Faculty Collaboration Database

Fatty acid transduction of nitric oxide signaling. Nitrolinoleic acid is a hydrophobically stabilized nitric oxide donor. J Biol Chem 2005 May 13;280(19):19289-97

Date

03/15/2005

Pubmed ID

15764811

DOI

10.1074/jbc.M414689200

Scopus ID

2-s2.0-21444449754 (requires institutional sign-in at Scopus site)   162 Citations

Abstract

The aqueous decay and concomitant release of nitric oxide (*NO) by nitrolinoleic acid (10-nitro-9,12-octadecadienoic acid and 12-nitro-9,12-octadecadienoic acid; LNO2) are reported. Mass spectrometric analysis of reaction products supports a modified Nef reaction as the mechanism accounting for the generation of *NO by the aqueous reactions of fatty acid nitroalkene derivatives. Nitrolinoleic acid is stabilized by an aprotic milieu, with LNO2 decay and *NO release strongly inhibited by phosphatidylcholine/cholesterol liposome membranes and detergents when present at levels above their critical micellar concentrations. The release of *NO from LNO2 was induced by UV photolysis and triiodide-based ozone chemiluminescence reactions currently used to quantify putative protein nitrosothiol and N-nitrosamine derivatives. This reactivity of LNO2 complicates the qualitative and quantitative analysis of biological oxides of nitrogen when applying UV photolysis and triiodide-based analytical systems to biological preparations typically abundant in nitrated fatty acids. The results reveal that nitroalkene derivatives of linoleic acid are pluripotent signaling mediators that act not only via receptor-dependent mechanisms, but also by transducing the signaling actions of *NO via pathways subject to regulation by the relative distribution of LNO2 to hydrophobic versus aqueous microenvironments.

Author List

Schopfer FJ, Baker PR, Giles G, Chumley P, Batthyany C, Crawford J, Patel RP, Hogg N, Branchaud BP, Lancaster JR Jr, Freeman BA

Author

Neil Hogg PhD Associate Dean, Professor in the Biophysics department at Medical College of Wisconsin

MESH terms used to index this publication - Major topics in bold

Animals
Chemistry
Cholesterol
Detergents
Dose-Response Relationship, Drug
Electron Spin Resonance Spectroscopy
Fatty Acids, Unsaturated
Horses
Hydrogen-Ion Concentration
Kinetics
Linoleic Acids
Lipid Bilayers
Liposomes
Mass Spectrometry
Micelles
Models, Chemical
Myoglobin
Nitric Oxide
Nitro Compounds
Nitrogen
Nitrosamines
Oxygen
Phosphatidylcholines
Signal Transduction
Spectrophotometry
Sulfhydryl Compounds
Time Factors
Ultraviolet Rays