Exploiting Benzophenone Photoreactivity To Probe the Phospholipid Environment and Insertion Depth of the Cell-Penetrating Peptide Penetratin in Model Membranes
Dr. Chen-Yu Jiao
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorDr. Emmanuelle Sachon
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Sorbonne Universités, Plateforme de Spectrométrie de Masse et Protéomique, IBPS, FRE3631, 7–9 quai St Bernard, 75005 Paris, France
Search for more papers by this authorDr. Isabel D. Alves
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Present address: Chemistry and Biology of Membranes and Nanoobjects, University of Bordeaux, Bat. B14, allée Geoffroy St Hilaire, 33600 Pessac, France
Search for more papers by this authorDr. Gérard Chassaing
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorDr. Gérard Bolbach
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Sorbonne Universités, Plateforme de Spectrométrie de Masse et Protéomique, IBPS, FRE3631, 7–9 quai St Bernard, 75005 Paris, France
Search for more papers by this authorCorresponding Author
Dr. Sandrine Sagan
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorDr. Chen-Yu Jiao
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorDr. Emmanuelle Sachon
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Sorbonne Universités, Plateforme de Spectrométrie de Masse et Protéomique, IBPS, FRE3631, 7–9 quai St Bernard, 75005 Paris, France
Search for more papers by this authorDr. Isabel D. Alves
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Present address: Chemistry and Biology of Membranes and Nanoobjects, University of Bordeaux, Bat. B14, allée Geoffroy St Hilaire, 33600 Pessac, France
Search for more papers by this authorDr. Gérard Chassaing
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorDr. Gérard Bolbach
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Sorbonne Universités, Plateforme de Spectrométrie de Masse et Protéomique, IBPS, FRE3631, 7–9 quai St Bernard, 75005 Paris, France
Search for more papers by this authorCorresponding Author
Dr. Sandrine Sagan
Department of Chemistry, Sorbonne Universités, UPMC Univ Paris 06, PSL Research University, Ecole Normale Supérieure, CNRS, Laboratoire des Biomolécules (LBM), 4 place Jussieu, 75005 Paris, France
Search for more papers by this authorAbstract
Penetratin (RQIKIWFQNRRMKWKK) enters cells by different mechanisms, including membrane translocation, thus implying that the peptide interacts with the lipid bilayer. Penetratin also crosses the membrane of artificial vesicles, depending on their phospholipid content. To evaluate the phospholipid preference of penetratin, as the first step of translocation, we exploited the benzophenone triplet kinetics of hydrogen abstraction, which is slower for secondary than for allylic hydrogen atoms. By using multilamellar vesicles of varying phospholipid content, we identified and characterized the cross-linked products by MALDI-TOF mass spectrometry. Penetratin showed a preference for negatively charged (vs. zwitterionic) polar heads, and for unsaturated (vs. saturated) and short (vs. long) saturated phospholipids. Our study highlights the potential of using benzophenone to probe the environment and insertion depth of membranotropic peptides in membranes.
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