Synthesis and Cellular Labeling of Caged Phosphatidylinositol Derivatives

Rainer Müller, Mevlut Citir, Sebastian Hauke, Carsten Schultz

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Phosphatidylinositol (PI) is the biosynthetic precursor for seven phosphoinositides, important signaling lipids in cells. A membrane-permeant caged PI derivative featuring a photo-removable coumarinyl group masking the negative charge of the phosphate, as well as two enzymatically removable butyrate esters for increased lipophilicity and for preventing phosphate migration, were synthesized. Rapid cell entry and cellular labeling in fixed cells was demonstrated by a photo-cross-linkable diazirine followed by attachment of a fluorophore through click chemistry. Using this technique, we found that the multifunctional caged PI derivative resided predominantly at internal membranes but rapidly changed to the plasma membrane after uncaging. Accordingly, a preliminary proteomic analysis of the lipid–protein conjugates revealed that the two major PI transport proteins PITPα and β were prime targets of the photo-cross-linked PI derivative.

Original languageEnglish (US)
Pages (from-to)384-389
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number2
DOIs
StatePublished - Jan 7 2020

Keywords

  • cellular labelling
  • crosslinking
  • phosphates
  • photochemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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