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Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN

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Abstract

This protocol describes the synthesis of cyclic anhydride precursors of the environment-sensitive fluorophores 4-dimethylaminophthalimide (4-DMAP) and 6-dimethylaminonaphthalimide (6-DMN). The condensation of these anhydrides with a primary amino group confers on molecules of interest solvatochromic properties. In particular, two strategies for the insertion of the chromophores into peptides are presented in two companion protocols. The anhydride syntheses can be completed on the gram scale in 2 d for the 4-DMAP precursor and 10–15 d for the 6-DMN precursor.

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Figure 1
Figure 2: Precursor synthesis.

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Acknowledgements

This research was supported by NSF CHE-0414243 (B.I.) and the Cell Migration Consortium (GM064346). The award of a Marie Curie Fellowship to M.S. is also gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, 02139-4307, Massachusetts, USA

    Matthieu Sainlos & Barbara Imperiali

  2. Department of Biology, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, 02139-4307, Massachusetts, USA

    Barbara Imperiali

Authors
  1. Matthieu Sainlos
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  2. Barbara Imperiali
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Correspondence to Barbara Imperiali.

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Competing interests

The authors declare that a patent on the environment–sensitive fluorophores is pending: “Fluorescent Probes for Biological Studies” by Imperiali et al. US Patent Application serial No. 11/106,349, filed April 13, 2005, pending.

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Sainlos, M., Imperiali, B. Synthesis of anhydride precursors of the environment-sensitive fluorophores 4-DMAP and 6-DMN. Nat Protoc 2, 3219–3225 (2007). https://doi.org/10.1038/nprot.2007.444

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