Antiviral activities of methylated nordihydroguaiaretic acids. 2. Targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor Tetra-O-methyl-NDGA

Journal of Medicinal Chemistry

Volumn 41, Issue 16, 1998, Pages 3001-3007

  Chen, Hongshan ^a   Teng, Li ^a   Li, Jian Nong ^a   Park, Richard ^b   Mold, David E ^b   Gnabre, John ^b   Hwu, Jih Ru ^c   Tseng, Wen Nan ^b,c   Huang, Ru Chih C ^b  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^c JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; NORDIHYDROGUAIARETIC ACID;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; DRUG CYTOTOXICITY; DRUG SENSITIVITY; HERPES SIMPLEX VIRUS; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; VERO CELL; VIRUS INHIBITION; VIRUS REPLICATION;

ACYCLOVIR; ANIMALS; ANTIVIRAL AGENTS; CELL LINE, TRANSFORMED; CERCOPITHECUS AETHIOPS; DRUG RESISTANCE, MICROBIAL; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; IMMEDIATE-EARLY PROTEINS; MUTATION; NORDIHYDROGUAIARETIC ACID; PLASMIDS; PROMOTER REGIONS (GENETICS); PROTEIN BINDING; SIMPLEXVIRUS; SP1 TRANSCRIPTION FACTOR; TRANSCRIPTION, GENETIC; TRANSFECTION; VERO CELLS; VIRUS REPLICATION;

EID: 0032581467     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980182w     Document Type: Article

References (31)

