Highly potent and selective inhibition of varicella-zoster virus replication by bicyclic furo [2,3-d]pyrimidine nucleoside analogues

Medicinal Research Reviews

Volumn 23, Issue 3, 2003, Pages 253-274

  De Clercq, Erik ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Dihydropyrimidine dehydrogenase; Furo 2,3 d pyrimidine nucleoside analogues; Thymidine kinase; Thymidine phosphorylase; Varicella zoster virus

Indexed keywords

5 (2 BROMOVINYL) 2' DEOXYURIDINE; ACICLOVIR; BICYCLIC FURO[2,3 D]PYRIMIDINE NUCLEOSIDE DERIVATIVE; CF 1368; CF 1742; CF 1743; DIHYDROPYRIMIDINE DEHYDROGENASE; FAMCICLOVIR; FLUOROURACIL; FURO[2,3 D]PYRIMIDINE NUCLEOSIDE DERIVATIVE; NETIVUDINE; PENCICLOVIR; PYRIMIDINE NUCLEOSIDE DERIVATIVE; THYMIDINE; THYMIDINE KINASE; THYMIDINE PHOSPHORYLASE; UNCLASSIFIED DRUG; URACIL; VALACICLOVIR; ZOSTEX;

ANTIVIRAL ACTIVITY; CHICKENPOX; CONCENTRATION RESPONSE; CROSS RESISTANCE; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME PHOSPHORYLATION; HERPES ZOSTER; MOLECULAR MODEL; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; VARICELLA ZOSTER VIRUS; VIRUS INHIBITION; VIRUS ISOLATION; VIRUS REPLICATION; VIRUS STRAIN;

ANIMALS; BICYCLO COMPOUNDS; HERPESVIRUS 3, HUMAN; HUMANS; PYRIMIDINE NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 0037404522     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/med.10035     Document Type: Review

References (39)

