Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 24, 2011, Pages 7664-7678

  Zhao, Jielu ^a   Bane, Susan ^b   Snyder, James P ^c   Hu, Haipeng ^c   Mukherjee, Kamalika ^b   Slebodnick, Carla ^a   Kingston, David G I ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b BINGHAMTON UNIVERSITY   (United States)

^c EMORY UNIVERSITY   (United States)

Author keywords

Antiproliferative activity; Bioactive conformation; Modeling; Paclitaxel; Simplified paclitaxel; T Taxol; Taxol; Tubulin; X ray

Indexed keywords

9 ALLYLOXY 10 BENZOYLOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3 BENZOYLAMINO 2' HYDROXY 3' (2 ALLYLPHENYL)PROPANOIC ACID; 9 ALLYLOXY 10 BENZOYLOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3 BENZOYLAMINO 2' HYDROXY 3' (2 ALLYPHENYL)PROPANOIC ACID; 9 ALLYLOXY 10 BENZOYLOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3 BENZOYLAMINO 2' HYDROXY 3' [2 (ALLYLOXY)PHENYL]PROPANOIC ACID; 9 ALLYLOXY 10 BENZOYLOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3 BENZOYLAMINO 2' HYDROXY 3' [2 (BUT 3 ENYLOXY)PHENYL]PROPANOIC ACID; ALCOHOL; ALDEHYDE; BETA LACTAM; HYDROXYPROLINE; PACLITAXEL; PACLITAXEL DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ANISOTROPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CELL PROLIFERATION; CONCENTRATION RESPONSE; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INHIBITION KINETICS; MICROTUBULE; PROTEIN POLYMERIZATION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEOPLASMS; PACLITAXEL; TUBULIN;

EID: 82255192184     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.10.010     Document Type: Article

References (66)

