Multifunctional Deuterated and Tritiated ‘Click’ Molecular Probes via ­Palladium-Mediated Reductive Deiodination of 5-Iodo-1,2,3-Triazoles

Abstract

Tritiated compounds are invaluable tools for in vitro and in vivo studies on bioactive molecules. Here we describe a ‘click-chemistry’-based strategy for deuteration and tritiation of multifunctional compounds and multimodal molecular imaging probes. The method relies on a palladium-mediated reductive deiodination of 5-iodo-1,2,3-triazoles in the presence of NaBD₄, deuterium or tritium gas.

Key words

tritium - ‘click’ chemistry - 1,2,3-triazole - deuterium - bioconjugation

• References

• 1 Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
• 2 Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696
• 3 van Dijk M, Rijkers DT. S, Liskamp RM. J, van Nostrum CF, Hennink WE. Bioconjugate Chem. 2009; 20: 2001
• 4 Hata S. J. Synth. Org. Chem. Jpn. 2011; 69: 1158
• 5 El-Sagheer AH, Brown T. Chem. Soc. Rev. 2010; 39: 1388
• 6 Lutz J, Zarafshani Z. Adv. Drug Delivery Rev. 2008; 60: 958
• 7 Waengler C, Schirrmacher R, Bartenstein P, Waengler B. Curr. Med. Chem. 2010; 17: 1092
• 8 Jia L, Cheng Z, Shi L, Li J, Wang C, Jiang D, Zhou W, Meng H, Qi Y, Cheng D, Zhang L. Appl. Radiat. Isot. 2013; 75: 64
• 9a Baskin JM, Bertozzi CR. Aldrichimica Acta 2010; 43: 15
• 9b Manabe Y. J. Synth. Org. Chem., Jpn. 2012; 70: 754
• 9c Gordon CG, Mackey JL, Jewett JC, Sletten EM, Houk KN, Bertozzi CR. J. Am. Chem. Soc. 2012; 134: 9199
• 10a Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed. 2009; 48: 8018
• 10b Bogdan AR, James K. Org. Lett. 2011; 13: 4060
• 11 Li L, Zhang G, Zhu A, Zhang L. J. Org. Chem. 2008; 73: 3630
• 12 Schwartz E, Breitenkamp K, Fokin VV. Abstracts of Papers of the American Chemical Society 2011; 242
• 13 Juricek M, Stout K, Kouwer PH. J, Rowan AE. Org. Lett. 2011; 13: 3494
• 14a Yan R, El-Emir E, Rajkumar V, Robson M, Jathoul AP, Pedley B, Årstad E. Angew. Chem. Int. Ed. 2011; 50: 6793
• 14b Yan R, Sander K, Galante E, Rajkumar V, Badar A, Robson M, El-Emir E, Lythgoe MF, Pedley RB, Arstad E. J. Am. Chem. Soc. 2013; 135: 703
• 15 Zhou Y, Lecourt T, Micouin L. Angew. Chem. Int. Ed. 2010; 49: 2607
• 16a Shao C, Wang X, Xu J, Zhao J, Zhang Q, Hu Y. J. Org. Chem. 2010; 75: 7002
• 16b Gonda Z, Loerincz K, Novak Z. Tetrahedron Lett. 2010; 51: 6275
• 16c Akula HK, Lakshman MK. J. Org. Chem. 2012; 77: 8896
• 17 See, for example: Frish K, Jakobsen S, Sorensen M, Munk OL, Alstrup AK. O, Ott P, Hoffmann AF, Keiding S. J. Nucl. Med. 2012; 53: 772
• 18 Avraamides CJ, Garmy-Susini B, Varner JA. Nat. Rev. Cancer 2008; 8: 604
• 19 Akers Y, Ye W, Xu B, Bloch S, Odonkor C, Achilefu S. Bioorg. Med. Chem. Lett. 2012; 22: 5405
• 20 Boturyn D, Dumy P. Tetrahedron Lett. 2001; 42: 2787
• 21a Jeong JM, Hong MK, Chang YS, Lee Y, Kim YJ, Cheon GJ, Lee DS, Chung J, Lee MC. J. Nucl. Med. 2008; 49: 830
• 21b Dumont RA, Deininger F, Haubner R, Maecke HR, Weber WA, Fani M. J. Nucl. Med. 2011; 52: 1276
• 21c Haubner R, Kuhnast B, Mang C, Weber WA, Kessler H, Wester HJ, Schwaiger M. Bioconjugate Chem. 2004; 15: 61
• 21d Dall’Angelo S, Zhang Q, Fleming IN, Piras M, Schweiger LF, O’Hagan D, Zanda M. Org. Biomol. Chem. 2013; 11: 4551
• 22a Boturyn D, Coll JL, Garanger E, Favrot MC, Dumy P. J. Am. Chem. Soc. 2004; 126: 5730
• 22b Piras M, Fleming IN, Zanda M. Synlett 2012; 23: 2899
• 23 Nagasaki T, Sakai K, Segawa M, Katsuyama Y, Haga N, Koike M, Kawada K, Takechi S. J. Labelled Compd. Radiopharm. 2001; 44: 993
• 24 Guella G, Zanchetta C, Patton B, Mioltello A. J. Phys. Chem. B 2006; 110: 17024
• 25 McCusker CF, Kocienski PJ, Boyle FT, Schatzlein AG. Bioorg. Med. Chem. Lett. 2002; 12: 547