Mechanism of inhibition of HIV-1 reverse transcriptase by 4′-ethynyl-2-fluoro-2′-deoxyadenosine triphosphate, a translocation-defective reverse transcriptase inhibitor

Journal of Biological Chemistry

Volumn 284, Issue 51, 2009, Pages 35681-35691

  Michailidis, Eleftherios ^a   Marchand, Bruno ^a   Kodama, Eiichi N ^b,g   Singh, Kamlendra ^a   Matsuoka, Masao ^b   Kirby, Karen A ^a   Ryan, Emily M ^a   Sawani, Ali M ^a   Nagy, Eva ^c   Ashida, Noriyuki ^d   Mitsuya, Hiroaki ^e,f   Parniak, Michael A ^c   Sarafianos, Stefan G ^a,h  

^a University of Missouri   (United States)

^b KYOTO UNIVERSITY   (Japan)

^c UNIVERSITY OF PITTSBURGH   (United States)

^d YAMASA CORPORATION   (Japan)

^e KUMAMOTO UNIVERSITY   (Japan)

^f NATIONAL INSTITUTES OF HEALTH   (United States)

^g TOHOKU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^h NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CHAINS; ANTIVIRAL ACTIVITIES; ANTIVIRAL NUCLEOSIDE; DE FACTO; DEOXYADENOSINE; DNA SYNTHESISS; ETHYNYL; HIV-1 REVERSE TRANSCRIPTASE; HUMAN IMMUNODEFICIENCY VIRUS; HYDROPHOBIC POCKETS; HYDROXYL GROUPS; HYDROXYL MOIETY; MECHANISM OF ACTION; MOLECULAR MODELING STUDIES; MONOPHOSPHATES; NATURAL SUBSTRATES; ORDERS OF MAGNITUDE; PERIPHERAL BLOOD MONONUCLEAR CELLS; PHOSPHOROLYSIS; REVERSE TRANSCRIPTASES; TRIPHOSPHATE;

BIOMOLECULES; DNA; ENZYME INHIBITION; FLUORINE CONTAINING POLYMERS; GENES; NUCLEIC ACIDS;

VIRUSES;

4' ETHYNYL 2 FLUORO 2' DEOXYADENOSINE TRIPHOSPHATE; ALANINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ASPARTIC ACID; METHIONINE; NUCLEIC ACID; PHENYLALANINE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; TYROSINE; UNCLASSIFIED DRUG; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CELL ACTIVATION; CONTROLLED STUDY; DNA SYNTHESIS; DRUG BINDING SITE; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SUBSTRATE; GENE TRANSLOCATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROPHOBICITY; MOLECULAR MODEL; NORMAL HUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; RESIDUE ANALYSIS; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

DEOXYADENINE NUCLEOTIDES; DNA, VIRAL; HIV INFECTIONS; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; HYDROPHOBICITY; LEUKOCYTES, MONONUCLEAR; MODELS, MOLECULAR; PROTEIN STRUCTURE, SECONDARY; REVERSE TRANSCRIPTASE INHIBITORS; REVERSE TRANSCRIPTION; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 72149100464     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.036616     Document Type: Article

References (50)

