title: Synthesis and cytotoxicity of novel indirubin-5-carboxamides.
abstract: Indirubins have been reported to act as potent inhibitors of protein kinases relevant to tumorigenesis and of tumor cell growth, but their development to antitumor drugs suffer from their poor water solubility. We synthesized a novel class of indirubin derivatives, indirubin-5-carboxamides, carrying amide substituents with basic centers. Quaternization or protonation of these alkylamino substituents provided indirubins with significantly improved solubility without loss of bioactivity.
authors.affiliation: Department of Chemistry, Division of Food Chemistry and Toxicology, University of Kaiserslautern, Kaiserslautern, Germany.
authors.forename: Xinlai
authors.initials: X
authors.lastname: Cheng
authors.forename: Paul
authors.initials: P
authors.lastname: Rasqué
authors.forename: Sandra
authors.initials: S
authors.lastname: Vatter
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: Merz
authors.forename: Gerhard
authors.initials: G
authors.lastname: Eisenbrand
mesh_terms: D000577:Amides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D011494:Protein Kinases / Q000737:chemistry / Q000378:metabolism; D012995:Solubility; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D007211:Indoles; D047428:Protein Kinase Inhibitors; D011494:Protein Kinases; C027185:indirubin