Anti-CyHV-3 effect of fluorescent, tricyclic derivative of acyclovir 6-(4-MeOPh)-TACV in vitro

1Adamek M., Rakus K.Ł., Chyb J., Brogden G., Huebner A., Irnazarow I., Steinhagen D.: Interferon type I responses to virus infections in carp cells: In vitro studies on Cyprinid herpesvirus 3 and Rhabdovirus carpio infections. Fish Shellfish Immunol 2012, 33, 482–493. https://doi.org/10.1016/j.fsi.2012.05.031 Adamek M. Rakus K.Ł. Chyb J. Brogden G. Huebner A. Irnazarow I. Steinhagen D. Interferon type I responses to virus infections in carp cells: In vitro studies on Cyprinid herpesvirus 3 and Rhabdovirus carpio infections Fish Shellfish Immunol 2012 33 482 493 https://doi.org/10.1016/j.fsi.2012.05.03110.1016/j.fsi.2012.05.031Search in Google Scholar

2Aljanabi S.M., Martinez I.: Universal and rapid salt-extraction of high quality genomic DNA for PCR-based techniques. Nucleic Acids Res 1997, 25, 4692–4693. https://doi.org/10.1093/nar/25.22.4692 Aljanabi S.M. Martinez I. Universal and rapid salt-extraction of high quality genomic DNA for PCR-based techniques Nucleic Acids Res 1997 25 4692 4693 https://doi.org/10.1093/nar/25.22.469210.1093/nar/25.22.4692Search in Google Scholar

3Balzarini J., Ostrowski T., Goslinski T., De Clercq E., Golankiewicz B.: Pronounced cytostatic activity and bystander effect of a novel series of fluorescent tricyclic acyclovir and ganciclovir derivatives in herpes simplex virus thymidine kinase gene-transduced tumor cell lines. Gene Ther 2002, 9, 1173– 1182. https://doi.org/10.1038/sj.gt.3301779 Balzarini J. Ostrowski T. Goslinski T. De Clercq E. Golankiewicz B. Pronounced cytostatic activity and bystander effect of a novel series of fluorescent tricyclic acyclovir and ganciclovir derivatives in herpes simplex virus thymidine kinase gene-transduced tumor cell lines Gene Ther 2002 9 1173 1182 https://doi.org/10.1038/sj.gt.330177910.1038/sj.gt.3301779Search in Google Scholar

4Boutier M., Ronsmans M., Ouyang P., Fournier G., Reschner A., Rakus K.Ł., Wilkie G.S., Farnir F., Bayrou C., Lieffrig F., Li H., Desmecht D., Davison A.J., Vanderplasschen A.: Rational development of an attenuated recombinant Cyprinid Herpesvirus 3 vaccine using prokaryotic mutagenesis and in vivo bioluminescent imaging. PLOS Pathog 2015, 11, e1004690. https://doi.org/10.1371/journal.ppat.1004690 Boutier M. Ronsmans M. Ouyang P. Fournier G. Reschner A. Rakus K.Ł. Wilkie G.S. Farnir F. Bayrou C. Lieffrig F. Li H. Desmecht D. Davison A.J. Vanderplasschen A. Rational development of an attenuated recombinant Cyprinid Herpesvirus 3 vaccine using prokaryotic mutagenesis and in vivo bioluminescent imaging PLOS Pathog 2015 11 e1004690 https://doi.org/10.1371/journal.ppat.100469010.1371/journal.ppat.1004690Search in Google Scholar

5Elion G.B.: Acyclovir: discovery, mechanism of action, and selectivity. J Med Virol Suppl 1993, 1, 2–6. https://doi.org/10.1002/jmv.1890410503 Elion G.B. Acyclovir: discovery, mechanism of action, and selectivity J Med Virol Suppl 1993 1 2 6 https://doi.org/10.1002/jmv.189041050310.1002/jmv.1890410503Search in Google Scholar

6Furman P.A., St Clair M.H., Fyfe J.A., Rideout J.L., Keller P.M., Elion G.B.: Inhibition of herpes simplex virus-induced DNA polymerase activity and viral DNA replication by 9-(2-hydroxyethoxymethyl)guanine and its triphosphate. J Virol 1979, 32, 72–77. Furman P.A. St Clair M.H. Fyfe J.A. Rideout J.L. Keller P.M. Elion G.B. Inhibition of herpes simplex virus-induced DNA polymerase activity and viral DNA replication by 9-(2-hydroxyethoxymethyl)guanine and its triphosphate J Virol 1979 32 72 7710.1128/jvi.32.1.72-77.1979Search in Google Scholar

