatives. Polymer Journal. 29:1997;374-379.
5. Dalgleish A.G., Weiss R.A. AIDS and the new viruses. 1990;Academic press, London.
6. Este J.A., Schols D., Vreese K.D., Laethm K.V., Vandamme A.M., Desmyter J., De Clercq E. Development of resistance of human immunodeficiency virus type 1 to dextran sulfate associated with the emergence of specific mutations in the envelope gp120 gycoprotein. Molecular Pharmacy. 52:1997;98-104.
7. Gordon, M., Guralnik, M., Kaneko, Y., Mimura, T., Baker, M., & Lang, T. (1994). A phase I study of curdlan sulfonate an HIV inhibitor. Tolerance, Pharmacokinetics and effects on coagulation and on CD4 lymphocytes. J. Medicine, 25, 163-179.
8. Hatanaka K., Uryu T. Synthesis and structural analysis of bioactive polysaccharide. Seisan-Kenkyu. 41:1989;167-170.
9. Hatanaka K., Yoshida T., Miyahara S., Sato T., Ono F., Uryu T., Kuzuhara H. Synthesis of new heparinoids with high anticoagulant activity. Journal of Medical Chemistry. 30:1987;810-814.
10. Hatanaka K., Nakajima I., Yoshida T., Uryu T., Yoshida O., Yamamoto N., Mimura T., Kaneko Y. Effect of degree of sulfation on anti-HIV activity of synthetic (1→5)-α-D-ribofuranan sulfate. Journal of Carbohydrate Chemistry. 10:1991;681-690.
11. Jagodzinski P.P., Wiarderkiewicz R., Kurzawski G., Kloczewiak M., Nakashima H., Hyjek E., Yamamoto N., Uryu T., Kaneko Y., Posner M.R., Kozbor D. Mechanism of the inhibitory effect of curdlan sulfate on HIV-1 infection in vitro. Virology. 202:1994;735-745.
12. Jagodzinski P.P., Wustner J., Kmieciak D., Wasik T.J., Fertala A., Sieron A.L., Takahashi M., Tsuji T., Mimura T., Fung M.S., Gorny M.K., Kloczewiak M., Kaneko Y., Kozbor D. Role of the V2, V3, and CD4-binding domains of gp120 in curdlan sulfate neutralization sensitivity of HIV-1 during infection of T lymphocytes. Virology. 226:1996;217-227.
13. Jeon K.W., Katsuraya K., Kaneko K., Mimura T., Uryu T. Studies on interaction mechanism of sulfated polysaccharides as an AIDS drug by NMR. Macromolecules. 30:1997;1997-2001.
14. Kaneko Y., Yoshida O., Nakagawa R., Yoshida T., Date M., Ogihara S., Matsuzawa Y., Nagashima N., Irie Y., Mimura T., Shinkai H., Yasuda N., Matsuzaki K., Uryu T., Yamamoto N. Inhibition of HIV-1 infectivity with curdlan sulfate in vivo. Biochemical Pharmacology. 39:1990;797-799.
15. Koyama Y., Harima K., Matsuzaki K., Uryu T. Cationic ring-opening polymerization of 1,4-anhydro-2,3-di-O-benzyl-α-L-arabinopyranose and synthesis of L-arabinofuranan. Journal of Polymer Science, Polymer Chemistry Edition. 23:1985;2989-2998.
16. Mitsuya H., Yarchoan R., Broder S. Molecular targets for AIDS therapy. Science. 249:1990;1533-1543.
17. Nakashima H., Kido Y., Kobayashi N., Motoki Y., Neushul M., Yamamoto N. Antiretroviral activity in a marine red alga: reverse transcriptase inhibition by an aqueous extract of Schizymenia pacifica. Journal of Cancer Research and Clinical Oncology. 113:1987;413-416.
18. Nagasawa K., Yoshidome H. Chemical & Pharmaceutical Bullitin. 17:1969;1316-1323.
19. Oscarsson L.G., Pejler G., Lindahl U. Location of the antithrombin-binding sequence in the heparin chain. Journal of Biological Chemistry. 264:1990;296-304.
20. Pauwels R., Balzarini J., Baba M., Snoeck R., Schols D., Herdewijn P., Desmyter J., De Clercq E. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. Journal of Virologial Methods. 20:1988;309-321.
21. Schuerch C. The chemical synthesis and properties of polysaccharides of biomedical interest. Cantow H.J. Advances in polymer science. Vol. 10:1972;173-194 Springer, Berlin.
22. Schuerch C. Synthesis and polymerization of anhydrosugars. Tipson R.S., Horton D. Advances in carbohydrate chemistry and biochemistry. Vol. 39:1981;157-212 Academic Press, New York.
23. Uryu T. Penczek S. Polysaccharides in models of biopolymers by ring-opening polymerization. 1990;133-233 CRC Press, Boca Raton.
24. Uryu T. Artificial polysaccharides and their biological activities. Vogel O. Progress in polymer science. Vol. 18:1993;717-761 Pergamon Press, New York.
25. Uryu T., Ikushima N., Katsuraya K., Shoji T., Takahashi N., Yoshida T., Kanno K., Murakami T., Nakashima H., Yamamoto N. Sulfated alkyl oligosaccharides with potent inhibitory effects on human immunodeficiency virus infection. Biochemical Pharmacology. 43:1992;2385-2392.
26. Uryu T., Yamanouchi J., Hayashi S., Tamaki H., Matsuzaki K. Selective ring-opening polymerization of 1,4-anhydro-2,3-di-O-benzyl-α-D-xylopyranose and synthesis of stereoregular (1→5)-α-D-xylofuranan. Macromolecules. 16:1983;320-326.
27. US Pharmacopoeia National Formulary, USP XXI (1985).
28. Villanueva G.B. Predictions of the secondary structure of antithrombin III and the location of the heparin-binding site. Journal of Biological Chemistry. 259:1984;2531-2536.
29. Yoshida T., Kida M., Uryu T. Selective ring-opening polymerization of di-O-t-butyldimethylsilylated and di-O-p-bromobenzylated 1,4-anhydro-α-L-arabinopyranoses and structural analysis of free arabinans. Polymer Journal. 19:1987;923-931.
30. Yoshida T., Arai T., Mukai Y., Uryu T. Synthesis of branched D-xylofuranan by selective ring-opening polymerization of silylated 1,5-anhydro-β-D-xylofuranose and its conversion into a blood anticoagulant. Carbohydrate Research. 177:1988;69-80.
31. Yoshida T., Hatanaka K., Uryu T., Kaneko Y., Suzuki E., Miyano H., Mimura T., Yoshida O., Yamamoto N. Synthesis and structural analysis of curdlan sulfate with a potent inhibitory effect in vitro of AIDS virus infection. Macromolecules. 23:1990;3717-3722.
32. Yoshida T., Katayama Y., Inoue S., Uryu T. Synthesis of branched ribofuranans and their sulfates with string anti-AIDS virus activity by selective ring-opening copolymerization of 1,4-anhydro-α-D-ribopyranose derivatives. Macromolecules. 25:1992;4051-4057.
33. Yoshida T., Wu C., Song L., Uryu T., Kaneko Y., Mimura T., Nakashima H., Yamamoto N. Synthesis of cellulose-type polyriboses and their branched sulfonates with anti-AIDS virus activity by selective ring-opening copolymerization of 1,4-anhydro-α-D-ribopyranose derivatives. Macromolecules. 27:1994;4422-4428.