1. Gnann JW, Jr., Whitley RJ. Herpes zoster. N Engl J Med 2002;347:340-346.
2. Gross G, Schöfer H, Wassilew S, Friese K, Timm A, Guthoff R, Pau HW, Malin JP, Wutzler P, Doerr HW. Herpes zoster. Guideline of the German Dermatology Society (DDG). J Clin Virol 2002; (Submitted).
3. McGuigan C, Yarnold CJ, Jones G, Velázquez S, Barucki H, Brancale A, Andrei G, Snoeck R, De Clercq E, Balzarini J. Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J Med Chem 1999;42:4479-4484.
4. Carangio A, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): Pd-catalysed synthesis of 5-aryl derivatives and their biological evaluation. Antiviral Chem Chemother 2001;12:187-197.
5. Brancale A, Srinivasan S, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Synthesis and antivaricella-zoster virus activity of some novel bicyclic nucleoside inhibitors: Effect of enhanced aqueous solubility. Antiviral Chem Chemother 2000;11:383-393.
6. Srinivasan S, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): The effect of terminal unsaturation in the side chain. Bioorg Med Chem Lett 2001;11:391-393.
7. Brancale A, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): The effect of a terminal halogen substitution in the side-chain. Bioorg Med Chem Lett 2000;10:1215-1217.
8. Brancale A, McGuigan C, Algain B, Savy P, Benhida R, Fourrey J-L, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic anti-VZV nucleosides: Thieno analogues retain full antiviral activity. Bioorg Med Chem Lett 2001;11:2507-2510.
9. McGuigan C, Pathirana RN, Jones G, Andrei G, Snoeck R, De Clercq E, Balzarini J. Anti-varicella-zoster virus bicyclic nucleosides: Replacement of furo by pyrro base reduces antiviral potency. Antiviral Chem Chemother 2000;11:343-348.
10. McGuigan C, Barucki H, Blewett S, Carangio A, Erichsen JT, Andrei G, Snoeck R, De Clercq E, Balzarini J. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. J Med Chem 2000;4993-4997.
11. Balzarini J, McGuigan C. Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides. Biochim Biophys Acta 2002;1587:287-295.
12. McGuigan C, Brancale A, Barucki H, Srinivasan S, Jones G, Pathirana R, Carangio A, Blewett S, Luoni G, Bidet O, Jukes A, Jarvis C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Furano pyrimidines as novel potent and selective anti-VZV agents. Antiviral Chem Chemother 2001;12:77-89.
13. Luoni G, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus: The effect of branching in the p-alkylphenyl side-chain. Abstracts of the Fifteenth International Conference on Antiviral Research, Prague, Czech Republic, 17-21 March 2002. Antiviral Res 2002;53: p A59 (no. 79).
14. Carangio A, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Anti-varicella-zoster virus bicyclic nucleosides: Synthesis and in vitro evaluation of 2′,3′-dideoxynucleoside derivatives. Abstracts of the Fifteenth International Conference on Antiviral Research, Prague, Czech Republic, 17-21 March 2002. Antiviral Res 2002;53: p A59, no. 80.
15. McGuigan C, Blewett S, Siccardi D, Erichsen JT, Andrei G, Snoeck R, De Clercq E, Balzarini J. Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility. Antiviral Chem Chemother 2002;13:91-99.
16. Bidet O, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Synthesis of unusual bicyclic nucleosides bearing an unsaturated side-chain, as potential inhibitors of varicella-zoster virus (VZV). XV International Round Table on Nucleosides, Nucleotides and Nucleic Acids, Leuven, Belgium, 10-14 September 2002. Abstracts, p 53.
17. Luoni G, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic furano pyrimidine nucleoside inhibitors of varicella-zoster virus: 5′-chloro and 3′-chloro derivatives. XV International Round Table on Nucleosides, Nucleotides and Nucleic Acids, Leuven, Belgium, 10-14 September 2002. Abstracts, p 87.
18. Carangio A, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus: Synthesis and biological evaluation of 2′,3′-dideoxy-3′-fluoro and 2′-deoxy-xylo derivatives. XV International Round Table on Nucleosides, Nucleotides and Nucleic Acids, Leuven, Belgium, 10-14 September 2002. Abstracts, p 88.
19. Sevillano LG, Angell A, McGuigan C, Andrei G, Snoeck R, De Clercq E, Balzarini J. Bicyclic thienopyrimidine nucleosides bearing an alkylaryl side chain as inhibitors of varicella-zoster virus. XV International Round Table on Nucleosides, Nucleotides and Nucleic Acids, Leuven, Belgium, 10-14 September 2002. Abstracts, p 99.