7Furman P.A., St Clair M.H., Spector T.: Acyclovir triphosphate is a suicide inactivator of the herpes simplex virus DNA polymerase. J Biol Chem 1984, 259, 9575–9579. Furman P.A. St Clair M.H. Spector T. Acyclovir triphosphate is a suicide inactivator of the herpes simplex virus DNA polymerase J Biol Chem 1984 259 9575 957910.1016/S0021-9258(17)42739-6Search in Google Scholar

8Gilad O., Yun S., Zagmutt-Vergara F.J., Bercovier C.M.L., Hedrick R.P.: Concentrations of a Koi herpesvirus (KHV) in tissues of experimentally-infected Cyprinus carpio koi as assessed by real-time TaqMan PCR. Dis Aquat Organ 2004, 60, 179–187. https://doi.org/10.3354/dao060179 Gilad O. Yun S. Zagmutt-Vergara F.J. Bercovier C.M.L. Hedrick R.P. Concentrations of a Koi herpesvirus (KHV) in tissues of experimentally-infected Cyprinus carpio koi as assessed by real-time TaqMan PCR Dis Aquat Organ 2004 60 179 187 https://doi.org/10.3354/dao06017910.3354/dao06017915521316Search in Google Scholar

9Golankiewicz B., Ostrowski T.: Tricyclic nucleoside analogues as antiherpes agents. Antiviral Res 2006, 71, 134–140. https://doi.org/10.1016/j.antiviral.2006.05.004 Golankiewicz B. Ostrowski T. Tricyclic nucleoside analogues as antiherpes agents Antiviral Res 2006 71 134 140 https://doi.org/10.1016/j.antiviral.2006.05.00410.1016/j.antiviral.2006.05.00416780965Search in Google Scholar

10Golankiewicz B., Ostrowski T., Goslinski T., Januszczyk P., Zeidler J., Baranowski D., de Clercq E.: Fluorescent tricyclic analogues of acyclovir and ganciclovir. A structure-antiviral activity study. J Med Chem 2001, 44, 4284–4287. https://pubs.acs.org/doi/abs/10.1021/jm010922s Golankiewicz B. Ostrowski T. Goslinski T. Januszczyk P. Zeidler J. Baranowski D. de Clercq E. Fluorescent tricyclic analogues of acyclovir and ganciclovir. A structure-antiviral activity study J Med Chem 2001 44 4284 4287 https://pubs.acs.org/doi/abs/10.1021/jm010922s10.1021/jm010922s11708929Search in Google Scholar

11Gotesman M., Soliman H., Besch R., El-Matbouli M.: In vitro inhibition of Cyprinid herpesvirus-3 replication by RNAi. J Virol Methods 2014, 206, 63–66. https://doi.org/10.1016/j.jviromet.2014.05.022 Gotesman M. Soliman H. Besch R. El-Matbouli M. In vitro inhibition of Cyprinid herpesvirus-3 replication by RNAi J Virol Methods 2014 206 63 66 https://doi.org/10.1016/j.jviromet.2014.05.02210.1016/j.jviromet.2014.05.022Search in Google Scholar

12Haetrakul T., Dunbar S.G., Chansue N.: Antiviral activities of Clinacanthus nutans (Burm.f.) Lindau extract against Cyprinid herpesvirus 3 in koi Cyprinus carpio koi J Fish Dis 2018, 41, 581–587. https://doi.org/10.1111/jfd.12757 Haetrakul T. Dunbar S.G. Chansue N. Antiviral activities of Clinacanthus nutans (Burm.f.) Lindau extract against Cyprinid herpesvirus 3 in koi Cyprinus carpio koi J Fish Dis 2018 41 581 587 https://doi.org/10.1111/jfd.1275710.1111/jfd.12757Search in Google Scholar

13Michel B., Fournier G., Lieffrig F., Costes B., Vanderplasschen A.: Cyprinid herpesvirus 3. Emerg Infect Dis 2010, 16, 1835–1843. https://doi.org/10.3201/eid1612.100593 Michel B. Fournier G. Lieffrig F. Costes B. Vanderplasschen A. Cyprinid herpesvirus 3 Emerg Infect Dis 2010 16 1835 1843 https://doi.org/10.3201/eid1612.10059310.3201/eid1612.100593Search in Google Scholar

14Miller W.H., Miller R.L.: Phosphorylation of acyclovir diphosphate by cellular enzymes. Biochem Pharmacol 1982, 31, 3879–3884. Miller W.H. Miller R.L. Phosphorylation of acyclovir diphosphate by cellular enzymes Biochem Pharmacol 1982 31 3879 388410.1016/0006-2952(82)90305-7Search in Google Scholar

15Mosmann T.: Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983, 65, 55–63. https://doi.org/10.1016/0022-1759(83)90303-4 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 1983 65 55 63 https://doi.org/10.1016/0022-1759(83)90303-410.1016/0022-1759(83)90303-4Search in Google Scholar

