Skip to main content
SpringerLink
Log in

N-Acyl-N-carboxymethyl-2-nitroaniline and its analogues: a new class of water-soluble photolabile precursor of carboxylic acids

  • Communication
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

The synthesis and photochemistry of a new class of water-soluble, photolabile protecting group, the N-carboxymethyl-2-nitroanilinyl (CNA) group, are described. All three CNA-caging compounds synthesized underwent clean photochemical reaction in aqueous buffer solution to produce the intended product of acetic acid, along with the corresponding nitroso aromatic.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Notes and references

  1. J. H. Kaplan, B. Forbush III and J. F. Hoffman, Rapid photolytic release of adenosine 5′-triphosphate from a protected analogue: Utilization by the Na:K pump of human red blood cell ghosts, Biochemistry, 1978, 17, 1929–1935.

    Article  CAS  Google Scholar 

  2. H. A. Lester and J. M. Nerbonne, Physiological and pharmacological manipulations with light flashes, Annu. Rev. Biophys. Bioeng., 1982, 11, 151–175.

    Article  CAS  Google Scholar 

  3. S. R. Adams and R. Y. Tsien, Controlling cell chemistry with caged compounds, Annu. Rev. Physiol., 1993, 55, 755–784.

    Article  CAS  Google Scholar 

  4. G. Marriott, Methods in Enzymology, Academic Press, San Diego, 1998, 291.

  5. M. Goeldner and R. Givens, Dynamic Studies in Biology, Wiley-VCH, Weinheim, 2005.

    Book  Google Scholar 

  6. G. Mayer and A. Heckel, Biologically active molecules with a “Light Switch”, Angew. Chem., Int. Ed., 2006, 45, 4900–4921.

    Article  CAS  Google Scholar 

  7. F. M. Rossi, M. Margulis, C.-M. Tang, J. P. Y. Kao, N-Nmoc-L-glutamate, a new caged glutamate with high chemical stability and low pre-photolysis activity, J. Biol. Chem., 1997, 272, 32933–32939.

    Article  CAS  Google Scholar 

  8. R. S. Givens, A. Jung, C.-H. Park, J. Weber and W. Bartlett, New photoactivated protecting proups. 7. p-Hydroxyphenacyl: A phototrigger for excitatory amino acids and peptides, J. Am. Chem. Soc., 1997, 119, 8369–8370.

    Article  CAS  Google Scholar 

  9. A. Specht, J.-S. Thomann, K. Alarcon, W. Wittayanan, D. Ogden, T. Furuta, Y. Kurakawa and M. Goeldner, New photoremovable protecting groups for carboxylic acids with high photolytic efficiencies at near-UV irradiation. Application to the photocontrolled release of L-glutamate, ChemBioChem, 2006, 7, 1690–1695.

    Article  CAS  Google Scholar 

  10. S. Gug, S. Charon, A. Specht, K. Alarcon, D. Ogden, B. Zietz, J. Léonard, S. Haacke, F. Bolze, J.-F. Nicoud and M. Goeldner, Photolabile glutamate protecting group with high one- and two-photon uncaging efficiencies, ChemBioChem, 2008, 9, 1303–1307.

    Article  CAS  Google Scholar 

  11. G. Papageorgiou, J. E. T. Corrie, Effects of Aromatic Substituents on the Photocleavage of 1-Acyl-7-nitroindolines, Tetrahedron, 2000, 56, 8197–8205.

    Article  CAS  Google Scholar 

  12. G. Papageorgiou, M. Lukeman, P. Wan, J. E. T. Corrie, An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease, Photochem. Photobiol. Sci., 2004, 3, 366–373.

    Article  CAS  Google Scholar 

  13. G. Papageorgiou, D. Ogden, G. Kelly, J. E. T. Corrie, Synthetic and photochemical studies of substituted 1-acyl-7-nitroindolines, Photochem. Photobiol. Sci., 2005, 4, 887–896.

    Article  CAS  Google Scholar 

  14. O. D. Fedoryak, J.-Y. Sul, P. G. Haydonb, G. C. R. Ellis-Davies, Synthesis of a caged glutamate for efficient one- and two-photon photorelease on living cells, Chem. Commun., 2005, 3664–3666.

    Google Scholar 

  15. T. Furuta, S. S.-H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk and R. Y. Tsien, Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis, Proc. Natl. Acad. Sci. U. S. A., 1999, 96, 1193–1200.

    Article  CAS  Google Scholar 

  16. V. R. Shembekar, Y. Chen, B. K. Carpenter and G. P. Hess, A protecting group for carboxylic acids that can be photolyzed by visible light, Biochemistry, 2005, 44, 7107–7114.

