Antiviral activities of 2,6-diaminopurine-based acyclic nucleoside phosphonates against herpesviruses: In vitro study results with pseudorabies virus (PrV, SuHV-1)

Veterinary Microbiology

Volumn 184, Issue , 2016, Pages 84-93

  Zouharova, Darina ^a   Lipenska, Ivana ^a   Fojtikova, Martina ^a   Kulich, Pavel ^a   Neca, Jiri ^a   Slany, Michal ^a   Kovarcik, Kamil ^a   Turanek Knotigova, Pavlina ^a   Hubatka, Frantisek ^a   Celechovska, Hana ^a   Masek, Josef ^a   Koudelka, Stepan ^a,b   Prochazka, Lubomir ^a   Eyer, Ludek ^a   Plockova, Jana ^a   Bartheldyova, Eliska ^a   Miller, Andrew D ^c,d   Ruzek, Daniel ^a,e   Raska, Milan ^a,f   Janeba, Zlatko ^g   Turanek, Jaroslav ^a   more..

^a VETERINARY RESEARCH INSTITUTE   (Czech Republic)

^b ST ANNE S UNIVERSITY HOSPITAL   (Czech Republic)

^c KING'S COLLEGE LONDON   (United Kingdom)

^d GlobalAcorn Ltd   (United Kingdom)

^e UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

^f PALACKÝ UNIVERSITY   (Czech Republic)

^g INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acyclic nucleoside phosphonates; Antiviral drugs; Cidofovir; DNA polymerase; DNA viruses; Pseudorabies

Indexed keywords

2,6 DIAMINOPURINE BASED ACYCLIC NUCLEOSIDE PHOSPHONATE DERIVATIVE; ACYCLIC NUCLEOSIDE; ANTIVIRUS AGENT; CYCLOPROPANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG; 2 AMINOPURINE; 2,6-DIAMINOPURINE;

ANIMAL CELL; ANIMAL CELL CULTURE; ANTIVIRAL ACTIVITY; ARTICLE; BIOAVAILABILITY; CYTOTOXICITY; DNA VIRUS; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES VIRUS INFECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; IN VITRO STUDY; MDCK CELL LINE; NONHUMAN; PSEUDORABIES; PSEUDORABIES VIRUS; TANDEM MASS SPECTROMETRY; VERO CELL LINE; VIRUS INHIBITION; VIRUS REPLICATION; ANALOGS AND DERIVATIVES; ANIMAL; CELL LINE; CHEMISTRY; DNA REPLICATION; DOG; DRUG EFFECTS; HERPESVIRIDAE; TRANSMISSION ELECTRON MICROSCOPY;

2-AMINOPURINE; ANIMALS; ANTIVIRAL AGENTS; CELL LINE; DNA REPLICATION; DOGS; HERPESVIRIDAE; IN VITRO TECHNIQUES; MADIN DARBY CANINE KIDNEY CELLS; MICROSCOPY, ELECTRON, TRANSMISSION; ORGANOPHOSPHONATES; PSEUDORABIES; VERO CELLS;

EID: 84957708402     PISSN: 03781135     EISSN: 18732542     Source Type: Journal    
DOI: 10.1016/j.vetmic.2016.01.010     Document Type: Article

References (41)