16Rakus K.Ł., Irnazarow I., Adamek M., Palmeira L., Kawana Y., Hirono I., Kondo H., Matras M., Steinhagen D., Flasz B., Brogden G., Vanderplasschen A., Aoki T.: Gene expression analysis of common carp Cyprinus carpio L.) lines during Cyprinid herpesvirus 3 infection yields insights into differential immune responses. Dev Comp Immunol 2012, 37, 65–76. https://doi.org/10.1016/j.dci.2011.12.006 Rakus K.Ł. Irnazarow I. Adamek M. Palmeira L. Kawana Y. Hirono I. Kondo H. Matras M. Steinhagen D. Flasz B. Brogden G. Vanderplasschen A. Aoki T. Gene expression analysis of common carp Cyprinus carpio L.) lines during Cyprinid herpesvirus 3 infection yields insights into differential immune responses Dev Comp Immunol 2012 37 65 76 https://doi.org/10.1016/j.dci.2011.12.00610.1016/j.dci.2011.12.006Search in Google Scholar

17Ramakrishnan M.A.: Determination of 50% endpoint titer using a simple formula. World J Virol 2016, 5, 85–86. https://doi.org/10.5501/wjv.v5.i2.85 Ramakrishnan M.A. Determination of 50% endpoint titer using a simple formula World J Virol 2016 5 85 86 https://doi.org/10.5501/wjv.v5.i2.8510.5501/wjv.v5.i2.85Search in Google Scholar

18Reichert M., Bergmann S.M., Hwang J., Buchholz R., Lindenberger C.: Antiviral activity of exopolysaccharides from Arthrospira platensis against koi herpesvirus. J Fish Dis 2017, 40, 1441–1450. https://doi.org/10.1111/jfd.12618 Reichert M. Bergmann S.M. Hwang J. Buchholz R. Lindenberger C. Antiviral activity of exopolysaccharides from Arthrospira platensis against koi herpesvirus J Fish Dis 2017 40 1441 1450 https://doi.org/10.1111/jfd.1261810.1111/jfd.12618Search in Google Scholar

19Riss T.L., Moravec R.A., Niles A.L., Duellman S., Benink H.A., Worzella T.J., Minor L.: Cell viability assays. in: Assay Guidance Manual. Edited by G.S. Sittampalam, N.P. Coussens, K. Brimacombe, A. Grossman, M. Arkin, D. Auld, C. Austin, J. Baell, B. Bejcek, J.M.M. Caaveiro, T.D.Y. Chung, J.L. Dahlin, V. Devanaryan, T.L. Foley, M. Glicksman, M.D. Hall, J.V. Haas, J. Inglese, P.W. Iversen, S.D. Kahl, S.C. Kales, M. Lal-Nag, Z. Li, J. McGee, O. McManus, T.L. Riss, O.J. Trask, J.R. Weidner, M.J. Wildey, M. Xia, X. Xu, Eli Lilly & Company and the National Center for Advancing Translational Sciences, Bethesda, 2004. Riss T.L. Moravec R.A. Niles A.L. Duellman S. Benink H.A. Worzella T.J. Minor L. Cell viability assays Assay Guidance Manual Edited by Sittampalam G.S. Coussens N.P. Brimacombe K. Grossman A. Arkin M. Auld D. Austin C. Baell J. Bejcek B. Caaveiro J.M.M. Chung T.D.Y. Dahlin J.L. Devanaryan V. Foley T.L. Glicksman M. Hall M.D. Haas J.V. Inglese J. Iversen P.W. Kahl S.D. Kales S.C. Lal-Nag M. Li Z. McGee J. McManus O. Riss T.L. Trask O.J. Weidner J.R. Wildey M.J. Xia M. Xu X. Eli Lilly & Company and the National Center for Advancing Translational Sciences Bethesda 2004Search in Google Scholar

20Ronen A., Perelberg A., Abramowitz J., Hutoran M., Tinman S., Bejerano I., Steinitz M., Kotler M.: Efficient vaccine against the virus causing a lethal disease in cultured Cyprinus carpio Vaccine 2003, 21, 4677–4684. https://doi.org/10.1016/S0264-410X(03)00523-1 Ronen A. Perelberg A. Abramowitz J. Hutoran M. Tinman S. Bejerano I. Steinitz M. Kotler M. Efficient vaccine against the virus causing a lethal disease in cultured Cyprinus carpio Vaccine 2003 21 4677 4684 https://doi.org/10.1016/S0264-410X(03)00523-110.1016/S0264-410X(03)00523-1Search in Google Scholar

