%0 Journal Article %1 RN213 %A Bahamonde-Padilla, V.E. %A Lopez-Cascales, J.J. %A Araya-Maturana, R. %A Martinez-Cifuentes, M. %A Lopez, B.E.W. %D 2014 %J Chemphyschem %K aqueous-solution, crystals, derivatives, dqcauchile dynamics, ewald, force-field, free-energy, lipid-bilayer, liquid membrane, mesh micelle microviscosity, molecular molecular-dynamics nmr particle quinones, resonance, simulations, spectroscopy, %N 7 %P 1422-1431 %R 10.1002/cphc.201301146 %T Thermodynamics and (Hnmr)-H-2 Study on the Insertion of Small Quinones into a Discotic Nematic Lyotropic Liquid Crystal %U /brokenurl#<Go to ISI>://WOS:000335515900018 %V 15 %X A detailed description of the distribution, interaction, and dynamics of molecules with biological activity dissolved in a hydrophobic bilayer, a simple model of a biological membrane, provides valuable information for a better understanding of drug functioning, which can be very useful in drug design. Here we present an H-2 NMR and molecular dynamics study on the insertion, distribution, interactions, and thermodynamics of two biologically active molecules, 9,10-dihydroxy-4,4-dimethyl-1,4,5,8-tetrahydroanthracen-1-one (HQ), with anticancer activity, and 4,4-dimethyl-1,4,5,8,9,10-hexahydroanthracen-1,9,10-trione (Q) a fungicide, dissolved in a nematic discotic lyotropic liquid crystal (ndllc) composed of sodium dodecylsulphate (SDS), decanol (DecOH) and Na2SO4 in water. H-2 NMR quadrupole splittings ((Q)) and longitudinal relaxation times (T-1) from HQ-d(6), Q-d(4), DecOH--d(2), partially deuterated water, and SDS-d(25) were measured and several molecular dynamics trajectories were also calculated. In particular, G, H, and S profiles for the process of both molecules crossing the bilayer were estimated. It was evidenced that the insertion of both molecules into the aggregate is a spontaneous process, and the molecules are mainly distributed in the internal side of the interface. Addition of HQ or Q decreased the mobility of all aggregate components, but this effect was more pronounced for HQ. The rotational correlation time of Q allowed an estimate of 5.3 cP for the microviscosity inside the ndllc aggregate, in the order of previously measured values in similar environments. Both guest molecules display similar free-energy profiles for the process of crossing the bilayer, with a calculated barrier height of 25 and 36 kJmol(-1) for HQ and Q, respectively.

@article{RN213, abstract = {A detailed description of the distribution, interaction, and dynamics of molecules with biological activity dissolved in a hydrophobic bilayer, a simple model of a biological membrane, provides valuable information for a better understanding of drug functioning, which can be very useful in drug design. Here we present an H-2 NMR and molecular dynamics study on the insertion, distribution, interactions, and thermodynamics of two biologically active molecules, 9,10-dihydroxy-4,4-dimethyl-1,4,5,8-tetrahydroanthracen-1-one (HQ), with anticancer activity, and 4,4-dimethyl-1,4,5,8,9,10-hexahydroanthracen-1,9,10-trione (Q) a fungicide, dissolved in a nematic discotic lyotropic liquid crystal (ndllc) composed of sodium dodecylsulphate (SDS), decanol (DecOH) and Na2SO4 in water. H-2 NMR quadrupole splittings ((Q)) and longitudinal relaxation times (T-1) from HQ-d(6), Q-d(4), DecOH--d(2), partially deuterated water, and SDS-d(25) were measured and several molecular dynamics trajectories were also calculated. In particular, G, H, and S profiles for the process of both molecules crossing the bilayer were estimated. It was evidenced that the insertion of both molecules into the aggregate is a spontaneous process, and the molecules are mainly distributed in the internal side of the interface. Addition of HQ or Q decreased the mobility of all aggregate components, but this effect was more pronounced for HQ. The rotational correlation time of Q allowed an estimate of 5.3 cP for the microviscosity inside the ndllc aggregate, in the order of previously measured values in similar environments. Both guest molecules display similar free-energy profiles for the process of crossing the bilayer, with a calculated barrier height of 25 and 36 kJmol(-1) for HQ and Q, respectively.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Bahamonde-Padilla, V.E. and Lopez-Cascales, J.J. and Araya-Maturana, R. and Martinez-Cifuentes, M. and Lopez, B.E.W.}, biburl = {https://www.bibsonomy.org/bibtex/2f7c117c3076e4e558b397535fd03e55c/dqcauchile}, doi = {10.1002/cphc.201301146}, interhash = {72486dee8d41963c2fd9caf8bc7abc10}, intrahash = {f7c117c3076e4e558b397535fd03e55c}, issn = {1439-4235}, journal = {Chemphyschem}, keywords = {aqueous-solution, crystals, derivatives, dqcauchile dynamics, ewald, force-field, free-energy, lipid-bilayer, liquid membrane, mesh micelle microviscosity, molecular molecular-dynamics nmr particle quinones, resonance, simulations, spectroscopy,}, number = 7, pages = {1422-1431}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Thermodynamics and (Hnmr)-H-2 Study on the Insertion of Small Quinones into a Discotic Nematic Lyotropic Liquid Crystal}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000335515900018}, volume = 15, year = 2014 }