1. M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, and A.T. McPhail J. Am. Chem. Soc. 93 1971 2325
2. M. Suffness, and M.E. Wall M. Suffness, Taxol: Science and Applications 1995 CRC Press Boca Raton, Fl 3
3. F. Gueritte-Voegelein, V. Senilh, B. David, D. Guenard, and P. Potier Tetrahedron 42 1986 4451
4. J. Crown, M. O'Leary, and W.-S. Ooi Oncologist 9 2004 24
5. E. Saloustros, D. Mavroudis, and V. Georgoulias Expert Opin. Pharmacother. 9 2008 2603
6. R.F. Ozols Semin. Oncol. 33 2006 S3
7. Y. Fu, S. Li, Y. Zu, G. Yang, Z. Yang, M. Luo, S. Jiang, M. Wink, and T. Efferth Curr. Med. Chem. 16 2009 3966
8. D.G.I. Kingston G.M. Cragg, D.G.I. Kingston, D.J. Newman, Anticancer Agents from Natural Products 2nd ed 2011 CRC Press Boca Raton, FL 89
9. D.G.I. Kingston, P.G. Jagtap, H. Yuan, and L. Samala W. Herz, H. Falk, G.W. Kirby, Progress in the Chemistry of Organic Natural Products Vol. 84 2002 Springer Wien 53
10. C. Ferlini, D. Gallo, and G. Scambia Expert Opin. Invest. Drugs 17 2008 335
11. D. Guenard, F. Gueritte-Voegelein, and P. Potier Acc. Chem. Res. 26 1993 160
12. M.D. Galsky, A. Dritselis, P. Kirkpatrick, and W.K. Oh Nat. Rev. Drug Disc. 9 2010 677
13. P.B. Schiff, J. Fant, and S.B. Horwitz Nature 277 1979 665
14. S.B. Horwitz, M.W. Davidson, and R.A. Holton Trends Pharmacol. Sci. 13 1992 134
15. J.J. Manfredi, J. Parness, and S.B. Horwitz J. Cell Biol. 94 1982 688
16. S. Rao, L. He, S. Chakravarty, I. Ojima, G.A. Orr, and S.B. Horwitz J. Biol. Chem. 274 1999 37990
17. S. Rao, N.E. Krauss, J.M. Heerding, C.S. Swindell, I. Ringel, G.A. Orr, and S.B. Horwitz J. Biol. Chem. 269 1994 3132
18. S. Rao, G.A. Orr, A.G. Chaudhary, D.G.I. Kingston, and S.B. Horwitz J. Biol. Chem. 270 1995 20235
19. J.F. Diaz, R. Strobe, Y. Engelborghs, A.A. Souto, and J.M. Andreu J. Biol. Chem. 275 2000 26265
20. Y. Li, J.R. Edsall, P.G. Jagtap, D.G.I. Kingston, and S. Bane Biochemistry 39 2000 616
21. S. Sengupta, T.C. Boge, Y. Liu, M. Hepperle, G.I. Georg, and R.H. Himes Biochemistry 36 1997 5179
22. J. Lowe, H. Li, K.H. Downing, and E. Nogales J. Mol. Biol. 313 2001 1045
23. E. Nogales, S.G. Wolf, and K.H. Downing Nature 39 1998 199
24. D.G. Vander Velde, G.I. Georg, G.L. Grunewald, C.W. Gunn, and L.A. Mitscher J. Am. Chem. Soc. 115 1993 11650
25. H.J. Williams, A.I. Scott, R.A. Dieden, C.S. Swindell, L.E. Chirlian, M.M. Francl, J.M. Heerding, and N.E. Krauss Can. J. Chem. 72 1994 252
26. J. Dubois, D. Guenard, F. Gueritte-Voeglein, N. Guedira, P. Potier, B. Gillet, and J.-C. Betoeil Tetrahedron 49 1993 6533
27. I. Ojima, S.D. Kuduk, S. Chakravarty, M. Ourevitch, and J.-P. Begue J. Am. Chem. Soc. 119 1997 5519
28. J.P. Snyder, N. Nevins, D.O. Cicero, and J. Jansen J. Am. Chem. Soc. 122 2000 724
29. J.P. Snyder, J.H. Nettles, B. Cornett, K.H. Downing, and E. Nogales Proc. Natl. Acad. Sci. U.S.A. 98 2001 5312
30. Y. Li, B. Poliks, L. Cegelski, M. Poliks, Z. Cryczynski, G. Piszczek, P.G. Jagtap, D.R. Studelska, D.G.I. Kingston, J. Schaefer, and S. Bane Biochemistry 39 2000 281
31. Y. Paik, C. Yang, B. Metaferia, S. Tang, S. Bane, R. Ravindra, N. Shanker, A.A. Alcaraz, S.A. Johnson, J. Schaefer, R.D. O'Connor, L. Cegelski, J.P. Snyder, and D.G.I. Kingston J. Am. Chem. Soc. 129 2007 361
32. T. Ganesh, R.C. Guza, S. Bane, R. Ravindra, N. Shanker, A.S. Lakdawala, J.P. Snyder, and D.G.I. Kingston Proc. Natl. Acad. Sci. U.S.A. 101 2004 10006
33. S.J. Danishefsky, J.J. Masters, W.B. Young, J.T. Link, L.B. Snyder, T.V. Magee, D.K. Jung, R.C.A. Isaacs, W.G. Bornmann, C.A. Alaimo, C.A. Coburn, and M.J. Di Grandi J. Am. Chem. Soc. 118 1996 2843
