The interaction of microtubules with stabilizers characterized at biochemical and structural levels

Topics in Current Chemistry

Volumn 286, Issue , 2009, Pages 121-149

  Diaz J F ^a   Andreu, J M ^a   Jimenez Barbero J ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

Antituniour drugs; Bioconformer; Microtubule stabilizing agents; Paclitaxel

Indexed keywords

EID: 69249159496     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2008_12     Document Type: Article

References (103)

1. Jordan MA, Wilson L (2004) Nat Rev Cancer 4:253
2. Weisenberg RC, Borisy GG, Taylor EW (1968) Biochemistry 7:4466
3. Ravelli RB, Gigant B, Curmi PA, Jourdain I, Lachkar S, Sobel A, Knossow M (2004) Nature 428:198
4. Gigant B, Wang C, Ravelli RB, Roussi F, Steinmetz MO, Curmi PA, Sobel A, Knossow M (2005) Nature 435:519
5. Nogales E, Wolf SG, Downing KH (1998) Nature 391:199
6. Schiff PB, Fant J, Horwitz SB (1979) Nature 277:665
7. Wall ME, Wani MC (1995) Cancer Res 55:753
8. Souto AA, Acuña AU, Andreu JM, Barasoain I, Abal M, Amat-Guerri F (1996) Angew Chem Int Ed Engl 34:2710
9. Evangelio JA, Abal M, Barasoain I, Souto AA, Lillo MP, Acuña AU, Amat-Guerri F, Andreu JM (1998) Cell Motil Cytoskeleton 39:73
10. Díaz JF, Strobe R, Engelborghs Y, Souto AA, Andreu JM (2000) J Biol Chem 275:26265
11. Andreu JM, Barasoain I (2001) Biochemistry 40:11975
12. Lowe J, Li H, Downing KH, Nogales E (2001) J Mol Biol 313:1045
13. Lowe J, Amos LA (1998) Nature 391:203
14. Huecas S, Llorca O, Boskovic J, Martin-Benito J, Valpuesta JM, Andreu JM (2008) Energetics and geometry of FtsZ polymers: nucleated self-assembly of single protofilaments. Biophys J 94, 1798
15. Wyman J, Gill SJ (1990) Binding and linkage. University Science Books, Mill Valley, CA
16. Menéndez M, Rivas G, Díaz JF, Andreu JM (1998) J Biol Chem 273:167
17. Pommier Y, Cherfils J (2005) Trends Pharmacol Sci 26:138
18. Andreu JM, Bordas J, Diaz JF, Garcia de Ancos J, Gil R, Medrano FJ, Nogales E, Pantos E, Towns-Andrews E (1992) J Mol Biol 226:169
19. Andreu JM, Díaz JF, Gil R, de Pereda JM, Garcia de Lacoba M, Peyrot V, Briand C, Towns- Andrews E, Bordas J (1994) J Biol Chem 269:31785
20. Buey RM, Barasoain I, Jackson E, Meyer A, Giannakakou P, Paterson I, Mooberry S, Andreu JM, Díaz JF (2005) Chem Biol 12:1269
21. Buey RM, Calvo E, Barasoain I, Pineda O, Edler MC, Matesanz R, Cerezo G, Vanderwal CD, Day BW, Sorensen EJ, Lopez JA, Andreu JM, Hamel E, Díaz JF (2007) Nat Chem Biol 3:117
22. Díaz JF, Barasoain I, Andreu JM (2003) J Biol Chem 278:8407
23. Díaz JF, Barasoain I, Souto AA, Amat-Guerri F, Andreu JM (2005) J Biol Chem 280:3928
