Experimental and theoretical studies of emodin interacting with a lipid bilayer of DMPC
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REVIEW
Experimental and theoretical studies of emodin interacting with a lipid bilayer of DMPC Antonio R. da Cunha 1,2 & Evandro L. Duarte 2 & Hubert Stassen 3 & M. Teresa Lamy 2 & Kaline Coutinho 2
Received: 7 June 2017 / Accepted: 29 August 2017 # International Union for Pure and Applied Biophysics (IUPAB) and Springer-Verlag GmbH Germany 2017
Abstract Emodin is one of the most abundant anthraquinone derivatives found in nature. It is the active principle of some traditional herbal medicines with known biological activities. In this work, we combined experimental and theoretical studies to reveal information about location, orientation, interaction and perturbing effects of Emodin on lipid bilayers, where we have taken into account the neutral form of the Emodin (EMH) and its anionic/deprotonated form (EM−). Using both UV/Visible spectrophotometric techniques and molecular dynamics (MD) simulations, we showed that both EMH and EM− are located in a lipid membrane. Additionally, using This article is part of a Special Issue on ‘Latin America’ edited by Pietro Ciancaglini and Rosangela Itri.
MD simulations, we revealed that both forms of Emodin are very close to glycerol groups of the lipid molecules, with the EMH inserted more deeply into the bilayer and more disoriented relative to the normal of the membrane when compared with the EM−, which is more exposed to interfacial water. Analysis of several structural properties of acyl chains of the lipids in a hydrated pure DMPC bilayer and in the presence of Emodin revealed that both EMH and EM− affect the lipid bilayer, resulting in a remarkable disorder of the bilayer in the vicinity of the Emodin. However, the disorder caused by EMH is weaker than that caused by EM−. Our results suggest that these disorders caused by Emodin might lead to distinct effects on lipid bilayers including its disruption which are reported in the literature.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s12551-017-0323-1) contains supplementary material, which is available to authorized users.
Keywords Emodin . Phospholipid bilayer . Molecular dynamic simulation . UV/Visible spectroscopy
* Kaline Coutinho [email protected] Antonio R. da Cunha [email protected] Evandro L. Duarte [email protected] Hubert Stassen [email protected] M. Teresa Lamy [email protected] 1
Universidade Federal do Maranhão, UFMA, Campus Balsas, Maranhão 06500-000, Brazil
2
Instituto de Física da Universidade de São Paulo, 05508-090, Cidade Universitária, São Paulo, Brazil
3
Grupo de Química Teórica, Instituto de Química, UFRGS, Av. Bento Gonçalves 9500, Porto Alegre 91540-000, Brazil
Introduction The interaction of a pharmacophore with cell membranes is a topic of great interest in biology and pharmacology due to the possible relevance in the pathway of action (Apostolova et al. 2003; Duarte et al. 2008; Peetla et al. 2009). There are several molecular features that govern the behavior of a drug in cell membranes such as size, shape, solubility, hydrophili
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