1. Aleman N., Quiroga M.I., Lopez-Pena M., Vazquez S., Guerrero F.H., Nieto J.M. L-Particle production during primary replication of pseudorabies virus in the nasal mucosa of swine. J. Virol. 2003, 77:5657-5667.
2. Cay A.B., Letellier C. Isolation of Aujeszky's disease virus from two hunting dogs in Belgium after hunting wild boars. Vlaams Diergeneeskundig Tijdschrift 2009, 78:194-195.
3. De Almeida A.P., Miranda M.M.F.S., Simoni I.C., Wigg M.D., Lagrota M.H.C., Costa S.S. Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion. Phytother. Res. 1998, 12:562-567.
4. De Clercq E. Antiviral agents that are active against CMV: potential of cidofovir for the treatment of CMV and other virus infections. Monogr. Virol. Basel. Karger 1998, 21:193-214.
5. De Clercq E. Cidofovir in the treatment of poxvirus infections. Antiviral Res. 2002, 55:1-13.
6. De Clercq E., Brancale A., Hodge A.V., Field H.J. Antiviral Chemistry & Chemotherapy's current antiviral agents FactFile 2006 (1st edition). Antivir. Chem. Chemother. 2006, 17:113-166.
7. Dong B., Zarlenga D.S., Ren X. An overview of live attenuated recombinant pseudorabies viruses for use as novel vaccines. J. Immunol. Res. 2014, 824630.
8. Field H.J. Chemotherapy of Aujeszky's disease (pseudorabies) in the mouse by means of nucleoside analogues: bromovinyldeoxyuridine acyclovir, and dihydropropoxymethylguanine. Antiviral Res. 1985, 5:157-168.
9. Fischer L., Barzu S., Andreoni C., Buisson N., Brun A., Audonnet J.C. DNA vaccination of neonate piglets in the face of maternal immunity induces humoral memory and protection against a virulent Pseudorabies virus challenge. Vaccine 2003, 21:1732-1741.
10. Garré B., Van der Meulen K., Nugent J., Neyts J., Croubels S., De Backer P., Nauwynck H. In vitro susceptibility of six isolates of equine herpesvirus1 to acyclovir ganciclovir, cidofovir, adefovir, PMEDAP and foscarnet. Vet. Microbiol. 2007, 122:43-51.
11. Holy A., Guenter J., Dvorakova H., Masojidkova M., Andrei G., Snoeck R., Balzarini J., De Clercq E. Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues 1. Derivatives Substituted at the carbon atoms of the base. J. Med. Chem. 1999, 42:2064-2086.
12. 6-substituted adenines 2,6-diaminopurines and related compounds. Collect. Czech Chem. Commun. 2001, 66:1545-1592.
13. Jansa P., Kolman V., Kostinova A., Dracinsky M., Mertlikova-Kaiserova H., Janeba Z. Efficient synthesis and biological properties of the 2'-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates. Collect. Czech Chem. Commun. 2011, 76:1187-1198.
14. Jansa P., Baszczynski O., Prochazkova E., Dracinsky M., Janeba Z. Microwave-assisted hydrolysis of phosphonate diesters: an efficient protocol for the preparation of phosphonic acids. Green Chem. 2012, 14:2282-2288.
15. Kim S.J., Kim H.K., Han Y.W., Aleyas A.G., George J.A., Yoon H.A., Yoo D.J., Kim K., Eo S.K. Multiple alternating immunizations with dna vaccine and replication incompetent adenovirus expressing gB of pseudorabies virus protect animals against lethal virus challenge. J. Microbiol. Biotechnol. 2008, 18:1326-1334.
16. Klupp B.G., Granzow H., Karger A., Mettenleiter T.C. Identification, subviral localization, and functional characterization of the pseudorabies virus UL17 protein. J. Virol. 2005, 79:13442-13453.
17. Klupp B.G., Granzow H., Mundt E., Mettenleiter T.C. Pseudorabies virus UL37 gene product is involved in secondary envelopment. J. Virol. 2001, 75:8927-8936.
18. Kong H., Zhang K., Liu Y., Shang Y., Wu B., Liu X. Attenuated live vaccine (Bartha-K16) caused pseudorabies (Aujeszky's disease) in sheep. Vet. Res. Commun. 2013, 37:329-332.
19. ®), entrapped in cationic liposomes: In vitro study on MDBK cell and BHV-1 virus. J. Control Release 2012, 160:330-338.
20. Kramer T., Enquist L.W. Directional spread of alphaherpesviruses in the nervous system. Viruses 2013, 5:678-707.
21. Krecmerova M., Jansa P., Dracinsky M., Sazelova P., Kasicka V., Neyts J., Auwerx J., Kiss E., Goris N., Stepan G., Janeba Z. 9-[2-(R)-(phosphonomethoxy)propyl]-2,6-diaminopurine (R)-PMPDAP and its prodrugs: optimized preparation, including identification of by-products formed, and antiviral evaluation in vitro. Bioorg. Med. Chem. 2013, 21:1199-1208.
