Anti-HIV activity of extracts and compounds from algae and cyanobacteria

Ecotoxicology and Environmental Safety

Volumn 45, Issue 3, 2000, Pages 208-227

  Schaeffer, David J ^a   Krylov, Victor S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

AIDS; Algae; Antiretroviral activity; Carrageenan; Cyanobacteria; Fucoidan; HIV; Seaweed; Sesquiterpene hydroquinones; Sulfated polysaccharides; Sulfogylcolipids

Indexed keywords

CARRAGEENAN; DEXTRAN SULFATE; FRESH WATER; FUCOIDIN; HYDROQUINONE; POLYSACCHARIDE; POLYSACCHARIDE SULFATE; SESQUITERPENE; SPERMICIDAL AGENT;

ALGA; ANTIVIRAL ACTIVITY; CYANOBACTERIUM; DRUG BINDING; DRUG SAFETY; DRUG TOLERANCE; EXTRACT; HERPES SIMPLEX VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IMMUNE DEFICIENCY; KAPOSI SARCOMA; MARINE ENVIRONMENT; RETROVIRUS; REVIEW; SEAWEED;

ALGAE; CHLOROPHYTA; CYANOBACTERIA; HERPES; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; SIMPLEXVIRUS; UNCULTURED CYANOBACTERIUM; UNIDENTIFIED RETROVIRUS;

EID: 0034102225     PISSN: 01476513     EISSN: None     Source Type: Journal    
DOI: 10.1006/eesa.1999.1862     Document Type: Review

References (115)

1. Abrams D., Pettinelli C., Power M., Kubacki V. B., Grieco M. H., Henry W. K. A phase I/II dose ranging trial of oral dextran sulfate in HIV p24 antigen positive individuals (ACTG 060): Results of a safety and efficacy trial. Int. Conf. AIDS. 5:1989a;404.
2. Abrams D. I., Kuno S., Wong R., Jeffords K., Nash M., Molaghan J. B., Gorter R., Ueno R. Oral dextran sulfate (UA001) in the treatment of the acquired immunodeficiency syndrome (AIDS) and AIDS-related complex. Ann. Intern. Med. 110:1989b;183-188.
3. Anand R., Nayyar S., Galvin T. A., Merril C. R., Bigelow L. B. Sodium pentosan polysulfate (SP-54), an anti-HIV agent also exhibits lymphocyte proliferative activity and synergism with AZT. Int. Conf. AIDS. 5:1989;635.
4. Anand R., Nayyar S., Galvin T. A., Merril C. R., Bigelow L. B. Sodium pentosan polysulfate (PPS), an anti-HIV agent also exhibits synergism with AZT, lymphoproliferative activity, and virus enhancement. AIDS Res. Hum. Retroviruses. 6:1990;679-689.
5. Anand R., Nayyar S., Pitha J. The sulfated sugar alpha-cyclodextrin sulfate (α-CDS) is a potent anti-HIV agent, has marked synergism with AZT, and exhibits lymphoproliferative activity. Int. Conf. AIDS. 6:1990;178.
6. Ayehunie S., Belay A., Baba T. W., Ruprecht R. M. Inhibition of HIV-1 replication by an aqueous extract of Spirulina platensis (Arthrospira platensis). J. Acquir. Immune. Defic. Syndr. Hum. Retrovirol. 18:1998;7-12.
7. Baba M., Nakajima M., Schols D., Pauwels R., Balzarini J., De Clercq E. Pentosan polysulfate, a sulfated oligosaccharide, is a potent and selective anti-HIV agent in vitro. Antiviral Res. 9:1988a;335-343.
8. 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. 32:1988b;1742-1745.
9. 4-positive cells with persistently HIV-1-infected cells. Int. Conf. AIDS. 5:1989;554-554.
10. 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. 3:1990;493-499.
11. Bagasra O., Lischner H. W., Halligen G. E., Heins B. Anti-HIV-1 activities of sulfated monosaccharides (SMS) and polysaccharides (SPS): Therapeutic indices (TI). Int. Conf. AIDS. 5:1989;660.
12. Bagasra O., Whittle P., Heins B., Pomerantz R. J. Anti-human immunodeficiency virus type 1 activity of sulfated monosaccharides: comparison with sulfated polysaccharides and other polyions. J. Infect. Dis. 164:1991;1082-1090.
