Polyanions - A lost chance in the fight against HIV and other virus diseases?

Antiviral Chemistry and Chemotherapy

Volumn 11, Issue 4, 2000, Pages 249-259

  Luscher Mattli M ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Antiviral agents; Dextran sulphate; Fusion; Influenza; Polyanions

Indexed keywords

ANTIVIRUS AGENT; CD4 ANTIGEN; IONIC SURFACTANT; MILK PROTEIN; POLYANION; POLYPHOSPHATE; POLYSACCHARIDE SULFATE; SERUM ALBUMIN; VIRUS ENVELOPE PROTEIN;

ANTICOAGULATION; ANTIVIRAL ACTIVITY; DRUG BIOAVAILABILITY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PRIORITY JOURNAL; REVIEW; SIDE EFFECT; SYNCYTIUM; T LYMPHOCYTE; THROMBOCYTOPENIA; VIRUS CELL INTERACTION; VIRUS INFECTIVITY; VIRUS REPLICATION;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; DRUG CARRIERS; HIV; HIV INFECTIONS; HUMANS; INFLUENZA, HUMAN; MOLECULAR STRUCTURE; POLYMERS;

EID: 0038809791     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (74)

1. Abrams DI, Kuno S, Wong R. Jeffords K, Nash M, Molaghan JB, Gorter R & Ueno R (1989) Oral dextran sulfate (Ua001) in the treatment of the acquired immunodeficiency syndrome (AIDS) and AIDS related complex. Annals of Internal Medicine 110:183-188.
2. Anonymous (1989) Dextran sulfate: Lost in a sea of confusion. Product Information (Pi) 6.
3. Baba M, Pauwels R, Balzarini J, Arnout J, Desmyter J & De Clercq E (1988) Mechanism of inhibitory effect of dextran sulfate and heparin on replication of human immunodeficiency virus in vitro. Proceedings of the National Academy of Sciences, USA 85:6132-6136.
4. Baba M, De Clercq E, Schols D, Pauwels R, Snoek R, Van Boeckel C, Van Dedem G, Kraijeveld N, Hobbelen P, Ottenheijm H & Den Hollander F (1990) Novel sulfated polysaccharides: dissociation of anti-human immunodeficiency virus activity from antithrombin activity. Journal of Infectious Diseases 161:208-213.
5. Balzarini J, Mitsuya H, De Clercq E & Broder S (1986) Aurintricarboxylic acid and Evans Blue represent two different classes of anionic compounds which selectively inhibit the cytopathogenicity of human T cell lymphotropic virus type III lymphadenopathy-associated virus. Biochemical Biophysical Research Communications 136:64-71.
6. Bengtson S (1965) Mechanism of dextran sulfate inhibition of attenuated poliovirus. Proceedings of the Society for Experimental Biology and Medicine 118:47-53.
7. Bettinger T, Remy JS, Erbacher P & Behr JP (1998) Convenient polymer-supported synthetic route to heterobifunctional polyethylene glycols. Bioconjugate Chemistry 6:842-846.
8. Carre V, Mbemba E, Letourneur D, Jozefonvicz J & Gattegno L (1995) Interactions of envelope glycoproteins with derivatized dextrans. Biochimica Biophysica Acta 12143:175-180.
9. Casu B (1985) Structure and biological activity of heparin. In Advances of Carbohydrate Chemistry and Biochemistry Vol 43, pp 43-134. Academic Press Inc.
10. Choi YS, Yoshida T, Mimura T, Kaneko Y, Nakashima H, Yamamoto N & Uryu T (1996) Synthesis of sulfated octadecyl ribo-oligosaccharides with potent anti-AIDS virus activity by ring-opening polymerization of a 1,4 anhydroribose derivative. Carbohydrate Research 282:113-123.
11. DR Reports (1998) Drug delivery systems: Technologies and commercial opportunities Decision Resources. Bay Colony Corporate Center, Waltham, Mass., USA.
