Copper Catalysis in Living Systems and In Situ Drug Synthesis

Angewandte Chemie - International Edition

Volumn 55, Issue 50, 2016, Pages 15662-15666

  Clavadetscher, Jessica ^a   Hoffmann, Scott ^b   Lilienkampf, Annamaria ^a   Mackay, Logan ^a   Yusop, Rahimi M ^c   Rider, Sebastien A ^b   Mullins, John J ^b   Bradley, Mark ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

^c UNIVERSITI KEBANGSAAN MALAYSIA   (Malaysia)

Author keywords

bioorthogonal chemistry; copper; heterogeneous catalysis; prodrugs

Indexed keywords

BIOLOGICAL SYSTEMS; CATALYSIS; CATALYSTS; COPPER; CYCLOADDITION; HYDROCARBONS;

ANTI-CANCER AGENTS; BIOORTHOGONAL CHEMISTRIES; CHEMICAL LIGATION; COPPER CATALYSIS; COPPER CATALYZED; CYCLOADDITION PROCESS; POLYMER FABRICATIONS; PRODRUGS;

COPPER COMPOUNDS;

ALKYNE; ANTINEOPLASTIC AGENT; AZIDE; COPPER; FLUORESCENT DYE; METAL NANOPARTICLE; TRIAZOLE DERIVATIVE;

ANIMAL; CATALYSIS; CELL LINE; CHEMISTRY; CLICK CHEMISTRY; CYCLOADDITION; HELA CELL LINE; HUMAN; PROCEDURES; SYNTHESIS; ZEBRA FISH;

ALKYNES; ANIMALS; ANTINEOPLASTIC AGENTS; AZIDES; CATALYSIS; CELL LINE; CLICK CHEMISTRY; COPPER; CYCLOADDITION REACTION; FLUORESCENT DYES; HELA CELLS; HUMANS; METAL NANOPARTICLES; TRIAZOLES; ZEBRAFISH;

EID: 85027943668     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201609837     Document Type: Article

References (50)