13. Balter M. Revealing HIV's T cell passkey. Science. 280:1998;1833-1834.
14. n-specific plant lectin from Urtica dioica are potentent and selective inhibitors of human immunodeficiency virus and cytomegalovirus replication in vitro. Antiviral Res. 18:1992;191-207.
15. 4-derived synthetic peptides. J. Biol. Chem. 267:1992;6664-6671.
16. Beress A., Wassermann O., Tahhan S., Bruhn T., Beress L., Kraiselburd E. N., Gonzalez L. V., de Motta G. E., Chavez P. I. A new procedure for the isolation of anti-HIV compounds (polysaccharides and polyphenols) from the marine alga Fucus vesiculosus. J. Nat. Prod. 56:1993;478-488.
17. Bewley C. A., Gustafson K. R., Boyd M. R., Covell D. G., Bax A., Clore G. M., Gronenborn A. M. Solution structure of cyanovirin-N, a potent HIV-inactivating protein. Nat. Struct. Biol. 5:1998;571-578.
18. Boyd M. R., Gustafson K., McMahon J., Shoemaker R. Discovery of cyanovirin-N, a novel HIV-inactivating protein from Nostoc ellipsosporum that targets viral gp120. Int. Conf. AIDS. 11:1996;71-71.
19. Boyd M. R., Gustafson K. R., McMahon J. B., Shoemaker R. H., O'Keefe B. R., Mori T., Gulakowski R. J., Wu L., Rivera M. I., Laurencot C. M., Currens M. J., Cardellina J. H., Buckheit R. W. J., Nara P. L., Pannell L. K., Sowder R. C., Henderson L. E. Discovery of cyanovirin-N, a novel human immunodeficiency virus-inactivating protein that binds viral surface envelope glycoprotein gp120: Potential applications to microbicide development. Antimicrob. Agents Chemother. 41:1997;1521-1530.
20. Burkholder P. R., Sharma G. M. Antimicrobial agents from the sea. Lloydia. 32:1969;466-483.
21. Cardellina J. H., Munro M. H., Fuller R. W., Manfredi K. P., McKee T. C., Tischler M., Bokesch H. R., Gustafson K. R., Beutler J. A., Boyd M. R. A chemical screening strategy for the dereplication and prioritization of HIV-inhibitory aqueous natural products extracts. J. Nat. Prod. 56:1993;1123-1129.
22. Carlucci M. J., Pujol C. A., Ciancia M., Noseda M. D., Matulewicz M. C., Damonte E. B., Cerezo A. S. Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity. Int. J. Biol. Macromol. 20:1997a;97-105.
23. Carlucci M. J., Scolaro L. A., Errea M. I., Matulewicz M. C., Damonte E. B. Antiviral activity of natural sulphated galactans on herpes virus multiplication in cell culture. Planta Med. 63:1997b;429-432.
24. Chamorro G., Salazar M., Favila L., Bourges H. Pharmacology and toxicology of Spirulina alga. Rev. Invest. Clin. 1996;389-399.
25. Codd G. A. Cyanobacterial toxins: Occurrence properties and biological significance. Water Sci. Technol. 32:1995;149-156.
26. Damonte E. B. Antiviral agents that act in the early phases of the viral cycle. Rev. Argent. Microbiol. 28:1996;204-216.
27. Damonte E. B., Matulewicz M. C., Cerezo A. S., Coto C. E. Herpes simplex virus-inhibitory sulfated xylogalactans from the red seaweed Nothogenia fastigiata. Chemotheraphy. 42:1996;57-64.
28. Damonte E. B., Neyts J., Pujol C. A., Snoeck R., Andrei G., Ikeda S., Witvrouw M., Reymen D., Haines H., Matulewicz M. C. Antiviral activity of a sulfated polysaccharide from the red seaweed Nothogenia fastigiata. Biochem. Pharmacol. 47:1994;2187-2192.
29. De Clercq E. Selective virus inhibitors. Microbiologica. 13:1990;165-178.
30. Deig E. F. Inhibition of herpes virus replication by marine algae extracts. Antimicrob. Agents Chemother. 6:1974;524-525.
31. Ehresmann D. W., Dieg E. F., Hatch M. T., DiSalvo L. H., Vedros N. A. Antiviral substances from California marine algae. J. Phycol. 13:1977;37-40.