24. Pryor DE, O'Brate A, Bilcer G, Diaz JF, Wang Y, Kabaki M, Jung MK, Andreu JM, Ghosh AK, Giannakakou P, Hamel E (2002) Biochemistry 41:9109
25. Gaitanos TN, Buey RM, Díaz JF, Northcote PT, Teesdale-Spittle P, Andreu JM, Miller JH (2004) Cancer Res 64:5063
26. Pineda O, Farras J, Maccari L, Manetti F, Botta M, Vilarrasa J (2004) Bioorg Med Chem Lett 14:4825
27. Jimenez-Barbero J, Canales A, Northcote PT, Buey RM, Andreu JM, Diaz JF (2006) J Am Chem Soc 128:8757
28. Dye RB, Fink SP, Williams RC (1993) J Biol Chem 268:6847
29. Elie-Caille C, Severin F, Helenius J, Howard J, Muller DJ, Hyman AA (2007) Current Biology 17:1765
30. Klein LE, Freeze BS, Smith AB, Horwitz SB (2005) Cell Cycle 4:501
31. Amos LA, Lowe J (1999) Chem Biol 6:R65
32. Li H, DeRosier DJ, Nicholson WV, Nogales E, Downing KH (2002) Structure (Camb) 10:1317
33. Díaz JF, Menéndez M, Andreu JM (1993) Biochemistry 32:10067
34. Oosawa F, Asakura S (1975) Thermodynamics of the polymerization of protein., Academic, London
35. Díaz JF, Andreu JM (1993) Biochemistry 32:2747
36. Buey RM, Díaz JF, Andreu JM, O'Brate A, Giannakakou P, Nicolaou KC, Sasmal PK, Ritzen A, Namoto K (2004) Chem Biol 11:225
37. Edler MC, Buey RM, Gussio R, Marcus AI, Vanderwal CD, Sorensen EJ, Diaz JF, Giannakakou P, Hamel E (2005) Biochemistry 44:11525
38. Carlomagno T, Blommers MJ, Meiler J, Jahnke W, Schupp T, Petersen F, Schinzer D, Altmann KH, Griesinger C (2003) Angew Chem Int Ed Engl 42:2511
39. Yang C, Barasoain I, Li X, Matesanz R, Liu R, Sharom FJ, Díaz JF, Fang W (2007) Chem Med Chem 2:691
40. Schiff PB, Horwitz SB (1981) Biochemistry 20:3247
41. Díaz JF, Valpuesta JM, Chacón P, Diakun G, Andreu JM (1998) J Biol Chem 273:33803
42. Nogales E, Wolf SG, Khan IA, Luduena RF, Downing KH (1995) Nature 375:424
43. Nogales E, Whittaker M, Milligan RA, Downing KH (1999) Cell 96:79
44. Díaz JF, Buey RM (2007) In: Zhou J (ed) Methods in molecular medicine, vol 137. Humana,Totowa, NJ p 245
45. Giannakakou P, Sackett DL, Kang YK, Zhan Z, Buters JT, Fojo T, Poruchynsky MS (1997) J Biol Chem 272:17118
46. Sato B, Muramatsu H, Miyauchi M, Hori Y, Takase S, Hino M, Hashimoto S, Terano H (2000) J Antibiot (Tokyo) 53:123
47. Sato B, Nakajima H, Hori Y, Hino M, Hashimoto S, Terano H (2000) J Antibiot (Tokyo) 53:204
48. Nicolaou KC, Roschangar F, Vourloumis D (1998) Angew Chem Int Ed Engl 37:2015
49. Kalesse M (2000) Chembiochem 1:171
50. Lindel T, Jensen PR, Fenical W, Long BH, Casazza AM, Carboni J, Fairchild CR (1997) J Am Chem Soc 119:8744
51. Rao S, He LF, Chakravarty S, Ojima I, Orr GA, Horwitz SB (1999) J Biol Chem 274:37990
52. Czaplinski KHA, Grunewald GL (1994) Bioorg Med Chem Lett 4:2211
53. Morita H, Gonda A, Wei L, Takeya K, Itokawa H (1997) Bioorg Med Chem Lett 7:2387
