CD4 mimics targeting the mechanism of HIV entry

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 1, 2010, Pages 354-358

  Yamada, Yuko ^a   Ochiai, Chihiro ^a   Yoshimura, Kazuhisa ^b   Tanaka, Tomohiro ^a   Ohashi, Nami ^a   Narumi, Tetsuo ^a   Nomura, Wataru ^a   Harada, Shigeyoshi ^b   Matsushita, Shuzo ^b   Tamamura, Hirokazu ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

Author keywords

CD4 mimic; CXCR4; HIV entry; Synergistic effect

Indexed keywords

CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; GLYCOPROTEIN GP 120; N (4 BROMOPHENYL) N' (2,2,6,6 TETRAMETHYLPIPERIDIN 4 YL)OXALAMIDE; N (4 CHLOROPHENYL) N' (2,2,6,6 TETRAMETHYLPIPERIDIN 4 YL)OXALAMIDE; T 140; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CD4+ T LYMPHOCYTE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; PROTEIN CONFORMATION; STRUCTURE ACTIVITY RELATION; SUPRAMOLECULAR CHEMISTRY; VIRUS ENTRY;

ANTI-HIV AGENTS; ANTIGENS, CD4; BINDING SITES; CELL LINE; HIV ENVELOPE PROTEIN GP120; HIV FUSION INHIBITORS; HUMANS; RECEPTORS, CXCR4; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 72049125590     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.098     Document Type: Article

References (32)

1. Mitsuya H., and Erickson J. In: Merigan T.C., Bartlett J.G., and Bolognesi D. (Eds). Textbook of AIDS Medicine (1999), Williams & Wilkins, Baltimore 751-780
2. Chan D.C., and Kim P.S. Cell 93 (1998) 681
3. Alkhatib G., Combadiere C., Broder C.C., Feng Y., Kennedy P.E., Murphy P.M., and Berger E.A. Science 272 (1996) 1955
4. Choe H., Farzan M., Sun Y., Sullivan N., Rollins B., Ponath P.D., Wu L., Mackay C.R., LaRosa G., Newman W., Gerard N., Gerard C., and Sodroski J. Cell 85 (1996) 1135
5. Deng H.K., Liu R., Ellmeier W., Choe S., Unutmaz D., Burkhart M., Marzio P.D., Marmon S., Sutton R.E., Hill C.M., Davis C.B., Peiper S.C., Schall T.J., Littman D.R., and Landau N.R. Nature 381 (1996) 661
6. Doranz B.J., Rucker J., Yi Y.J., Smyth R.J., Samson M., Peiper S.C., Parmentier M., Collman R.G., and Doms R.W. Cell 85 (1996) 1149
7. Dragic T., Litwin V., Allaway G.P., Martin S.R., Huang Y., Nagashima K.A., Cayanan C., Maddon P.J., Koup R.A., Moore J.P., and Paxton W.A. Nature 381 (1996) 667
8. Feng Y., Broder C.C., Kennedy P.E., and Berger E.A. Science 272 (1996) 872
9. Wild C.T., Greenwell T.K., and Matthews T.J. AIDS Res. Hum. Retroviruses 9 (1993) 1051
10. Dorr P., Westby M., Dobbs S., Griffin P., Irvine B., Macartney M., Mori J., Rickett G., Smith-Burchnell C., Napier C., Webster R., Armour D., Price D., Stammen B., Wood A., and Perros M. Antimicrob. Agents Chemother. 49 (2005) 4721
11. Price D.A., Armour D., De Groot M., Leishman D., Napier C., Perros M., Stammen B.L., and Wood A. Bioorg. Med. Chem. Lett. 16 (2006) 4633
12. Cahn P., and Sued O. Lancet 369 (2007) 1235
13. Grinsztejn B., Nguyen B.-Y., Katlama C., Gatell J.M., Lazzarin A., Vittecoq D., Gonzalez C.J., Chen J., Harvey C.M., and Isaacs R.D. Lancet 369 (2007) 1261
14. Tamamura H., Xu Y., Hattori T., Zhang X., Arakaki R., Kanbara K., Omagari A., Otaka A., Ibuka T., Yamamoto N., Nakashima H., and Fujii N. Biochem. Biophys. Res. Commun. 253 (1998) 877
15. Fujii N., Oishi S., Hiramatsu K., Araki T., Ueda S., Tamamura H., Otaka A., Kusano S., Terakubo S., Nakashima H., Broach J.A., Trent J.O., Wang Z., and Peiper S.C. Angew. Chem., Int. Ed. 42 (2003) 3251
16. Tanaka T., Nomura W., Narumi T., Esaka A., Oishi S., Ohashi N., Itotani K., Evans B.J., Wang Z., Peiper S.C., Fujii N., and Tamamura H. Org. Biomol. Chem. 7 (2009) 3805
17. Otaka A., Nakamura M., Nameki D., Kodama E., Uchiyama S., Nakamura S., Nakano H., Tamamura H., Kobayashi Y., Matsuoka M., and Fujii N. Angew. Chem., Int. Ed. 41 (2002) 2937
18. Zhao Q., Ma L., Jiang S., Lu H., Liu S., He Y., Strick N., Neamati N., and Debnath A.K. Virology 339 (2005) 213
19. Schön A., Madani N., Klein J.C., Hubicki A., Ng D., Yang X., Smith III A.B., Sodroski J., and Freire E. Biochemistry 45 (2006) 10973
20. Madani N., Schön A., Princiotto A.M., LaLonde J.M., Courter J.R., Soeta T., Ng D., Wang L., Brower E.T., Xiang S.-H., Do Kwon Y., Huang C.-C., Wyatt R., Kwong P.D., Freire E., Smith III A.B., and Sodroski J. Structure 16 (2008) 1689
21. Haim H., Si Z., Madani N., Wang L., Courter J.R., Princiotto A., Kassa A., DeGrace M., McGee-Estrada K., Mefford M., Gabuzda D., Smith III A.B., and Sodroski J. ProS Pathogens 5 (2009) 1
22. 475, and included residues located within a radius 4.4 Å. The ligand was considered to be flexible, and all other options were set to their default values. Figures were generated with ViewerLite version 5.0 (Accelrys Inc., San Diego, CA).
23. + 318.2182, found 318.2173.
24. McFarland C., Vicic D.A., and Debnath A.K. Synthesis (2006) 807
25. + 349.1876, found 349.1871.
26. Yoshimura K., Shibata J., Kimura T., Honda A., Maeda Y., Koito A., Murakami T., Mitsuya H., and Matsushita S. AIDS 20 (2006) 2065
27. Chapman N.B., and Shorter J. Advances in Linear Free Energy Relationship (1972), Plenum Press, London
28. Chapman N.B., and Shorter J. Correlation Analysis in Chemistry (1978), Plenum Press, London
29. Hansch C., Leo A.J., and Hoekman D. Exploring QSAR, Hydrophobic, Electronic, and Steric Constants (1995), American Chemical Society, Washington, DC
30. Taft R.W. In: Newman M.S. (Ed). Steric Effects in Organic Chemistry (1956), John Wiley, New York 556
31. Chou T.C., and Talalay P. J. Biol. Chem. 252 (1977) 6438
32. Chou T.C., and Hayball M.P. CalcuSyn. 2nd ed. (1996), Biosoft, Cambridge, UK