32. Elias C. J., Coggins C., Alvarez F., Brache V., Fraser I. S., Lacarra M., Lahteenmaki P., Massai R., Mishell D. R. Jr., Phillips D. M., Salvatierra A. M. Colposcopic evaluation of a vaginal gel formulation of iota-carrageenan. Contraception. 56:1997;387-389.
33. 4-induced conformational changes in gp120. J. Virol. 73:1999;4360-4371.
34. Filalimouhim R., Hours M. Antiviral activities of sulfated polysaccharides. Acta Botanica Gallica. 142:1995;125-130.
35. Flexner C., Braditch-Crovo P. A., Kornhauser D. M., Farzadegan H., Nerhood L. J., Chaisson R. E., Bell K. M., Lorentsen K. J., Hendrix C. W., Petty B. G. Pharmacokinetics, toxicity, and activity of intravenous dextran sulfate in human immunodeficiency virus infection. Antimicrob. Agents Chemother. 35:1991;2544-2550.
36. Fogg G. E. The Metabolism of Algae. 1953;Methuen, London.
37. Gerber P., Dutcher J. D., Adams E. V., Sherman J. H. Protective effect of seaweed extracts for chicken embryos infected with influenza B or mumps. Proc. Soc. Exp. Biol. Med. 99:1958;590-593.
38. Gonzalez M. E., Alarcon B., Carrasco L. Polysaccharides as antiviral agents: Antiviral activity of carrageenan. Antimicrob. Agents Chemother. 31:1987;1388-1393.
39. Grippo P., Orlando P., Carretta F., Pastore M., Strazzullo G., Manzari V., Sinibaldi P., Silvestri I. Inhibition of HTLV1 replication by Kelletinin A. Int. Conf. AIDS. 7:1991;103.
40. Gustafson K. R., Cardellina J. H., Fuller R. W., Weislow O. S., Kiser R. F., Snader K. M., Patterson G. M., Boyd M. R. AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae). J. Natl. Cancer Inst. 81:1989;1254-1258.
41. Gustafson K. R., Sowder R. C., Henderson L. E., Cardellina J. H., McMahon J. B., Rajamani U., Pannell L. K., Boyd M. R. Isolation, primary sequence determination, and disulfide bond structure of cyanovirin-N, an anti-HIV (human immunodeficiency virus) protein from the cyanobacterium Nostoc ellipsosporum. Biochem. Biophys. Res. Commun. 238:1997;223-228.
42. Gustafson K. R., Sowder R., Henderson L., Pannel L., Cardellina J., McMahon J., Shoemaker R., Boyd M. Sequence determination and chemical characteristics of a novel anti-HIV protein, cyanovirin-N, isolated from the cyanobacterium Nostoc ellipsosporum. Int. Cont. AIDS. 11:1996;70.
43. Hansen J. E., Nielsen C. M., Nielsen C., Heegaard P., Mathiesen L. R., Nielsen J. O. Correlation between carbohydrate structures on the envelope glycoprotein gp120 of HIV-1 and HIV-2 and syncytium inhibition with lectins. AIDS. 3:1989;635-641.
44. Harwood J. Sulfolipids. Stumpf P. K. The Biochemistry of Plants. 9:1987;275-289 Academic Press, New York.
45. Hasui M., Matsuda M., Okutani K., Shigeta S. In vitro antiviral activities of sulfated polysaccharides from a marine microalga (Cochlodinium polykrikoides) against human immunodeficiency virus and other enveloped viruses. Int. J. Biol. Macromol. 17:1995;293-297.
46. Hayashi K., Hayashi T., Morita M. An extract of Spirulina platensis is a selective inhibitor of herpes simplex virus type-1 penetration into HeLa cells. Phytother. Res. 7:1992;7680-7680.
47. Hayashi T., Hayashi K., Maeda M., Kojima I. Calcium spirulan, an inhibitor of enveloped virus replication, from a blue-green alga Spirulina platensis. J. Nat. Prod. 59:1996a;83-87.
48. Hayashi K., Hayashi T., Kojima I. 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 Res. Hum. Retroviruses. 12:1996b;1463-1471.
49. Hayashi K., Hamada J., Hayashi T. A screening strategy for selection of anti-HSV-1 and anti-HIV extracts from algae. Phytother. Res. 10:1996c;233-237.