54. Wang M, Xia X, Kim Y, Hwang D, Jansen JM, Botta M, Liotta DC, Snyder JP (1999) Org Lett 1:43
55. Jiménez-Barbero J, Amat-Guerri F, Snyder JP (2002) Curr Med Chem Anti-Canc Agents 2:91
56. Kingston DGI, Bane S, Snyder JP (2005) Cell Cycle 4:279
57. Giannakakou P, Gussio R, Nogales E, Downing KH, Zaharevitz D, Bollbuck B, Poy G, Sackett D, Nicolaou KC, Fojo T (2000) Proc Natl Acad Sci USA 97:2904
58. Gueritte-Voegelein F, Guenard D, Mangatal L, Potier P, Guilhem J, Cesario M, Pascard C (1990) Acta Cryst C 46:781
59. Snyder JP, Nettles JH, Cornett B, Downing KH, Nogales E (2001) Proc Natl Acad Sci USA 98:5312
60. Vandervelde DG, Georg GI, Grunewald GL, Gunn GW, Mitscher LA (1993) J Am Chem Soc 115:11650
61. Williams HJ, Scott AI, Dieden RA, Swindell CS, Chirlian LE, Francl MM, Heerding JM, Krauss NE (1994) Can J Chem 72:252
62. Snyder JP, Nevins N, Cicero DO, Jasen J (2000) J Am Chem Soc 122:724
63. Johnson SA, Alcaraz AA, Snyder JP (2005) Org Lett 7:5549
64. Zhu QQ, Guo ZR, Huang N, Wang MM, Chu FM (1997) J Med Chem 40:4319
65. Moyna G, Williams HJ, Scott AI, Ringel I, Gorodetsky R, Swindell CS (1997) J Med Chem 40:3305
66. Mastropaolo D, Camerman A, Luo YG, Brayer GD, Camerman N (1995) Proc Natl Acad Sci USA 92:6920
67. Gómez Paloma L, Guy RK, Wrasidlo W, Nicolaou KC (1994) Chem Biol 1:107
68. Dubois J, Guenard D, Gueritte-Voegelein F, Guedira N, Potier P, Gillet B, Beloeil JC (1993) Tetrahedron 49:6533
69. Cachau RE, Gussio R, Beutler JA, Chmurny GN, Hilton BD, Muschik GM, Erickson JW (1994) Int J Supercomput Appl High Perform Comput8:24
70. Boge TC, Himes RH, Vandervelde DG, Georg GI (1994) J Med Chem 37:3337
71. Ojima I, Kuduk SD, Chakravarty S, Ourevitch M, Begue JP (1997) J Am Chem Soc 119:5519
72. Georg GI, Harriman GCB, Hepperle M, Clowers JS, VanderVelde DG, Himes RH (1996) J Org Chem 61:2664
73. Jiménez-Barbero J, Souto AA, Abal M, Barasoain I, Evangelio JA, Acuña AU, Andreu JM, Amat-Guerri F (1998) Bioorg Med Chem 6:1857
74. Ojima I, Chakravarty S, Inoue T, Lin S, He L, Horwitz SB, Kuduk SD, Danishefsky SJ (1999) Proc Natl Acad Sci USA 96:4256
75. Magnani M, Ortuso F, Soro S, Alcaro S, Tramontano A, Botta M (2006) Febs J 273:3301
76. Shanker N, Kingston DGI, Ganesh T, Yang C, Alcaraz AA, Geballe MT, Banerjee A, McGee D, Snyder JP, Bane S (2007) Biochemistry 46:11514
77. Li YK, Poliks B, Cegelski L, Poliks M, Gryczynski Z, Piszczek G, Jagtap PG, Studelska DR, Kingston DGI, Schaefer J, Bane S (2000) Biochemistry 39:281
78. Geney R, Sun L, Pera P, Bernacki RJ, Xia SJ, Horwitz SB, Simmerling CL, Ojima I (2005) Chem Biol 12:339
79. Ojima I, Inoue T, Chakravarty S (1999) J Fluorine Chem 97:3
