Brief Communication | Published:

Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry

Nature Chemical Biology volume 6, pages 205207 (2010) | Download Citation

Abstract

Alkyne-modified phospholipids can be unambiguously identified and differentiated from native species in complex mixtures by formation of dicobalthexacarbonyl complexes. This reaction is specific for alkynes and is unaffected by other glycerophospholipid-related moieties. Enrichment of cells with alkyne-derivatized fatty acids or glycerophospholipids followed by solid-phase sequestration and release is a promising new method for unequivocally monitoring individual glycerophospholipids following incorporation into cells. This technique also facilitates lipidomic analysis of substrates and products.

  • Compound C18H28O2

    (9Z,12Z)-Octadeca-9,12-dien-17-ynoic acid

  • Compound C20H28O2

    (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraen-19-ynoic acid

  • Compound C42H76NO8P

    1-Hexadecanoyl-2-(9Z,12Z-octadecadien-17-ynoyl)-sn-glycero-3-phosphocholine

  • Compound C48H76Co2NO14P

    1-Hexadecanoyl-2-(9Z,12Z-octadecadien-17-ynoyl)-sn-glycero-3-phosphocholine dicobalt hexacarbonyl complex

  • Compound C40H72NO8P

    1,2-Dihexadecan-15-ynoyl-sn-glycero-3-phosphocholine

  • Compound C39H69O8P

    1,2-Dihexadecan-15-ynoyl-sn-glycero-3-phosphobutanol

  • Compound C19H36O4

    (Z)-Methyl 12,13-dihydroxyoctadec-9-enoate

  • Compound C21H36O4

    (5Z,8Z,11Z)-Methyl 14,15-dihydroxyicosa-5,8,11-trienoate

  • Compound C13H24O3

    (Z)-Methyl 12-hydroxydodec-9-enoate

  • Compound C12H21IO2

    (Z)-12-Iodododec-9-enoic acid

  • Compound C30H36IO2P

    (Z)-12-(Iodotriphenylphosphoranyl)dodec-9-enoic acid

  • Compound C15H24O3

    (5Z,8Z,11Z)-Methyl 14-hydroxytetradeca-5,8,11-trienoate

  • Compound C14H21IO2

    (5Z,8Z,11Z)-14-Iodotetradeca-5,8,11-trienoic acid

  • Compound C32H36IO2P

    (5Z,8Z,11Z)-14-(Iodotriphenylphosphoranyl)tetradeca-5,8,11-trienoic acid

  • Compound C16H30O

    Hexadec-15-yn-1-ol

  • Compound C16H28O2

    Hexadec-15-ynoic acid

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Acknowledgements

The authors thank P. Ivanova and D. Myers for technical assistance and many helpful conversations. This work was partially supported by the US National Institutes of Health (P01-ES013125 to H.A.B., L.J.M. and N.A.P.), a Vanderbilt Institute of Chemical Biology Pilot Program grant (H.A.B. and N.A.P.) and National Institutes of Health Grant Lipid Maps U54 GM69338 (H.A.B.).

Author information

Author notes

    • Stephen B Milne
    •  & Keri A Tallman

    These authors contributed equally to this work.

Affiliations

  1. Department of Pharmacology, Vanderbilt University, Nashville, Tennessee, USA.

    • Stephen B Milne
    • , Michelle D Armstrong
    • , Lawrence J Marnett
    •  & H Alex Brown
  2. Department of Chemistry, Vanderbilt University, Nashville, Tennessee, USA.

    • Keri A Tallman
    • , Remigiusz Serwa
    • , Lawrence J Marnett
    • , Charles M Lukehart
    • , Ned A Porter
    •  & H Alex Brown
  3. Department of Biochemistry, Vanderbilt University, Nashville, Tennessee, USA.

    • Carol A Rouzer
    • , Lawrence J Marnett
    • , Ned A Porter
    •  & H Alex Brown
  4. Vanderbilt Institute for Chemical Biology, Vanderbilt University, Nashville, Tennessee, USA.

    • Lawrence J Marnett
    • , Ned A Porter
    •  & H Alex Brown
  5. Vanderbilt Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee, USA.

    • Lawrence J Marnett
    •  & H Alex Brown

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Contributions

S.B.M. analyzed cell extract samples by mass spectrometry. K.A.T. and R.S. performed chemical synthesis, purification and analysis. S.B.M. and C.M.L. developed the alkyne lipid cobalt derivatization protocol. K.A.T. and S.B.M. developed the capture and release methodology. M.D.A. and C.A.R. contributed to the lipid enrichment procedures. L.J.M., N.A.P. and H.A.B. were responsible for overall project direction and experimental design. All authors discussed the results and modified the manuscript.

Competing interests

The authors declare no competing financial interests.

Corresponding author

Correspondence to H Alex Brown.

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    Supplementary Figures 1–4 and Supplementary Methods

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DOI

https://doi.org/10.1038/nchembio.311

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