50. Hiebert L. M., Wice S. M., Jaques L. B., Williams K. E., Conly J. M. Orally administered dextran sulfate is absorbed in HIV-positive individuals. J. Lab. Clin. Med. 133:1999;161-170.
51. Hoshino T., Hayashi T., Hayashi K., Hamada J., Lee J. B., Sankawa U. An antivirally active sulfated polysaccharide from Sargassum horneri (TURNER) C. AGARDH. Biol. Pharm. Bull. 21:1998;730-734.
52. Husson G. P., Subra F., Lai-Kuen R., Vilagines R. Antiviral activity of hydroalcoholic extract from Haemanthus albiflos on the Moloney murine leukemia virus and the human immunodeficiency virus. C. R. Seances. Soc. Biol. Fil. 191:1997;473-485.
53. Ito M., Baba M., Hirabayashi K., Matsumoto T., Suzuki M., Suzuki S., Shigeta S., De Clercq E. In vitro activity of mannan sulfate, a novel sulfated polysaccharide, against human immunodeficiency virus type 1 and other enveloped viruses. Eur. J. Clin. Microbiol. Infect. Dis. 8:1989;171-173.
54. Itoh W., Sugawara I., Kimura S., Tabata K., Hirata A., Kojima T., Mori S., Shimada K. Immunopharmacological study of sulfated schizophyllan (SPG). I. Its action as a mitogen and anti-HIV agent. Int. J. Immunopharmacol. 12:1990;225-233.
55. Jagodzinski P. P., Wiaderikiewicz R., Kurzawski G., Kloczewiak M., Nakashima H., Hyjek E., Yamamoto N., Uryu T., Kaneko Y., Posner M. R. Mechanism of the inhibitory effect of curdlan sulfate on HIV-1 infection in vitro. Virology. 202:1994;735-745.
56. Khan S. A., Wickstrom M. L., Haschek W. M., Schaeffer D. J., Ghosh S., Beasley V. R. Microcystin-LR and kinetics of cytoskeletal reorganization in hepatocytes, kidney cells, and fibroblasts. Nat. Toxins. 4:1996;206-214.
57. Knubel G., Larsen L. K., Moore R. E., Levine I. A., Patterson G. M. Cytotoxic, antiviral indolocarbazoles from a blue-green alga belonging to the Nostocaceae. J Antibiot. (Tokyo). 43:1990;1236-1239.
58. Kolender A. A., Pujol C. A., Damonte E. B., Matulewicz M. C., Cerezo A. S. The system of sulfated alpha-(1→3)-linked D-mannans from the red seaweed Nothogenia fastigiata: Structures, antitherpetic and anticoagulant properties. Carbohydr. Res. 304:1997;53-60.
59. Krylov V. S. C., Hassell J. D., Strickland J. W., Schaeffer D. J. Retrospective epidemiological study using medical records to determine which diseases are improved by Aphanizomenon flos-aquae supplements. Med. Hypotheses. 1999.
60. Larsen L. K., Moore R. E., Patterson G. M. beta-Carbolines from the blue-green alga Dichothrix baueriana. J. Nat. Prod. 57:1994;419-421.
61. Lau A. F., Siedlecki J., Anleitner J., Patterson G. M., Caplan F. R., Moore R. E. Inhibition of reverse transcriptase activity by extracts of cultured blue-green algae (cyanophyta). Planta Med. 59:1993;148-151.
62. Lifson J., Coutre S., Huang E., Engleman E. Role of envelope glycoprotein carbohydrate in human immunodeficiency virus (HIV) infectivity and virus-induced cell fusion. J. Exp. Med. 164:1986;2101-2106.
63. Lopezrodas V., Costas E. Characterization of morphospecies and strains of Microcystis (cyanobacteria) from natural populations and laboratory clones using cell probes (lectins and antibodies). J. Phycol. 33:1997;446-454.
64. Lorentsen K., Hendrix C., Collins J., Eckel R., Petty B., Lietman P. Dextran sulfate is poorly absorbed after oral administration. Int. Conf. AIDS. 5:1989a;336.
