Preparation of thermocleavable conjugates based on ansamitocin and superparamagnetic nanostructured particles by a chemobiosynthetic approach

Chemistry - A European Journal

Volumn 20, Issue 52, 2014, Pages 17541-17551

  Mancuso, Lena ^a   Knobloch, Tobias ^a   Buchholz, Jessica ^a   Hartwig, Jan ^a   Möller, Lena ^a   Seidel, Katja ^a   Collisi, Wera ^b   Sasse, Florenz ^b   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

Antitumor agents; Hyperthermia; Maytansinoids; Mutasynthesis; Nanoparticles

Indexed keywords

BIOCHEMISTRY; CELL CULTURE; CHEMOTHERAPY; ELECTROMAGNETIC FIELDS; IRON OXIDES; NANOPARTICLES; SILICA; SUPERPARAMAGNETISM;

ANTI-PROLIFERATIVE ACTIVITIES; ANTI-TUMOR AGENTS; HYPERTHERMIA; MAYTANSINOIDS; MUTASYNTHESIS; OSCILLATING ELECTROMAGNETIC FIELDS; SILICA CORE SHELL PARTICLES; SUPERPARAMAGNETIC IRON OXIDES;

IRON COMPOUNDS;

EID: 84920154661     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404502     Document Type: Article

References (98)

