Two Polymorphic Crystal Structures of Cholesteryl 2,4-Dichlorobenzoate

Park, Young Ja

doi:10.5012/bkcs.2004.25.5.751

Bulletin of the Korean Chemical Society

2004

DOI: 10.5012/bkcs.2004.25.5.751

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Two Polymorphic Crystal Structures of Cholesteryl 2,4-Dichlorobenzoate

Young Ja Park

Abstract: Cholesterol derivatives are important constituents of pathological conditions such as atherosclerosis, the formation of thick deposits on the inner surfaces of blood vessels.1 The crystal structures of cholesteryl 2,4-dichlorobenzoate are of interest because their mode of crystallization and packing might be useful in understanding their deposition in arteries.

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Cited by 6 publications

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Hemolytic mechanism of dioscin proposed by molecular dynamics simulations

Wang

2009

J Mol Model

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Saponins are a class of compounds containing a triterpenoid or steroid core with some attached carbohydrate modules. Many saponins cause hemolysis. However, the hemolytic mechanism of saponins at the molecular level is not yet fully understood. In an attempt to explore this issue, we have studied dioscin-a saponin with high hemolytic activity-through extensive molecular dynamics (MD) simulations. Firstly, all-atom MD simulations of 8 ns duration were conducted to study the stability of the dioscin-cholesterol complex and the cholesterol-cholesterol complex in water and in decane, respectively. MM-GB/SA computations indicate that the dioscin-cholesterol complex is energetically more favorable than the cholesterol-cholesterol complex in a non-polar environment. Next, several coarse-grained MD simulations of 400 ns duration were conducted to directly observe the distribution of multiple dioscin molecules on a DPPC-POPC-PSM-CHOL lipid bilayer. Our results indicate that dioscin can penetrate into the lipid bilayer, accumulate in the lipid raft micro-domain, and then bind cholesterol. This leads to the destabilization of lipid raft and consequent membrane curvature, which may eventually result in the hemolysis of red cells. This possible mechanism of hemolysis can well explain some experimental observations on hemolysis.

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Hemolytic mechanism of dioscin proposed by molecular dynamics simulations

Wang

2009

J Mol Model

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Combinatorial Approach for the Rapid Determination of Thermochromic Behavior of Binary and Ternary Cholesteric Liquid Crystalline Mixtures

2012

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A combinatorial approach was developed for the rapid determination of thermochromic behavior of a large number of binary and ternary sterol based thermochromic liquid crystalline formulations. A binary mixture containing cholesteryl oleyl carbonate and cholesteryl nonanoate, and ternary mixtures also containing a third component, either cholesteryl oleate, cholesteryl benzoate, cholesteryl 2,4-dichlorobenzoate or cholesteryl propionate, were formulated via solvent deposition into a black Teflon coated aluminum 96 well plate. The temperature of the well plate was then varied, and the color appearance of the deposited mixture in each well was recorded. This approach allowed expedient examination of the thermochromic behavior for a large range of liquid crystal formulations. The accuracy of the rapid combinatorial technique was validated on selected thermochromic liquid crystal mixture compositions by comparing well thermochromic output with that observed using UV-vis spectroscopy on material produced in gram quantities.

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Cholesteryl isobutylcarbonate

2005

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Key indicatorsSingle-crystal X-ray study T = 173 K Mean (C-C) = 0.005 Å Disorder in main residue R factor = 0.058 wR factor = 0.169 Data-to-parameter ratio = 8.6For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2005 International Union of Crystallography Printed in Great Britain -all rights reservedCholesteryl isobutylcarbonate, C 32 H 54 O 3 , contains two molecules (A and B) in the asymmetric unit. The isobutylcarbonate chain of molecule A and the isoprenoid tail of molecule B are each conformationally disordered over two positions. The two distinct molecules form separate stacks along the screw axes so that they are arranged in an antiparallel array, forming monolayers with a thickness of d 001 = 19.412 Å . The central regions of the monolayers are characterized by efficient molecular packing and are separated by interface regions, which are more loosely packed.

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Two Polymorphic Crystal Structures of Cholesteryl 2,4-Dichlorobenzoate

Cited by 6 publications

References 5 publications

Hemolytic mechanism of dioscin proposed by molecular dynamics simulations

Hemolytic mechanism of dioscin proposed by molecular dynamics simulations

Combinatorial Approach for the Rapid Determination of Thermochromic Behavior of Binary and Ternary Cholesteric Liquid Crystalline Mixtures

Cholesteryl isobutylcarbonate

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