65. Lorentsen K., Hendrix C., Collins J. M., Kornhauser D. M., Petty B. G., Klecker R. W., Flexner C., Eckel R. H., Lietman P. S. Dextran sulfate is poorly absorbed after oral administration. Ann. Intern. Med. 111:1989b;561-566.
66. Loya S., Bakhanashvili M., Kashman Y., Hizi A. Peyssonols A and B, two novel inhibitors of the reverse transcriptases of human immunodeficiency virus types 1 and 2. Arch. Biochem. Biophys. 316:1995;789-796.
67. Loya S., Reshef V., Mizrachi E., Silberstein C., Rachamim Y., Carmeli S., Hizi A. The inhibition of the reverse transcriptase of HIV-1 by the natural sulfoglycolipids from cyanobacteria: Contribution of different moieties to their high potency. J. Nat. Prod. 61:1998;891-895.
68. 4-gp120 interaction, but do not inhibit monocyte infection. J. Leukoc. Biol. 56:1994;266-272.
69. Maass G., Immendoerfer U., Koenig B., Leser U., Mueller B., Goody R., Pfaff E. Viral resistance to the thiazolo-iso-indolinones, a new class of nonnucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 37:1993;2612-2617.
70. Mariner J. M., McMahon J. B., O'Keefe B. R., Nagashima K., Boyd M. R. The HIV-inactivating protein, cyanovirin-N, does not block gp120-mediated virus-to-cell binding. Biochem. Biophys. Res. Commun. 248:1998;841-845.
71. Matulewicz M. C., Cerezo A. S. Water-soluble sulfated polysaccharides from the red seaweed Chaetangium fatigiatum. Analysis of the system and structures of the α-D-(1→3)-linked mannans. Carbohyd. Pol. 7:1987;121-132.
72. McClure M. O., Moore J. P., Blanc D. F., Scotting P., Cook G. M., Keynes R. J., Weber J. N., Davies D., Weiss R. A. Investigations into the mechanism by which sulfated polysaccharides inhibit HIV infection in vitro. AIDS Res. Hum. Retroviruses. 8:1992;19-26.
73. McClure M. O., Whitby D., Patience C., Gooderham N. J., Bradshaw A., Cheingsong P. R., Weber J. N., Davies D. S., Cook G. M. W. Dextrin sulphate and fucoidan are potent inhibitors of HIV infection in vitro. Antiviral Chem. Chemother. 2:1991;149-156.
74. Mizumoto K., Sugawara I., Ito W., Kodama T., Hayami M., Mori S. Sulfated homopolysaccharides with immunomodulating activities are more potent anti-HTLV-III agents than sulfated heteropolysaccharides. Jpn. J. Exp. Med. 58:1988;145-151.
75. Moen L. K., Clark G. F. A novel reverse transcriptase inhibitor from Fucus vesiculosus. Int. Conf. AIDS. 9:1993;145-161.
76. Mori T., Gustafson K. R., Pannell L. K., Shoemaker R. H., Wu L., McMahon J. B., Boyd M. R. Recombinant production of cyanovirin-N, a potent human immunodeficiency virus-inactivating protein derived from a cultured cyanobacterium. Protein Expr. Purif. 12:1998;151-158.
77. Mori T., Shoemaker R. H., Gulakowski R.J., Krepps B. L., McMahon J. B., Gustafson K. R., Pannell L. K., Boyd M. R. Analysis of sequence requirements for biological activity of cyanovirin-N, a potent HIV (human immunodeficiency virus)-inactivating protein. Biochem. Biophys. Res. Commun. 238:1997a;218-222.
78. Mori T., Shoemaker R. H., McMahon J. B., Gulakowski R. J., Gustafson K. R., Boyd M. R. Construction and enhanced cytotoxicity of a [cyanovirin-N]-[Pseudomonas exotoxin] conjugate against human immunodeficiency virus-infected cells. Biochem. Biophys. Res. Commun. 239:1997b;884-888.
79. Mori T., Shoemaker R., McMahon J., Gustafson K., Boyd M. Analysis of sequence requirements for biological activity of recombinant cyanovirin-N, a novel anti-HIV virucidal protein. Int. Conf. AIDS. 11:1996;70.
80. 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. J. Cancer Res. Clin. Oncol. 113:1987a;413-416.