22. Krishnan B.R. Current status of DNA vaccines in veterinary medicine. Adv. Drug Deliv. Rev. 2000, 43:3-11.
23. Li X., Turanek J., Knoetigova P., Kudlackova H., Masek J., Pennington D.B., Rankin S.E., Knuton B.L., Lehmler H.J. Synthesis and biocompatibility evaluation of fluorinated: single-tailed glucopyranoside surfactants. New J. Chem. 2008, 32:2169-2179.
24. Li X., Turanek J., Knotigova P., Kudlackova H., Masek J., Pennington D.B., Rankin S.E., Knuton B.L., Lehmler H.J. Hydrophobic tail length: degree of fluorination and headgroup stereochemistry are determinants of the biocompatibility of (fluorinated) carbohydrate surfactants. Colloids Surf. B Biointerfaces 2009, 73:65-74.
25. Ma W., Kelly M., Lager K.M., Richt J.A., Stoffregen W.A., Zhou F., Yoon K.J. Development of real-time polymerase chain reaction assays for rapid detection and differentiation of wild-type pseudorabies and gene-deleted vaccine viruses. J. Vet. Diagn. Invest. 2008, 20:440-447.
26. McGeoch D.J., Cook S. Molecular phylogeny of the alphaherpesvirinae subfamily and a proposed evolutionary timescale. J. Mol. Biol. 1994, 22:9-22.
27. Olson G.R., Miller L.D. Studies on the pathogenesis of heart lesions in dogs infected with pseudorabies virus. Can. J. Vet. Res. 1986, 50:245-250.
28. Pancheva S.N. Potentiating effect of ribavirin on the anti-herpes activity of acyclovir. Antiviral Res. 1991, 16:151-161.
29. Pomeranz L.E., Reynolds A.E., Hengartner C.J. Molecular biology of pseudorabies virus: impact on neurovirology and veterinary medicine. Microbiol. Mol. Biol. Rev. 2005, 69:462-500.
30. Ren X., Sui X., Yin J. The effect of Houttuynia cordata injection on pseudorabies herpesvirus (PrV) infection in vitro. Pharm. Biol. 2011, 49:161-166.
31. Robbins A.K., Whealy M.E., Watson R.J., Enquist L.W. Pseudorabies virus gene encoding glycoprotein glll is not essential for growth in tissue culture. J. Virol. 1986, 59:635-645.
32. Slana I., Kaevska M., Kralik P., Horvathova A., Pavlik I. Distribution of Mycobacterium avium subsp avium and M: a. hominissuis in artificially infected pigs studied by culture and IS901 and IS1245 quantitative real time PCR. Vet. Microbiol. 2010, 144:437-443.
33. Slana I., Kralik P., Kralova A., Pavlik I. On-farm spread of Mycobacterium avium subsp: paratuberculosis in raw milk studied by IS900 and F57 competitive real time quantitative PCR and culture examination. Intl. J. Food Microbiol. 2008, 128:250-257.
34. Sui X., Yin J., Ren X. Antiviral effect of diammonium glycyrrhizinate and lithium chloride on cell infection by pseudorabies herpesvirus. Antiviral Res. 2010, 85:346-353.
35. Van Alstine W., Anderson T., Reed D., Wheeler J. Vaccine induced pseudorabies in lambs. J. Am. Vet. Med. Assoc. 1984, 185:409-410.
36. Van Rooij E.M., Rijsewijk F.A., Moonen-Leusen H.W., Bianchi A.T., Rziha H.J. Comparison of different prime-boost regimes with DNA and recombinant Orf virus based vaccines expressing glycoprotein D of pseudorabies virus in pigs. Vaccine 2010, 28:1808-1813.
37. Williams D.L., Robinson J.C., Lay E., Field H. Efficacy of topical aciclovir for the treatment of feline herpetic keratitis: results of a prospective clinical trial and data from in vitro investigations. Vet. Rec. 2005, 157:254-257.
38. Wittmann G., Jakubik J., Ahl R. Multiplication and distribution of Aujeszky's disease (pseudorabies) virus in vaccinated and non-vaccinated pigs after intranasal infection. Arch. Virol. 1980, 66:227-240.
39. Woodland D.L. Jump-starting the immune system: prime-boosting comes of age. Trends Immunol. 2004, 25:98-104.
40. Yoon H.A., Aleyas A.G., George J.A., Park S.O., Han Y.W., Kang S.H., Cho J.G., Eo S.K. Differential segregation of protective immunity by encoded antigen in DNA vaccine against pseudorabies virus. Immunol. Cell Biol. 2006, 84:502-511.
41. Zhang L., Zhong C., Wang J., Lu Z., Liu L., Yang W., Lyu Y. Pathogenesis of natural and experimental pseudorabies virus infections in dogs. Virol. J. 2015, 12:44.