1. Hammer, S. M., Saag, M. S., Schechter, M., Montaner, J. S., Schooley, R. T., Jacobsen, D. M., Thompson, M. A., Carpenter, C. C., Fischl, M. A., Gazzard, B. G., Gatell, J. M., Hirsch, M. S., Katzenstein, D. A., Richman, D. D., Vella, S., Yeni, P. G., and Volberding, P. A. (2006) Top. HIV Med. 14, 827-843
2. Schinazi, R. F., Hernandez-Santiago, B. I., and Hurwitz, S. J. (2006) Antiviral Res. 71, 322-334
3. Parniak, M. A., and Sluis-Cremer, N. (2000) Adv. Pharmacol. 49, 67-109
4. De Clercq, E. (2007) Verh. K. Acad. Geneeskd. Belg. 69, 81-104
5. Sluis-Cremer, N., and Tachedjian, G. (2008) Virus Res. 134, 147-156
6. Deval, J. (2009) Drugs 69, 151-166
7. Sharma, P. L., Nurpeisov, V., Hernandez-Santiago, B., Beltran, T., and Schinazi, R. F. (2004) Curr. Top. Med. Chem. 4, 895-919
8. Sarafianos, S. G., Marchand, B., Das, K., Himmel, D. M., Parniak, M. A., Hughes, S. H., and Arnold, E. (2009) J. Mol. Biol. 385, 693-713
9. Gallois-Montbrun, S., Schneider, B., Chen, Y., Giacomoni-Fernandes, V., Mulard, L., Morera, S., Janin, J., Deville-Bonne, D., and Veron, M. (2002) J. Biol. Chem. 277, 39953-39959
10. Kodama, E. I., Kohgo, S., Kitano, K., Machida, H., Gatanaga, H., Shigeta, S., Matsuoka, M., Ohrui, H., and Mitsuya, H. (2001) Antimicrob. Agents Chemother. 45, 1539-1546
11. Ohrui, H., and Mitsuya, H. (2001) Curr. Drug Targets Infect. Disord. 1, 1-10
12. Ohrui, H., Kohgo, S., Hayakawa, H., Kodama, E., Matsuoka, M., Nakata, T., and Mitsuya, H. (2006) Nucleic Acids Symp. Ser. (Oxf.) 2006, 1-2
13. Kawamoto, A., Kodama, E., Sarafianos, S. G., Sakagami, Y., Kohgo, S., Kitano, K., Ashida, N., Iwai, Y., Hayakawa, H., Nakata, H., Mitsuya, H., Arnold, E., and Matsuoka, M. (2008) Int. J. Biochem. Cell Biol. 40, 2410-2420
14. White, K. L., Chen, J. M., Feng, J. Y., Margot, N. A., Ly, J. K., Ray, A. S., Macarthur, H. L., McDermott, M. J., Swaminathan, S., and Miller, M. D. (2006) Antivir. Ther. 11, 155-163
15. Mascolini, M., Larder, B. A., Boucher, C. A., Richman, D. D., and Mellors, J. W. (2008) Antivir. Ther. 13, 1097-1113
16. Le Grice, S. F., and Grüninger-Leitch, F. (1990) Eur. J. Biochem. 187, 307-314
17. Meyer, P. R., Matsuura, S. E., So, A. G., and Scott, W. A. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 13471-13476
18. Bøyum, A., Løvhaug, D., Tresland, L., and Nordlie, E. M. (1991) Scand. J. Immunol. 34, 697-712
19. Marchand, B., and Götte, M. (2003) J. Biol. Chem. 278, 35362-35372
20. Biaglow, J. E., and Kachur, A. V. (1997) Radiat. Res. 148, 181-187
21. Siddiqui, M. A., Hughes, S. H., Boyer, P. L., Mitsuya, H., Van, Q. N., George, C., Sarafinanos, S. G., and Marquez, V. E. (2004) J. Med. Chem. 47, 5041-5048
22. Stewart, J. J. P. (1989) J. Comput. Chem. 10, 209-220
23. Hattori, S., Ide, K., Nakata, H., Harada, H., Suzu, S., Ashida, N., Kohgo, S., Hayakawa, H., Mitsuya, H., and Okada, S. (2009) Antimicrob. Agents Chemother. 53, 3887-3893
24. Quan, Y., Liang, C., Inouye, P., and Wainberg, M. A. (1998) Nucleic Acids Res. 26, 5692-5698
25. Tong, W., Lu, C. D., Sharma, S. K., Matsuura, S., So, A. G., and Scott, W. A. (1997) Biochemistry 36, 5749-5757
26. Sluis-Cremer, N., Arion, D., and Parniak, M. A. (2000) Cell. Mol. Life Sci. 57, 1408-1422
27. Arion, D., Kaushik, N., McCormick, S., Borkow, G., and Parniak, M. A. (1998) Biochemistry 37, 15908-15917
