4′-modified nucleoside analogs: Potent inhibitors active against entecavir-resistant hepatitis B virus

Hepatology

Volumn 62, Issue 4, 2015, Pages 1024-1036

  Takamatsu, Yuki ^a   Tanaka, Yasuhito ^b   Kohgo, Satoru ^c,d   Murakami, Shuko ^b   Singh, Kamalendra ^e   Das, Debananda ^a   Venzon, David J ^a   Amano, Masayuki ^f   Higashi Kuwata, Nobuyo ^c,f   Aoki, Manabu ^a,f,g   Delino, Nicole S ^a   Hayashi, Sanae ^b   Takahashi, Satoru ^b   Sukenaga, Yoshikazu ^c   Haraguchi, Kazuhiro ^d   Sarafianos, Stefan G ^e   Maeda, Kenji ^a,c   Mitsuya, Hiroaki ^a,c,f  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NAGOYA CITY UNIVERSITY GRADUATE SCHOOL OF MEDICAL SCIENCES   (Japan)

^c NATIONAL CENTER FOR GLOBAL HEALTH AND MEDICINE   (Japan)

^d NIHON PHARMACEUTICAL UNIVERSITY   (Japan)

^e UNIVERSITY OF MISSOURI   (United States)

^f KUMAMOTO UNIVERSITY   (Japan)

^g KUMAMOTO HEALTH SCIENCE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4' C CYANO 2 AMINO 2' DEOXYADENOSINE; ANTIVIRUS AGENT; ENTECAVIR; NUCLEOSIDE ANALOG; SERUM ALBUMIN; UNCLASSIFIED DRUG; 4'-C-CYANO-2-AMINO-2'-DEOXYADENOSINE; DEOXYADENOSINE DERIVATIVE; GUANINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; HEPATITIS B; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IC50; MOLECULAR MODEL; MOUSE; NONHUMAN; PRIORITY JOURNAL; VIREMIA; VIRUS INHIBITION; ANALOGS AND DERIVATIVES; ANIMAL; ANTIVIRAL RESISTANCE; DRUG EFFECTS; HUMAN IMMUNODEFICIENCY VIRUS 1;

ANIMALS; DEOXYADENOSINES; DRUG RESISTANCE, VIRAL; GUANINE; HEPATITIS B VIRUS; HIV-1; MICE;

EID: 84942551464     PISSN: 02709139     EISSN: 15273350     Source Type: Journal    
DOI: 10.1002/hep.27962     Document Type: Article

References (38)

