Solubilization of organic compounds by arginine-derived polymers

Poor aqueous solubility of drugs is one of the major challenges in the pharmaceutical science. In this study, a guanidinium-containing polymer based on arginine was designed and synthesized, and was evaluated as a solubility enhancing additive for three model organic compounds (coumarin, pyrene and doxorubicin). At a guanidinium group concentration of 100 mmol/L, the polymer could significantly increase the solubility of pyrene and doxorubicin by 6- and 11-fold respectively, much more effective than arginine (2- and 3-fold, respectively). In contrast, its effect on the solubility of coumarin was less effective than arginine. The solubilizing effect may be explained by the enhanced interaction between the guanidinium group in the polymer and the aromatic compounds.

Graphical abstractWith multiple guanidinium side groups, arginine-derived polymers are very effective to solubilize large aromatic compounds in the aqueous solutions.Figure optionsDownload full-size imageDownload as PowerPoint slide