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Journal of Biochemistry Advance Access published online on June 26, 2008
Journal of Biochemistry, doi:10.1093/jb/mvn078
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© 2008 The Japanese Biochemical Society

Arginine Increases the Solubility of Coumarin: Comparison with Salting-In and Salting-Out Additives

Atsushi Hirano1, Tsutomu Arakawa2 and Kentaro Shiraki1,*

1Institute of Applied Physics, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan; and 2Alliance Protein Laboratories, Thousand Oaks, CA 91360, United States.

*To whom correspondence should be addressed. Institute of Applied Physics, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan. Fax: +81-29-853-5215. Tel: +81-29-853-5306. E-mail: shiraki{at}bk.tsukuba.ac.jp

Received March 22, 2008; Accepted May 23, 2008


  Abstract

Summary

Poor aqueous solubility of low molecular weight drug substances hampers their development as pharmacological agents. Here we have examined the effects of arginine on the solubility of organic compounds, coumarin, caffeine and benzyl alcohol, in aqueous solution. Arginine increased the solubility of aromatic coumarin, but not non-aromatic caffeine, concentration dependently, suggesting the favorable interaction of arginine with the aromatic structure. Consistent with this, arginine also increased the solubility of aromatic benzyl alcohol. Guanidine hydrochloride, urea, and salting-in salts increased both coumarin and caffeine solubilities, while salting-out salts decreased them. These results suggest the specific interaction of arginine with aromatic groups, leading to increased solubility of coumarin. However, the effect of 1 M arginine on coumarin solubility was at most ~2-fold, which may limit its applications as a solubility enhancing agent.

Key Words: arginine, caffeine, coumarin, solubility, surface tension


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