1. J. A. Prescher, C. R. Bertozzi, Nat. Chem. Biol. 2005, 1, 13–21.
2. M. Boyce, C. R. Bertozzi, Nat. Methods 2011, 8, 638–642.
3. R. K. V. Lim, Q. Lin, Chem. Commun. 2010, 46, 1589–1600.
4. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004–2021;
5. Angew. Chem. 2001, 113, 2056–2075.
6. H.-W. Shih, D. N. Kamber, J. A. Prescher, Curr. Opin. Chem. Biol. 2014, 21, 103–111.
7. C. W. Tornøe, M. Meldal in Pept. Wave Futur. Proc. Second Int. Seventeenth Am. Pept. Symp. (Eds.: M. Lebl, R. A. Houghten), Springer Netherlands, Dordrecht, 2001, pp. 263–264.
8. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596–2599;
9. Angew. Chem. 2002, 114, 2708–2711.
10. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057–3064.
11. R. Kharb, P. C. Sharma, M. S. Yar, J. Enzyme Inhib. Med. Chem. 2011, 26, 1–21.
12. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128–1137.
13. L. M. Gaetke, C. K. Chow, Toxicology 2003, 189, 147–163.
14. D. C. Kennedy, C. S. McKay, M. C. B. Legault, D. C. Danielson, J. A. Blake, A. F. Pegoraro, A. Stolow, Z. Mester, J. P. Pezacki, J. Am. Chem. Soc. 2011, 133, 17993–18001.
15. T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853–2855.
16. V. Hong, S. I. Presolski, C. Ma, M. G. Finn, Angew. Chem. Int. Ed. 2009, 48, 9879–9883;
17. Angew. Chem. 2009, 121, 10063–10067.
18. D. Soriano del Amo, W. Wang, H. Jiang, C. Besanceney, A. C. Yan, M. Levy, Y. Liu, F. L. Marlow, P. Wu, J. Am. Chem. Soc. 2010, 132, 16893–16899.
19. V. Hong, N. F. Steinmetz, M. Manchester, M. G. Finn, Bioconjugate Chem. 2010, 21, 1912–1916.
20. C. Besanceney-Webler, H. Jiang, T. Zheng, L. Feng, D. Soriano del Amo, W. Wang, L. M. Klivansky, F. L. Marlow, Y. Liu, P. Wu, Angew. Chem. Int. Ed. 2011, 50, 8051–8056;
21. Angew. Chem. 2011, 123, 8201–8206.
22. C. Uttamapinant, A. Tangpeerachaikul, S. Grecian, S. Clarke, U. Singh, P. Slade, K. R. Gee, A. Y. Ting, Angew. Chem. Int. Ed. 2012, 51, 5852–5856;
23. Angew. Chem. 2012, 124, 5954–5958.
24. V. Bevilacqua, M. King, M. Chaumontet, M. Nothisen, S. Gabillet, D. Buisson, C. Puente, A. Wagner, F. Taran, Angew. Chem. Int. Ed. 2014, 53, 5872–5876;
25. Angew. Chem. 2014, 126, 5982–5986.
26. Y. Bai et al., J. Am. Chem. Soc. 2016, 138, 11077–11080.
27. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 15046–15047.
28. P. Agarwal, B. J. Beahm, P. Shieh, C. R. Bertozzi, Angew. Chem. Int. Ed. 2015, 54, 11504–11510;
29. Angew. Chem. 2015, 127, 11666–11672.
30. K. E. Beatty, J. D. Fisk, B. P. Smart, Y. Y. Lu, J. Szychowski, M. J. Hangauer, J. M. Baskin, C. R. Bertozzi, D. A. Tirrell, ChemBioChem 2010, 11, 2092–2095.
31. T. Völker, E. Meggers, Curr. Opin. Chem. Biol. 2015, 25, 48–54.
32. M. Yang, J. Li, P. R. Chen, Chem. Soc. Rev. 2014, 43, 6511–6526.
33. P. K. Sasmal, C. N. Streu, E. Meggers, Chem. Commun. 2013, 49, 1581–1587.
34. M. I. Sánchez, C. Penas, M. E. Vazquez, J. L. Mascarenas, Chem. Sci. 2014, 5, 1901–1907.
35. H.-T. Hsu, B. M. Trantow, R. M. Waymouth, P. A. Wender, Bioconjugate Chem. 2016, 27, 376–382.
36. J. Li et al., Nat. Chem. 2014, 6, 352–361.
37. J. Li, P. R. Chen, Nat. Chem. Biol. 2016, 12, 129–137.
38. T. Völker, F. Dempwolff, P. L. Graumann, E. Meggers, Angew. Chem. Int. Ed. 2014, 53, 10536–10540;
39. Angew. Chem. 2014, 126, 10705–10710.
40. M. Tomás-Gamasa, M. Martínez-Calvo, J. R. Couceiro, J. L. Mascareñas, Nat. Commun. 2016, 7, 12538.
41. R. M. Yusop, A. Unciti-Broceta, E. M. V. Johansson, R. M. Sanchez-Martin, M. Bradley, Nat. Chem. 2011, 3, 239–243.
42. J. T. Weiss, J. C. Dawson, K. G. Macleod, W. Rybski, C. Fraser, C. Torres-Sánchez, E. E. Patton, M. Bradley, N. O. Carragher, A. Unciti-Broceta, Nat. Commun. 2014, 5, 3277.
43. G. Y. Tonga et al., Nat. Chem. 2015, 7, 597–603.
44. K. Sivakumar, F. Xie, B. M. Cash, S. Long, H. N. Barnhill, Q. Wang, Org. Lett. 2004, 6, 4603–4606.
45. R. A. J. Smith, C. M. Porteous, A. M. Gane, M. P. Murphy, Proc. Natl. Acad. Sci. USA 2003, 100, 5407–5412.
46. G. M. Tozer, V. E. Prise, J. Wilson, R. J. Locke, B. Vojnovic, M. R. L. Stratford, M. F. Dennis, D. J. Chaplin, Cancer Res. 1999, 59, 1626–1634.
47. C. Kanthou, G. M. Tozer, Int. J. Exp. Pathol. 2009, 90, 284–294.
48. G. C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, A. A. Genazzani, J. Med. Chem. 2006, 49, 3033–3044.
49. K. Odlo, J. Fournier-Dit-Chabert, S. Ducki, O. A. B. S. M. Gani, I. Sylte, T. V. Hansen, Bioorg. Med. Chem. 2010, 18, 6874–6885.
50. O. W. Akselsen, K. Odlo, J. J. Cheng, G. Maccari, M. Botta, V. T. Hansen, Bioorg. Med. Chem. 2012, 20, 234–242.