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Determining the Effects of Lipophilic Drugs on Membrane Structure by Solid-State NMR Spectroscopy: The Case of the Antioxidant Curcumin
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Present address: Department of Fine Chemistry, Seoul National University of Technology, Seoul, Korea.
Section:Abstract
Curcumin is the active ingredient of turmeric powder, a natural spice used for generations in traditional medicines. Curcumin’s broad spectrum of antioxidant, anticarcinogenic, antimutagenic, and anti-inflammatory properties makes it particularly interesting for the development of pharmaceutical compounds. Because of curcumin’s various effects on the function of numerous unrelated membrane proteins, it has been suggested that it affects the properties of the bilayer itself. However, a detailed atomic-level study of the interaction of curcumin with membranes has not been attempted. A combination of solid-state NMR and differential scanning calorimetry experiments shows curcumin has a strong effect on membrane structure at low concentrations. Curcumin inserts deep into the membrane in a transbilayer orientation, anchored by hydrogen bonding to the phosphate group of lipids in a manner analogous to cholesterol. Like cholesterol, curcumin induces segmental ordering in the membrane. Analysis of the concentration dependence of the order parameter profile derived from NMR results suggests curcumin forms higher order oligomeric structures in the membrane that span and likely thin the bilayer. Curcumin promotes the formation of the highly curved inverted hexagonal phase, which may influence exocytotic and membrane fusion processes within the cell. The experiments outlined here show promise for understanding the action of other drugs such as capsaicin in which drug-induced alterations of membrane structure have strong pharmacological effects.
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
Effects of Curcumin Concentration and Temperature on the Spectroscopic Properties of Liposomal Curcumin
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Yumeng Niu, Xiaoyong Wang, Shaohu Chai, Zhiyun Chen, Xueqin An, and Weiguo ShenJournal of Agricultural and Food Chemistry2012 Article ASAPThe spectroscopic properties of liposomal curcumin in pH 7.0 sodium phosphate buffer were studied at various curcumin concentrations and temperatures. At 25 °C, liposomal curcumin exhibited much higher values than free curcumin in absorption maximum, ...
Spectrometric Study on the Interaction of Dodecyltrimethylammonium Bromide with Curcumin
Dan Ke, Xiaoyong Wang, Qianqian Yang, Yumeng Niu, Shaohu Chai, Zhiyun Chen, Xueqin An, and Weiguo ShenLangmuir2011 27 (23), 14112-14117Spectrometric Study on the Interaction of Dodecyltrimethylammonium Bromide with Curcumin
Dan Ke, Xiaoyong Wang, Qianqian Yang, Yumeng Niu, Shaohu Chai, Zhiyun Chen, Xueqin An, and Weiguo ShenLangmuir2011 27 (23), 14112-14117The interaction between dodecyltrimethylammonium bromide (DTAB) and curcumin has been studied in pH 5.0 sodium phosphate buffer using absorption and fluorescence measurements. With increasing DTAB concentration (CDTAB) from 0 to 20 mM, the absorption peak ...
Temperature Dependence of the Fluorescence Properties of Curcumin
Yuval Erez, Itay Presiado, Rinat Gepshtein, and Dan HuppertThe Journal of Physical Chemistry A2011 115 (40), 10962-10971Temperature Dependence of the Fluorescence Properties of Curcumin
Yuval Erez, Itay Presiado, Rinat Gepshtein, and Dan HuppertThe Journal of Physical Chemistry A2011 115 (40), 10962-10971Steady-state and time-resolved techniques were employed to study the nonradiative process of curcumin dissolved in ethanol and 1-propanol in a wide range of temperatures. We found that the nonradiative rate constants at temperatures between 175–250 K ...
A Proton Spin Diffusion Based Solid-State NMR Approach for Structural Studies on Aligned Samples
Jiadi Xu, Pieter E. S. Smith, Ronald Soong, and Ayyalusamy RamamoorthyThe Journal of Physical Chemistry B2011 115 (16), 4863-4871A Proton Spin Diffusion Based Solid-State NMR Approach for Structural Studies on Aligned Samples
Jiadi Xu, Pieter E. S. Smith, Ronald Soong, and Ayyalusamy RamamoorthyThe Journal of Physical Chemistry B2011 115 (16), 4863-4871Rapidly expanding research on nonsoluble and noncrystalline chemical and biological materials necessitates sophisticated techniques to image these materials at atomic-level resolution. Although their study poses a formidable challenge, solid-state NMR is ...
Copper Curcuminoids Containing Anthracene Groups: Fluorescent Molecules with Cytotoxic Activity
Núria Aliaga-Alcalde, Patricia Marqués-Gallego, Mirte Kraaijkamp, Coral Herranz-Lancho, Hans den Dulk, Helmut Görner, Olivier Roubeau, Simon J. Teat, Thomas Weyhermüller, and Jan ReedijkInorganic Chemistry2010 49 (20), 9655-9663Copper Curcuminoids Containing Anthracene Groups: Fluorescent Molecules with Cytotoxic Activity
Núria Aliaga-Alcalde, Patricia Marqués-Gallego, Mirte Kraaijkamp, Coral Herranz-Lancho, Hans den Dulk, Helmut Görner, Olivier Roubeau, Simon J. Teat, Thomas Weyhermüller, and Jan ReedijkInorganic Chemistry2010 49 (20), 9655-9663The coordination chemistry of the new curcuminoid ligand, 1,7-(di-9-anthracene-1,6-heptadiene-3,5-dione), abbreviated 9Accm has been studied, resulting in two new copper-9Accm compounds. Compound 1, [Cu(phen)Cl(9Accm)], was synthesized by reacting 9Accm ...
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History
- Published In Issue April 01, 2009
- Article ASAPMarch 03, 2009
- Received: November 25, 2008
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