1. A. Kirschning, F. Hahn, Angew. Chem. 2012, 124, 4086-4096
2. Angew. Chem. Int. Ed. 2012, 51, 4012-4022.
3. a) S. Weist, R. D. Süssmuth, Appl. Microbiol. Biotechnol. 2005, 68, 141-150
4. b) A. Kirschning, F. Taft, T. Knobloch, Org. Biomol. Chem. 2007, 5, 3245-3295
5. c) J. Kennedy, Nat. Prod. Rep. 2008, 25, 25-34
6. d) K. Weissman, Trends Biotechnol. 2007, 25, 139-142.
7. R. Thiericke, J. Rohr, Nat. Prod. Rep. 1993, 10, 265-289.
8. a) F. Taft, M. Brünjes, H. G. Floss, N. Czempinski, S. Grond, F. Sasse, A. Kirschning, ChemBioChem 2008, 9, 1057-1060
9. b) A. Deb Roy, S. Griischow, N. Cairns, R.J.M. Goss, J. Am. Chem. Soc. 2010, 134, 1224-12245
10. c) K. Harmrolfs, L. Mancuso, B. Drung, F. Sasse, A. Kirschning, Beilstein J. Org. Chem. 2014, 10, 535-543.
11. F. Taft, K. Harmrolfs, I. Nickeleit, A. Heutling, M. Kiene, N. Malek, F. Sasse, A. Kirschning, Chem. Eur. J. 2012, 18, 880-886.
12. a) B. Kusebauch, N. Brendel, H. Kirchner, H.-M. Dahse, C. Hertweck, ChemBioChem 2011, 12, 2284-2288
13. b) S. Weist, C. Kittel, D. Bischoff, B. Bister, V. Pfeifer, G. J. Nicholson, W. Wohlleben, R. D. Süssmuth, J. Am. Chem. Soc. 2004, 126, 5942-5943
14. c) R. D. Süssmuth, W. Wohlleben, Appl. Microbiol. Biotechnol. 2004, 63, 344-350
15. d) S. Weist, B. Bister, O. Puk, D. Bischoff, S. Pelzer, G.J. Nicholson, W. Wohlleben, G. Jung, R. D. Süssmuth, Angew. Chem. 2002, 114, 3531-3534
16. Angew. Chem. Int. Ed. 2002, 41, 3383-3385.
17. The term maytansinoids relates to the macrolactam antibiotic Maytansine (6) which was first isolated from the plant Maytenus serrata: S. M. Kupchan, Y Komoda, W. A. Court, G.J. Thomas, R. M. Smith, A. Karim, C.J. Gilmore, R.C. Haltiwanger, R. F. Bryan, J. Am. Chem. Soc. 1972, 94, 1354-1356.
18. a) J.M. Cassady, K. K. Chan, H.G. Floss, E. Leistner, Chem. Pharm. Bull. 2004, 52, 1-26
19. b) A. Kirschning, K. Harmrolfs, T. Knobloch, C. R. Chim. 2008, 11, 1523-1543.
20. a) T Kubota, M. Brünjes, T. Frenzel, J. Xu, A. Kirschning, H.G. Floss, ChemBioChem 2006, 7, 1221-1225
21. b) A. Meyer, M. Brünjes, F. Taft, T. Frenzel, F. Sasse, A. Kirschning, Org. Lett. 2007, 9, 1489-1492
22. c) F. Taft, M. Brünjes, T. Knobloch, H. G. Floss, A. Kirschning, J. Am. Chem. Soc. 2009, 131, 3812-3813
23. d) K. Harmrolfs, M. Brünjes, G. Dräger, H.G. Floss, F. Sasse, F. Taft, A. Kirschning, ChemBioChem 2010, 11, 2517-2520
24. e) T Knobloch, H.G. Floss, K. Harmrolfs, F. Sasse, F. Taft, B. Thomaszewski, A. Kirschning, ChemBioChem 2011, 12, 540-547
25. f) T. Knobloch, G. Dräger, W. Collisi, F. Sasse, A. Kirschning, Beilstein J. Org. Chem. 2012, 8, 861-869
26. g) L. Mancuso, G. Jürjens, J. Hermane, K. Harmrolfs, S. Eichner, J. Fohrer, W. Collisi, F. Sasse, A. Kirschning, Org. Lett. 2013, 15, 4442-4445.
27. CT. Walsh, S.W. Haynes, B.D. Ames, Nat. Prod. Rep. 2012, 29, 37-59.
28. S. Eichner, T. Knobloch, H. G. Floss, G. J. Fohrer, K. Harmrolfs, J. Hermane, A. Schulz, F. Sasse, P. Spiteller, F. Taft, A. Kirschning, Angew. Chem. 2012, 124, 776-781
29. Angew. Chem. Int. Ed. 2012, 51, 752-757.
30. a) P. Workman, Curr. Cancer Drug Targets 2003, 3, 297-300
31. b) L. Neckers, K. Neckers, Expert Opin. Emerging Drugs 2005, 10, 137-149
32. c) L. Whitesell, S. L. Lindquist, Nat. Rev. Cancer 2005, 5, 761-772
