Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

Article English OPEN
Anderson, James C.; Grounds, Helen; Jathoul, Amit; Murray, James Augustus Henry; Pacman, Steven J.; Tisi, Laurence;

Infra-luciferin, an alkene linked analogue of luciferin, gives bioluminescence emission >700 nm and has the potential to be used for multiparametric in vivo imaging. We report here a high yielding, scalable and convergent synthesis of infra-luciferin which will allow th... View more
  • References (19)
    19 references, page 1 of 2

    1 F. Fan and K. V. Wood, Assay Drug Dev. Technol., 2007, 5, 127.

    2 J. A. Prescher and C. H. Contag, Curr. Opin. Chem. Biol., 2010, 14, 80.

    3 Y. Ando, K. Niwa, N. Yamada, T. Enomoto, T. Irie, H. Kubota, Y. Ohmiya and H. Akiyama, Nat. Photonics, 2008, 2, 44.

    4 (a) P. E. De Almeida, J. R. M. Van Rappard and J. C. Wu, Am. J. Physiol.: Heart Circ. Physiol., 2011, 301, H663; (b) R. T. Sadikot and T. S. Blackwell, Methods Mol. Biol., 2008, 477, 383; (c) J. Duda, M. Karimi, R. S. Negrin and G. H. Contag, Methods Mol. Med., 2007, 134, 17; (d) C. E. Badr and B. A. Tannous, Trends Biotechnol., 2011, 29, 624.

    5 B. W. Rice, M. D. Cable and M. B. Nelson, J. Biomed. Opt., 2001, 6, 432.

    6 (a) S. T. Adams Jr and S. C. Miller, Curr. Opin. Chem. Biol., 2014, 21, 112; (b) M. A. Paley and J. A. Prescher, Med. Chem. Commun., 2014, 5, 255.

    7 (a) S. Maki, JP2009184932, 2009; (b) S. Iwano, R. Obata, C. Miura, M. Kiyama, K. Hama, M. Nakurama, Y. Amano, S. Kojima, T. Hirano, S. Maki and H. Niva, Tetrahedron, 2013, 69, 3847; (c) C. Miura, M. Kiyama, S. Iwano, K. Ito, R. Obata, T. Hirano, S. Maki and H. Niwa, Tetrahedron, 2013, 69, 9726; (d) T. Kuchimaru, S. Iwano, M. Kiyama, S. Mitsumata, T. Kadosono, H. Niwa, S. Maki and S. Kizaka-Kondoh, Nat. Commun., 2016, 7, 11856, DOI: 10.1038/ncomms11856.

    8 A. P. Jathoul, H. Grounds, J. C. Anderson and M. A. Pule, Angew. Chem., Int. Ed., 2014, 53, 13059.

    9 D. C. McCutcheon, M. A. Paley, R. C. Steinhardt and J. A. Prescher, J. Am. Chem. Soc., 2012, 134, 7604.

    10 E. Pfund, T. Lequeux, S. Masson and M. Vazeux, Org. Lett., 2002, 4, 843.

  • Related Organizations (4)
  • Metrics
Share - Bookmark