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Retention behavior of flavonoids on immobilized artificial membrane chromatography and correlation with cell‐based permeability
Author(s) -
Tsopelas Fotios,
Tsagkrasouli Maria,
Poursanidis Pavlos,
Pitsaki Maria,
Vasios George,
Danias Panagiotis,
Panderi Irene,
TsantiliKakoulidou Anna,
Giaginis Constantinos
Publication year - 2018
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.4108
Subject(s) - chemistry , chromatography , molecular descriptor , permeability (electromagnetism) , octanol , membrane , partition coefficient , membrane permeability , quantitative structure–activity relationship , stereochemistry , biochemistry
The aim of the study was to investigate the immobilized artificial membrane (IAM) retention mechanism for a set of flavonoids and to evaluate the potential of IAM chromatography to model Caco‐2 permeability. For this purpose, the retention behavior of 41 flavonoid analogs on two IAM stationary phases, IAM.PC.MG and IAM.PC.DD2, was investigated. Correlations between retention factors, log k w(IAM) and octanol–water partitioning (log P ) were established and the role of hydroxyl groups of flavonoids to the underlying retention mechanism was explored. IAM retention and log P values were used to establish sound linear models with Caco‐2 permeability (log P app ) taken from the literature. Both stepwise regression and multivariate analysis confirmed the contribution of hydrogen bond descriptors, as additional parameters in the either log k w(IAM) or log P models. Retention factors on both IAM stationary phases showed comparable performance with n ‐octanol–water partitioning towards Caco‐2 permeability.