title: pH-dependent, stereoselective dimerization of sinomenine.
abstract: In a continuing study on discovery of more potent derivatives of sinomenine (1), a clinically available alkaloid for rheumatoid arthritis (RA) treatment, oxidation of sinomenine provided two unique stereoisomers, disinomenines 2 and 3. The structure of 3 was determined by MS, NMR, and X-ray analysis. The formation of 2 and 3 via oxidation of sinomenine by potassium permanganate (KMnO4) exhibited a pH-dependent stereoselectivity. The bioassay results using human synovial sarcoma cells (SW982) showed that 2 inhibited, while 3 stimulated, IL-6 production.
authors.affiliation: Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
authors.forename: Zhang-Shuang
authors.initials: ZS
authors.lastname: Deng
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
authors.forename: Cui-Cui
authors.initials: CC
authors.lastname: He
authors.forename: Jie
authors.initials: J
authors.lastname: Jin
authors.forename: Yun-Mian
authors.initials: YM
authors.lastname: He
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Li
mesh_terms: D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D019281:Dimerization; D006801:Humans; D006863:Hydrogen-Ion Concentration; D015850:Interleukin-6 / Q000096:biosynthesis; D009019:Morphinans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010084:Oxidation-Reduction; D013584:Sarcoma, Synovial / Q000378:metabolism; D013237:Stereoisomerism; D000093242:Interleukin-6 Inhibitors
chemical_list: D015850:Interleukin-6; D009019:Morphinans; D000093242:Interleukin-6 Inhibitors; C009271:sinomenine