1. Shepard CW, Simard EP, Finelli L, Fiore AE, Bell BP. Hepatitis B virus infection: epidemiology and vaccination. Epidemiol Rev 2006;28:112-125.
2. Daniels D, Grytdal S, Wasley A. Surveillance for acute viral hepatitis-United States, 2007. MMWR Surveill Summ 2009;58:1-27.
3. Wasley A, Kruszon-Moran D, Kuhnert W, Simard EP, Finelli L, McQuillan G, et al. The prevalence of hepatitis B virus infection in the United States in the era of vaccination. J Infect Dis 2010;202:192-201.
4. Thio CL, Seaberg EC, Skolasky R, Jr., Phair J, Visscher B, Munoz A, et al. HIV-1, hepatitis B virus, and risk of liver-related mortality in the Multicenter Cohort Study (MACS). Lancet 2002;360:1921-1926.
5. Levy V, Grant RM. Antiretroviral therapy for hepatitis B virus-HIV-coinfected patients: promises and pitfalls. Clin Infect Dis 2006;43:904-910.
6. Lau GK, Piratvisuth T, Luo KX, Marcellin P, Thongsawat S, Cooksley G, et al. Peginterferon Alfa-2a, lamivudine, and the combination for HBeAg-positive chronic hepatitis B. N Engl J Med 2005;352:2682-2695.
7. Buster EH, Flink HJ, Cakaloglu Y, Simon K, Trojan J, Tabak F, et al. Sustained HBeAg and HBsAg loss after long-term follow-up of HBeAg-positive patients treated with peginterferon alpha-2b. Gastroenterology 2008;135:459-467.
8. Levine S, Hernandez D, Yamanaka G, Zhang S, Rose R, Weinheimer S, et al. Efficacies of entecavir against lamivudine-resistant hepatitis B virus replication and recombinant polymerases in vitro. Antimicrob Agents Chemother 2002;46:2525-2532.
9. Fisher EJ, Chaloner K, Cohn DL, Grant LB, Alston B, Brosgart CL, et al. The safety and efficacy of adefovir dipivoxil in patients with advanced HIV disease: a randomized, placebo-controlled trial. AIDS 2001;15:1695-1700.
10. Karras A, Lafaurie M, Furco A, Bourgarit A, Droz D, Sereni D, et al. Tenofovir-related nephrotoxicity in human immunodeficiency virus-infected patients: three cases of renal failure, Fanconi syndrome, and nephrogenic diabetes insipidus. Clin Infect Dis 2003;36:1070-1073.
11. Ohrui H. 2′-Deoxy-4′-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity. Chem Rec 2006;6:133-143.
12. Nakata H, Amano M, Koh Y, Kodama E, Yang G, Bailey CM, et al. Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4′-ethynyl-2-fluoro-2′-deoxyadenosine. Antimicrob Agents Chemother 2007;51:2701-2708.
13. Kawamoto A, Kodama E, Sarafianos SG, Sakagami Y, Kohgo S, Kitano K, et al. 2′-Deoxy-4′-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants. Int J Biochem Cell Biol 2008;40:2410-2420.
14. Hattori S, Ide K, Nakata H, Harada H, Suzu S, Ashida N, et al. Potent activity of a nucleoside reverse transcriptase inhibitor, 4′-ethynyl-2-fluoro-2′-deoxyadenosine, against human immunodeficiency virus type 1 infection in a model using human peripheral blood mononuclear cell-transplanted NOD/SCID Janus kinase 3 knockout mice. Antimicrob Agents Chemother 2009;53:3887-3893.
15. Michailidis E, Marchand B, Kodama EN, Singh K, Matsuoka M, Kirby KA, et al. Mechanism of inhibition of HIV-1 reverse transcriptase by 4′-Ethynyl-2-fluoro-2′-deoxyadenosine triphosphate, a translocation-defective reverse transcriptase inhibitor. J Biol Chem 2009;284:35681-35691.
16. Murphey-Corb M, Rajakumar P, Michael H, Nyaundi J, Didier PJ, Reeve AB, et al. Response of simian immunodeficiency virus to the novel nucleoside reverse transcriptase inhibitor 4′-ethynyl-2-fluoro-2′-deoxyadenosine in vitro and in vivo. Antimicrob Agents Chemother 2012;56:4707-4712.
17. Merck Signs Two Deals for Novel HIV Drug Candidates and Initiates Phase II Clinical Trial of MK-1439 for HIV. MERCK. Available at: http://www.merck.com/licensing/our-partnership/Merck-chimerix-partnership.html. Accessed December 9, 2014.
18. Kohgo S, Yamada K, Kitano K, Iwai Y, Sakata S, Ashida N, et al. Design, efficient synthesis, and anti-HIV activity of 4′-C-cyano- and 4′-C-ethynyl-2′-deoxy purine nucleosides. Nucleosides Nucleotides Nucleic Acids 2004;23:671-690.
19. Sugiyama M, Tanaka Y, Kato T, Orito E, Ito K, Acharya SK, et al. Influence of hepatitis B virus genotypes on the intra- and extracellular expression of viral DNA and antigens. Hepatology 2006;44:915-924.
20. Sells MA, Chen ML, Acs G. Production of hepatitis B virus particles in HepG2 cells transfected with cloned hepatitis B virus DNA. Proc Natl Acad Sci U S A 1987;84:1005-1009.
21. Birkus G, Hitchcock MJ, Cihlar T. Assessment of mitochondrial toxicity in human cells treated with tenofovir: comparison with other nucleoside reverse transcriptase inhibitors. Antimicrob Agents Chemother 2002;46:716-723.
22. Weckbecker G, Cory JG. 2, 6-Diaminopurinedeoxyriboside as a prodrug of deoxyguanosine in L1210 cells. Cancer Res 1987;47:2218-2223.
23. Mitsuya H, Weinhold KJ, Furman PA, St Clair MH, Lehrman SN, Gallo RC, et al. 3′-Azido-3′-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A 1985;82:7096-7100.
24. Mitsuya H, Broder S. Strategies for antiviral therapy in AIDS. Nature 1987;325:773-778.
25. Das K, Xiong X, Yang H, Westland CE, Gibbs CS, Sarafianos SG, et al. Molecular modeling and biochemical characterization reveal the mechanism of hepatitis B virus polymerase resistance to lamivudine (3TC) and emtricitabine (FTC). J Virol 2001;75:4771-4779.
26. Allen MI, Deslauriers M, Andrews CW, Tipples GA, Walters KA, Tyrrell DL, et al. Identification and characterization of mutations in hepatitis B virus resistant to lamivudine. Lamivudine Clinical Investigation Group. Hepatology 1998;27:1670-1677.
27. Bartholomeusz A, Tehan BG, Chalmers DK. Comparisons of the HBV and HIV polymerase, and antiviral resistance mutations. Antivir Ther 2004;9:149-160.
28. Maag H, Rydzewski RM, McRoberts MJ, Crawford-Ruth D, Verheyden JP, Prisbe EJ. Synthesis and anti-HIV activity of 4′-azido- and 4′-methoxynucleosides. J Med Chem 1992;35:1440-1451.
29. O-Yang C, Wu HY, Fraser-Smith EB, Walker KAM. Synthesis of 4′-cyanothymidine and analogs as potent inhibitors of HIV. Tetrahedron Lett 1992;33:37-40.
30. Kohgo S, Kodama E, Shigeta S, Saneyoshi M, Machida H, Ohrui H. Synthesis of 4′-substituted nucleosides and their biological evaluation. Nucleic Acids Symp Ser 1999;42:127-128.
31. Kodama EI, Kohgo S, Kitano K, Machida H, Gatanaga H, Shigeta S, et al. 4′-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro. Antimicrob Agents Chemother 2001;45:1539-1546.
32. Maeda K, Desai DV, Aoki M, Nakata H, Kodama EN, Mitsuya H. Delayed emergence of HIV-1 variants resistant to 4′-ethynyl-2-fluoro-2′-deoxyadenosine: comparative sequential passage study with lamivudine, tenofovir, emtricitabine and BMS-986001. Antivir Ther 2014;19:179-189.
33. Michailidis E, Huber AD, Ryan EM, Ong YT, Leslie MD, Matzek KB, et al. 4′-Ethynyl-2-fluoro-2′-deoxyadenosine (EFdA) inhibits HIV-1 reverse transcriptase with multiple mechanisms. J Biol Chem 2014;289:24533-24548.
34. Dienstag JL. Hepatitis B virus infection. N Engl J Med; 2008;359:1486-1500.
35. Seok JI, Lee DK, Lee CH, Park MS, Kim SY, Kim HS, et al. Long-term therapy with clevudine for chronic hepatitis B can be associated with myopathy characterized by depletion of mitochondrial DNA. Hepatology 2009;49:32080-2086.
36. Seifer M, Hamatake RK, Colonno RJ, Standring DN. In vitro inhibition of hepadnavirus polymerases by the triphosphates of BMS-200475 and lobucavir. Antimicrob Agents Chemother 1998;42:3200-3208.
37. Hayashi S, Murakami S, Omagari K, Matsui T, Iio E, Isogawa M, et al. Characterization of novel entecavir resistance mutations. J Hepatol 2015 Mar 25. pii: S0168-8278(15)00203-2. doi: 10.1016/j.jhep.2015.03.020. [Epub ahead of print]
38. Srinivas RV, Robbins BL, Connelly MC, Gong YF, Bischofberger N, Fridland A. Metabolism and in vitro antiretroviral activities of bis(pivaloyloxymethyl) prodrugs of acyclic nucleoside phosphonates. Antimicrob Agents Chemother 1993;37:2247-2250.