Tetrahydroxy cyclic urea-potent inhibitor for HIV-1 protease wild type and mutant type - A computational design

E-Journal of Chemistry

Volumn 5, Issue 3, 2008, Pages 584-592

  Sree Kanth, S ^a   Vijjulatha, M ^a  

^a OSMANIA UNIVERSITY   (India)

Author keywords

ADME; CU (Cyclic urea); Docking; MMFF94s; OPLS AA; THCU (Terahydroxy cyclic urea)

Indexed keywords

EID: 52649117641     PISSN: None     EISSN: 09734945     Source Type: Journal    
DOI: 10.1155/2008/154030     Document Type: Article

References (33)

1. (a) Tomasselli A G, Howe W J, Sawyer T K, Wlodawer A and Heinrikson R L, Chimica Ogg.,1991, 6-27.
2. (b) Huff J R, Med. Chem J, 1991, 34, 2305-2314.
3. (c) Norbeck D W and Kempf D J, Annu. Rep, Med. Chem, 1991, 26, 141-160.
4. (d) Debouck C, AIDS Res. Hum. Retroviruses, 1992, 8, 153-164.
5. (e) Katz R A and Skalka A M, Annu. Rev. Biochem, 1994, 63, 133-173.
6. (a) Wei X, Gosh S K, Taylor M E, Johnson V A, Emini E A, Deutsch P, Lifson J D, Bonhoeffer S, Nowak M A, Hahn B H, Saag M S and Shaw G M, Nature, 1995, 373 117-122.
7. (b) Ho D D, Neumann A U, Perelson A S, Chen W, Leonard J M and Markowitz M, Nature, 1995, 373,123-126.
8. (c) Kempf D, Marsh K C, Denissen J F, McDonald E, Vasavanonda S, Flentge C A, Green B G, Fino L, Park C H, Kong X P, Wideburg N E, Saldivar A, Ruiz L, Kati W M, Sham H L, Robins T, Stewart K D, Hsu A, Plattner J J, Leonard J M and Norbeck D W, Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2484-2488.
9. Rutenber E, Fauman E B, Keenan R J, Fong S, Furth S P, Oritizde P R, Montellano D L, DeCamp, Babe L M and Craik C S, Proc. Natl. Acad. Sci, USA, 1990, 87, 6644-6648.
10. Humber D C, Cammack N, Coates J, Cobley K N, Orr D C, Storer R, Weingarten G G and Weir M P, J. Med. Chem, 1992, 35, 3080-3081.
11. Lam S P Y, Jadhav P K, Eyermann C J, Hodge C N, Ru Y, Bacheler L T, Meek J L, Otto M J, Rayner M M, Wong Y N, Chang C H, Weber P C, Sharpe T R, Jackson D A and Erickson-Viitanen S, Science, 1994, 263, 380-384.
12. Schrödinger, LLC, New York, NY, Glide, Version 4.0, 2005.
13. QikProp, Version 2.5, Schrödinger, LLC, New York, NY, 2005.
14. Sham H L, Zhao C, Stewert K D, Betebenner D A, Lin S, Park C H, Knong X P, Rosenbrook W J, Herrin T, Madigan D, Vasavaononda S, Lyons N, Molla A, Saldivar A, Marsh K C, McDonald E, Wideburg N E, Platter J F and Norbeck D W, J. Med. Chem, 1996, 39, 392-397.
15. Yamazaki T, Hinck A P, WangY X, Nicholson L K, Torichia D A, Wingfield P, Stahl S J, Kanfman J D, Chang C H, Domaille P J and Lam P Y, Protein Sci, 1996, 5, 495-506.
16. Backbro K, Lowgran S, Osterlund K, Atepo J, Unge T, Hulten. J, Bonham N M, Schaal W, Karlen A and Halberg A, J. Med. Chem, 1997, 40, 898-902.
17. Abdel-Meguid S S, Netcalf B W, Carr T J, Demarsh P, Desjarlais R L, Fisher S, Green D W, Ivanoff L, Lambert D M and Murthy K H, Biochemistry, 994, 33, 11671-11677.
18. Chen Z, Li Y, Chen E, Hall D L, Darke P L, Culberson C, Shafer J A and Kho L C, J. Biol. Chem, 1994, 263, 344-348.
19. Thaisrivongs S, Watenpaugh K D, Howe W J, Tomich P K, Doluk L A, Chong K T, Tomich C C, Tomasselli A G, Turner S R and Strohbach J W, J. Med. Chem,1995, 38, 3624-3637.
20. Ala P J, Huston E E, Klabe R M, McCabe D D, Duke J L, Rizzo C J, Korant B D, Deloskey R J, Lam PY, Hodge C N and Chang C H, Biochemistry, 1997, 36, 1573-1580.
21. Richard A Friesner, Jay L Banks, Robert Bm Murphy, Thomas A Halgren, Jasna J Klicic, Daniel T Mainz, Matthew P Repasky, Eric H Knoll, Mee Shelley, Jason K. Perry, David E Shaw, Perry Francis, and Peter S Shenkin J. Med. Chem, 2004, 47, 1739-174
22. Carlson H A and Masukawa K M, McCammon J A, J. Phys. Chem,1999,103,10213-10219.
23. Carlson H A, Masukawa K M, Rubins K, Bushman F D, Jorgensen W L, Lins R D, Briggs J M, McCammon J A, J. Med. Chem. 2000, 43, 2100-2114.
24. Lam PY S, Yu Ru, Jadhav P K, Aldrich P E, DeLucca G V, Eyermann C J, Chang C H, Emmet G, Holler E R, Daneker W F, Li L, Confalone P N, Bacheler L T, Rayner M M, Klabe R M, Shum L, Winslow D L, Kornahouse D M, Jackson D A, Erickson-Viitanen S and C N Hodge, J. Med. Chem. 1996, 39, 3514-3525.
25. Jadhav P K, Ala P, Woerner F J, Chang C H, Garber S S, Anton E D and Bacheler L T, J. Med. Chem. 1997, 40,181-191.
26. Jadhav P K, Woerner F J, Lam PY S, Hodge C N, Eyermann C J, Hon-Wah Man, Daneker W F, Bacheler L T, Rayner M M, Meek J L, Erickson-Viitanen S, Jackson D A, Calabrese J C, Schadt M and Chang C H, J. Med. Chem. 1998, 41, 1446-1455.
27. Rodgers J D, Johnson B L, Wang H, Erickson-Viitanen S, Klabe R M, Bacheler L T, Cordova B C and Chang C H, Bioorg, Med. Chem, Lett.. 1998, 8, 715-720.
28. Patel M, Bacheler L T, Rayner M M, Cordova B C, Klabe R M, Erickson Viitanen S, and Sitz S P, Bioorg. Med. Chem, Lett. 1998, 8, 823-828.
29. Patel M, Kaltenbach III R F, Nugie D A, Mchugh Jr R J, Jadhav P K, Bacheler L T, Cordova B C, Klabe R M, Erickson-Viitanen S, Garber S S, Ried C and Sitz S P, Bioorg. Med. Chem, Lett. 1998, 8, 1077-1082.
30. Bhanuprakash K, Irena B, Fabio B and Stanisalav M, Biochem. Biophy. Res. Comm, 2000, 268, 384-389.
31. th Congress of the world association of theoretically oriented chemists.
32. Lipinski C A, Lombardo F, Dominy B W and Feeney P J, Adv. Drug. Deliver. Rev. 1997, 23, 3-25.
33. Lipinski C A, Lombardo F, Dominy B W, Feeney P J, Adv. Drug. Deliver. Rev. 2001, 46, 3-26.