Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins.

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Ogata N, Shibata T

Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins.

Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73.

PubMed ID

11334365 [ View in PubMed

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Abstract

Wood creosote, primarily a mixture of simple alkyl- and/or alkoxy-substituted phenolic compounds with closely related structures, has long been used as an oral antidiarrheal agent. The use of wood creosote as a parenteral antidiarrheal agent was investigated, and for basic pharmacokinetic data we measured the extent of equilibrium binding of its six major constituent phenolic compounds to human serum proteins using an ultrafiltration method. The percent binding of these major constituent phenolic compounds, namely phenol, guaiacol, p-cresol, o-cresol, creosol and 4-ethylguaiacol, bound to 40-mg/ml human serum albumin was 15.5+/-0.9, 28.0+/-1.5, 37.2+/-0.7, 52.3+/-5.3, 36.8+/-2.0 and 56.7+/-2.4%, respectively, while percent binding to human serum (68 mg protein/ml) was 41.3+/-0.7, 42.6+/-0.5, 64.8+/-0.4, 70.1+/-1.6, 65.7+/-0.2 and 83.1+/-0.1% (mean +/- standard deviation, n = 4), respectively, when tested individually at a concentration of 500 micromol/l. Saturation of binding was not observed for the phenolic compounds up to a concentration of 50 mmol/l. Phenolic compounds with a lipophilic substituent showed higher percent binding to proteins than those without it. We conclude that simple phenolic compounds having alkyl- and/or alkoxy-substituents bind to serum proteins to a considerable extent and that the binding is hydrophobic and nonspecific.

DrugBank Data that Cites this Article

Drug Targets

Drug	Target	Kind	Organism	Pharmacological Action	Actions
Guaiacol	Serum albumin	Protein	Humans	Unknown	Not Available	Details
Phenol	Serum albumin	Protein	Humans	Unknown	Not Available	Details