title: Gossypol-cross-linked boronic acid-modified hydrogels: a functional matrix for the controlled release of an anticancer drug.
abstract: Anticancer drug gossypol cross-links phenylboronic acid-modified acrylamide copolymer chains to form a hydrogel matrix. The hydrogel is dissociated in an acidic environment (pH 4.5), and its dissociation is enhanced in the presence of lactic acid (an α-hydroxy carboxylic acid) as compared to formic acid. The enhanced dissociation of the hydrogel by lactic acid is attributed to the effective separation of the boronate ester bridging groups through the formation of a stabilized complex between the boronic acid substituent and the lactic acid. Because lactic acid exists in cancer cells in elevated amounts and the cancer cells' environment is acidic, the cross-linked hydrogel represents a stimuli-responsive matrix for the controlled release of gossypol. The functionality is demonstrated and characterized by rheology and other spectroscopic means.
authors: Institute of Chemistry, The Center for Nanoscience and Nanotechnology, The Hebrew University of Jerusalem , Jerusalem 91904, Israel.
authors: Vered
authors: V
authors: Heleg-Shabtai
authors: Ruth
authors: R
authors: Aizen
authors: Ron
authors: R
authors: Orbach
authors: Miguel Angel
authors: MA
authors: Aleman-Garcia
authors: Itamar
authors: I
authors: Willner
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003692:Delayed-Action Preparations / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D006072:Gossypol / Q000737:chemistry*; D020100:Hydrogels / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D019344:Lactic Acid / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D001897:Boronic Acids; D003692:Delayed-Action Preparations; D005561:Formates; D020100:Hydrogels; C030544:formic acid; D019344:Lactic Acid; D006072:Gossypol