Latrunculin analogues with improved biological profiles by "diverted total synthesis": Preparation, evaluation, and computational analysis

Chemistry - A European Journal

Volumn 13, Issue 1, 2007, Pages 135-149

  Fürstner, Alois ^a   Kirk, Douglas ^a   Fenster, Michaël D B ^a   Aïssa, Christophe ^a   De Souza, Dominic ^a   Nevado, Cristina ^a   Tuttle, Tell ^a   Thiel, Walter ^a   Müller, Oliver ^b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

Actin; Chemical biology; Computational chemistry; Macrolides; Metathesis; Total synthesis

Indexed keywords

HYDROGEN BONDS; MOLECULAR STRUCTURE; MOLYBDENUM; SYNTHESIS (CHEMICAL); BINDING SITES; CHEMICAL MODIFICATION; COMPLEX NETWORKS; COMPUTATIONAL CHEMISTRY; FUNCTIONAL GROUPS; LIGANDS; METABOLITES; MOLYBDENUM COMPOUNDS;

ACTIN; CHEMICAL BIOLOGY; COMPUTATIONAL CHEMISTRY; MACROLIDES; METATHESIS;

ORGANIC COMPOUNDS; PROTEINS;

ACTIN; FUSED HETEROCYCLIC RINGS; LATRUNCULIN A; LATRUNCULIN B; THIAZOLIDINE DERIVATIVE;

ANIMAL; ARTICLE; CATALYSIS; CELL STRAIN 3T3; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; HYDROGEN BOND; MOUSE; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

ACTINS; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NIH 3T3 CELLS; THERMODYNAMICS; THIAZOLIDINES;

ACTIN; CHEMICAL BIOLOGY; MACROLIDES; METATHESIS; TOTAL SYNTHESIS;

EID: 33845951511     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601136     Document Type: Article

References (97)