    Article  CAS  Google Scholar 

  17. N. Senda, A. Momotake and T. Arai, Synthesis and photocleavage of 7-[s(carboxymethyl)aminocoumarin-4-yl]methyl-caged neurotransmitters, Bull. Chem. Soc. Jpn., 2007, 80, 2384–2388.

    Article  CAS  Google Scholar 

  18. O. D. Fedoryak and T. M. Dore, Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation, Org. Lett., 2002, 4, 3419–3422.

    Article  CAS  Google Scholar 

  19. E. J. Petersson, G. S. Brandt, N. M. Zacharias, D. A. Dougherty and H. A. Lester, Methods Enzymol., 2003, 360, 258.

    Article  CAS  Google Scholar 

  20. G. Marriott, P. Roy and K. Jacobson, Methods Enzymol., 2003, 360, 274.

    Article  CAS  Google Scholar 

  21. D. S. Lawrence, The preparation and in vivo applications of caged peptides and proteins, Curr. Opin. Chem. Biol., 2005, 9, 570–575.

    Article  CAS  Google Scholar 

  22. H. Li, J.-M. Hah and D. S. Lawrence, Light-mediated liberation of enzymatic activity: “Small Molecule” caged protein equivalents, J. Am. Chem. Soc., 2008, 130, 10474–10475.

    Article  CAS  Google Scholar 

  23. H. Ando, T. Furuta, R. Y. Tsien and H. Okamoto, Photo-mediated gene activation using caged RNA/DNA in zebrafish embryos, Nat. Genet., 2001, 28, 317–325.

    Article  CAS  Google Scholar 

  24. P. Wenter, B. Fürtig, A. Hainard, H. Schwalbe and S. Pitsch, Kinetics of photoinduced RNA refolding by real-time NMR spectroscopy, Angew. Chem., Int. Ed., 2005, 44, 2600–2603.

    Article  CAS  Google Scholar 

  25. C. Hobartner and S. K. Silverman, Modulation of RNAtertiary folding by incorporation of caged nucleotides, Angew. Chem., Int. Ed., 2005, 44, 7305–7309.

    Article  CAS  Google Scholar 

  26. G. C. R. Ellis-Davies, Neurobiology with caged calcium, Chem. Rev., 2008, 108, 1603–1613.

    Article  CAS  Google Scholar 

  27. A. Momotake, N. Lindegger, E. Niggli, R. J. Barsotti, G. C. R. Ellis-Davies, The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells, Nat. Methods, 2006, 3, 35–40.

    Article  CAS  Google Scholar 

  28. S. R. Adams, J. P. Y. Kao and G. Grynkiewicz, Biologically useful chelators that release Ca2+ upon illumination, A. V. Minta and R. Y. Tsien, J. Am. Chem. Soc., 1988, 110, 3212–3220.

    Article  CAS  Google Scholar 

  29. S. R. Adams, V. Lev-Ram and R. Y. Tsien, A new caged Ca2+, azid-1, is far more photosensitive than nitrobenzyl-based chelators, Chem. Biol., 1997, 4, 867.

    Article  CAS  Google Scholar 

  30. G. C. R. Ellis-Davies and J. H. Kaplan, Nitrophenyl-EGTA, a photolabile chelator that selectively binds Ca2+ with high affinity and releases it rapidly upon photolysis, Proc. Natl. Acad. Sci. U. S. A., 1994, 91, 187–191.

    Article  CAS  Google Scholar 

  31. N. Obi, A. Momotake, Y. Kanemoto, M. Matsuzaki, H. Kasai and T. Arai, 1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids, Tetrahedron Lett., 2010, 51, 1642–1647.

    Article  CAS  Google Scholar 

  32. P. V. Fish, C. G. Barber, D. G. Brown, R. Butt, M. G. Collis, R. P. Dickinson, B. T. Henry, V. A. Horne, J. P. Huggins, E. King, M. O’Gara, D. McCleverty, F. McIntosh, C. Phillips and R. Webster, Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-sulfonamidoisoquinolinyl)guanidines, J. Med. Chem., 2007, 50, 2341–2351.

    Article  CAS  Google Scholar 

  33. K. Smith, T. Gibbins, R. W. Millar and R. P. Claridge, A novel method for the nitration of deactivated aromatic compounds, J. Chem. Soc., Perkin Trans. 1, 2000, 2753–2758.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8577, Japan

    Takuya Honda, Atsuya Momotake & Tatsuo Arai

Authors
  1. Takuya Honda
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Atsuya Momotake
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tatsuo Arai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tatsuo Arai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Honda, T., Momotake, A. & Arai, T. N-Acyl-N-carboxymethyl-2-nitroaniline and its analogues: a new class of water-soluble photolabile precursor of carboxylic acids. Photochem Photobiol Sci 11, 493–496 (2012). https://doi.org/10.1039/c2pp05322e

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c2pp05322e

Search

Navigation