Next Article in Journal
Proteomic and Bioinformatic Profiling of Transporters in Higher Plant Mitochondria
Next Article in Special Issue
Insight into the Anticancer Activity of Copper(II) 5-Methylenetrimethylammonium-Thiosemicarbazonates and Their Interaction with Organic Cation Transporters
Previous Article in Journal
C. elegans Models to Study the Propagation of Prions and Prion-Like Proteins
Previous Article in Special Issue
Attenuation of Inflammatory Symptoms by Icariside B2 in Carrageenan and LPS-Induced Inflammation Models via Regulation of MAPK/NF-κB Signaling Cascades
Open AccessArticle

Free-Radical-Mediated Formation of Trans-Cardiolipin Isomers, Analytical Approaches for Lipidomics and Consequences of the Structural Organization of Membranes

1
Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via Piero Gobetti 101, 40129 Bologna, Italy
2
Department of Pharmacy and Biotechnology, University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy
3
Center for Advanced Technologies, Adam Mickiewicz University, 61-614 Poznań, Poland
*
Authors to whom correspondence should be addressed.
This article is dedicated to Prof. Bronisław Marciniak, an example of unswerving motivation toward progress, in the occasion of his 70th birthday.
Biomolecules 2020, 10(8), 1189; https://doi.org/10.3390/biom10081189
Received: 20 July 2020 / Revised: 1 August 2020 / Accepted: 12 August 2020 / Published: 15 August 2020
(This article belongs to the Special Issue 2020 Feature Papers by Biomolecules’ Editorial Board Members)
Free-radical-mediated processes, such as peroxidation, isomerization and hydrogenation affecting fatty acid integrity and biological functions, have a trans-disciplinary relevance. Cardiolipins (CL, (1,3-diphosphatidyl-sn-glycerol)) and tetra-linoleoyl-CL are complex phospholipids, exclusively present in the Inner Mitochondrial Membrane (IMM) lipids, where they maintain membrane integrity and regulate enzyme functionalities. Peroxidation pathways and fatty acid remodeling are known causes of mitochondrial disfunctions and pathologies, including cancer. Free-radical-mediated isomerization with the change of the cis CL into geometrical trans isomers is an unknown process with possible consequences on the supramolecular membrane lipid organization. Here, the formation of mono-trans CL (MT-CL) and other trans CL isomers (T-CL) is reported using CL from bovine heart mitochondria and thiyl radicals generated by UV-photolysis from 2-mercaptoethanol. Analytical approaches for CL isomer separation and identification via 1H/13C NMR are provided, together with the chemical study of CL derivatization to fatty acid methyl esters (FAME), useful for lipidomics and metabolomics research. Kinetics information of the radical chain isomerization process was obtained using γ-irradiation conditions. The CL isomerization affected the structural organization of membranes, as tested by the reduction in unilamellar liposome diameter, and accompanied the well-known process of oxidative consumption induced by Fenton reagents. These results highlight a potential new molecular modification pathway of mitochondrial lipids with wide applications to membrane functions and biological consequences. View Full-Text
Keywords: cardiolipin; linoleic acid; free radicals; cis-trans isomerization; γ-irradiation; Fenton reaction; liposome dimension cardiolipin; linoleic acid; free radicals; cis-trans isomerization; γ-irradiation; Fenton reaction; liposome dimension
Show Figures

Graphical abstract

MDPI and ACS Style

Vetica, F.; Sansone, A.; Meliota, C.; Batani, G.; Roberti, M.; Chatgilialoglu, C.; Ferreri, C. Free-Radical-Mediated Formation of Trans-Cardiolipin Isomers, Analytical Approaches for Lipidomics and Consequences of the Structural Organization of Membranes. Biomolecules 2020, 10, 1189.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop