Retinazone inhibits certain blood-borne human viruses including Ebola virus Zaire

Antiviral Chemistry and Chemotherapy

Volumn 23, Issue 5, 2014, Pages 197-215

  Kesel, Andreas J ^a   Huang, Zhuhui ^b   Murray, Michael G ^b   Prichard, Mark N ^c   Caboni, Laura ^d   Nevin, Daniel K ^d   Fayne, Darren ^d   Lloyd, David G ^d   Detorio, Mervi A ^e,f   Schinazi, Raymond F ^e,f  

^a Southern Research Institute ^*  (Germany)

^b SOUTHERN RESEARCH INSTITUTE   (United States)

^c University of Alabama at Birmingham   (United States)

^d TRINITY COLLEGE DUBLIN   (Ireland)

^e EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^f ATLANTA VA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENHANCED GREEN FLUORESCENT PROTEIN; GLUCOCORTICOID RECEPTOR; RETINAZONE; RETINOID; RETONAVIR; RITONAVIR; THIOSEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG; VIRUS DNA; ZIDOVUDINE; ANTIVIRUS AGENT; RETINOL; THIOSEMICARBAZONE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; EBOLA VIRUS; EBOLA VIRUS ZAIRE 1976 STRAIN MAYINGA; HEPATITIS B VIRUS; HEPATITIS C VIRUS SUBTYPE 1B; HUMAN; HUMAN CELL; HUMAN GENOME; HUMAN HERPESVIRUS 6; HUMAN HERPESVIRUS 8; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROVIRUS; VIROGENESIS; VIRUS INHIBITION; VIRUS REPLICATION; VIRUS STRAIN; WILD TYPE; ANALOGS AND DERIVATIVES; CHEMISTRY; CLASSIFICATION; DRUG EFFECTS; HEPACIVIRUS; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; EBOLAVIRUS; HEPACIVIRUS; HEPATITIS B VIRUS; HIV-1; HUMANS; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSEMICARBAZONES; VITAMIN A;

EID: 84898463043     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.3851/IMP2568     Document Type: Article

References (70)

1. Hemelaar J. The origin and diversity of the HIV-1 pandemic. Trends Mol Med 2012; 18: 182-192.
2. Marcellin P. Hepatitis B and hepatitis C in 2009. Liver Int 2009; 29 Suppl 1: 1-8.
3. Liang TJ, Heller T. Pathogenesis of hepatitis C-associated hepatocellular carcinoma. Gastroenterology 2004; 127 Suppl 1: S62-S71.
4. Beasley RP, Hwang L-Y, Lin C-C, Chien C-S. Hepatocellular carcinoma and hepatitis B virus-a prospective study of 22 707 men in Taiwan. Lancet 1981; 318: 1129-1133.
5. Ly KN, Xing J, Klevens RM, Jiles RB, Ward JW, Holmberg SD. The increasing burden of mortality from viral hepatitis in the United States between 1999 and 2007. Ann Intern Med 2012; 156: 271-278.
6. Sterling RK. Triple infection with human immunodeficiency virus, hepatitis C virus, and hepatitis B virus: a clinical challenge. Am J Gastroenterol 2003; 98: 2130-2134.
7. Dominguez G, Dambaugh TR, Stamey FR, Dewhurst S, Inoue N, Pellett PE. Human herpesvirus 6B genome sequence: coding content and comparison with human herpesvirus 6A. J Virol 1999; 73: 8040-8052.
8. Cathomas G. Kaposi's sarcoma-associated herpesvirus (KSHV)/human herpesvirus 8 (HHV-8) as a tumour virus. Herpes 2003; 10: 72-77.
9. Feldmann H, Geisbert TW. Ebola haemorrhagic fever. Lancet 2011; 377: 849-862.
10. Leroy EM, Kumulungui B, Pourrut X, et al. Fruit bats as reservoirs of Ebola virus. Nature 2005; 438: 575-576.
11. Kesel AJ. Broad-spectrum antiviral activity including human immunodeficiency and hepatitis C viruses mediated by a novel retinoid thiosemicarbazone derivative. Eur J Med Chem 2011; 46: 1656-1664.
12. Wain-Hobson S, Vartanian J-P, Henry M, et al. LAV revisited: origins of the early HIV-1 isolates from Institut Pasteur. Science 1991; 252: 961-965.
13. Woerz I, Lohmann V, Bartenschlager R. Hepatitis C virus replicons: dinosaurs still in business? J Viral Hepat 2009; 16: 1-9.
14. Towner JS, Paragas J, Dover JE, et al. Generation of eGFP expressing recombinant Zaire ebolavirus for analysis of early pathogenesis events and high-throughput antiviral drug screening. Virology 2005; 332: 20-27.
15. Sanger F, Coulson AR, Hong GF, Hill DF, Petersen GB. Nucleotide sequence of bacteriophage l DNA. J Mol Biol 1982; 162: 729-773.
16. Vizard DL, Ansevin AT. High resolution thermal denaturation of DNA: thermalites of bacteriophage DNA. Biochemistry 1976; 15: 741-750.
17. MacHattie LA, Thomas CA, Jr. DNA from bacteriophage lambda: molecular length and conformation. Science 1964; 144: 1142-1144.
18. Schinazi RF, Sommadossi J-P, Saalmann V, et al. Activities of 3′-azido-3′-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1. Antimicrob Agents Chemother 1990; 34: 1061-1067.
19. Spira TJ, Bozeman LH, Holman RC, Warfield DT, Phillips SK, Feorino PM. Micromethod for assaying reverse transcriptase of human T-cell lymphotropic virus type III/lymphadenopathy-associated virus. J Clin Microbiol 1987; 25: 97-99.
20. Stuyver LJ, Lostia S, Adams M, et al. Antiviral activities and cellular toxicities of modified 2′, 3′-dideoxy-2′, 3′-didehydrocytidine analogues. Antimicrob Agents Chemother 2002; 46: 3854-3860.
21. Korba BE, Gerin JL. Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral Res 1992; 19: 55-70.
22. Stachulski AV, Pidathala C, Row EC, et al. Thiazolides as novel antiviral agents. 1. Inhibition of hepatitis B virus replication. J Med Chem 2011; 54: 4119-4132.
23. Galibert F, Mandart E, Fitoussi F, Tiollais P, Charnay P. Nucleotide sequence of the hepatitis B virus genome (subtype ayw) cloned in E. coli. Nature 1979; 281: 646-650.
24. Morrey JD, Korba BE, Beadle JR, Wyles DL, Hostetler KY. Alkoxyalkyl esters of 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine are potent and selective inhibitors of hepatitis B virus (HBV) replication in vitro and in HBV transgenic mice in vivo. Antimicrob Agents Chemother 2009; 53: 2865-2870.
25. Lohmann V, Körner F, Koch J-O, Herian U, Theilmann L, Bartenschlager R. Replication of subgenomic hepatitis C virus RNAs in a hepatoma cell line. Science 1999; 285: 110-113.
