Universität zu Köln

Dokoohaki, Maryam Heydari, Zolghadr, Amin Reza and Klein, Axel ORCID: 0000-0003-0093-9619 (2020). Impact of the chemical structure on the distribution of neuroprotective N-alkyl-9H-carbazoles at octanol/water interfaces. New J. Chem., 44 (4). S. 1211 - 1221. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1369-9261

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Abstract

All-atom molecular dynamics (MD) simulations were performed to systematically analyse the distribution and agglomeration of a series of small neuroprotective N-(3-anilinopropyl)-9H-carbazole based molecules at octanol/water interfaces along with a detailed assessment of their structural and dynamical properties, such as density profiles, distribution functions, average orientations, hydrogen bonding (H-bonding), and mean-square displacements. Our simulations show that the biologically active neuroprotective molecules easily migrate from the water phase to the octanol phase during the simulation trajectories. However, biologically inactive derivatives agglomerated in the water phase. Calculated radial distribution functions (RDFs) clearly underpin the necessity of the two 3,6-dibromo substituents on the carbazole core for a sufficient hydrophobic character. Furthermore, we could show that H-bonding from F, or OH groups located on the propyl unit with octanol or water molecules are decisive structural requirements for their distribution between the two liquid phases.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Dokoohaki, Maryam Heydari UNSPECIFIED UNSPECIFIED UNSPECIFIED Zolghadr, Amin Reza UNSPECIFIED UNSPECIFIED UNSPECIFIED Klein, Axel UNSPECIFIED orcid.org/0000-0003-0093-9619 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-348171
DOI:	10.1039/c9nj04251b
Journal or Publication Title:	New J. Chem.
Volume:	44
Number:	4
Page Range:	S. 1211 - 1221
Date:	2020
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1369-9261
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Inorganic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language COSMO-RS; AMINOPROPYL CARBAZOLES; ALZHEIMERS-DISEASE; SMALL MOLECULES; HYDROGEN-BOND; MONTE-CARLO; MOUSE MODEL; DYNAMICS; WATER; DISCOVERY Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/34817