NDLI: Phospholipophilicity of CxHyN+ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes

Please wait, while we are loading the content...

In situ speciation of dissolved inorganic antimony in surface waters and sediment porewaters: development of a thiol-based diffusive gradients in thin films technique for Sb^III

Occurrence and fate of nitrification and urease inhibitors in the aquatic environment

Phospholipophilicity of C_xH_yN⁺ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes

Re-analysis of narcotic critical body residue data using the equilibrium distribution concept and refined partition coefficients

Sorption selectivity of birnessite particle edges: a d-PDF analysis of Cd(ii) and Pb(ii) sorption by δ-MnO₂ and ferrihydrite

The dilemma in prioritizing chemicals for environmental analysis: known versus unknown hazards

A theoretical assessment of microplastic transport in river catchments and their retention by soils and river sediments

Chronic exposure to triclosan sustains microbial community shifts and alters antibiotic resistance gene levels in anaerobic digesters

Sticking to (first) principles: quantum molecular dynamics and Bayesian probabilistic methods to simulate aquatic pollutant absorption spectra

Wildfires and water chemistry: effect of metals associated with wood ash

Chemical controls on abiotic and biotic release of geogenic arsenic from Pleistocene aquifer sediments to groundwater

Correction: The dilemma in prioritizing chemicals for environmental analysis: known versus unknown hazards

Back cover

Environmental Science: Processes & Impacts Vol - 18 Issue - 7

Environmental Science: Processes & Impacts Vol - 18 Issue - 6

Environmental Science: Processes & Impacts Vol - 18 Issue - 5

Phospholipophilicity of C_xH_yN⁺ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes

Content Provider	Royal Society of Chemistry (RSC)
Author	Droge, S. T. J. Hermens, J. L. M. Gutsell, S. Hodges, G. Rabone, J.
Copyright Year	2016
Abstract	Using immobilized artificial membrane high-performance liquid chromatography (IAM-HPLC) the sorption affinity of 70 charged amine structures to phospholipids was determined. The amines contained only 1 charged moiety and no other polar groups, the rest of the molecule being aliphatic and/or aromatic hydrocarbon groups. We systematically evaluated the influence of the amine type (1°, 2°, 3° amines and quaternary ammonium), alkyl chain branching, phenyl ring positioning, charge positioning (terminal vs. central in the molecule) on the phospholipid-water partitioning coefficient (KPLIPW). These experimental results were compared with quantum-chemistry based three-dimensional (3D) molecular simulations of the partitioning of charged amines, including the most likely solute conformers, using a hydrated phospholipid bilayer in the COSMOmic module of COSMOtherm software. Both IAM-HPLC retention data and the simulations suggest that the molecular orientation of charged amines at the location in the bilayer with the lowest calculated Gibbs free energy exerts a strong influence over the partitioning within the membrane. The most favourable position of charged amines coincides with the region where the phosphate anions in the phospholipid bilayer are most abundant. Hydrocarbon units oriented in this layer are located more towards the aqueous phase and contribute less to the overall membrane affinity than hydrocarbon units extending into the more hydrophobic core of the bilayer. COSMOmic simulations explain most of the trends between the structural differences observed in IAM-HPLC based KPLIPW. For this set of cationic structures, the mean absolute difference between COSMOmic simulations and IAM-HPLC data, accounting only for amine type corrective increments, is 0.31 log units.
Starting Page	1011
Ending Page	1023
Page Count	13
File Format	HTM / HTML PDF
ISSN	20507887
Volume Number	18
Issue Number	8
Journal	Environmental Science: Processes & Impacts
DOI	10.1039/c6em00118a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	KPLIPW Gibbs Synthetic membrane High-performance liquid chromatography Sorption Aliphatic compound Quaternary ammonium cation Alkyl Phenyl group Three-dimensional space Lipid bilayer Gibbs free energy Phosphate Hydrophobe Absolute difference
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Public Health, Environmental and Occupational Health Management, Monitoring, Policy and Law

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Predicting the phospholipophilicity of monoprotic positively charged amines

Gemini quaternary ammonium salt waterborne biodegradable polyurethanes with antibacterial and biocompatible properties

Thermal polycondensation of poly(diol citrate)s with tethered quaternary ammonium biocides

Bactericidal and corrosion-inhibiting activity of quaternary ammonium salts synthesized from aliphatic amines and alkenyl halides

Soil water solutes reduce the critical micelle concentration of quaternary ammonium compounds.

Long alkyl chain quaternary ammonium-based ionic liquids and potential applications

Syntheses of quaternary ammonium-containing, trithiocarbonate RAFT agents and hemi-telechelic cationomers

Mixed-mode capillary electrochromatographic separation of anionic analytes

High performance aliphatic-heterocyclic benzyl-quaternary ammonium radiation-grafted anion-exchange membranes †

Phospholipophilicity of C_xH_yN⁺ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes

Similar Documents

Predicting the phospholipophilicity of monoprotic positively charged amines

Gemini quaternary ammonium salt waterborne biodegradable polyurethanes with antibacterial and biocompatible properties

Thermal polycondensation of poly(diol citrate)s with tethered quaternary ammonium biocides

Bactericidal and corrosion-inhibiting activity of quaternary ammonium salts synthesized from aliphatic amines and alkenyl halides

Soil water solutes reduce the critical micelle concentration of quaternary ammonium compounds.

Long alkyl chain quaternary ammonium-based ionic liquids and potential applications

Syntheses of quaternary ammonium-containing, trithiocarbonate RAFT agents and hemi-telechelic cationomers

Mixed-mode capillary electrochromatographic separation of anionic analytes

High performance aliphatic-heterocyclic benzyl-quaternary ammonium radiation-grafted anion-exchange membranes †

Phospholipophilicity of CxHyN+ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes

Phospholipophilicity of C_xH_yN⁺ amines: chromatographic descriptors and molecular simulations for understanding partitioning into membranes