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Investigation of lipophilicity of anticancer‐active thioquinoline derivatives
Author(s) -
Bajda Marek,
Boryczka Stanisław,
Wietrzyk Joanna,
Malawska Barbara
Publication year - 2007
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.706
Subject(s) - lipophilicity , chemistry , chromatography , partition coefficient , acetonitrile , high performance liquid chromatography , stereochemistry
The lipophilicity of a series of anticancer propargylthioquinoline derivatives has been investigated using chromatographic and computational methods. The parameters of relative lipophilicity ( R MO and log k 0 ) of the tested compounds were determined experimentally both by reversed‐phase thin layer (RP‐TLC), and high‐performance liquid chromatographic methods (RP‐HPLC, LiChrospher RP 18 column), with mixtures of acetonitrile and water as mobile phases. Their phospholipophilicity (log k 0IAM ) was determined using immobilized artificial membrane HPLC (IAM . PC DD2 Regis column). Mobile phase acetonitrile concentrations were in the ranges 50–90% (RP‐TLC), 55–90% (RP‐HPLC) and 35–60% (IAM‐HPLC). The R M , log k and log k IAM values of the compounds investigated were linearly dependent on acetonitrile concentration. The analysis led to the calculation of R MO , log k 0 and log k 0IAM parameter values for each of the tested compounds. Their partition coefficients (log P ) were also calculated with the Pallas and CAChe programs. The obtained results indicated that, among experimental methods, both RP‐TLC and RP‐HPLC gave similar results, and these methods enable the determination of lipophilicity of derivatives of thioquinolines. Using the IAM‐HPLC technique a simple method of estimation of phospholipoplilicity was described. The CAChe program might better predict calculated lipophilicity log P values, and therefore is a useful tool for the early stage of design of new propargyl thioquinolines. Copyright © 2006 John Wiley & Sons, Ltd.