Harnessing Clickable Acylated Glycerol Probes as Chemical Tools for Tracking Glycerolipid Metabolism

Author:

Ancajas Christelle F.1ORCID,Carr Adam J.1ORCID,Lou Jinchao1ORCID,Sagar Ruhani1ORCID,Zhou Yue2,Reynolds Todd B.2ORCID,Best Michael D.1ORCID

Affiliation:

1. Department of Chemistry University of Tennessee 1420 Circle Drive Knoxville TN, 37996 USA

2. Department of Microbiology University of Tennessee 1311 Cumberland Avenue Knoxville TN, 37996 USA

Abstract

AbstractWe report the use of clickable monoacylglycerol (MAG) analogs as probes for the labeling of glycerolipids during lipid metabolism. Incorporation of azide tags onto the glycerol region was pursued to develop probes that would label glycerolipids, in which the click tag would not be removed through processes including acyl chain and headgroup remodeling. Analysis of clickable MAG probes containing acyl chains of different length resulted in widely variable cell imaging and cytotoxicity profiles. Based on these results, we focused on a probe bearing a short acyl chain (C4‐MAG‐N3) that was found to infiltrate natural lipid biosynthetic pathways to produce click‐tagged versions of both neutral and phospholipid products. Alternatively, strategic blocking of the glycerol sn‐3 position in probe C4‐MEG‐N3 served to deactivate phospholipid tagging and focus labeling on neutral lipids. This work shows that lipid metabolic labeling profiles can be tuned based on probe structures and provides valuable tools for evaluating alterations to lipid metabolism in cells.

Funder

National Institute of General Medical Sciences

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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