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Diphenylhexatriene Membrane Probes DPH and TMA-DPH: A Comparative Molecular Dynamics Simulation Study

Diphenylhexatriene Membrane Probes DPH and TMA-DPH: A Comparative Molecular Dynamics Simulation Study

António M T M do Canto, João R Robalo, Patrícia D Santos, Alfredo J Palace Carvalho, J P Prates Ramalho, Luís M S Loura

Biochim Biophys Acta. 2016 Nov;1858(11):2647-2661.

PMID: 27475296

Abstract:

Fluorescence spectroscopy and microscopy have been utilized as tools in membrane biophysics for decades now. Because phospholipids are non-fluorescent, the use of extrinsic membrane probes in this context is commonplace. Among the latter, 1,6-diphenylhexatriene (DPH) and its trimethylammonium derivative (TMA-DPH) have been extensively used. It is widely believed that, owing to its additional charged group, TMA-DPH is anchored at the lipid/water interface and reports on a bilayer region that is distinct from that of the hydrophobic DPH. In this study, we employ atomistic MD simulations to characterize the behavior of DPH and TMA-DPH in 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and POPC/cholesterol (4:1) bilayers. We show that although the dynamics of TMA-DPH in these membranes is noticeably more hindered than that of DPH, the location of the average fluorophore of TMA-DPH is only ~3-4Å more shallow than that of DPH. The hindrance observed in the translational and rotational motions of TMA-DPH compared to DPH is mainly not due to significant differences in depth, but to the favorable electrostatic interactions of the former with electronegative lipid atoms instead. By revealing detailed insights on the behavior of these two probes, our results are useful both in the interpretation of past work and in the planning of future experiments using them as membrane reporters.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP484049049	DPH		484049-04-9	Price

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