26. Pietschmann T, Lohmann V, Kaul A, et al. Persistent and transient replication of full-length hepatitis C virus genomes in cell culture. J Virol 2002; 76: 4008-4021.
27. Ma S, Boerner JE, TiongYip C, et al. NIM811, a cyclophilin inhibitor, exhibits potent in vitro activity against hepatitis C virus alone or in combination with alpha interferon. Antimicrob Agents Chemother 2006; 50: 2976-2982.
28. Hopkins S, Scorneaux B, Huang Z, et al. SCY-635, a novel nonimmunosuppressive analog of cyclosporine that exhibits potent inhibition of hepatitis C virus RNA replication in vitro. Antimicrob Agents Chemother 2010; 54: 660-672.
29. Kinch MS, Yunus AS, Lear C, et al. FGI-104: a broadspectrum small molecule inhibitor of viral infection. Am J Transl Res 2009; 1: 87-98.
30. Shurtleff AC, Biggins JE, Keeney AE, et al. Standardization of the filovirus plaque assay for use in preclinical studies. Viruses 2012; 4: 3511-3530.
31. Cook PD, Rousseau RJ, Mian AM, Dea P, Meyer RB, Jr., Robins RK. Synthesis of 3-deazaguanine, 3-deazaguanosine, and 3-deazaguanylic acid by a novel ring closure of imidazole precursors. J Am Chem Soc 1976; 98: 1492-1498.
32. Repetto G, del Peso A, Zurita JL. Neutral red uptake assay for the estimation of cell viability/cytotoxicity. Nat Protoc 2008; 3: 1125-1131.
33. Williams-Aziz SL, Hartline CB, Harden EA, et al. Comparative activities of lipid esters of cidofovir and cyclic cidofovir against replication of herpesviruses in vitro. Antimicrob Agents Chemother 2005; 49: 3724-3733.
34. Prichard MN, Frederick SL, Daily S, et al. Benzimidazole analogs inhibit human herpesvirus 6. Antimicrob Agents Chemother 2011; 55: 2442-2445.
35. Prichard MN, Daily SL, Jefferson GM, Perry AL, Kern ER. A rapid DNA hybridization assay for the evaluation of antiviral compounds against Epstein-Barr virus. J Virol Methods 2007; 144: 86-90.
36. James SH, Hartline CB, Harden EA, et al. Cyclopropavir inhibits the normal function of the human cytomegalovirus UL97 kinase. Antimicrob Agents Chemother 2011; 55: 4682-4691.
37. Prichard MN, Quenelle DC, Hartline CB, et al. Inhibition of herpesvirus replication by 5-substituted 4′-thiopyrimidine nucleosides. Antimicrob Agents Chemother 2009; 53: 5251-5258.
38. Oñate SA, Tsai SY, Tsai M-J, O'Malley BW. Sequence and characterization of a coactivator for the steroid hormone receptor superfamily. Science 1995; 270: 1354-1357.
39. Jung-Testas I, Baulieu E-E. Inhibition of glucocorticosteroid action in cultured L-929 mouse fibroblasts by RU 486, a new anti-glucocorticosteroid of high affinity for the glucocorticosteroid receptor. Exp Cell Res 1983; 147: 177-182.
40. Kesel AJ, Sonnenbichler I, Polborn K, et al. A new antioxidative vitamin B6 analogue modulates pathophysiological cell proliferation and damage. Bioorg Med Chem 1999; 7: 359-367.
41. Mascal M, Hafezi N, Meher NK, Fettinger JC. Oxatriquinane and oxatriquinacene: extraordinary oxonium ions. J Am Chem Soc 2008; 130: 13532-13533.
42. Mascal M, Hafezi N, Toney MD. 1, 4, 7-Trimethyloxatriquinane: SN2 Reaction at tertiary carbon. J Am Chem Soc 2010; 132: 10662-10664.
43. Mangelsdorf DJ, Thummel C, Beato M, et al. The nuclear receptor superfamily: the second decade. Cell 1995; 83: 835-839.
44. Tur-Kaspa R, Burk RD, Shaul Y, Shafritz DA. Hepatitis B virus DNA contains a glucocorticoid-responsive element. Proc Natl Acad Sci U S A 1986; 83: 1627-1631.
45. Tur-Kaspa R, Shaul Y, Moore DD, et al. The glucocorticoid receptor recognizes a specific nucleotide sequence in hepatitis B virus DNA causing increased activity of the HBV enhancer. Virology 1988; 167: 630-633.
46. Vandevyver S, Dejager L, Libert C. On the trail of the glucocorticoid receptor: into the nucleus and back. Traffic 2012; 13: 364-374.
47. Schoneveld OJLM, Gaemers IC, Lamers WH. Mechanisms of glucocorticoid signalling. Biochim Biophys Acta 2004; 1680: 114-128.
48. George AA, Schiltz RL, Hager GL. Dynamic access of the glucocorticoid receptor to response elements in chromatin. Int J Biochem Cell Biol 2009; 41: 214-224.
49. Slater EP, Rabenau O, Karin M, Baxter JD, Beato M. Glucocorticoid receptor binding and activation of a heterologous promoter by dexamethasone by the first intron of the human growth hormone gene. Mol Cell Biol 1985; 5: 2984-2992.
