Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors

Chemistry - A European Journal

Volumn 17, Issue 44, 2011, Pages 12257-12261

  Rotstein, Benjamin H ^a   Mourtada, Rida ^a   Kelley, Shana O ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

fluorescent probes; isocyanides; macrocycles; multicomponent reactions; peptides; solvatochromism

Indexed keywords

FLUORESCENT PROBES; ISOCYANIDES; MACROCYCLES; MULTI-COMPONENT REACTIONS; SOLVATOCHROMISMS;

CYANIDES; LINEAR CONTROL SYSTEMS; SCAFFOLDS (BIOLOGY);

PEPTIDES;

CYANIDE; CYCLOPEPTIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORESCENT DYE; MACROCYCLIC COMPOUND;

ARTICLE; CELL MEMBRANE PERMEABILITY; CHEMICAL STRUCTURE; CHEMISTRY;

CELL MEMBRANE PERMEABILITY; CYANIDES; FLUORESCENT DYES; INDICATORS AND REAGENTS; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC;

EID: 80054744507     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102096     Document Type: Article

References (74)

1. E. Vives, J. Schmidt, A. Pelegrin, Biochim. Biophys. Acta 2008, 1786, 126
2. S. B. Fonseca, M. P. Pereira, S. O. Kelley, Adv. Drug Delivery Rev. 2009, 61, 953.
3. D. H. Kwan, H.-M. Chen, K. Ratananikom, S. M. Hancock, Y. Watanabe, P. T. Kongsaeree, A. L. Samuels, S. G. Withers, Angew. Chem. Int. Ed. 2011, 50, 300
4. J. M. Baumes, J. J. Gassensmith, J. Giblin, J.-J. Lee, A. G. White, W. J. Culligan, W. M. Leevy, M. Kuno, B. D. Smith, Nat. Chem. 2010, 2, 1025
5. J. Dommerholt, S. Schmidt, R. Temming, L. J. A. Hendriks, F. P. J. T. Rutjes, J. C. M. van Hest, D. J. Lefeber, P. Friedl, F. L. van Delft, Angew. Chem. 2010, 122, 9612
6. Angew. Chem. Int. Ed. 2010, 49, 9422
7. T. Tanaka, W. Nomura, T. Narumi, A. Masuda, H. Tamamura, J. Am. Chem. Soc. 2010, 132, 15899
8. Y. K. Kim, H.-H. Ha, J.-S. Lee, X. Bi, Y.-H. Ahn, J.-J. Lee, Y.-T. Chang, J. Am. Chem. Soc. 2010, 132, 576
9. N. K. Devaraj, S. Hiderbrand, R. Upadhyay, R. Mazitschek, R. Weissleder, Angew. Chem. 2010, 122, 2931
10. Angew. Chem. Int. Ed. 2010, 49, 2869
11. C. Ran, X. Xu, S. B. Raymond, B. J. Ferrara, K. Neal, B. J. Bacskai, Z. Medarova, A. Moore, J. Am. Chem. Soc. 2009, 131, 15257
12. X. Zhang, Y. Xiao, X. Qian, Angew. Chem. 2008, 120, 8145
13. Angew. Chem. Int. Ed. 2008, 47, 8025
14. S. T. Laughlin, J. M. Baskin, S. L. Amacher, C. R. Bertozzi, Science 2008, 320, 664
15. A. Watzke, G. Kosec, M. Kindermann, V. Jeske, H.-P. Nestler, V. Turk, B. Turk, K. U. Wendt, Angew. Chem. 2008, 120, 412
16. Angew. Chem. Int. Ed. 2008, 47, 406
17. M.-K. So, C. Xu, A. M. Loening, S. S. Gambhir, J. Rao, Nat. Biotechnol. 2006, 24, 339
18. F. Galindo, M. I. Burguete, L. Vigara, S. V. Luis, N. Kabir, J. Gavrilovic, D. A. Russell, Angew. Chem. 2005, 117, 6662