1. a) I. Spector, N. R. Shochet, Y. Kashman, A. Groweiss, Science 1983, 219, 493-495;
2. b) review: I. Spector, N. R. Shochet, D. Blasberger, Y. Kashman, Cell Motil. Cytosketeton 1989, 13, 127-144.
3. a) A. Groweiss, U. Shmueli, Y. Kashman, J. Org. Chem. 1983, 48, 3512-3516;
4. b) Y. Kashman, A. Groweiss, R. Lidor, D. Blasberger, S. Carmely, Tetrahedron 1985, 41, 1905-1914.
5. a) J. R. Peterson, T. J. Mitchison, Chem. Biol. 2002, 9, 1275-1285;
6. b) I. Spector, F. Braet, N. R. Shochet, M. R. Bubb, Microsc. Res. Tech. 1999, 47, 18-37;
7. c) K. Ayscough, Methods Enzymol. 1998, 298, 18-25;
8. d) T. M. A. Gronewold, F. Sasse, H. Lünsdorf, H. Reichenbach, Cell Tissue Res. 1999, 295, 121-129.
9. a) I. Spector, N. R. Shochet, D. Blasberger, Y. Kashman, J. Cell Biol. 1986, 103, A393;
10. b) K. A. El Sayed, D. T. A. Youssef, D. Marchetti, J. Nat. Prod. 2006, 69, 219-223.
11. a) P. Sheterline, J. Clayton, J. C. Sparrow, Actin, 4th ed., Oxford University Press, New York, 1999;
12. b) T. D. Pollard, L. Blanchoin, R. D. Mullins, Annu. Rev. Biophys. Biomol. Struct. 2000, 29, 545-576;
13. c) H. Lodish, D. Baltimore, A. Berk, S. L. Zipursky, P. Matsudaira, J. Darnell, Molecular Cell Biology, 3rd ed., Scientific American Books, New York, 1995;
14. d) A. Giganti, E. Friederich, in Prog. Cell Cycle Res., Vol. 5 (Eds.: L. Meijer, A. Jézéquel, M. Roberge), Springer, Berlin, 2003, pp. 511-523;
15. e) G. Fenteany, S. Zhu, Curr. Top. Med. Chem. 2003, 3, 593-616;
16. f) M. A. Jordan, L. Wilson, Curr. Opin. Cell Biol. 1998, 10, 123-130.
17. W. M. Morton, K. R. Ayscough, P. J. McLaughlin, Nat. Cell Biol. 2000, 2, 376-378.
18. See also: E. G. Yarmola, T. Somasundaram, T. A. Boring, I. Spector, M. R. Bubb, J. Biol. Chem. 2000, 275, 28 120-28 127.
19. The non-basic endocyclic ester oxygen cannot serve as a hydrogen-bond acceptor.
20. T. R. Hoye, S.-E. N. Ayyad, B. M. Eklov, N. E. Hashish, W. T. Shier, K. A. El Sayed, M. T. Hamann, J. Am. Chem. Soc. 2002, 124, 7405-7410.
21. Note that Glu214 (E214) is erroneously assigned as D214 in ref. [6]. The structure deposited in the database (PDB ID: 1ESV) clearly identifies this residue as a glutamic acid moiety.
22. A. Fürstner, D. De Souza, L. Turet, M. D. B. Fenster, L. Parra-Rapado, C. Wirtz, R. Mynott, C. W. Lehmann, Chem. Eur. J. 2006, 12, 115-134.
23. Although previously practiced, the expression "diverted total synthesis" was coined only recently by Danishefsky. For a discussion and an instructive case, see: a) R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006. DOI: 10.1021/jo0610053;
24. b) C. Gaul, J. T. Njardarson, D. Shan, D. C. Dorn, K.-D. Wu, W. P. Tong, X.-Y. Huang, M. A. S. Moore, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 11326-11337;
25. c) short review: I. Paterson, E. A. Anderson, Science 2005, 310, 451-453;
26. d) for a discussion of "natural product like" compounds and "natural product hybrids" see: L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. 2003, 115, 4128-4160;
27. Angew. Chem. Int. Ed. 2003, 42, 3996-4028.
28. Preliminary communication: A. Fürstner, D. Kirk, M. D. B. Fenster, C. Aïssa, D. De Souza, O. Müller, Proc. Natl. Acad. Sci. USA 2005, 102, 8103-8108.
29. Preliminary communications: a) A. Fürstner, D. De Souza, L. ParraRapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518;
30. Angew. Chem. Int. Ed. 2003, 42, 5358-5360;
31. b) A. Fürstner, L. Turet, Angew. Chem. 2005, 117, 3528-3532;
32. Angew. Chem. Int. Ed. 2005, 44, 3462-3466.
33. a) A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624-629;
34. b) B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943-3949;
35. c) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863;
36. d) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635;
37. Angew. Chem. Int. Ed. 2002, 41, 609-612;
38. e) G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950-3952.
39. D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112, 8215-8216.
40. a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull Chem. Soc. Jpn. 1979, 52, 1989-1993;
41. b) for advanced applications from this laboratory see: O. Lepage, E. Kattnig, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 15970-15971;
42. c) A. Fürstner, E. Kattnig, O. Lepage, J. Am. Chem. Soc. 2006, 128, 9194-9204;
43. d) J. Mlynarski, J. Ruiz-Caro, A. Fürstner, Chem. Eur. J. 2004, 10, 2214-2222.
44. For another instructive case in which an attempted Yamaguchi esterification of an α,β-unsaturated acid was unsuccessful see: a) A. Fürstner, C. Aïssa, C. Chevrier, F. Teplý, C. Nevado, M. Tremblay, Angew. Chem. 2006, 118, 5964-5969;
45. Angew. Chem. Int. Ed. 2006, 45, 5832-5837;
46. b) A. Fürstner, C. Nevado, M. Tremblay, C. Chevrier, F. Teplý, C. Aïssa, M. Waser, Angew. Chem. 2006, 118, 5969-5974;
47. Angew. Chem. Int. Ed. 2006, 45, 5837-5842.
48. O. Mitsunobu, Synthesis 1981, 1-28.
49. a) A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320;
50. b) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760;
51. Angew. Chem. Int. Ed. 1998, 37, 1734-1736.
52. Applications of RCAM in natural product synthesis: a) A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11 799-11 805;
