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In silico modelling for predicting the cationic hydrophobicity and cytotoxicity of ionic liquids towards the Leukemia rat cell line, Vibrio fischeri and Scenedesmus vacuolatus based on molecular interaction potentials of ions
Abstract
In this study we present prediction models for estimating in silico the cationic hydrophobicity and the cytotoxicity (log [1/EC50]) of ionic liquids (ILs) towards the Leukemia rat cell line (IPC-81), the marine bacterium Vibrio fischeri and the limnic green algae Scenedesmus vacuolatus using linear free energy relationship (LFER) descriptors computed by COSMO calculations. The LFER descriptors used for the prediction model (i.e. excess molar refraction (E), dipolarity/polarizability (S), hydrogen-bonding acidity (A), hydrogen-bonding basicity (B) and McGowan volume (V)) were calculated using sub-descriptors (sig2, sig3, HBD3, HBA4, MR, and volume) derived from COSMO–RS, COSMO and OBPROP. With the combination of two solute descriptors (B, V) of the cation we were able to predict cationic hydrophobicity values (log ko ) with r 2 = 0.987 and standard error (SE) = 0.139 log units. By using the calculated log k o values, we were able to deduce a linear toxicity prediction model. In the second prediction study for the cytotoxicity of ILs, analysis of descriptor sensitivity helped us to determine that the McGowan volume (V) terms of the cation was the most important predictor of cytotoxicity and to simplify prediction models for cytotoxicity of ILs towards the IPC-81 (r 2 of 0.778, SE of 0.450 log units), Vibrio fischeri (r 2 of 0.762, SE of 0.529 log units) and Scenedesmus vacuolatus (r 2 of 0.776, SE of 0.825 log units). The robustness and predictivity of the two models for IPC-81 and Vibrio fischeri were checked by comparing the calculated SE and r 2 (coefficient of determination) values of the test set.
Authors (9)
-
Chul-Woong Cho
- University of Bremen Centre for Environmental Research and Sustainable Technology (UFT)
-
Johannes Ranke
- University of Bremen Centre for Environmental Research and Sustainable Technology (UFT)
-
Jurgen Arning
- University of Bremen Centre for Environmental Research and Sustainable Technology (UFT)
-
Jorg THöMING
- University of Bremen Centre for Environmental Research and Sustainable Technology (UFT)
-
Ulrich Preiss
- Ruhr–Universität Bochum Interdisciplinary Centre for Advanced Materials Simulation (ICAMS)
-
M. Diedenhofen
- COSMOlogic GmbH & Co. KG COSMOlogic GmbH & Co. KG
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Ingo Krossing
- University of Freiburg Institut für Anorganische und Analytische Chemie
-
Stefan Stolte
- University of Bremen Centre for Environmental Research and Sustainable Technology (UFT)
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
SAR AND QSAR IN ENVIRONMENTAL RESEARCH
no. 24,
edition 10,
pages 863 - 882,
ISSN: 1062-936X - Language:
- English
- Publication year:
- 2013
- Bibliographic description:
- Cho C., Ranke J., Arning J., Thöming J., Preiss U., Jungnickel C., Diedenhofen M., Krossing I., Stolte S.: In silico modelling for predicting the cationic hydrophobicity and cytotoxicity of ionic liquids towards the Leukemia rat cell line, Vibrio fischeri and Scenedesmus vacuolatus based on molecular interaction potentials of ions// SAR AND QSAR IN ENVIRONMENTAL RESEARCH. -Vol. 24, iss. 10 (2013), s.863-882
- Verified by:
- Gdańsk University of Technology
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