Application of a water-soluble pyridyl disulfide amine linker for use in Cu-free click bioconjugation

Tetrahedron Letters

Volumn 52, Issue 33, 2011, Pages 4316-4319

  Thomas, Joshua D ^a,b   Burke Jr , Terrence R ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b Mersana Therapeutics Inc   (United States)

Author keywords

Bioconjugation; Cleavable linker; Cu free click reaction; Pyridyl disulfide

Indexed keywords

AMINE; COPPER; DISULFIDE; MACROGOL; PYRIDYL DISULFIDE; REAGENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIOCONJUGATION; CHEMICAL STRUCTURE; CLICK CHEMISTRY; CONJUGATION; SOLUBILITY;

EID: 79960267447     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.042     Document Type: Article

References (26)

1. T. Hofer, J.D. Thomas, T.R. Burke Jr. , and C. Rader Proc. Natl. Acad. Sci. U.S.A. 105 2008 12451
2. T. Hofer, L.R. Skeffington, C.M. Chapman, and C. Rader Biochemistry 48 2009 12047
3. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem. Int. Ed. 40 2001 2004
4. J.C. Jewett, and C.R. Bertozzi Chem. Soc. Rev. 39 2010 1272
5. G. Saito, J.A. Swanson, and K.-D. Lee Adv. Drug Delivery Rev. 55 2003 199
6. I. Ojima Acc. Chem. Res. 41 2008 108
7. P.J. Carter, and P.D. Senter Cancer J. 14 2008 154
8. P.S. Low, and S.A. Kularatne Curr. Opin. Chem. Biol. 13 2009 256
9. A.J. van der Vlies, C.P. O'Neil, U. Hasegawa, N. Hammond, and J.A. Hubbell Bioconjugate Chem. 21 2010 653
10. C.P. Leamon, and P.S. Low J. Biol. Chem. 267 1992 24966
11. L. Zhu, and R.I. Mahato Bioconjugate Chem. 21 2010 2119
12. A. Meister, and M.E. Anderson Annu. Rev. Biochem. 52 1983 711
13. A.F. Howie, L.M. Forrester, M.J. Glancey, J.J. Schlager, G. Powis, G.J. Beckett, J.D. Hayes, and C.R. Wolf Carcinogenesis 11 1990 451
14. G.K. Balendiran, R. Dabur, and D. Fraser Cell Biochem. Funct. 22 2004 343
15. G.T. Zugates, D.G. Anderson, S.R. Little, I.E.B. Lawhorn, and R. Langer J. Am. Chem. Soc. 128 2006 12726
16. Breitenkamp, K.; Sill, Kevin, N.; Skaff, H. In Patent Cooperation Treaty (PCT); Organization, Publication WO 2007/127473 A2, November 8, 2007.
17. M.A. Pilkington-Miksa, S. Sarkar, M.J. Writer, S.E. Barker, P.A. Shamlou, S.L. Hart, H.C. Hailes, and A.B. Tabor Eur. J. Org. Chem. 2008 2900
18. A.C. French, A.L. Thompson, and B.G. Davis Angew. Chem. Int. Ed. 48 2009 1248
19. L. Field, T.F. Parsons, and D.E. Pearson J. Org. Chem. 31 1966 3550
20. P.G.M. Wuts, and T.W. Greene Greene's Protective Groups in Organic Synthesis 4th ed. 2007 Wiley-Interscience Hoboken, NJ 07030-5774
21. M. Lapeyre, J.M.M. Leprince, H. Oulyadi, P.Y. Renard, A. Romieu, G. Turcatti, and H. Vaudry Chem. Eur. J. 12 2006 3655
22. M. de Arruda, C.A. Cocchiaro, C.M. Nelson, C.M. Grinnell, B. Janssen, A. Haupt, and T. Barlozzari Cancer Res. 55 1995 3085
23. R. Pipkorn, W. Waldeck, B. Didinger, M. Koch, G. Mueller, M. Wiessler, and K. Braun J. Pept. Sci. 15 2009 235
24. M.L. Blackman, M. Royzen, and J.M. Fox J. Am. Chem. Soc. 130 2008 13518
25. Thomas Joshua, D.; Rader, C.; Burke, T. R., Jr. Unpublished results 2011.
26. M.J.O. Anteunis, and C. van der Auwera Int. J. Pept. Protein Res. 31 1988 301