81. Nakashima H., Kido Y., Kobayashi N., Motoki Y., Neushul M., Yamamoto N. Purification and characterization of an avian myeloblastosis and human immunodeficiency virus reverse transcriptase inhibitor, sulfated polysaccharides extracted from sea algae. Antimicrob. Agents Chemother. 31:1987b;1524-1528.
82. Nakashima H., Tanabe A., Tochikura T. S., Yamamoto N. Rapid screening method with a cell multizier for inhibitors of human immunodeficiency virus-induced cell fusion in vitro. J. Clin. Microbiol. 26:1988;1229-1232.
83. Nowotny A., Mentel R., Wegner U., Mundt S., Lindequist U. Antiviral activity of an aqueous extract of the cyanobacterium Microcystis aeruginosa. Phytother. Res. 11:1997;93-96.
84. O'Connor T. J., Jeffries D. J. Strategies for the inhibition of sexual transmission by topical antiviral agents. Int. Conf. AIDS. 11:1996;313.
85. Ohta K., Mizushina Y., Hirata N., Takemura M., Sugawara F., Matsukage A., Yoshida S., Sakaguchi K. Sulfoquinovosyldiacylglycerol, KM043, a new potent inhibitor of eukaryotic DNA polymerases and HIV-reverse transcriptase type 1 from a marine red alga, Gigartina tenella. Chem. Pharm. Bull. (Tokyo). 46:1998;684-686.
86. Ohta K., Mizushina Y., Hirata N., Takemura M., Sugawara F., Matsukage A., Yoshida S., Sakaguchi K. Action of a new mammalian DNA polymerase inhibitor, sulfoquinovosyldiacylglycerol. Biol. Pharm. Bull. 22:1999;111-116.
87. 4 molecule. Proximity to the HIV-gp120 binding region. J. Immunol. 145:1990;1188-1195.
88. Pearce-Pratt R., Phillips D. M. Sulfated polysaccharides inhibit lymphocyte-to-epithelial transmission of human immunodeficiency virus-1. Biol. Reprod. 54:1996;173-182.
89. Piot P. The science of AIDS: A tale of two worlds. Science. 280:1998;1844-1845.
90. Pluda J. M., Shay L. E., Foli A., Tannenbaum S., Cohen P. J., Goldspiel B. R., Adamo D., Cooper M. R., Broder S., Yarchoan R. Administration of pentosan polysulfate to patients with human immunodeficiency virus-associated Kaposi's sarcoma. J. Natl. Cancer Inst. 85:1993;1585-1592.
91. Pratt R., Fong J. Studies on Chlorella vulgaris. Further evidence that chlorella cells form a growth inhibiting substance. Am. J. Bot. 27:1940;431-436.
92. Pratt R., Mautner R. H., Gardner G. M., Sha Y., Dufenoy J. Report on antibiotic activity of seaweed extracts. J. Am. Pharm. Assoc. 40:1951;575-579.
93. Pujol C. A., Coto C. E., Damonte E. B. Determination of the antiviral activity of a naturally occurring sulfated xylomannan under various experimental conditions. Rev. Argent. Microbiol. 27:1995;91-98.
94. Reshef V., Mizrachi E., Maretzki T., Silberstein C., Loya S., Hizi A., Carmeli S. New acylated sulfoglycolipids and digalactolipids and related known glycolipids from cyanobacteria with a potential to inhibit the reverse transcriptase of HIV-1. J. Nat. Prod. 60:1997;1251-1260.
95. Richards J. T. K. E. R., Glasgow L. A., Overall J. C. Jr., Deig E. F., Hatch M. T. Antiviral activity of extracts from marine algae. Antimicrob. Agents Chemother. 14:1978;24-30.
96. Rizzuto C. D., Wyatt R., Hernández-Ramos N., Sun Y., Kwong P. D., Hendrickson W. A., Sodroski J. A conserved HIV gp120 glycoprotein structure involved in chemokine receptor binding. Science. 280:1998;1949-1953.
97. Sarin P. S., Sun D., Thornton A., Muller W. E. Inhibition of replication of the etiologic agent of acquired immune deficiency syndrome (human T-lymphotropic retrovirus/lymphadenopathy-associated virus) by avarol and avarone. J. Natl. Cancer Inst. 78:1987;663-666.
98. + cells. J. Acquir. Immune Defic. Syndr. 2:1989;10-15.
99. 4 cell receptor. Proc. Natl. Acad. Sci. USA. 86:1989;3322-3326.
