Journal of Chemical Biology

, Volume 5, Issue 3, pp 119–123 | Cite as

In situ synthesis of fluorescent membrane lipids (ceramides) using click chemistry

  • María Garrido
  • José Luis Abad
  • Alicia Alonso
  • Félix M. Goñi
  • Antonio Delgado
  • L.-Ruth MontesEmail author


Ceramide analogues containing azide groups either in the polar head or in the hydrocarbon chains are non-fluorescent. When incorporated into phospholipid bilayers, they can react in situ with a non-fluorescent 1,8-naphthalimide using click chemistry giving rise to fluorescent ceramide derivatives emitting at ≈440 nm. When incorporated into giant unilamellar vesicles, two-photon excitation at 760 nm allows visualization of the ceramide-containing bilayers. This kind of method may be of general applicability in the study of model and cell membranes.


Ceramide GUV Fluorescence Click chemistry 





Nuclear magnetic resonance


High-resolution mass spectrometry


Egg phosphatidylcholine



This work was supported in part by Spanish Ministerio de Ciencia e Innovación grants BFU2011-28566 (AA), SAF 2011-22444 (JLA/AD) and BFU 2007-62062 (FMG), and by Generalitat de Catalunya grant SGR 2009-1072 (JLA/AD). LRM is grateful to Consejo Superior de Investigaciones Científicas for a JAEdoc fellowship and MG for a JAEpredoc fellowship.

Supplementary material

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Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • María Garrido
    • 1
  • José Luis Abad
    • 1
  • Alicia Alonso
    • 2
  • Félix M. Goñi
    • 2
  • Antonio Delgado
    • 1
    • 3
  • L.-Ruth Montes
    • 2
    Email author
  1. 1.Consejo Superior de Investigaciones Científicas (CSIC), Research Unit on Bioactive Molecules (RUBAM)Institut de Química Avançada de Catalunya (IQAC-CSIC)BarcelonaSpain
  2. 2.Unidad de Biofísica (CSIC-UPV/EHU), and Departamento de BioquímicaUniversidad del País VascoBilbaoSpain
  3. 3.Facultad de Farmacia, Unidad de Química Farmacéutica (Unidad Asociada al CSIC)Universidad de Barcelona (UB)BarcelonaSpain

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