34. R.A. Holton, H.-B. Kim, C. Somoza, F. Liang, R.J. Biediger, P.D. Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N. Gentile, and J.H. Liu J. Am. Chem. Soc. 116 1994 1599
35. H. Kusama, R. Hara, S. Kawahara, T. Nishimori, H. Kashima, N. Nakamura, K. Morihira, and I. Kuwajima J. Am. Chem. Soc. 122 2000 3811
36. T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y.-I. Tani, M. Hasegawa, K. Yamada, and K. Saitoh Chem. Eur. J. 5 1999 121
37. K.C. Nicolaou, Z. Yang, J.J. Liu, H. Ueno, P.G. Nantermet, R.K. Guy, C.F. Claiborne, J. Renaud, E.A. Couladouros, K. Paulvannan, and E.J. Sorensen Nature 367 1994 630
38. P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E. Glass, C. Granicher, J.B. Houze, J. Janichen, D. Lee, D.G. Marquess, P.L. McGrane, W. Meng, T.P. Mucciaro, M. Muhlebach, M.G. Natchus, H. Paulsen, D.B. Rawlins, J. Satkofsky, A.J. Shuker, J.C. Sutton, R.E. Taylor, and K. Tommoka J. Am. Chem. Soc. 119 1997 2755
39. P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E. Glass, J.B. Houze, N.E. Krauss, D. Lee, D.G. Marquess, P.L. McGrane, W. Meng, M.G. Natchus, A.J. Shuker, J.C. Sutton, and R.E. Taylor J. Am. Chem. Soc. 119 1997 2757
40. F. Almqvist, S. Manner, V. Thornqvist, U. Berg, M. Wallin, and T. Frejd Org. Biomol. Chem. 2 2004 3085
41. X. Geng, R. Geney, P. Pera, J. Bernacki, and I. Ojima Bioorg. Med. Chem. Lett. 14 2004 3491
42. U. Klar, H. Graf, O. Schenk, B. Rohr, and H. Schulz Bioorg. Med. Chem. Lett. 8 1998 1397
43. L. Sun, J.M. Veith, P. Pera, R.J. Bernacki, and I. Ojima Bioorg. Med. Chem. 18 2010 7101
44. T. Ganesh, A. Norris, S. Sharma, S. Bane, A.A. Alcaraz, J.P. Snyder, and D.G.I. Kingston Bioorg. Med. Chem. 14 2006 3447
45. A.L. Spek J. Appl. Cryst. 36 2003 7
46. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, D.E. Shaw, M. Shelley, J.K. Perry, L.C. Sander, and P.S. Shenkin J. Med. Chem. 47 2004 1739
47. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz J. Med. Chem. 49 2006 6177
48. C.R. Guimaraes, and M. Cardozo J. Chem. Inf. Model. 48 2008 958
49. A.P. Graves, D.M. Shivakumar, S.E. Boyce, M.P. Jacobson, D.A. Case, and B.K. Shoichet J. Mol. Biol. 377 2008 914
50. M. Biel, P. Deck, A. Giannis, and H. Waldmann Chem. Eur. J. 12 2006 4121
51. X.-l. Qiu, and F.-l. Qing J. Org. Chem. 67 2002 7162
52. X. Zhang, A.C. Schmitt, and W. Jiang Tetrahedron Lett. 42 2001 5335
53. E. Piers, C.L. Harrison, and C. Zetina-Rocha Org. Lett. 3 2001 3245
54. T. Ganesh, C. Yang, A. Norris, T.E. Glass, S. Bane, R. Ravindra, A. Banerjee, B. Metaferia, S.L. Thomas, P. Giannakakou, A.A. Alcaraz, A.S. Lakdawala, J.P. Snyder, and D.G.I. Kingston J. Med. Chem. 50 2007 713
55. P. Compain Adv. Synth. Catal. 349 2007 1829
56. J.F. Diaz, J.M. Andres, and J. Jimenez-Barbero Topics in Current Chemistry (Tubulin Binding Agents) Vol. 2 2009 Springer Berlin p 121
57. M. Seto, K. Morihira, Y. Horiguchi, and I. Kuwajima J. Org. Chem. 59 1994 3165
58. J. Seidler, S.L. McGovern, T.N. Doman, and B.K. Shoichet J. Med. Chem. 46 2003 4477
59. K.E.D. Coan, D.A. Maltby, A.L. Berlingame, and B.K. Shoichet J. Med. Chem. 52 2009 2067
60. B. Bonne, C. Heuséle, C. Simon, and D. Pantaloni J. Biol. Chem. 260 1985 2819
61. D.M. Barron, S.K. Chatterjee, R. Ravindra, R. Roof, E. Baloglu, D.G.I. Kingston, and S. Bane Anal. Biochem. 315 2003 49
62. CrysAlisPro 171.33.31. Oxford Diffraction: Wroclaw, Poland, 2009.
63. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112
64. H.D. Flack Acta Crystallogr., Sect. A 39 1983 876
65. R.W.W. Hooft, L.H. Straver, and A.L. Spek J. Appl. Cryst. 41 2008 96
66. E. Pan, L. Harinantenaina, P. Brodie, M. Callmander, S. Rakotonandrasana, E. Rakotobe, V.E. Rasamison, K. TenDyke, Y. Shen, E.M. Suh, and D.G.I. Kingston Bioorg. Med. Chem. 19 2011 422