33. d) C. Prodromou, S. M. Roe, R. O'Brien, J. E. Ladbury, P. W. Piper, L. H. Pearl, Cell 1997, 90, 65-75
34. e) K. Hatano, E. Higashide, S. Akiyama, M. Yoneda, Agric. Biol. Chem. 1984, 48, 1721-1729
35. f) S. Bandi, Y. J. Kim, S. O. Sa, Y-K. Chang, J. Microbiol. Biotechnol. 2005, 15, 930-937.
36. M. A. Biamonte, R. van de Water, J.W. Arndt, R.H. Scannevin, R.H. Perret, D. Perret, W.-C. Lee, J. Med. Chem. 2010, 53, 3-17.
37. FDA approval see: http://www.accessdata.fda.gov/drugsatfda-docs/label/2013/125427lbl.pdf.
38. P. Spiteller, L. Bai, G. Shang, B.J. Carroll, T.-W. Yu, H.G. Floss, J. Am. Chem. Soc. 2003, 125, 14236-14237.
39. a) C. G. Kim, T.W. Yu, C.B. Fryhle, S. Handa, H.G. Floss, J. Biol. Chem. 1998, 273, 6030-6040
40. b) K. Arakawa, R. Müller, T. Mahmud, T.W. Yu, H.G. Floss, J. Am. Chem. Soc. 2002, 124, 10644-10645
41. c) T-W. Yu, R. Müller, M. Müller, X. Zhang, G. Dräger, C.-G. Kim, E. Leistner, H. G. Floss, J. Biol. Chem. 2001, 276, 12546-12555.
42. T.-W. Yu, L. Bai, D. Clade, D. Hoffmann, S. Toelzer, K. Q. Trinh, J. Xu, S. J. Moss, E. Leistner, H.G. Floss, Proc. Natl. Acad. Sci. USA 2002, 99, 7968-7973.
43. S. C. Wenzel, R. M. Williamson, C. Grünanger, J. Xu, K. Gerth, R. A. Martinez, S. J. Moss, B.J. Carroll, S. Grond, C.J. Unkefer, R. Müller, H. G. Floss, J. Am. Chem. Soc. 2006, 128, 14325-14336.
44. a) E. W. Hafner, B. W. Holley, K. S. Holdom, S. E. Lee, R. G. Wax, D. Beck, H. A. I. McArthur, W. C. Wernau, J. Antibiot. 1991, 44, 349-356
45. b) H. B. Bode, P. Meiser, T. Klefisch, N.S. d.J. Cortina, D. Krug, A. Gçhring, G. Schwär, T Mahmud, Y. A. Elnakady, R. Müller, ChemBioChem 2007, 8, 2139-2144.
46. a) A. Kawai, H. Akimoto, Y. Kozai, K. Ootsu, S. Tanida, N. Hashimoto, H. Nomura, Chem. Pharm. Bull. 1984, 32, 3441-3451
47. b) W. C. Widdison, R. V. J. Chari (Immunogen Inc., Cambridge, MA), Patent No. US20070112188.
48. W. C. Widdison, S.D. Wilhelm, E. E. Cavanagh, K. R. Whiteman, B. A. Leece, Y. Kovtun, V. S. Goldmacher, H. Xie, R. M. Stevens, R. J. Lutz, R. Zhao, L. Wang, W. A. Blättler, R.V.J. Chari, J. Med. Chem. 2006, 49, 4392-3408.
49. a) D. Ortega, Q. A. Pankhurst, Nanoscience 2013, 1, 60-88
50. b) J. van der Zee, Ann. Oncol. 2002, 13, 1173-1184
51. c) M. H. Falk, R. D. Issels, Int. J. Hyperthermia 2001, 17, 1-18.
52. D. Yoo, H. Jeong, S.-H. Noh, J.-H. Lee, J. Cheon, Angew. Chem. 2013, 125, 13285-13289
53. Angew. Chem. Int. Ed. 2013,52, 13047-13051.
54. a) J. van Overbeek, M. E. Conklin, A. F. Blakeslee, Science 1941, 94, 350-351
55. b) J. van Overbeek, Science 1966, 152, 721-731.
56. a) C. Thorpe, Trends Biochem. Sci. 1989, 14, 148-151
57. 4-Pentynoic acid as inhibitor of b-oxidation: b) Y. Yoshizawa, Z. Li, P. B. Reese, J. C. Vederas, J. Am. Chem. Soc. 1990, 112, 3212-3213
58. c) D. E. Cane, G. Luo, C. Khosla, C. M. Kao, L. Katz, J. Antibiot. 1995, 48, 647-651.
59. 2-Methylpent-4-ynoic acid: C. J. Dutton, S. P. Gibson, A. C. Goudie, K. S. Holdom, M. S. Pacey, J. C. Ruddock, J. D. Bu'Lock, M. K. Richards, J. Antibiot. 1991, 44, 357-365.
60. a) Y. Matsumura, T. Shiozawa, H. Matsushita, Y. Terao, Biol. Pharm. Bull. 1995, 18, 1805-1807
61. b) M. A. A. Sarhan, J. Appl. Sci. Res. 2007, 3, 886-889.
62. Details are given in the Supporting Information.
