Interaction of amino acids with a non-homologous series of anticancer drugs.
The interaction of amino acids with 14 commercial anticancer drugs was studied by charge-transfer reversed-phase thin-layer chromatography and the retention matrix was evaluated by principal component analysis. The majority of amino acids had a negligible effect on the retention of anticancer drugs. Only dicarboxy amino acids and Trp exerted a considerable impact on the retention of drugs, indicating the involvement of hydrophilic forces (probably hydrogen bond formation) and stacking interactions in the binding of drugs to amino acids. Stepwise regression analysis proved that both the pI value of amino acids and the pK value of the amino acid side chain significantly influence the strength of interaction. The findings support the hypothesis that the binding of anticancer drugs to proteins may involve both hydrophilic forces occurring between the corresponding polar sub-structures of drugs and amino acids and stacking interactions between the various ring structures. The relative importance of these interactions depends on the character of the amino acid residue and the chemical structure of drugs.
Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest.
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Cserháti
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Holló
D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism*; D002855:Chromatography, Thin Layer / Q000379:methods; D004347:Drug Interactions; D007700:Kinetics; D012044:Regression Analysis
D000596:Amino Acids; D000970:Antineoplastic Agents