Polysulfonates derived from metal thiolate complexes as inhibitors of HIV-1 and various other enveloped viruses in vitro

Antiviral Chemistry and Chemotherapy

Volumn 13, Issue 3, 2002, Pages 185-195

  Bergstrom, Donald E ^a,b   Lin, Xiaoping ^a   Wood, Troy D ^c   Witvrouw, Myriam ^d   Ikeda, Satoru ^d   Andrei, Graciela ^d   Snoeck, Robert ^d   Schols, Dominique ^d   De Clercq, Erik ^d  

^a PURDUE UNIVERSITY   (United States)

^b WALTHER CANCER INSTITUTE   (United States)

^c UNIVERSITY AT BUFFALO   (United States)

^d REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral; HIV; Palladium; Platinum; Polyanion

Indexed keywords

DEXTRAN SULFATE; PALLADIUM; PALLADIUM COMPLEX; PLATINUM DERIVATIVE; SILVER; SILVER DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOL DERIVATIVE; ZINC; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIVIRUS AGENT; DRUG DERIVATIVE; MESNA; METAL;

ANTIVIRAL ACTIVITY; ARENAVIRUS; ARTICLE; CYTOMEGALOVIRUS; CYTOTOXICITY; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; INFLUENZA VIRUS A; JUNIN VIRUS; NONHUMAN; PRIORITY JOURNAL; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; SINDBIS VIRUS; STATISTICAL SIGNIFICANCE; VESICULAR STOMATITIS VIRUS; VIRUS ENVELOPE; VIRUS INHIBITION; VIRUS TRANSMISSION; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; PHYSIOLOGY; VIRUS REPLICATION;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; CELL LINE; HIV-1; HUMANS; MESNA; METALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; VIRUS REPLICATION;

EID: 2342573756     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632020201300305     Document Type: Article

References (57)

1. Ahmed SP, Cardin AD, Bridges CG, Jackson RL, Mullins MJ & Tyms AS (1995) Potent inhibition of herpes simplex virus by MDL 101028, a novel biphenyldisulfonic acid urea co-polymer. Antiviral Chemistry & Chemotherapy 6:34-42.
2. Alemany P &. Hoffmann R (1993) Toroidal nickel thiolates: structure and bonding. Journal of the American Chemical Society 115:8290-8297.
3. Appleton TG, Connor JW, Hall JR & Prenzler PD (1989) NMR study of the reactions of the cis-diamminediaquaplatinum(II) cation with glutathione and amino acids containing a thiol group. Inorganic Chemistry 28:2030-2037.
4. Baba M, Snoeck R, Pauwels R & De Clercq E (1988) Sulfated polysaccharides are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, and human immunodeficiency virus. Antimicrobial Agents and Chemotherapy 32:1742-1745.
5. Barrera H, Bayon JC, Suades J, Germain C & Declerq JP (1984) Metal complexes of mercaptoamines - III. Different behavior of β-and γ-(N, N-dimethyl)mercaptoamines. Polyhedron 3:969-975.
6. 1H} DEPT NMR. Journal of Inorganic Biochemistry 38:305-326.
7. 2. Canadian Journal of Chemistry 60:2075-2081.
8. Blower PJ & Dilworth JR. (1987) Thiolate-complexes of the transition metals. Coordination Chemistry Reviews 76:121-185.
9. 12], a cyclic hexameric homothiolate of nickel. Polyhedron 8:1253-1259.
10. Chatt J & Hart FA (1953) The Nature of the Co-ordinate Link. Part VIII. Geometrical isomerism and simple reactions of ethylthio-bridged complexes of platinum(II) and palladium(II). Journal of the Chemical Society 2363-2371.
11. Clanton DJ, Moran RA, McMahon JB, Weislow OS, Buckheit RW Jr, Hollingshead MG, Ciminale V, Felber BK, Pavlakis GN & Bader JP (1992) Sulfonic acid dyes: inhibition of the human immunodeficiency virus and mechanism of action. Journal of Acquired Immune Deficiency Syndromes 5:771-781.
12. 2. Angewandte Chemie International Edition in English 25:165-166.
13. Cushman M, Wang P, Stowell JG, Schols D & De Clercq E (1992) Structural investigation and anti-HIV activities of high molecular weight ATA polymers. Journal of Organic Chemistry 57:7241-7248.
14. Dance IG (1977) On the molecularity of crystalline cyclohexanethiolatosilver(I). Inorganica Chimica Acta 25:L17-L18.
15. 3OH)(SPh)], a model for zinc-thiolate metalloenzymes. Journal of the American Chemical Society 102:3445-3451.
16. Dance IG (1981) The zinc-benzenethiolate-halide system. Synthesis and structure of the hexakis(μ-(benzenethiolato))-bis(benzenethiolato) dichlorotetrazincate(II) dianion. Inorganic Chemistry 20:2155-2160.
17. 8 molecules in solution. Inorganic Chemistry 22:3785-3788.
18. 16, a receptive octagonal toroid. Inorganic Chemistry 24:1201-1208.
19. Dance IG (1986) The structural chemistry of metal thiolate complexes. Polyhedron 5:1037-1104.
20. 2. analogies with microporous aluminosilicate frameworks. Inorganic Chemistry 26:4057-4064.
21. Dance IG, Fisher KJ, Herath Banda RM & Scudder ML (1991) Layered structure of crystalline compounds AgSR. Inorganic Chemistry 30:183-187.
22. Debnath AK, Radigan L & Jiang S (1999) Structure-based identification of small molecule antiviral compounds targeted to the gp41 core structure of the human immunodeficiency virus type 1. Journal of Medicinal Chemistry 42:3203-3209.
23. De Clercq E, Luczak M, Reepmeyer JC, Kirk KL & Cohen LA (1975) Fluoroimidazoles as antiviral agents and inhibitors of polynucleotide biosynthesis. Life Sciences 17:187-194.
24. De Clercq E, Descamps J, Verhelst G, Walker RT, Jones AS, Torrence PF & Shugar D (1980) Comparative Efficacy of Antiherpes Drugs against Different Strains of Herpes Simplex Virus. Journal of Infectious Diseases 141:563-574.
25. De Clercq E, Holy A, Rosenberg I, Sakuma T, Balzarini J & Maudgal PC (1986) A Novel Selective Broad-Spectrum Anti-DNA Virus Agent. Nature 323:464-467.
26. Djuran MI, Lempers ELM & Reedijk J (1991) Reactivity of chloro- and aqua(diethylenetriamine)platinum(II) ions with glutathione, S-methylglutathione, and guanosine 5-monophosphate in relation to the antitumor activity and toxicity of platinum complexes. Inorganic Chemistry 30:2648-2652.
27. Gaete W, Ros J, Solans X, Font-Altaba M & Brianso JL (1984) Synthesis and crystal and molecular structure of cyclotetrakis[bis(μ-N- methylpiperidine-4-thiolato)nickel(II)]. Inorganic Chemistry 23:39-43.
28. Gibson D & Lippard SJ (1986) Preparation and structural characteristics of a novel hexanuclear complex of platinum(II) with 2-aminoethanethiolate. Inorganic Chemistry 25:219-222.
29. Gould RO & Harding MM (1970) Nickel and palladium complexes of 1-hydroxyethane-2-thiol and analogues. Part I. crystal structure of cyclohexakis[bis(μ-1-hydroxyethane-2-thiolato)]nickel(II). Journal of the Chemical Society (A), 875-881.
30. Harada S, Koyanagi Y & Yamamoto N (1985) Infection of HTLV-III/LAV in HTLV-1 carrying cell MT-2 and TT-4 and application in a plaque assay. Science 229:563-566.
31. Hencher JL, Khan M, Said FF & Tuck DG (1981) Electrochemical preparation and structure of an unusual zinc(II) thiolato anionic cluster. Inorganic and Nuclear Chemistry Letters 17:287-290.
32. Herold BC, Bourne N, Marcellino D, Kirkpatrick R, Strauss DM, Zaneveld LJD, Waller DP, Anderson RA, Chany CJ, Barham BJ, Stanberry LR & Cooper MD (2000) Poly(sodium 4-styrenesulfonate): an effective candidate topical antimicrobial for the prevention of sexually transmitted diseases. Journal of Infectious Diseases 181:770-773.
33. 12. Inorganica Chimica Acta 145:247-252.
34. 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 composition of the target amino acid sequences of the viral envelope glycoproteins. Antimicrobial Agents and Chemotherapy 35:2515-2520.
35. Inouye Y, Tokutake Y, Kunihara J, Yoshida T, Yamase T, Nakata A & Nakamura S (1992) Suppressive effect of polyoxometalates on the cytopathogenicity of human immunodeficiency virus type 1 (HIV-1) In Vitro and their inhibitory activity against HIV-1 reverse transcriptase. Chemical & pharmaceutical bulletin 40:805-807.
36. 5, a pentametallic tiara structure. Polyhedron 7:1397-1399.
37. Krebs B & Menhel B (1991) Transition-metal thiolates: from molecular fragments of sulfidic solids to models for active centers in biomolecules. Angewandte Chemie International Edition in English 30:769-788.
38. 8], a homoleptic nickel thiolate. Angewandte Chemie International Edition in English 28:61-62.
39. Kunchur NR (1968) The crystal structure of palladium n-propyl mercaptide. Acta crystallographica B24:1623-1633.
40. Lüscher-Mattli M (2000) Polyanions - a lost chance in the fight against HIV and other virus diseases? Antiviral Chemistry & Chemotherapy 11:249-259.
41. 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.
42. Moriya T, Kurita H, Matsumoto K, Otake T, Mori H, Morimoto M, Ueba N & Kunita N (1991) Potent inhibitory effect of a series of modified cyclodextrin sulfates (mCDS) on the replication of HIV-1 in vitro. Journal of Medicinal Chemistry 34:2301-2304.
43. Nakanishi I, Matsumoto K & Ooi S (1991) Structures of benzenethiolato complexes of palladium (II) and platinum (II). Acta crystallographica C47:2073-2076.
44. Neyts J, Snoeck R, Wutzler P, Cushman M, Klöcking R, Helbig B, Wang P & De Clercq E (1992) Poly(hydroxy)carboxylates as selective inhibitors of cytomegalovirus and herpes simplex virus replication. Antiviral Chemistry & Chemotherapy 3:215-222.
45. Pauwels R, De Clercq E, Desmyter J, Balzarini J, Goubau P, Herdewijn P, Vanderhaeghe H & Vandeputte M (1987) Sensitive and rapid assay on MT-4 cells for detection of antiviral compounds against the AIDS Virus. Journal of Virological Methods 16:171-185.
46. Schols D, De Clercq E, Balzarini J, Baba M, Witvrouw M, Hosoya M, Andrei G, Snoeck R, Neyts J, Pauwels R, Nagy M, Györgyi-Edelényi J, Machovich R, Horváth I & Löw M, Görög 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 toga-, arena- and retroviruses. Antiviral Chemistry & Chemotherapy 1:233-240.
47. Schols D, De Clercq E, Witvrouw M, Nakashima H, Snoeck R, Pauwels R, Van Schepdael A & Claes P (1991) Sulphated cyclodextrins are potent anti-HIV agents acting synergistically with 2′,3′-dideoxynucleoside analogues. Antiviral Chemistry & Chemotherapy 2:45-53.
48. Shaw IC & Graham MI (1987) Mesna - A short review. Cancer Treatment Reviews 14:67-86.
49. Take Y, Tokutake Y, Inouye Y, Yoshida T, Yamamoto A, Yamase T & Nakamura S (1991) Inhibition of proliferation of human immunodeficiency virus type 1 by novel heteropolyoxotungstates in vitro. Antiviral Research 15:113-124.
50. n. Inorganic Chemistry 26:1488-1497.
51. Taylor DL, Brennan TM, Bridges CG, Mullins MJ, Tyms AS, Jackson R & Cardin AD (1995) Potent inhibition of human immunodeficiency virus by MDL 101028, a novel sulphonic acid polymer. Antiviral Research 28:159-173.
52. Tunaboylu K & Schwarzenbach G (1971) Silbermercaptide und - mercaptokomplexe. Helvetica Chimica Acta 54:2166-2071.
53. Witvrouw M, Schols D, Andrei G, Snoeck R, Ikeda S, Pauwels R, Van Schepdael A, Arnout J, Claes P, Desmyter J & De Clercq E (1992) New polyacetal polysulphate active against human immunodeficiency virus and other enveloped viruses. Antiviral Chemistry & Chemotherapy 3:351-360.
54. Witvrouw M, Fikkert V, Phuymers W, Matthews B, Mardel K, Schols D, Raff J, Debyser Z, De Clercq E, Holan G & Pannecouque C (2000) Polyanionic (i.e. polysulfonate) dendrimers can inhibit the replication of human immunodefiency virus by interfering with both virus adsorption and later steps (reverse transcriptase/integrase) in the virus replicative cycle. Molecular Pharmacology 58:1100-1108.
55. 6. Journal of the American Chemistry Society 87:5251-5253.
56. Yamamoto N, Schols D, De Clercq E, Debyser Z, Pauwels R, Balzarini J, Nakashima H, Baba M, Hosoya M, Snoeck R Neyts J, Andrei G, Murrer BA, Theobald B, Bossard G, Henson G, Abrams M & Picker D (1992) Mechanism of anti-human immunodeficiency virus action of polyoxometalates, a class of broad-spectrum antiviral agents. Molecular Pharmacology 42:1109-1117.
57. 6. Bulletin of the Chemical Society of Japan 61:1975-1978.