12. De Clercq E (1989) New acquisitions in the development of anti-HIV agents. Antiviral Research 12:1-20.
13. Désormeaux A & Bergeron MG (1998) Liposomes as drug delivery system: a strategic approach for the treatment of HIV infection. Journal of Drug Targeting 6:1-15.
14. Drusano GL (1993) Pharmacodynamics of antiretroviral chemotherapy. Clinical Pharmacology of Antibiotics 14:530-536.
15. Dutch RE, Joshi SB & Lamb RA (1998) Membrane fusion promoted by increasing surface densities of the paramyxovirus F and HN Proteins: Comparison of fusion reactions mediated by Simian virus 5F, human parainfluenza virus type 3F, and influenza virus HA. Journal of Virology 72:7745-7753.
16. Erbacher P, Remy JS & Behr JP (1999) Gene transfer with synthetic virus-like particles via the integrin-mediated endocytosis pathway. Gene Therapy 6:138-145.
17. Fass D & Kim KS (1995) Dissection of a retrovirus envelope protein reveals structural similarity to influenza haemagglutinin. Current Biology 5:1377-1383.
18. Fletcher CV (1996) Pharmacologic considerations for antiviral drug development. The Annals Of Pharmacotherapy 30:972-977.
19. Flexner Ch, Barditch-Crovo PA, Kornhauser DM, Farzadegan H, Nerhood LJ, Chaisson RE, Bell KM, Lorentsen KJ, Hendrix CW, Petty BG & Lietman PS (1991) Pharmacokinetics, toxicity, and activity of intravenous dextran sulfate. Antimicrobial Agents and Chemotherapy 35:2544-2550.
20. Gianese F & Lucchelli PE (1991) A survey of the clinical experience with dermatan sulfate. Seminars In Thrombosis And Hemostasis 17(Suppl. 20):199-204.
21. Gordon LM, Waring AJ, Curtain CC, Kirkpatrick A, Leung C, Faull K & Mobley PW (1995) Antivirals that target the amino-terminal domain of HIV type 1 glycoprotein gp41. AIDS Research and Human Retroviruses 11:677-686.
22. Hartmann NL, Johns DG & Mitsuya H (1990) Pharmacokinetic analysis of dextran sulfate in rats as pertains to 1st clinical usefulness for therapy of HIV infection. AIDS Research and Human Retroviruses 6:805-812.
23. Hayashi K, Hayashi T & Kojima I (1996) A natural sulfated polysaccharide, calcium spirulan, isolated from Spirulina Platensis: In vitro and ex vivo evaluation of anti-herpes simplex virus and anti human immunodeficiency virus activities. AIDS Research and Human Retroviruses 12:1463-1471.
24. Herrmann A, Korte TH, Arnold K & Hillebrecht B (1992) The influence of dextran sulfate on influenza A virus fusion with erythrocyte membranes. Antiviral Research 19:295-311.
25. Hiti AL et al. (1991) (Title unavailable) Virology 111:113-124.
26. Hosoya M, Balzarini J, Shigeta S & De Clercq E (1991) Differential inhibitory effects of sulfated polysaccharides and polymers on the replication of various myxoviruses and retroviruses,depending on the target amino acid sequences of the viral envelope glycoprotein. Antimicrobial Agents and Chemotherapy 35:2515-2520.
27. Ikeda S, Neyts J, Verma S, Wickramasinghe A, Mohan P & De Clercq E (1994) In vitro and in vivo inhibition of ortho- and paramyxovirus infections by a new class of sulfonic acid polymers interacting with virus-cell binding and/or fusion. Antimicrobial Agents and Chemotherapy 38:256-259.
28. Ito M, Baba M, Sato A, Pauwels R, De Clercq E & Shigeta S (1987) Inhibitory effect of dextran sulfate and heparin on the replication of human immunodeficiency virus (HIV) in vitro. Antiviral Research 7:361-367
29. Jansen RW, Molema G, Pauwels R, Schols D, De Clercq E & Meijer DKF (1991) Potent in vitro anti-human immunodeficiency virus-1 activity of modified human serum albumins. Molecular Pharmacology 39:818-823.
