Anti-HIV-1 activity of combinations and covalent conjugates of negatively charged human serum albumins (NCAs) and AZT

Journal of Drug Targeting

Volumn 6, Issue 5, 1999, Pages 323-335

  Kuipers, M E ^a   Swart, P J ^a   Witvrouw, M ^b   Este J A ^b   Reymen, D ^b   De Clercq, E ^b   Meijer, D K F ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Aco HSA; AZT; HIV; Polyanion; Suc HSA; Synergy

Indexed keywords

ANTIVIRUS AGENT; GLYCOPROTEIN GP 120; HUMAN SERUM ALBUMIN; ZIDOVUDINE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL FUSION; CONCENTRATION RESPONSE; CONTROLLED STUDY; HUMAN IMMUNODEFICIENCY VIRUS 1; MOUSE; NONHUMAN; PRIORITY JOURNAL; SYNCYTIUM; T LYMPHOCYTE; TARGET CELL; VIRUS REPLICATION;

EID: 0032962307     PISSN: 1061186X     EISSN: None     Source Type: Journal    
DOI: 10.3109/10611869908996840     Document Type: Article

References (58)

1. Ames, G.F.-L. and Lecar, H. (1992). ATP-dependent bacterial transporters and cystic fibrosis: Analogy between channels and transporters. FASEB J., 6: 2660-2666.
2. Anand, R., Nayyar, S., Galvin, T.A., Merril, C.R. and Bigelow, L.B. (1990). Sodium pentosan polysulfate (PPS). an anti-HIV agent also exhibits synergism with AZT, lymphoproliferative activity, and virus enhancement. AIDS Res. Hum. Retroriruses, 6: 679-689.
3. Baba, M., Ito, M., Shigela, S. and De Clercq, E. (1984). Synergistic antiviral effects of antiherpes compounds and human leukocyte interferon on varicella-zoster virus in vitro. Antimicrob. Agents Chemother., 25: 515-517.
4. Baba, M., Schols, D., Pauwels, R., Nakashima, H. and De Clercq, E. (1990). Sulfated polysaccharides as potent inhibitors of HIV-induced syncytium formation: a new strategy towards AIDS chemotherapy. J. Acquir. Immune Defic. Syndr., 3: 493-499.
5. Bergeron, L., Sullivan, N. and Sodroski, J. (1992). Target cell-specific determinants of membrane fusion within the human immunodeficiency virus type 1 gp120 third variable region and gp41 amino terminus. J. Virol., 66: 2389-2397.
6. Borman, A.M., Paulous, S. and Clavel, F. (1996). Resistance of human immunodeficiency virus type 1 to protease inhibitors: selection of resistance mutations in the presence and absence of the drug. J. Gen. Virol., 77: 419-426.
7. Breen, E.G., Rezai, A.R., Nakajima, K., Beall, G.N., Mitsuyasu, R.T., Hirano, T., Kishimoto, T. and Martinez Maza, O. (1990). Infection with HIV is associated with elevated IL-6 levels and production. J. Immunol., 144: 480-484.
8. Brighty, D.W., Rosenberg, M., Chen, I.S. and Ivey Hoyle, M. (1991). Envelope proteins from clinical isolates of human immunodeficiency virus type 1 that are refractory to neutralization by soluble CD4 possess high affinity for the CD4 receptor. Proc. Natl. Acad. Sci. USA, 88: 7802-7805.
9. Collier, A.C., Coombs, R.W., Schoenfeld, D.A., Bassett, R.L., Timpone, J., Baruch, A., Jones, M., Facey, K., Whitacre, C., McAuliffe, V.J., Friedman, H.M., Merigan, T.C., Reichman, R.C., Hooper, C. and Corey, L. (1996). Treatment of human immunodeficiency virus infection with saquinavir, zidovudine and zalcitabine. N. Engl. J. Med., 334: 1011-1017.
10. De Clercq, E. (1987). Perspectives for the chemotherapy of AIDS. Anticancer Res., 7: 1023-1038.
11. De Clercq, E., Yamamoto, N., Pauwels, R., Baba, M., Schols, D., Nakashima, H., Balzarini, J., Debyser, Z., Murrer, B.A., Schwartz, D., Thornton, D., Bridger, G., Fricker, S., Henson, G., Abrams, M. and Picker, D. (1992). Potent and selective inhibition of human immunodeficiency virus (HIV)-1 and HIV-2 replication by a class of bicyclams interacting with a viral uncoating event. Proc. Natl. Acad. Sci. USA, 89: 5286-5290.