19. Angew. Chem. Int. Ed. 2005, 44, 6504.
20. G. Blum, S. R. Mullins, K. Keren, M. Fonovič, C. Jedesko, M. J. Rice, B. F. Sloane, M. Bogyo, Nat. Chem. Biol. 2005, 1, 203
21. G. Blum, G. von Degenfeld, M. J. Merchant, H. M. Blau, M. Bogyo, Nat. Chem. Biol. 2007, 3, 668.
22. M. E. Vázquez, J. B. Blanco, B. Imperiali, J. Am. Chem. Soc. 2005, 127, 1300
23. M. Sainlos, W. S. Iskenderian, B. Imperiali, J. Am. Chem. Soc. 2009, 131, 6680
24. G. Loving, B. Imperiali, J. Am. Chem. Soc. 2008, 130, 13630
25. G. Loving, B. Imperiali, Bioconjugate Chem. 2009, 20, 2133.
26. H. Kessler, Angew. Chem. 1982, 94, 509
27. Angew. Chem. Int. Ed. Engl. 1982, 21, 512
28. J. DiMaio, T. M.-D. Nguyen, C. Lemieux, P. W. Schiller, J. Med. Chem. 1982, 25, 1432
29. J. Ying, X. Gu, M. Cai, M. Dedek, J. Vagner, D. B. Tivedi, V. J. Hruby, J. Med. Chem. 2006, 49, 6888
30. J. D. A. Tyndall, T. Nall, D. P. Fairlie, Chem. Rev. 2005, 105, 973
31. W. S. Horne, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009, 121, 4812
32. Angew. Chem. Int. Ed. 2009, 48, 4718.
33. S. Hess, Y. Linde, O. Ovadia, E. Safrai, D. E. Shalev, A. Swed, E. Halbfinger, T. Lapidot, I. Winkler, Y. Gabinet, A. Faier, D. Yarden, Z. Xiang, F. P. Portillo, C. Haskell-Luevano, C. Gilon, A. Hoffman, J. Med. Chem. 2008, 51, 1026
34. J. M. Fletcher, C. J. Morton, R. A. Zwar, S. S. Murray, P. D. O'Leary, R. A. Hughes, J. Biol. Chem. 2008, 283, 33375
35. D. R. Witty, J. Bateson, G. J. Hervieu, K. Al-Barazanji, P. Jeffrey, D. Hamprecht, A. Haynes, C. N. Johnson, A. I. Muir, P. J. O'Hanlon, G. Stemp, A. J. Stevens, K. Thewlis, K. Y. Winborn, Bioorg. Med. Chem. Lett. 2006, 16, 4872
36. M. Pakkala, C. Hekim, P. Soininen, J. Leinonen, H. Koistinen, J. Weisell, U.-H. Stenman, J. Vepsäläinen, A. Närvänen, J. Pept. Sci. 2007, 13, 348.
37. O. S. Gudmundsson, S. D. S. Jois, D. G. Vander Velde, T. J. Siahaan, B. Wang, R. T. Borchardt, J. Peptide Res. 1999, 53, 383
38. K. Matsuzaki, S. Yoneyama, N. Fujii, K. Miyajima, K. Yamada, Y. Kirino, K. Anzai, Biochemistry 1997, 36, 9799.
39. T. Rezai, B. Yu, G. L. Millhauser, M. P. Jacobson, R. S. Lokey, J. Am. Chem. Soc. 2006, 128, 14073.
40. D. Lössner, H. Kessler, G. Thumshirn, C. Dahmen, B. Wiltschi, M. Tanaka, W. Knoll, E.-K. Sinner, U. Reuning, Anal. Chem. 2006, 78, 4524
41. M. Pfaff, K. Tangemann, B. Müller, M. Gurrath, G. Müller, H. Kessler, R. Timpl, J. Engel, J. Biol. Chem. 1994, 269, 20233.
42. R. Hili, V. Rai, A. K. Yudin, J. Am. Chem. Soc. 2010, 132, 2889
43. B. H. Rotstein, V. Rai, R. Hili, A. K. Yudin, Nat. Protoc. 2010, 5, 1813.
44. I. Bolz, D. Schaarschmidt, T. Rüffer, H. Lang, S. Spange, Angew. Chem. 2009, 121, 7576