100. Schussler A., Meyer T., Gehrig H., Kluge M. Variations of lectin binding sites in extracellular glycoconjugates during the life cycle of Nostoc punctiforme, a potentially endosymbiotic cyanobacterium. Eur. J. Phycol. 32:1997;233-239.
101. Shaunak S., Gooderham N. J., Edwards R. J., Payvandi N., Javan C. M., Baggett N., MacDermot J., Weber J. N., Davies D. S. Infection by HIV-1 blocked by binding of dextrin 2-sulfate to the cell surface of activated human peripheral blood mononuclear cells and cultured T-cells. Br. J. Pharmacol. 113:1994;151-158.
102. Shaunak S., Thornton M., John S., Teo I., Peers E., Mason P., Krausz T., Davies D. S. Reduction of the viral load of HIV-1 after the intraperitoneal administration of dextrin 2-sulfate in patients with AIDS. AIDS. 12:1998;399-409.
103. Shoemaker R. H., Wu L., Smythe A., Gulakowski R., McMahon J., Gustafson K., Boyd M. Construction and expression in E. coli of a synthetic gene coding for cyanovirin-N, a novel anti-HIV protein originally isolated from a cultured cyanobacterium. Int. Conf. AIDS. 11:1996;70.
104. Stafford M. K., Cain D., Rosenstein I., Fontaine E. A., McClure M., Flanagan A. M., Smith J. R., Taylor-Robinson D., Weber J., Kitchen V. S. A placebo-controlled, double-blind prospective study in healthy female volunteers of dextrin sulfate gel: A novel potential intravaginal virucide. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 14:1997;213-218.
105. Sugawara I., Itoh W., Kimura S., Mori S., Shimada K. Further characterization of sulfated homopolysaccharides as anti-HIV agents. Experientia. 45:1989;996-998.
106. Ueno R., Kuno S. Anti-HIV synergism between dextran sulphate and zidovudine [letter]. Lancet. 2:1987a;796-797.
107. Ueno R., Kuno S. Dextran sulphate, a potent anti-HIV agent in vitro having synergism with zidovudine [letter]. Lancet. 1:1987b;1379.
108. Weislow O. S., Kiser R., Fine D. L., Bader J., Shoemaker R. H., Boyd M. R. New soluble formazan assay for HIV cytopathic effect: applications for high flux screening of synthetic and natural products for AIDS-antiviral activity. J. Nat. Cancer Inst. 81:1989;577-586.
109. Wickstorm M. L., Khan S. A., Haschek W. M., Wyman J. F., Eriksson J. E., Schaeffer D. J., Beasley V. R. Alterations in microtubules, intermediate filaments, and microfilaments induced by microcystin-LR in cultured cells. Toxicol. Pathol. 23:1995;326-337.
110. Witvrouw M., De Clercq E. Sulfated polysaccharides extracted from sea algae as potential antiviral drugs. Gen. Pharmacol. 29:1997;497-511.
111. Witvrouw M., Este J. A., Quinones Mateu M. E., Reymen D., Andrei G., Snoeck R., Ikeda S., Pauwels R., Vittori Bianchini N., Desmyter J., De Clercq E. Antiviral activity of a sulfated polysaccharide extracted from the red seaweed Aghardhiella tenera against human immunodeficiency virus and other enveloped viruses. Antiviral Chem. Chemother. 5:1994;297-303.
112. Yang F., Bewley C. A., Louis J. M., Gustafson K. R., Boyd M. R., Gronenborn A. M., Clore G. M., Wlodawer A. Crystal structure of cyanovirin-N, a potent HIV-inactivating protein, shows unexpected domain swapping. J. Mol. Biol. 288:1999;403-412.
113. Zacharopoulos V. R., Phillips D. M. Cell-mediated HTLV-I infection of a cervix-derived epithelial cell line. Microb. Pathog. 23:1997;225-233.
114. Zeitlin L., Whaley K. J., Hegarty T. A., Moench T. R., Cone R. A. Tests of vaginal microbicides in the mouse genital herpes model. Contraception. 56:1997;329-335.
115. Zhang X., Smith C. D. Microtubule effects of welwistatin, a cyanobacterial indolinone that circumvents multiple drug resistance. Mol. Pharmacol. 49:1996;288-294.