21Saotome K., Morita H., Umeda M.: Cytotoxicity test with simplified crystal violet staining method using microtitre plates and its application to injection drugs. Toxicol Vitro Int J Publ Assoc BIBRA 1989, 3, 317–321. https://doi.org/10.1016/0887-2333(89)90039-8 Saotome K. Morita H. Umeda M. Cytotoxicity test with simplified crystal violet staining method using microtitre plates and its application to injection drugs Toxicol Vitro Int J Publ Assoc BIBRA 1989 3 317 321 https://doi.org/10.1016/0887-2333(89)90039-810.1016/0887-2333(89)90039-8Search in Google Scholar

22Sunarto A., Rukyani A., Itami T.: Indonesian experience on the outbreak of koi herpesvirus in koi and carp Cyprinus carpio Bull Fish Res Agency 2005, 2, 15–21. Sunarto A. Rukyani A. Itami T. Indonesian experience on the outbreak of koi herpesvirus in koi and carp Cyprinus carpio Bull Fish Res Agency 2005 2 15 21Search in Google Scholar

23Tadmor-Levi R., Asoulin E., Hulata G., David L.: Studying the genetics of resistance to CyHV-3 disease using introgression from feral to cultured common carp strains. Front Genet 2017, 8, 1–13. https://doi.org/10.3389/fgene.2017.00024 Tadmor-Levi R. Asoulin E. Hulata G. David L. Studying the genetics of resistance to CyHV-3 disease using introgression from feral to cultured common carp strains Front Genet 2017 8 1 13 https://doi.org/10.3389/fgene.2017.0002410.3389/fgene.2017.00024534489528344591Search in Google Scholar

24Troszok A., Kolek L., Szczygieł J., Wawrzeczko J., Borzym E., Reichert M., Kamińska T., Ostrowski T., Jurecka P., Adamek M., Rakus K.Ł., Irnazarow I.: Acyclovir inhibits Cyprinid herpesvirus 3 multiplication in vitro J Fish Dis 2018, 41, 1709– 1718. https://doi.org/10.1111/jfd.12880 Troszok A. Kolek L. Szczygieł J. Wawrzeczko J. Borzym E. Reichert M. Kamińska T. Ostrowski T. Jurecka P. Adamek M. Rakus K.Ł. Irnazarow I. Acyclovir inhibits Cyprinid herpesvirus 3 multiplication in vitro J Fish Dis 2018 41 1709 1718 https://doi.org/10.1111/jfd.1288010.1111/jfd.1288030144085Search in Google Scholar

25Uchii K., Minamoto T., Honjo M. N., Kawabata Z.: Seasonal reactivation enables Cyprinid herpesvirus 3 to persist in a wild host population. FEMS Microbiol. Ecol 2014, 87, 536–542. https://doi.org/10.1111/1574-6941.12242 Uchii K. Minamoto T. Honjo M. N. Kawabata Z. Seasonal reactivation enables Cyprinid herpesvirus 3 to persist in a wild host population FEMS Microbiol. Ecol 2014 87 536 542 https://doi.org/10.1111/1574-6941.1224210.1111/1574-6941.1224224256414Search in Google Scholar

26Uchii K., Telschow A., Minamoto T., Yamanaka H., Honjo M. N., Matsui K., Kawabata Z.: Transmission dynamics of an emerging infectious disease in wildlife through host reproductive cycles. ISME J 2011, 5, 244–251. https://doi.org/10.1038/ismej.2010.123 Uchii K. Telschow A. Minamoto T. Yamanaka H. Honjo M. N. Matsui K. Kawabata Z. Transmission dynamics of an emerging infectious disease in wildlife through host reproductive cycles ISME J 2011 5 244 251 https://doi.org/10.1038/ismej.2010.12310.1038/ismej.2010.123310570620740025Search in Google Scholar

27Wils P., Warnery A., Phung-Ba V., Legrain S., Scherman D.: High lipophilicity decreases drug transport across intestinal epithelial cells. J Pharmacol Exp Ther 1994, 269, 654–658. Wils P. Warnery A. Phung-Ba V. Legrain S. Scherman D. High lipophilicity decreases drug transport across intestinal epithelial cells J Pharmacol Exp Ther 1994 269 654 658Search in Google Scholar

28Zielenkiewicz W., Golankiewicz B., Perlovich G.L., Koźbiał M.: Aqueous solubilities, infinite dilution activity coefficients and octanol–water partition coefficients of tricyclic analogs of acyclovir. J Solut Chem 1999, 28, 731–745. https://doi.org/10.1023/A:1021720128725 Zielenkiewicz W. Golankiewicz B. Perlovich G.L. Koźbiał M. Aqueous solubilities, infinite dilution activity coefficients and octanol–water partition coefficients of tricyclic analogs of acyclovir J Solut Chem 1999 28 731 745 https://doi.org/10.1023/A:102172012872510.1023/A:1021720128725Search in Google Scholar