53. b) A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758-8762;
54. c) A. Fürstner, A. Rumbo, J. Org. Chem. 2000, 65, 2608-2611;
55. d) A. Fürstner, G. Seidel, J. Organomet. Chem. 2000, 606, 75-78;
56. e) A. Fürstner, A.-S. Castanet, K. Radkowski, C. W. Lehmann, J. Org. Chem. 2003, 68, 1521-1528;
57. f) A. Fürstner, C. Mathes, K. Grela, Chem. Commun. 2001, 1057-1059;
58. g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871;
59. h) A. Fürstner, K. Grela, Angew. Chem. 2000, 112, 1292-1294;
60. Angew. Chem. Int. Ed. 2000, 39, 1234-1236;
61. D. Song, G. Blond, A. Fürstner, Tetrahedron 2003, 59, 6899-6904;
62. j) B. Aguilera, L. B. Wolf, P. Nieczypor, F. P. J. T. Rutjes, H. S. Overkleeft, J. C. M. van Hest, H. E. Schoemaker, B. Wang, J. C. Mol, A. Fürstner, M. Overhand, G. A. van der Marel, J. H. van Boom, J. Org. Chem. 2001, 66, 3584-3589;
63. k) N. Ghalit, A. J. Pool, A. Fürstner, D. T. S. Rijkers, R. M. J. Liskamp, Org. Lett. 2005, 7, 2961-2964;
64. l) M. IJsselstijn, B. Aguilera, G. A. van der Marel, J. H. van Boom, F. L. van Delft, H. E. Schoemaker, H. S. Overkleeft, F. P. J. T. Rutjes, M. Overhand, Tetrahedron Lett. 2004, 45, 4379-4382;
65. m) A. Fürstner, T. Dierkes, Org. Lett. 2000, 2, 2463-2465;
66. n) A. Fürstner, C. Mathes, Org. Lett. 2001, 3, 221-223;
67. o) J. Chan, T. F. Jamison, J. Am. Chem. Soc. 2004, 126, 10682-10691.
68. a) A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453-9454;
69. b) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
70. a) J. H. Freudenberger, R. R. Schrock, M. R. Churchill, A. L. Rheingold, J. W. Ziller, Organometallics 1984, 3, 1563-1573;
71. b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11 108-11 113.
72. a) The short supply has already led to first attempts to grow N. magnifica in aquaculture, cf. E. Hadas, M. Shpigel, M. Ilan, Aquaculture 2005, 244, 159-169;
73. b) moreover, a recent study strongly suggests a non-symbiotic origin of latrunculin B, cf: O. Gillor, S. Carmeli, Y. Rahamim, Z. Fishelson, M. Ilan, Mar. Biotechnol. 2000, 2, 213-223.
74. CHARMM, V.c31b1, 2004.
75. C. L. Brooks, M. Karplus, J. Chem. Phys. 1983, 79, 6312-6325.
76. A. D. MacKerell, Jr., B. Brooks, C. L. Brooks, L. Nilsson, B. Roux, Y. Won, M. Karplus, in Encyclopedia of Computational Chemistry, Vol. 1 (Ed.: P. von R. Schleyer), Wiley, Chichester, 1998, pp. 271-277.
77. ChemShell, V. 3.0a3, 2004.
78. P. Sherwood, et al., THEOCHEM 2003, 632, 1-28.
79. W. Thiel, MNDO99, V. 6.1, Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr (Germany), 2004.
80. K. Y. Burstein, A. N. Isaev, Theor. Chim. Acta 1984, 64, 397-401.
81. M. J. S. Dewar, W. Thiel, J. Am. Chem. Soc. 1977, 99, 4899-4907.
82. N. Foloppe, A. D. MacKerell, Jr., J. Comput. Chem. 2000, 21, 86-104.
83. A. D. MacKerell, Jr. N. K. Banavali, J. Comput. Chem. 2000, 21, 105.
84. A. D. MacKerell, Jr., D. Bashford, M. Bellott, R. L. Dunbrack, Jr., J. D. Evanseck, M. J. Field, S. Fischer, J. Gao, H. Guo, S. Ha, D. Joseph-McCarthy, L. Kuchnir, K. Kuczera, F. T. K. Lau, C. Mattos, S. Michnick, T. Ngo, D. T. Nguyen, B. Prodhom, W. E. Reiher, III, B. Roux, M. Schlenkrich, J. C. Smith, R. Stole, J. Straub, M. Watanabe, J. Wiorkiewicz-Kuczera, D. Yin, M. Karplus, J. Phys. Chem. B 1998, 102, 3586-3616.
85. D. Bakowies, W. Thiel, J. Phys. Chem. 1996, 100, 10580-10594.
86. A. H. de Vries, P. Sherwood, S. J. Collins, A. M. Rigby, M. Rigutto, G. J. Kramer, J. Phys. Chem. B 1999, 103, 6133-6141.
87. There are H-bonds between the oxygen atoms of the macrocycle and surrounding waters, however, these will also be present in thesolvent and should therefore have only a minor influence on the binding energy.
88. Since the independent optimizations of the complexes are not directly comparable due to the distance criteria used in determining the active atoms during each optimization, the 2/- and 44/G-actin complexes were re-optimized for the sake of consistency. Using the 1/G-actin complex as the starting point, the 2/- and 44/G-actin complexes were created by subsequently deleting the additional groups (i.e., for 2 the HC=CH linkage in the macrocycle, and then the methyl substituents to create the 44/G-actin complex), followed by an optimization with smaller distance criteria (10 Å) for the active region (see Supporting Information for further details).
89. L. R. Otterbein, P. Graceffa, R. Dominguez, Science 2001, 293, 708-711.
90. J. A. McCammon, S. H. Northrup, Nature 1981, 295, 316-317.
91. H.-X. Zhou, S. T. Wlodek, J. A. McCammon, Proc. Natl. Acad. Sci. USA 1998, 95, 9280-9283.
92. M. P. Sibi, D. Rutherford, P. A. Renhowe, B. Li, J. Am. Chem. Soc. 1999, 121, 7509-7516.
93. S. Ma, X. Lu, Z. Li, J. Org. Chem. 1992, 57, 709-713.
94. a) U. S. Racheria, Y. Liao, H. C. Brown, J. Org. Chem. 1992, 57, 6614-6617;
95. b) H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092-2093.
96. G. M. Sheldrick, SHELXS-97, Program for the determination of crystal structures, University of Göttingen (Germany), 1997.
97. G. M. Sheldrick, SHELXL-97, Program for least-squares refinement of crystal structures, University of Göttingen (Germany), 1997.