50. Horie-Inoue K, Takayama K, Bono HU, Ouchi Y, Okazaki Y, Inoue S. Identification of novel steroid target genes through the combination of bioinformatics and functional analysis of hormone response elements. Biochem Biophys Res Commun 2006; 339: 99-106.
51. Pereira LA, Bentley K, Peeters A, Churchill MJ, Deacon NJ. A compilation of cellular transcription factor interactions with the HIV-1 LTR promoter. Nucleic Acids Res 2000; 28: 663-668.
52. Mitra D, Sikder SK, Laurence J. Role of glucocorticoid receptor binding sites in the human immunodeficiency virus type 1 long terminal repeat in steroid-mediated suppression of HIV gene expression. Virology 1995; 214: 512-521.
53. Soudeyns H, Geleziunas R, Shyamala G, Hiscott J, Wainberg MA. Identification of a novel glucocorticoid response element within the genome of human immunodeficiency virus type 1. Virology 1993; 194: 758-768.
54. Marin M, Rose KM, Kozak SL, Kabat D. HIV-1 Vif protein binds the editing enzyme APOBEC3G and induces its degradation. Nat Med 2003; 9: 1398-1403.
55. Chono K, Katsumata K, Kontani T, et al. ASP2151, a novel helicase-primase inhibitor, possesses antiviral activity against varicella-zoster virus and herpes simplex virus types 1 and 2. J Antimicrob Chemother 2010; 65: 1733-1741.
56. Zhang W, Li H, Li Y, et al. Effective inhibition of HCMV UL49 gene expression and viral replication by oligonucleotide external guide sequences and RNase P. Virol J 2010; 7: 100.
57. Bonnafous P, Boutolleau D, Naesens L, Deback C, Gautheret-Dejean A, Agut H. Characterization of a cidofovir-resistant HHV-6 mutant obtained by in vitro selection. Antiviral Res 2008; 77: 237-240.
58. Chen Y, Ciustea M, Ricciardi RP. Processivity factor of KSHV contains a nuclear localization signal and binding domains for transporting viral DNA polymerase into the nucleus. Virology 2005; 340: 183-191.
59. Bechtel JT, Shenk T. Human cytomegalovirus UL47 tegument protein functions after entry and before immediate-early gene expression. J Virol 2002; 76: 1043-1050.
60. Kuny CV, Chinchilla K, Culbertson MR, Kalejta RF. Cyclindependent kinase-like function is shared by the beta-and gamma-subset of the conserved herpesvirus protein kinases. PLoS Pathog 2010; 6: e1001092.
61. Mockenhaupt T, Reschke M, Bogner E, Reis B, Radsak K. Structural analysis of the US-segment of a viable temperature sensitive human cytomegalovirus mutant. Arch Virol 1994; 137: 161-169.
62. Baines JD, Roizman B. The open reading frames UL3, UL4, UL10, and UL16 are dispensable for the replication of herpes simplex virus 1 in cell culture. J Virol 1991; 65: 938-944.
63. Lee M-A, Yates JL. BHRF1 of Epstein-Barr virus, which is homologous to human proto-oncogene bcl2, is not essential for transformation of B cells or for virus replication in vitro. J Virol 1992; 66: 1899-1906.
64. Warren TK, Warfield KL, Wells J, et al. Antiviral activity of a small-molecule inhibitor of filovirus infection. Antimicrob Agents Chemother 2010; 54: 2152-2159.
65. Castro EF, Fabian LE, Caputto ME, et al. Inhibition of bovine viral diarrhea virus RNA synthesis by thiosemicarbazone derived from 5, 6-dimethoxy-1-indanone. J Virol 2011; 85: 5436-5445.
66. Choudhary SK, Margolis DM. Curing HIV: pharmacologic approaches to target HIV-1 latency. Annu Rev Pharmacol Toxicol 2011; 51: 397-418.
67. Chun T-W, Murray D, Justement JS, et al. Relationship between residual plasma viremia and the size of HIV proviral DNA reservoirs in infected individuals receiving effective antiretroviral therapy. J Infect Dis 2011; 204: 135-138.
68. Germann MW, Johnson CN, Spring AM. Recognition of damaged DNA: structure and dynamic markers. Med Res Rev 2012; 32: 659-683.
69. Meeks RG, Zaharevitz D, Chen RF. Membrane effects of retinoids: possible correlation with toxicity. Arch Biochem Biophys 1981; 207: 141-147.
70. Horwitz J, Heller J. Properties of the chromophore binding site of retinol-binding protein from human plasma. J Biol Chem 1974; 249: 4712-4719.