45. Angew. Chem. Int. Ed. 2009, 48, 7440
46. Y. Suzuki, K. Yokoyama, Angew. Chem. 2007, 119, 4175
47. Angew. Chem. Int. Ed. 2007, 46, 4097.
48. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300
49. Angew. Chem. Int. Ed. 2000, 39, 3168
50. J. Zhu, Eur. J. Org. Chem. 2003, 1133
51. A. Dömling, Chem. Rev. 2006, 106, 17
52. L. A. Wessjohann, D. G. Rivera, O. E. Vercillo, Chem. Rev. 2009, 109, 796.
53. G. Rouschias, B. L. Shaw, J. Chem. Soc. D 1970, 183
54. Y. Yu, A. R. Sadique, J. M. Smith, T. R. Dugan, R. E. Cowley, W. W. Brennessel, C. J. Flaschenriem, E. Bill, T. R. Cundari, P. L. Holland, J. Am. Chem. Soc. 2008, 130, 6624.
55. M. Tobisu, S. Imoto, S. Ito, N. Chatani, J. Org. Chem. 2010, 75, 4835.
56. Z.-Q. Wu, K. Nagai, M. Banno, K. Okoshi, K. Onitsuka, E. Yashima, J. Am. Chem. Soc. 2009, 131, 6708
57. Y. Hase, K. Nagai, H. Iida, K. Maeda, N. Ochi, K. Sawabe, K. Okoshi, E. Yashima, J. Am. Chem. Soc. 2009, 131, 10719.
58. A. Czarna, B. Beck, S. Srivastava, G. M. Popowicz, S. Wolf, Y. Huang, M. Bista, T. A. Holak, A. Dömling, Angew. Chem. 2010, 122, 5480
59. Angew. Chem. Int. Ed. 2010, 49, 5352
60. T. Yue, M.-X. Wang, D.-X. Wang, G. Masson, J. Zhu, Angew. Chem. 2009, 121, 6845
61. Angew. Chem. Int. Ed. 2009, 48, 6717
62. J.-M. Grassot, G. Masson, J. Zhu, Angew. Chem. 2008, 120, 961
63. Angew. Chem. Int. Ed. 2008, 47, 947
64. S.-X. Wang, M.-X. Wang, D.-X. Wang, J. Zhu, Angew. Chem. 2008, 120, 394
65. Angew. Chem. Int. Ed. 2008, 47, 388
66. A. Dömling, B. Beck, U. Eichelberger, S. Sakamuri, S. Menon, Q.-Z. Chen, Y. Lu, L. A. Wessjohann, Angew. Chem. 2006, 118, 7393
67. Angew. Chem. Int. Ed. 2006, 45, 7235.
68. An alternative strategy involving a fluorescently labeled diaminocarboxylic acid residue within the peptide sequence was also investigated. 4-DMNA (see ref. [3c]) was synthesized and was compatible with our standard macrocyclization conditions as an amino acid or within a dipeptide. Synthesis of larger peptides incorporating the 4-DMNA residue requires cumbersome orthogonal protection strategies. See the Supporting Information for details.: K. L. Horton, K. M. Stewart, S. B. Fonseca, Q. Guo, S. O. Kelley, Chem. Biol. 2008, 15, 375
69. L. Yousif, K. M. Stewart, K. L. Horton, S. O. Kelley, ChemBioChem 2009, 10, 2081.
70. M. J. Jebrail, A. H. C. Ng, V. Rai, R. Hili, A. K. Yudin, A. R. Wheeler, Angew. Chem. 2010, 122, 8807
71. Angew. Chem. Int. Ed. 2010, 49, 8625.
72. J. Aimi, Y. Nagamine, A. Tsuda, A. Muranaka, M. Uchiyama, T. Aida, Angew. Chem. 2008, 120, 5231
73. Angew. Chem. Int. Ed. 2008, 47, 5153
74. M. Koeck, H. Kessler, D. Seebach, A. Thaler, J. Am. Chem. Soc. 1992, 114, 2676.