title: Synthesis of genistein coupled with sugar derivatives and their inhibitory effect on nitric oxide production in macrophages.
abstract: The isoflavone genistein 1 and some derivatives modulate IL-12, TNF-α and NO production by macrophages and lung cancer cell lines, and improve the clinical signs of experimental autoimmune encephalomyelitis (EAE). Seven genistein derivatives connected at C-6 position of a sugar, such as d-glucose and d-galactose, were synthesized. The ability to modulate macrophage response was evaluated, showing variable inhibition capacity of NO and TNF-α production in J774.A1 and RAW 264.7. Five of the seven compounds were non-cytotoxic; compound 8 was more effective to inhibit NO and TNF-α production, without affecting cell viability.
authors.affiliation: Department of Chemistry, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Celso O R
authors.initials: CO
authors.lastname: Junior
authors.affiliation: Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Sandra B R
authors.initials: SB
authors.lastname: Castro
authors.affiliation: Department of Chemistry, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Adriane A
authors.initials: AA
authors.lastname: Pereira
authors.affiliation: Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Caio C S
authors.initials: CC
authors.lastname: Alves
authors.affiliation: Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Erick E
authors.initials: EE
authors.lastname: Oliveira
authors.affiliation: Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Renata T
authors.initials: RT
authors.lastname: Rêgo
authors.affiliation: Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil.
authors.forename: Ana Paula
authors.initials: AP
authors.lastname: Ferreira
authors.affiliation: Department of Chemistry, Federal University of Juiz de Fora, Juiz de Fora, MG, Brazil. Electronic address: mauro.almeida@ufjf.edu.br.
authors.forename: Mauro V
authors.initials: MV
authors.lastname: de Almeida
mesh_terms: D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005690:Galactose / Q000737:chemistry*; D019833:Genistein / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005947:Glucose / Q000737:chemistry*; D007371:Interferon-gamma / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism*; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis*; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis
chemical_list: D008070:Lipopolysaccharides; D014409:Tumor Necrosis Factor-alpha; D009569:Nitric Oxide; D007371:Interferon-gamma; D019833:Genistein; D005947:Glucose; D005690:Galactose
keywords: Carbohydrate; Genistein; J774A.1; Nitric oxide; RAW 264.7; TNF-α