1. Richman, D. D.; Havlir, D.; Corbein, J.; Looney, D.; Ignacio, C.; Spector, S. T.; Sullivan, J.; Cheeseman, S.; Barringer, K.; Pauletti, D.; Shih, C.-K.; Myers, M.; Griffin, J. Nevirapine resistance mutations of human immunodeficiency virus type 1 selected during therapy. J. Virol. 1994, 68, 1660-1666.
2. De Clercq, E. HIV resistance to reverse transcriptase inhibitors. Biochem. Pharmacol. 1994, 47, 155-169.
3. Condra, J. H.; Schleif, W. A.; Blahy, O. M.; Gabryelski, L. J.; Graham, D. J.; Quintero, J. C.; Rhodes, A.; Robbins, H. L.; Roth E.; Shivaprakash, M.; Titus, D.; Yang, T.; Teppler, H.; Squires, K. E.; Deutsch, P. J.; Emini, E. A. In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors. Nature 1995, 374, 569-571.
4. Baba, M. Mini Review. Cellular factors as alternative targets for inhibition of HIV-1. Antiviral Res. 1997, 33, 1441-152.
5. Gnabre, J. N.; Brady, J.; Clanton, D.; Ito, Y.; Dittmer, J.; Bates, R. B.; Chao, Y.; Ho, D.; Huang, R. C. Inhibition of human immunodeficiency virus type 1 transcription and replication by DNA sequence-selective plant lignans. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 11239-11243.
6. Gnabre, J. N.; Ito, Y.; Ma, Y.; Huang, R. C. Isolation and anti-HIV-1 lignans from Larrea tridentata by counter-current chromatography. J. Chromatogr. A 1996, 719, 353-364.
7. Gnabre, J. N.; Huang, R. C.; Bates, R. B.; Burns, J. J.; Caldera, S.; Malcomson, M. E.; McClure, K. J. Characterization of Anti-HIV lignans from Larrea tridentata. Tetrahedron 1995, 51, 12203-12210.
8. Hwu, J. R.; Tseng, W. N.; Gnabre, J.; Giza, P.; Huang, R. C. C. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of Tat-regulated HIV transactivation. J. Med. Chem. 1998, 41, 2994-3000.
9. Honess, R. W.; Roizman, B. Regulation of herpes virus macromolecular synthesis. I. Cascade regulation of the synthesis of three groups of viral proteins. J. Virol. 1974, 14, 8.
10. Mackem, S.; Roizman, B. Structural features of the herpes simplex a gene 4, 0, 27 promoter-regulatory sequences which confer a regulation on chimeric thymidine kinase genes. J. Virol. 1982, 44, 939.
11. ApRhys, C. M. J. Trans-activation by the herpes simplex virion component VP16, Cis and trans-acting requirements. Ph.D. Thesis, Johns Hopkins University, 1991.
12. Lai, J. S.; Cleary, M. A.; Herr, W. A single amino acid exchange transfers VPIG-induced positive control from the Oct-1 to Oct-2 homeodomain. Genes Dev. 1992, 6, 2058-2065.
13. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahonn, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Nat. Cancer Institute 1990, 82, 1107-1112.
14. Dittmer, J.; Gregonne, A.; Gitlin, S. D.; Glysdale, J.; Brady, J. N. Regulation of parathyroid hormone-related protein (PTHrP) gene expression. J. Biol. Chem. 1994, 269, 21428-21434.
15. Jones, K. A.; Tjian, R. Sp1 binds to promoter sequences and activates herpes simplex virus "immediate-early" gene transcription in vitro. Nature 1985, 317, 179.
16. Pauwels, R.; Balzanini, J.; Baba, M.; Snolck, R.; Schols, D.; Herdewijin, P.; Desmyter, J.; DeClercq, E. Rapid and automated tetrazolium-based colorimetric assay for detection of anti-HIV compounds. J. Vir. Methods 1988, 20, 309-321.
17. Staszewski, S.; Miller, V.; Rehmet, S.; et al. Virological and immunological analysis of a triple combination pilot study with loviride, lamivudine and zidovudine in HIV-1-infected patients. AIDS 1996, 10, F1-F7.
18. Furman, P. A.; Fyte, J. A.; St. Clair, M. H.; Weinhold, K.; Rideout, J. L.; Freeman, G. A.; Nusinoff, L. S.; Bolognesi, D. P.; Broder, S.; Mitsuya, H.; Barry, D. W. Phosphorylation of 3′-azido-3′-deoxythymine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8333-8337.
19. Elion, G. B.; Furman, P. A.; Fyte, J. A.; DeMiranda, P.; Beauchamp, L.; Schaeffer, H. J. Selectivity of action of an antitherapeutic agent g-(2-hydroxyethoxymethyl) guanine. Proc. Natl. Acad. Sci. U.S.A. 1977, 12, 5716-5720.
20. Courey, A. J.; Tjian, R. Analysis of Sp1 in vivo reveals multiple transcription domains, including a novel glutamine-rich activation motif. Cell 1988, 55, 887.
21. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
22. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
23. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
24. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
25. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
26. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
27. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
28. Some of the Sp1-regulated cellular genes: Sartorelli, V.; Webster, K. A.; Kedes, L. Muscle-specific expression of the cardiac alpha-actin gene requires myoD1, CArG-hox binding factor and Sp1. Gene Dev. 1990, 4, 1811. Dailey, L.; Roberts, S. B.; Heintz, N. Purification of the histone H4 gene-specific transcription factor, H4TF-1 and H4TF-2. Gene Dev. 1988, 2, 1700. Means, A. L.; Farnham, P. J. Transcription initiation form the dihydrogolate reductase promoter is positioned by HIP-1 binding at the initiation site. Mol. Cell Biol. 1990, 10, 653. Abravaya, K.; Phillips, B.; Morimoto, R. I. Heat shock-induced interactions of heat shock transcription factor and human hsp70 promoter examined by in vivo footprinting. Mol. Cell Biol. 1991, 11, 586. Leask, A.; Rosenberg, M.; Vassar, R.; Fuchs, E. Regulation of a human epidermal keratin gene: Sequences and nuclear factors involved in keratinocyte-specific transcription. Gene Dev. 1990, 4, 1985. Desjardins, E.; Hay, N. Repeated CT elements bound by zinc finger proteins control the absolute and relative activities of the two principal huyman c-myc promoter. Mol. Cell Biol. 1993, 13, 5710. Sanchez, H. B.; Yieh, L.; Osborne, T. F. Cooperation by sterol regulatory element-binding protein and Sp1 in sterol regulation of low-density lipoprotein receptor gene. J. Biol. Chem. 1995, 270, 1161. Lemaigre, F. P., Lafontaine, D. A.; Courtois, S. J.; Durviaux, S. M., Rousseau, G. G. Sp1 can displace GHF-1 from its distal binding site and stimulate transcription form growth hormone gene promoter. Mol. Cell. Biol. 1990, 10, 1811.
29. Chatis, P. A.; Crumpacker, C. S. Analysis of the thymidine kinase gene for clinically isolated acyclovir-resistant herpes simplex viruses. Virology 1991, 180, 793-797.
30. O'Hare, P.; Hayward, G. S. Comparison of upstream sequence requirements for positive and negative regulation of a herpes simplex virus immediate-early gene by three virus-encoded trans-acting factors. J. Virol. 1987, 61, 190-199.
31. McLaren, C.; Ellis, M. N.; Hunter, G. A. A colorimetric assay for the measurement of the sensitivity of herpes simplex viruses to antiviral agents. Antiviral Res. 1983, 3, 223-234.