12. De Clercq, E. (1995). Antiviral therapy for human immunodeficiency virus infections. Clin. Microbiol. Rev., 8: 200-239.
13. Dimitrov, D.S. and Blumenthal, R. (1994). Photoinactivation and kinetics of membrane fusion mediated by the human immunodeficiency virus type 1 envelope glycoprotein. J. Virol, 68: 1956-1961.
14. Elion, G.B., Singer, S. and Hitchings, G.H. (1954). Antagonists of nucleic acid derivatives VIII. Synergism in combination of biochemically related antimetabolites. J. Biol. Chem., 208: 477-488.
15. Fitzgibbon, J.E., Howell. R.M., Haberzettl, C.A., Sperber, S.J., Gocke, D.J. and Dubin, D.T. (1992). Human immunodefi-ciency virus type 1 pol gene mutations which cause decreased susceptibility to 2′,3′-dideoxycytidine. Antimicrob. Agents Chemother., 36: 153-157.
16. Gordon, L.M., Waring, A.J., Curtain, C.C., Kirkpatrick, A., Leung, C., Faull, K. and Mobley, P.W. (1995). Antivirals that target the amino-terminal domain of HIV type 1 glycoprotein 41. AIDS Res. Hum. Retroviruses, 11: 677-686.
17. Groenink, M., Swart, PJ., Broersen, S., Kuipers, M.E., Meijer, D.K.F. and Schuitemaker, H. (1997). Potent inhibition of replication of primary HIV-1 isolates by negatively charged human serum albumin. AIDS Res. Hum. Retroviruses, 13: 179-185.
18. Habeeb, A.F.S.A. (1966). Determination of free amino groups in proteins by trinitrobenzenesulfonic acid. Anal. Biochem., 14: 328-336.
19. Halloran, M.J. and Parker. C.W. (1966). The preparation of nucleotide-protein conjugates: carbodiimides as coupling agents. J. Immunol., 96: 373-378.
20. Haseltine, W.A. (1988). Replication and pathogenesis of the AIDS virus. J. Acquir. Immune. Defic. Syndr., 1: 217-240.
21. Hayashi, S., Fine, R.L., Chou, T.C., Currens, M.J., Broder, S. and Mitsuya, H. (1990). In vitro inhibition of the infectivity and replication of human immunodeficiency virus type-1 by combination of antiretroviral 2′,3′-dideoxynucleosides and virus-binding inhibitors. Antimicrob. Agents Chemother., 34: 82-88.
22. Jansen, R.W., Molema, G., Pauwels, R., Schols, D., De Clercq, E. and Meijer, D.K.F. (1991). Potent in vitro antihuman immunodeficiency virus-1 activity of modified human serum albumins. Mol. Pharmacol., 39: 818-823.
23. Jansen, R.W., Olinga, P., Harms, G. and Meijer, D.K.F. (1993a). Pharmacokinetic analysis and cellular distribution of the anti-HIV compound succinylated human serum albumin (Suc-HSA) in vivo and in the isolated perfused rat liver. Pharm. Res., 10: 1611-1614.
24. Jansen, R.W., Schols, D., Pauwels, R., De Clercq, E. and Meijer, D.K.F. (1993b). Novel, negatively charged, human serum albumins display potent and selective in vitro anti-human immunodeficiency virus type 1 activity. Mol. Pharmacol., 44: 1003-1007.
25. Katzenstein, D.A. and Holodniy, M. (1995). HIV viral load quantification, HIV resistance, and antiretroviral therapy. AIDS Clin. Rev., 1995-1996, 277-303.
26. Kennedy, C.J. (1987) AZT in the treatment of AIDS and ARC. In HIV and Other Highly Pathogenic Viruses, R.A. Smith (ed.), Academic Press, Inc.; Harcourt Brace Jovanovich, Publishers, San Diego, New York, Berkeley, Boston, London, Sydney, Tokyo, Toronto, pp. 81-93.
27. Kuipers, M.E., Swart, P.J., Hendriks, M.M.W.B. and Meijer, D.K.F. (1995). Optimization of the reaction conditions for the synthesis of neoglycoprotein-AZT-monophosphate conjugates. J. Med. Chem., 38: 883-889.
28. Kuipers, M.E., Huisman. J.G., Swart, P.J., de Béthune, M., Pauwels, R., De Clercq, E., Schuitemaker, H. and Meijer, D.K.F. (1996a). Mechanism of anti-HIV activity of negatively charged albumins: biomolecular interaction with the HIV-1 envelope protein gp!20. J. Acq. Immun. Defic. Synd. Hum. R., 11:419-429.