20. McGuigan C, Pathirana RN, Carangio A, Andrei G, Snoeck R, De Clercq E, Balzarini J. Discovery of a new family of anti-CMV nucleosides based on lipophilic dideoxyribofurano pyrimidines. XV International Round Table on Nucleosides, Nucleotides and Nucleic Acids, Leuven, Belgium, 10-14 September 2002. Abstracts, p 105.
21. De Clercq E, Degreef H, Wildiers J, de Jonge G, Drochmans A, Descamps J, De Somer P. Oral (E)-5-(2-bromovinyl)-2′-deoxyuridine in severe herpes zoster. Br Med J 1980;281:1178.
22. Shigeta S, Yokota T, Iwabuchi T, Baba M, Konno K, Ogata M, De Clercq E. Comparative efficacy of antiherpes drugs against various strains of varicella-zoster virus. J Infect Dis 1983;147:576-584.
23. De Clercq E. The antiviral spectrum of (E)-5-(2-bromovinyl)-2′-deoxyuridine. J Antimicrob Chemother 1984;14(Suppl A):85-95.
24. Andrei G, Snoeck R, Reymen D, Liesnard D, Goubau P, Desmyter J, De Clercq E. Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. Eur J Clin Microbiol Infect Dis 1995;14:318-328.
25. Andrei G, Sienaert R, Naesens L, De Clercq E, McGuigan C, Balzarini J, Snoeck R. Susceptibilities of several drug-resistant varicella-zoster virus (VZV) strains to bicyclic pyrimidine nucleoside analogues (BCNAs). Abstracts of the Fifteenth International Conference on Antiviral Research, Prague, Czech Republic, 17-21 March 2002. Antiviral Res 2002;53: p A59, no. 81.
26. Safrin S, Berger TG, Gilson I, Wolfe PR, Wofsy CB, Mills J, Biron KK. Foscarnet therapy in five patients with AIDS and acyclovir-resistant varicella-zoster virus infection Ann Intern Med 1991;115:19-21.
27. Sienaert R, Naesens L, Brancale A, De Clercq E, McGuigan C, Balzarini J. Specific recognition of the bicyclic pyrimidine nucleoside analogs, a new class of highly potent and selective inhibitors of varicella-zoster virus (VZV), by the VZV-encoded thymidine kinase. Mol Pharmacol 2002;61:249-254.
28. Desgranges C, Razaka G, Rabaud M, Bricaud H, Balzarini J, De Clercq E. Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted 2′-deoxyuridines by purified human thymidine phosphorylase and intact blood platelets. Biochem Pharmacol 1983;32:3583-3590.
29. Liermann B, Hermann G. (E)-5-(2-Bromovinyl)-2′-deoxyuridine: A good substrate for mammalian pyrimidine nucleoside phosphorylases. Biomed Biochim Acta 1983;42:K35-K38.
30. Balzarini J, Sienaert R, Liekens S, Van Kuilenburg A, Carangio A, Esnouf R, De Clercq E, McGuigan C. Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase. Mol Pharmacol 2002;61:1140-1145.
31. Walter MR, Cook WJ, Cole LB, Short SA, Koszalka GW, Krenitsky TA, Ealick SE. Three-dimensional structure of thymidine phosphorylase from Escherichia coli at 2.8 Å resolution. J Biol Chem 1990;265:14016-14022.
32. Esnouf R. Further additions of MolScript version 1.4, including reading and contouring of the electron-density maps. Acta Crystallogr 1999;D 55:938-940.
33. Desgranges C, Razaka G, De Clercq E, Herdewijn P, Balzarini J, Drouillet F, Bricaud H. Effect of (E)-5-(2-bromovinyl)uracil on the catabolism and antitumor activity of 5-fluorouracil in rats and leukemic mice. Cancer Res 1986;46:1094-1101.
34. Diasio RB. Sorivudine and 5-fluorouracil: A clinically significant drug-drug interaction due to inhibition of dihydropyrimidine dehydrogenase. Br J Clin Pharmacol 1998;46:1-4.
35. Nakayama H, Kinouchi T, Kataoka K, Akimoto S, Matsuda Y, Ohnishi Y. Intestinal anaerobic bacteria hydrolyse sorivudine, producing the high blood concentration of 5-(E)-5-(2-bromovinyl)uracil that increases the level and toxicity of 5-fluorouracil. Pharmacogenetics 1997;7:5-43.
36. Okuda H, Ogura K, Kato A, Takubo H, Watabe T. A possible mechanism of eighteen patient deaths caused by interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs. J Pharmacol Exp Ther 1998;287:791-799.
37. De Clercq E, Walker RT. Chemotherapeutic agents for herpesvirus infections. In: Ellis GP, West GB, editors. Progress in medicinal chemistry. Amsterdam, the Netherlands: Elsevier Science Publishers B.V. (Biomedical Division); 1986. Vol. 23: p 187-218.
38. De Clercq E. Towards a selective chemotherapy of virus infections. Development of bromovinyldeoxyuridine as a highly potent and selective anti-herpetic drug. Verh K Acad Geneesk Belg 1986;48:261-290.
39. De Clercq E. Antiviral activity of nucleoside analogues: The BVDU connection. In: Chu D, editor. Recent Advances in Nucleosides: Chemistry and Chemotherapy. New York, NY, USA: Elsevier Science B.V.; 2002, 433-454.