80. Paik Y, Yang C, Metaferia B, Tang SB, Bane S, Ravindra R, Shanker N, Alcaraz AA, Johnson SA, Schaefer J, O'Connor RD, Cegelski L, Snyder JP, Kingston DGI (2007) J Am Chem Soc 129:361
81. Alcaraz AA, Mehta AK, Johnson SA, Snyder JP (2006) J Med Chem 49:2478
82. Ganesh T, Guza RC, Bane S, Ravindra R, Shanker N, Lakdawala AS, Snyder JP, Kingston DGI (2004) Proc Natl Acad Sci USA 101:10006
83. Ganesh T, Yang C, Norris A, Glass T, Bane S, Ravindra R, Banerjee A, Metaferia B, Thomas SL, Giannakakou P, Alcaraz AA, Lakdawala AS, Snyder JP, Kingston DGI (2007) J Med Chem 50:713
84. Höfle G, Bedorf N, Steinmetz H, Schomburg D, Gerth K, Reichenbach H (1996) Angew Chem Int Ed Engl 35:1567
85. Taylor RE, Zajicek J (1999) J Org Chem 64:7224
86. Lange A, Schupp T, Petersen F, Carlomagno T, Baldus M (2007) Chemmedchem 2:522
87. Carlomagno T, Sanchez VM, Blommers MJ, Griesinger C (2003) Angew Chem Int Ed Engl 42:2515
88. Nettles JH, Li H, Cornett B, Krahn JM, Snyder JP, Downing KH (2004) Science 305:866
89. Reese M, Sanchez-Pedregal VM, Kubicek K, Meiler J, Blommers MJJ, Griesinger C, Carlomagno T (2007) Angew Chem Int Ed Engl 46:1864
90. Nicolaou KC, Scarpelli R, Bollbuck B, Werschkun B, Pereira MMA, Wartmann M, Altmann KH, Zaharevitz D, Gussio R, Giannakakou P (2000) Chem Biol 7:593
91. Sanchez-Pedregal VM, Kubicek K, Meiler J, Lyothier I, Paterson I, Carlomagno T (2006) Angew Chem Int Ed Engl 45:7388
92. Gunasekera SP, Gunasekera M, Longley RE, Schulte GK (1990) J Org Chem 55:4912
93. Paterson I, Britton R, Delgado O, Meyer A, Poullennec KG (2004) Angew Chem Int Ed Engl 43:4629
94. Canales A, Matesanz R, Gardner NM, Andreu JM, Paterson I, Díaz JF, Jiménez-Barbero J (2008) The bound conformation of microtubule- stabilizing agents (II): NMR insights on the bioactive 3D structure of discodermolide and dictyostatin. Chemistry (DOI: 10.1002/chem.200800039
95. Smith AB III, LaMarche MJ, Falcone-Hindley M (2001) Org Lett 3:695
96. Monteagudo E, Cicero DO, Cornett B, Myles DC, Snyder JP (2001) J Am Chem Soc 123:6929
97. Paterson I, Britton R, Delgado O, Wright AE (2004) Chem Commun (Camb):632
98. West LM, Northcote PT, Battershill CN (2000) J Org Chem 65:445
99. Liao XB, Wu YS, De Brabander JK (2003) Angew Chem Int Ed Engl 42:1648
100. Snyder JP, Nevins N, Jímenez-Barbero J, Cicero D, Jansen JM. Unpublished
101. Matesanz R, Barasoain I, Yang CG, Wang L, Li X, de Inés C, Coderch C, Gago F, Barbero JJ, Andreu JM, Fang WS, Diaz JF. (2008) Chem Biol.15:573
102. Erdélyi M, Pfeiffer B, Hauenstein K, Fohrer J, Gertsch J, Altmann KH, Carlomagno T. (2008) J Med Chem. 51:1469
103. Huzil JT, Chik JK, Slysz GW, Freedman H, Tuszynski J, Taylor RE, Sackett DL, Schriemer DC. (2008) J Mol Biol. 378:1016