63. a) R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, 1-176
64. b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
65. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
66. c) C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3062
67. d) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
68. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
69. a) J.-F. Lutz, Z. Zarafshani, Adv. Drug Delivery Rev. 2008, 60, 958-970
70. b) E. M. Sletten, CR. Bertozzi, Angew. Chem. 2009, 121, 7108-7133
71. Angew. Chem. Int. Ed. 2009, 48, 6974-6998.
72. S.-K. Choi, Synthetic Multivalent Molecules: Concepts and Biomedical Applications, Wiley, Hoboken, 2004.
73. S. Kumar, D. P. Arya, J. Am. Chem. Soc. 2011, 133, 7361-7375.
74. This concept was shown to work well, if the biological target operates as a homodimer, as was recently shown for the inhibition of heat shock protein Hsp90: H. Wahyudi, Y Wang, S. R. McAlpine, Org. Biomol. Chem. 2014, 12, 765-773.
75. Reviews on superparamagnetic nanoparticles: a) A. Kirschning, L. Kupracz, J. Hartwig, Chem. Lett. 2012, 41, 562-570
76. b) A.-H. Lu, E. L. Salabas, F. Schüth, Angew. Chem. 2007, 119, 1242-1266
77. Angew. Chem. Int. Ed. 2007, 46, 1222-1244
78. c) Y-W. Jun, J.-S. Choi, J. Cheon, Chem. Commun. 2007, 1203-1214
79. d) X. K. Zhang, Y F. Li, J.Q. Xiao, E. D. Wetzel, J. Appl. Phys. 2003, 93, 7124-7126.
80. a) A.M. Wu, P.D. Senter, Nat. Biotechnol. 2005, 23, 1137-1146
81. b) R.V. Chari, Acc. Chem. Res. 2008, 41, 98-107
82. c) S. C. Alley, N. M. Okeley, P. D. Senter, Curr. Opin. Chem. Biol. 2010, 14, 529-537.
83. P.S. Low, W. A. Henne, D.D. Doorneweerd, Acc. Chem. Res. 2008, 41, 120-129.
84. a) W. Arap, R. Pasqualini, E. Ruoslahti, Science 1998, 279, 377-380
85. b) M. L. Janssen, W.J. Oyen, I. Dijkgraaf, L. F Massuger, C. Frielink, D. S. Edwards, M. Rajopadhye, H. Boonstra, F. H. Corstens, O. C Boerman, Cancer Res. 2002, 62, 6146-6151.
86. Review: L F. Tietze, K. Schmuck, Curr. Pharm. Des. 2011, 17, 3527-3547.
87. L. F. Tietze, J. M. von Hof, M. Müller, B. Krewer, I. Schuberth, Angew. Chem. 2010, 122, 7494-7497.
88. L. F. Tietze, R. Hannemann, W. Buhr, M. Lçgers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Dçring, I. Schuberth, Angew. Chem. 1996, 108, 2840-2842
89. Angew. Chem. Int. Ed. 1996, 35, 2674-2677.
90. Target specific drug conjugates were recently reviewed by A. Mullard, Nat. Rev. Drug Discovery 2013, 12, 329-333.
91. Ansamitocin and its derivatives are stable in refluxing toluene for 22 h; see ref. [9].
92. S. D. Bergman, F. Wudl, J. Mat. Chem. 2008, 18, 41-62.
93. TT N'Guyen, H.TT Duong, J. Basuki, V. Montembault, S. Pascual, C. Guibert, J. Fresnai, C. Boyer, M. R. Whittaker, T. P. Davis, L. Fontaine, Angew. Chem. 2013, 125, 14402-14406
94. Angew. Chem. Int. Ed. 2013, 52, 14152-14156.
95. H. I. Lim, P. M. Oliver, J. Marzillier, D. V. Vezenov, Anal. Bioanal. Chem. 2010, 397, 1861-1872.
96. Ringer's solution is an aqueous solution of several salts. It resembles an isotonic solution.
97. A. Gagnoud, IEEE Trans. Magn. 2004, 40, 29-36.
98. Use of SAG 471 anti-foam for fermentation of A. pretiosum was suggested in Patent No. US6790954 (J. Chung, G. S. Byng; Immunogen Inc., Cambridge, MA; Genentech Inc., South San Francisco, CA).