Synthesis and Cellular Labeling of Caged Phosphatidylinositol Derivatives.
cellular labelling
crosslinking
phosphates
photochemistry
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
07 Jan 2020
07 Jan 2020
Historique:
received:
13
08
2019
revised:
22
09
2019
pubmed:
25
9
2019
medline:
17
1
2020
entrez:
25
9
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 31550056
doi: 10.1002/chem.201903704
pmc: PMC6973124
doi:
Substances chimiques
Phosphatidylinositols
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
384-389Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM127631
Pays : United States
Organisme : Deutsche Forschungsgemeinschaft
ID : TRR186, TRR83
Organisme : NIGMS NIH HHS
ID : R01GM127631
Pays : United States
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Biochim Biophys Acta. 2014 Aug;1841(8):1085-96
pubmed: 24713581
Nat Chem Biol. 2010 May;6(5):324-6
pubmed: 20364126
Bioorg Med Chem. 2003 Mar 20;11(6):885-98
pubmed: 12614874
Angew Chem Int Ed Engl. 2013 Jun 10;52(24):6330-4
pubmed: 23720390
Angew Chem Int Ed Engl. 2006 Jul 24;45(30):4900-21
pubmed: 16826610
ACS Chem Biol. 2016 Sep 16;11(9):2541-50
pubmed: 27384741
Angew Chem Int Ed Engl. 2001;40(16):3004-8
pubmed: 12203630
Chem Sci. 2019 Jan 10;10(9):2687-2692
pubmed: 30996985
Curr Opin Cell Biol. 2018 Aug;53:97-104
pubmed: 30015291
J Biol Chem. 1993 Mar 25;268(9):6316-22
pubmed: 8384207
Science. 2017 Jun 30;356(6345):1397-1401
pubmed: 28619718
FEBS Lett. 2016 Aug;590(15):2454-68
pubmed: 27391591
J Lipid Res. 2019 Feb;60(2):242-268
pubmed: 30504233
Sci Signal. 2014 Jan 14;7(308):ra5
pubmed: 24425787
Angew Chem Int Ed Engl. 2016 Dec 23;55(52):16026-16030
pubmed: 27874234
Angew Chem Int Ed Engl. 2001 Mar 16;40(6):1045-1048
pubmed: 11268067
Mol Cell. 2016 Jul 21;63(2):181-183
pubmed: 27447982
Chemistry. 2020 Jan 7;26(2):384-389
pubmed: 31550056
Angew Chem Int Ed Engl. 2013 Apr 2;52(14):4033-8
pubmed: 23450850
ACS Chem Biol. 2016 Jan 15;11(1):222-30
pubmed: 26555438
Proc Natl Acad Sci U S A. 2017 Feb 14;114(7):1566-1571
pubmed: 28154130
Biol Chem. 2003 Sep;384(9):1321-6
pubmed: 14515995
Angew Chem Int Ed Engl. 2011 Apr 11;50(16):3811-4
pubmed: 21404403
Elife. 2015 Nov 27;4:
pubmed: 26613410