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Determination of lipophilic descriptors of antihelmintic 6,7‐diaryl‐pteridine derivatives useful for bioactivity predictions
Author(s) -
Reta Mario,
Giacomelli Liliana,
Santo Marisa,
Cattana Rosa,
Silber Juana J,
Ochoa Carmen,
Rodriguez Mercedes,
Chana Antonia
Publication year - 2003
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.227
Subject(s) - chemistry , lipophilicity , partition coefficient , chromatography , pteridine , aqueous solution , acetonitrile , octanol , solubility , stereochemistry , organic chemistry , enzyme
The liquid chromatographic retention factors extrapolated to pure water, k ′ w , for several 6,7‐diaryl‐pteridine derivatives in both an octadecylsilane (ODS) and an immobilized articial membrane column (IAM.PC.DD2), using acetonitrile–aqueous buffer pH = 7.45 as mobile phase, were obtained. The logarithms of the k ′ w values in the IAM.PC.DD2 column, log k ′ w IAM , show good correlation with the calculated values of the octanol–water partition coefcients, log P o/w , showing that the chromatographic parameter can be used as lipophilicity descriptor for the studied pteridines. However, interactions other than the lipophilic ones seem to be involved in the ODS column. Previous studies have shown that pteridines have antihelmintic properties. In spite of the complexity of the studied biological system as compared with the chromatographic one, good correlation between the descriptors obtained in the IAM column and biological activity (expressed as the log of the inhibitory concentration required to obtain up to 50% in the reduction of population growth of nematodes, log IC 50 ) was observed. Copyright © 2003 John Wiley & Sons, Ltd.