28. Meyer, P. R., Matsuura, S. E., Mian, A. M., So, A. G., and Scott, W. A. (1999) Mol. Cell 4, 35-43
29. Sarafianos, S. G., Clark, A. D., Jr., Das, K., Tuske, S., Birktoft, J. J., Ilankumaran, P., Ramesha, A. R., Sayer, J. M., Jerina, D. M., Boyer, P. L., Hughes, S. H., and Arnold, E. (2002) EMBO J. 21, 6614-6624
30. Sarafianos, S. G., Clark, A. D., Jr., Tuske, S., Squire, C. J., Das, K., Sheng, D., Ilankumaran, P., Ramesha, A. R., Kroth, H., Sayer, J. M., Jerina, D. M., Boyer, P. L., Hughes, S. H., and Arnold, E. (2003) J. Biol. Chem. 278, 16280-16288
31. Tuske, S., Sarafianos, S. G., Clark, A. D., Jr., Ding, J., Naeger, L. K., White, K. L., Miller, M. D., Gibbs, C. S., Boyer, P. L., Clark, P., Wang, G., Gaffney, B. L., Jones, R. A., Jerina, D. M., Hughes, S. H., and Arnold, E. (2004) Nat. Struct. Mol. Biol. 11, 469-474
32. Yang, G., Wang, J., Cheng, Y., Dutschman, G. E., Tanaka, H., Baba, M., and Cheng, Y. C. (2008) Antimicrob. Agents Chemother. 52, 2035-2042
33. Sluis-Cremer, N., Arion, D., Parikh, U., Koontz, D., Schinazi, R. F., Mellors, J. W., and Parniak, M. A. (2005) J. Biol. Chem. 280, 29047-29052
34. Marchand, B., White, K. L., Ly, J. K., Margot, N. A., Wang, R., McDermott, M., Miller, M. D., and Götte, M. (2007) Antimicrob. Agents Chemother. 51, 2911-2919
35. Feng, J. Y., Murakami, E., Zorca, S. M., Johnson, A. A., Johnson, K. A., Schinazi, R. F., Furman, P. A., and Anderson, K. S. (2004) Antimicrob. Agents Chemother. 48, 1300-1306
36. Nakata, H., Amano, M., Koh, Y., Kodama, E., Yang, G., Bailey, C. M., Kohgo, S., Hayakawa, H., Matsuoka, M., Anderson, K. S., Cheng, Y. C., and Mitsuya, H. (2007) Antimicrob. Agents Chemother. 51, 2701-2708
37. Strerath, M., Cramer, J., Restle, T., and Marx, A. (2002) J. Am. Chem. Soc. 124, 11230-11231
38. Boyer, P. L., Julias, J. G., Marquez, V. E., and Hughes, S. H. (2005) J. Mol. Biol. 345, 441-450
39. Boyer, P. L., Julias, J. G., Ambrose, Z., Siddiqui, M. A., Marquez, V. E., and Hughes, S. H. (2007) J. Mol. Biol. 371, 873-882
40. Tchesnokov, E. P., Obikhod, A., Schinazi, R. F., and Götte, M. (2008) J. Biol. Chem. 283, 34218-34228
41. Summerer, D., and Marx, A. (2005) Bioorg. Med. Chem. Lett. 15, 869-871
42. Di Pasquale, F., Fischer, D., Grohmann, D., Restle, T., Geyer, A., and Marx, A. (2008) J. Am. Chem. Soc. 130, 10748-10757
43. Maag, H., Rydzewski, R. M., McRoberts, M. J., Crawford-Ruth, D., Verheyden, J. P., and Prisbe, E. J. (1992) J. Med. Chem. 35, 1440-1451
44. Chen, M. S., Suttmann, R. T., Papp, E., Cannon, P. D., McRoberts, M. J., Bach, C., Copeland, W. C., and Wang, T. S. (1993) Biochemistry 32, 6002-6010
45. Chen, M. S., Suttmann, R. T., Wu, J. C., and Prisbe, E. J. (1992) J. Biol. Chem. 267, 257-260
46. Maag, H., Nelson, J. T., Steiner, J. L., and Prisbe, E. J. (1994) J. Med. Chem. 37, 431-438
47. Nitanda, T., Wang, X., Kumamoto, H., Haraguchi, K., Tanaka, H., Cheng, Y. C., and Baba, M. (2005) Antimicrob. Agents Chemother. 49, 3355-3360
48. Tanaka, H., Haraguchi, K., Kumamoto, H., Baba, M., and Cheng, Y. C. (2005) Antivir. Chem. Chemother. 16, 217-221
49. Hsu, C. H., Hu, R., Dutschman, G. E., Yang, G., Krishnan, P., Tanaka, H., Baba, M., and Cheng, Y. C. (2007) Antimicrob. Agents Chemother. 51, 1687-1693
50. Yang, G., Dutschman, G. E., Wang, C. J., Tanaka, H., Baba, M., Anderson, K. S., and Cheng, Y. C. (2007) Antiviral Res. 73, 185-191