29. Kuipers, M.E., Swart, P.J., Smit, C. and Meijer, D.K.F. (1996b). Binding of negatively charged human serum albumins to lymphocytes: implications for shielding of HIV-1 binding and fusion. Chapter 4. Thesis Biomolecular and pharmacokinetic studies on drug delivery preparations with dual activity on HlV-1, University of Groningen, The Netherlands, ISBN 90-90009738-4.
30. Kuipers, M.E., Swart, P.J., Schutten, M., Smit, C., Osterhaus, A.D.M.E. and Meijer, D.K.F. (1997). Pharmacokinetics and anti-hiv-1 efficacy of negatively charged human serum albumins in mice. Antiviral Res., 33: 99-108.
31. Lafeuillade, A., Poggi, C., Tamalet, C., Profizi, N., Tourres, C. and Costes, O. (1997). Effects of a combination of zidovudine, didanosine, and lamivudine on primary human immunodeficiency virus type 1 infection. J. Infect. Dis., 175: 1051-1055.
32. Lambert, D.M., Bartus, H., Fernandez, A. V., Bratby-Anders, C., Leary, J.J., Dreyer, G.B., Metcalf, B.W. and Petteway, S.R., Jr. (1993). Synergistic drug interactions of an HIV-1 protease inhibitor with AZT in different in vitro models of HIV-1 infection. Antiviral Res., 21: 327-342.
33. Larder, B.A., Darby, G. and Richman, D.D. (1989). HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy. Science, 243: 1731-1734.
34. Larder, B.A. and Kemp, S.D. (1989). Multiple mutations in HIV-1 reverse transcriptase confer high-level resistance to zidovudine (AZT). Science, 246: 1155-1158.
35. Lifson, J.D., Feinberg, M.B., Reyes, G.R., Rabin, L., Banapour, B., Chakrabarti, S., Moss, B., Wong Staal, F., Steimer, K.S. and Engleman, E.G. (1986). Induction of CD4-dependent cell fusion by the HTLV-III/LAV envelope glycoprotein. Nature, 323: 725-728.
36. Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951). Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193: 265-275.
37. Machida, A., Kishimoto, S., Ohnuma, H., Baba, K., Ito, Y., Miyamoto, H., Funatsu, G., Oda, K., Usuda, S.T.S, Nakamura, T., Miyakawa, Y. and Mayumi, M. (1984). A polypeptide containing 55 amino acid residues coded by the pre-S region of hepatitis B virus deoxyribonucleic acid bears the receptor for polymerized human as well as chimpanzee albumins. Gastroenterology, 86: 910-918.
38. Meng, T.-C, Fischl, M.A., Boota, A.M., Spector, S.A., Bennett, D., Bassiakos, Y., Lai, S., Wright, B. and Richman, D.D. (1992). Combination therapy with zidovudine and dideoxycytidine in patients with advanced human immunodeficiency virus infection: a phase I/II study. Ann. Intern. Med., 116:13-20.
39. Meshcheryakova, D., Andreev, S., Tarasova, S., Sidorova, M., Vafina, M., Kornilaeva, G., Karamov, E. and Khaitov, R. (1993). CD4-derived peptide and sulfated polysaccharides have similar mechanisms of anti-HIV activity based on electrostatic interactions with positively charged gp120 fragments. Mol. Immunol., 30: 993-1001.
40. Molema, G., Jansen, R.W., Pauwels, R., De Clercq, E. and Meijer, D.K.F. (1990). Targeting of antiviral drugs to T-4 lymphocytes: Anti-HIV activity of neoglycoprotein-AZTMP conjugates in vitro. Biochem. Pharmacol., 40: 2603-2610.
41. Molema, G., Jansen, R.W., Visser, J., Herdewijn, P., Moolenaar, F. and Meijer, D.K.F. (1991). Neoglycoproteins as carriers for antiviral drugs: synthesis and analysis of protein-drug conjugates. J. Med. Chem., 34: 1137-1141.
42. Molema, G. (1992) Delivery of the anti-HIV drug azidothymidine (AZT) to T-lymphocytes with neoglycoprotein carriers. Chapter 6. Thesis: Delivery of the anti-HIV drug azidothymidine (AZT) to T-lymphocytes with neoglycoprotein carriers, University Groningen, The Netherlands, ISBN 90-90005402-2.
