Literature DB >> 26926421

Both idebenone and idebenol are localized near the lipid-water interface of the membrane and increase its fluidity.

Victoria Gómez-Murcia1, Alejandro Torrecillas1, Ana M de Godos1, Senena Corbalán-García1, Juan C Gómez-Fernández1.   

Abstract

Idebenone is a synthetic analog of coenzyme Q; both share a quinone moiety but idebenone has a shorter lipophilic tail ending with a hydroxyl group. Differential scanning calorimetry experiments showed that both idebenone and idebenol widened and shifted the phase transition of 1,2-dipalmitoylphosphatidylcholine (DPPC) to a lower temperature and a phase separation with different concentrations of these molecules was observed. Also small angle X-ray diffraction and wide angle X-ray diffraction revealed that both, idebenone and idebenol, induced laterally separated phases in fluid membranes when included in DPPC membranes. Electronic profiles showed that both forms, idebenone and idebenol, reduced the thickness of the fluid membrane. (2)H NMR measurements showed that the order of the membrane decreased at all temperatures in the presence of idebenone or idebenol, the greatest disorder being observed in the segments of the acyl chains close to the lipid-water interface. (1)H NOESY MAS NMR spectra were obtained using 1-palmitoyl-2-oleoyl-phosphatidylcholine membranes and results pointed to a similar location in the membrane for both forms, with the benzoquinone or benzoquinol rings and their terminal hydroxyl group of the hydrophobic chain located near the lipid/water interface of the phospholipid bilayer and the terminal hydroxyl group of the hydrophobic chain of both compounds located at the lipid/water interface. Taken together, all these different locations might explain the different physiological behavior shown by the idebenone/idebenol compared with the ubiquinone-10/ubiquinol-10 pair in which both compounds are differently localized in the membrane.
Copyright © 2016 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  (1)H NOESY MAS-NMR; (2)H NMR; DSC; Idebenone; Membranes; SAXD; WAXD

Mesh:

Substances:

Year:  2016        PMID: 26926421     DOI: 10.1016/j.bbamem.2016.02.034

Source DB:  PubMed          Journal:  Biochim Biophys Acta        ISSN: 0006-3002


  4 in total

1.  Ceramide-mediation of diffusion in supported lipid bilayers.

Authors:  Masroor Hossain; G J Blanchard
Journal:  Chem Phys Lipids       Date:  2021-05-07       Impact factor: 3.570

2.  X-ray diffraction and NMR data for the study of the location of idebenone and idebenol in model membranes.

Authors:  Victoria Gómez-Murcia; Alejandro Torrecillas; Ana M deGodos; Senena Corbalán-García; Juan C Gómez-Fernández
Journal:  Data Brief       Date:  2016-03-24

3.  Electron Transport Lipids Fold Within Membrane-Like Interfaces.

Authors:  Margaret M Braasch-Turi; Jordan T Koehn; Kateryna Kostenkova; Cameron Van Cleave; Jacob W Ives; Heide A Murakami; Dean C Crick; Debbie C Crans
Journal:  Front Chem       Date:  2022-03-08       Impact factor: 5.221

Review 4.  Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives.

Authors:  Margaret Braasch-Turi; Debbie C Crans
Journal:  Molecules       Date:  2020-09-29       Impact factor: 4.411

  4 in total

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