30. Jansen RW, Schols D, Pauwels R, De Clercq E & Meijer DKF (1993) Novel negatively charged human serum albumins display potent and selective in vitro anti-human immunodeficiency virus type1 activity. Molecular Pharmacology 44:1003-1007.
31. Joshi SB, Dutch RE & Lamb RA (1998) A core trimer of the paramyxovirus fusion protein: parallels to influenza hemagglutinin and HIV-1 gp41. Virology 248:20-34.
32. Kamps JA, Swart PJ, Morselt HWM, Pauwels R, De Bethune MP, De Clercq E, Meijer DKF & Scherphof GL (1996) Preparation and characterization of conjugates of (modified) human serum albumin and liposomes: drug carriers with an intrinsic anti-HIV activity. Biochimica et Biophysica Acta 1278:183-190.
33. Kamps JA, Morselt HW, Swart PJ, Meijer DKF & Scherphof GL (1997) Massive targeting of liposomes, surface-modified with anionized albumins,to hepatic endothelial cells. Proceedings of the National Academy of Sciences, USA 94:11681-11685.
34. Koff WC & Fidler IJ (1985) The potential use of liposome-mediated antiviral therapy. Antiviral Research 5:179-190.
35. Krust B, Callebaut CH & Honavessian AG (1993) Inhibition of entry of HIV into cells by poly (A)-poly(U). AIDS Research And Human Retroviruses 9:1087-1090.
36. Kuipers ME, Huismann JG, Swart PJ, de Bethune MP, Pauwels R, Schuitemaker H, De Clercq E & Meijer DK (1996) Mechanism of anti-HIV activity of negatively charged albumins: biomolecular interaction with the HIV-1 envelope protein gp 120. Journal of Acquired Immune Deficiency Syndromes and Human Retrovirology 11:419-429.
37. Leydet A, Barthelemi P, Boyer B, Lamathy G, Roque JP, Bousseau A, Evers M, Henin Y, Snoek R, Andrei G et al. (1995) Polyanion inhibitors of human immunodeficiency virus and other viruses. 1 Polymerized anionic surfactants. Journal of Medicinal Chemistry 38:2433-2440.
38. Leydet A, El Hachemi H, Boyer B, Lamaty G, Roque JP, Schols D, Snoek R, Andrei G, Ikeda S, Neyts J, Reymen D, Este J, Witrouw M & De Clercq E (1996) Polyanion inhibitors of human immunodeficiency virus and other viruses. Part 2. Polymerized anionic surfactants derived from amino acids and dipeptides. Journal of Medicinal Chemistry 39:1626-1634.
39. Leydet A, Barragan V, Boyer B, Montero JL, Roque JP, Witvrouw M, Este J, Snoek R, Andrei G & De Clercq E (1997) Polyanion inhibitors of human immunodeficiency virus and other viruses 5. Telomerized anionic surfactants derived from amino acids. Journal of Medicinal Chemistry 40:342-349.
40. Leydet A, Moullet C, Roque JP, Witvrouw M, Pannecouque C, Andrei G, Snoek R, Neyts J, Schols D & De Clercq E (1998) Polyanion inhibitors of HIV and other viruses 7. Polyanionic compounds and zwitterionic compounds derived from cyclodextrins as inhibitors of HIV transmission. Journal of Medicinal Chemistry 41:4927-4932.
41. Lorentsen KJ, Hendrix CW & Collins JM (1989) Dextran sulfate is poorly absorbed after oral administration. Annals of Internal Medicine 111:561-566.
42. Lorenz B, Leuck J, Köhl D, Muller WE & Schroder HC (1997) Anti-HIV activity of inorganic polyphosphates. Journal of Acquired Immunodeficiency Syndrome and Human Retrovirology 14:110-118.
43. Luescher-Mattli M & Glueck R (1990) Dextran sulfate inhibits the fusion of influenza virus with model membranes, and suppresses influenza replication in vivo. Antiviral Research 14:39-50.
44. Luescher-Mattli M, Glueck R, Kempf CH & Zanoni-Grassi M (1993) A comparative study of the effect of dextran sulfate on the fusion and the in vitro replication of influenza A and B, Semliki Forest, vesicular stomatis, rabies, sendai and mumps virus. Archives Virology 130:317-326.
45. Mehvar R & Shepard TL (1992) Molecular-weight-dependent pharmacokinetics of fluorescein-labeled dextrans in rats. Journal of Pharmaceutical Sciences 81:908-912.
46. Meijer DKF, Jansen RW & Molema G (1992) Drug targeting systems for antiviral agents: Options and limitations. Antiviral Research 18:215-258.
47. Mitsuya H, Popovic M, Yarchoan R, Matsushita S, Gallo RC & Broder S (1984) Suramin protection of T cells in vitro against infectivity and cytopathic effect of HTLV-III. Science 226:172-174.
48. Mitsuya H, Looney DJ, Kuno S, Ueno R, Wong-Staal F & Broder S (1988) Dextran sulfate suppression of viruses in the HIV family: inhibition of virion binding to CD4+ cells Science 240:646-649.
49. Mohan P, Schols D, Baba M & De Clercq E (1992) Sulfonic acid polymers as a new class of human immunodeficiency virus inhibitors. Antiviral Research 18:139-150.
50. Montefiori DC & Mitchell WM (1987) Antiviral activity of mismatched double stranded RNA against human immunodeficiency virus in vitro. Proceedings of the National Academy of Sciences USA 84:2985-2989.
51. Nakashima H, Yoshida O, Tochikura TS, Yoshida T, Mimura T, Kido Y, Motoki Y, Kaneko Y, Uryu T & Yamamoto N (1987) Sulfation of polysaccharides generates potent and selective inhibitors of human immunodeficiency virus infection and replication in vitro. Japanese Journal of Cancer Research 78:1164-1168.
52. Nakashima H, Yoshida O, Baba M, De Clercq E & Yamamoto N (1989) Anti-HIV activity of dextran sulfate as determined under different experimental conditions. Antiviral Research 11:233-246.
53. Neyts J, Reymen D, Letourneur D, fozefonvics J, Schols D, Este J, Andrei G, McKenna P, Witvrouw M, Ikeda S, et al. (1995) Differential antiviral activity of derivatized dextrans. Biochemical Pharmacology 50:743-751.
54. Ohki S, Arnold K, Srinivasakumar N & Flanagan TD (1991) Effect of dextran sulfate on fusion of Sendai virus with human erythrocyte ghosts. Biomedica Biochimica Acta 50:199-206.
55. Ono M, Wada Y, Wu Y, Nemori R, Jinbo Y, Wang H, Lo KM, Yamaguchi N, Brunkhorst B, Otomo H, Wesolowski J, Way JC, Itoh I, Gillies S & Chen LB (1997) FP-21399 blocks HIV envelope protein-mediated membrane fusion and concentrates in lymph nodes. Natural Biotechnology 15:343-348.
56. Pavào MSG (1996) Unique sulfated polysaccharides from ascidians (Chordata,Tunicata). Brazilian Journal of Medical and Biological Research 29:1227-1233.
57. Rubas W & Schreier H (1991) Liposomen: fortschritte in herstellungs-technologie und therapie. Pharmazie in Unserer Zeit 6:255-270.
58. Schoen P, Corver J, Meijer DKF, Wilschut J & Swart PJ (1997) Inhibition of influenza virus fusion by polyanionic proteins. Biochemical Pharmacology 53:995-1003.
59. Schols D, Pauwels R, Baba M, Desmyter J & De Clercq E (1989) Syncytium formation and destruction of bystander CD4+ cells cocultured with T cells persistently nfected with human immundeficiency virus as demonstrated by flow cytometry. Journal of General Virology 70:2398-2408.