43. Molla, A., Korneyeva, M., Gao, Q., Vasavanonda, S., Schipper, P.J., Mo, H.M., Markowitz, M., Chernyavskiy, T., Niu, P., Lyons, N., Hsu, A., Granneman, G.R., Ho, D.D., Boucher, C.A., Leonard, J.M., Norbeck, D.W. and Kempf, D.J. (1996). Ordered accumulation of mutations in HIV protease confers resistance to ritonavir. Nat. Med., 2: 760-766.
44. Moyle, G. and Gazzard, B. (1996). Current knowledge and future prospects for the use of HIV protease inhibitors. Drugs, 51:701-712.
45. Pauwels, R., Balzarini, J., Baba, M., Snoeck, R., Schols, D., Herdewijn, P., Desmyter, J. and De Clercq, E. (1988). Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods, 20: 309-321.
46. Pinter, A., Honnen, W.J. and Tilley, S.A. (1993). Conformational changes affecting the V3 and CD4-binding domains of human immunodeficiency virus type 1 gp120 associated with env processing and with binding of ligands to these sites. J. Virol., 67: 5692-5697.
47. Schols, D., Pauwels, R., Desmyter, J. and De Clercq, E. (1990). Dextran sulfate and other polyanionic anti-HIV compounds specifically interact with the viral gp)20 glycoprotein expressed by the T-cells persistently infected with HIV-1. Virology, 175: 556-561.
48. St. Clair, M.H., Hartigan, P.M., Andrews, J.C., Vavro, C.L., Simberkoff, M.S. and Hamilton, J.D. (1993). Zidovudine resistance, syncytium-inducing phenotype, and HIV disease progression in a case-control study. The VA Cooperative Study Group. J. Acquir. Immune. Defic. Syndr., 6: 891-897.
49. St. Clair, M.H., Martin, J.L., Tudor-Williams, G., Bach, M.C., Vavro, C.L., King, D.M., Kellam, P., Kemp, S.D. and Larder, B.A. (1991). Resistance to ddl and sensitivity to AZT induced by a mutation in HIV-1 reverse transcriptase. Science, 253: 1557-1559.
50. Swart, P.J., Schutten, M., Smit, C., Van Amerongen, G., Proost, J.H., Osterhaus, A.D.M.E. and Meijer, D.K.F. (1996a). Pharmacokinetics of succinylated serum albumin in wistar rats and cynomolgus monkeys: implications for dosage regiments in the therapy of HIV-infection. Drug Delivery, 3: 165-171.
51. Swart, P.J., Smit, C., Pasma, A., Beljaars, E., Schuitemaker, H. and Meijer, D.K.F. (1996b). Comparative pharmacokinetics, immunologic and hematologic studies on the anti-HIV-l/-2 compouds succinylated and aconitylated HSA. Journal of Drug Targeting, 4: 109-116.
52. Swart, P.J. and Meijer, D.K.F. (1994). Negatively-charged albumins: A novel class of polyanionic proteins with a potent anti-HIV activity. Antiviral News, 2: 69-71.
53. Tisdale, M., Myers, R.E., Maschera, B., Parry, N.R., Oliver, N.M. and Blair, E.D. (1995). Cross-resistance analysis of human immunodeficiency virus type 1 variants individually selected for resistance to five different protease inhibitors. Antimicrob. Agents Chemother., 39: 1704-1710.
54. Ueno, R. and Kuno, S. (1987). Dextran sulphate, a potent anti-HIV agent in vitro having synergism with zidovudine (letter). Lancet, Jun. 13, 1(8546): 1379.
55. van 't Wout, A.B., Ran, L.J., de Jong, M.D., Bakker, M., van Leeuwen, R., Notermans, D.W., Loeliger, A.E., De Wolf, F., Danner, S.A., Reiss, P., Boucher, C.A., Lange, J.M.A. and Schuitemaker, H. (1997). Selective inhibition of syncytium inducing and non-syncytium inducing HIV-1 variants in individuals receiving didanosine or zidovudine respectively. J. Clin. Invest., 100: 2325-2332.
56. Vella, S. (1995). Rationale and experience with reverse transcriptase inhibitors and protease inhibitors. J. Acquit. Immune. Defic. Syndr. Hum. Retrovirol., 10: S58-S61.
57. Wilde, M.I. and Langtry, H.D. (1993). Zidovudine. An update of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs, 46: 515-578.
58. Witvrouw, M., Desmyter, J. and De Clercq, E. (1994). Antiviral portrait series: 4. Polysulfates as inhibitors of HIV and other enveloped viruses. Antiviral Chem. Chemother., 5: 345-359.