60. Schols D, De Clercq E, Balzarini J, Baba M, Witvrouw M, Hosoya M, Andrei G, Snoek R, Neyts J, Pauwels R, Nagy M, Gyorgyi-Edelenyi J, Machowich R, Horvath I, Low M & Gorog S (1990) Sulphated polymers are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, respiratory syncytial virus, and togaarena-and retroviruses. Antiviral Chemistry and Chemotherapy 1:233-240.
61. Schols D, Pauwels R, Witvrouv M, Desmyter J & De Clercq E (1992) Differential activity of polyanionic compounds and castanospermine against HIV replication and HIV-induced syncytium formation depending on virus strain and cell type. Antiviral Chemistry and Chemotherapy 3:23-29.
62. Sinangil F, Loyter A & Volsky DJ (1988) Quantitative measurement of fusion beween human immunodeficiency virus and cultured cells using membrane fluorescence quenching. Federation of European Biochemical Societies 238:88-92.
63. Stegmann T, Delfino JM, Richards FM & Helenius A (1991) The HA2 subunit of influenza hemagglutinin inserts into the target membrane prior to fusion. Journal of Biological Chemistry 266:18404-18410.
64. Swart PJ & Meijer DKF (1994) Negatively charged albumins:a novel class of polyanionic proteins with a potent anti-HIV activity. International Antiviral News 2:69-71.
65. Swart PJ, Kuipers ME, Smit C, Pauwels R, de Bethune MP, De Clercq E, Meijer DK & Huisman JG (1996) Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. AIDS Research and Human Retroviruses 12:769-775.
66. Takakura Y (1996) Development of drug delivery systems for macromolecular drugs. Yakugaku Zasshi 116:519-532.
67. Tan GT, Wickramasinghe A, Verma S, Hughes SH, Pezzuto JM, Baba M & Mohan P (1993) Sulfonic acid polymers are potent inhibitors of HIV-1 induced cytopathogenicity and the reverse transcriptases of both HIV 1 and HIV 2. Biochimica et Biophysica Acta 1181:183-188.
68. Taugner R, Karsunki KP & Metz J (1971) Zur Pharmakokinetik des 'heparinartigen' sulfatierten polyanions SP 54. Archives Internationales de Pharmacodynamie 189:250-280.
69. Tsurudome M, Glück R, Graf R, Falchetto R, Schaller U & Brunner J (1992) Lipid interactions of the hemagglutinin Ha2 NH2-terminal segment during influenza virus-induced membrane fusion. Journal of Biological Chemistry 267:20225-20232.
70. Ueno R & Kuno S (1987) Dextran sulphate, a potent anti-HIV agent in vitro, having synergism with zidovudine. The Lancet 1:1379.
71. Witvrouw M, Baba M, Balzarini J, Pauwels R & De Clercq E (1990) Establishment of a bioassay to determine serum levels of dextran sulfate and pentosan polysulfate, two potent inhibitors of human immunodeficiency virus. Journal of Acquired Immunodeficiency Syndromes 3:343-347.
72. Witrvrouv M, Schols D, Andrei G, Snoek R, Hosoya M, Pauwels R, Balzarini J & De Clercq E (1991) Antiviral activity of of low MW dextran sulfate (derived from dextran MW 1000) compared to dextran sulfate samples of higher MW. Antiviral Chemistry and Chemotherapy 2:171-179.
73. Witvrouv M, Este JA, Quinones Mateu ME, Reymen D, Andrei G, Snoek R, Ikeda S, Pauwels R, Vittori Bianchini N, Desmyter J & De Clercq E (1994) Activity of a sulfated poysaccharide extracted from the red seaweed Aghardhiella tenera agauinst human immunodeficiency virus and other enveloped viruses. Antiviral Chemistry and Chemotherapy 5:297-303.
74. Witvrouw M & De Clercq E (1997) Sulfated polysaccharides extracted from sea algae as potent antiviral drugs. General Pharmacology 29:497-511.