title: Synthesis and cytotoxic properties of tryptamine derivatives.
abstract: The cyclopropyliminium and subsequent Grandberg rearrangements of cyclopropylketone hydrozones lead to the formation of tryptamines, which were additionally substituted at either the aromatic ring atoms or the amino group. The products were tested for their cytotoxic properties against HepG2, Jurkat and HEK293 cell lines using MTT assay. The highest activity as well as the highest selectivity was found amongst the compounds derived with one benzyl substituent at the amino group. The flow cytometry technique revealed cell-type specificity in terms of the mechanism of viability inhibition. Thus, the compounds were found to induce mainly apoptosis in HEK293 and HepG2 cells, while Jurkat cells displayed late apoptotic and necrotic responses. The apoptosis pathway is most likely to include mitochondrial damage.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation.
authors.forename: Rinat F
authors.initials: RF
authors.lastname: Salikov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation; Higher Chemical College, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: Aleksandr Yu
authors.initials: AY
authors.lastname: Belyy
authors.affiliation: Institute of Biochemistry and Genetics Ufa Science Centre of the Russian Academy of Sciences, Ufa, Russian Federation.
authors.forename: Nailya S
authors.initials: NS
authors.lastname: Khusnutdinova
authors.affiliation: Institute of Biochemistry and Genetics Ufa Science Centre of the Russian Academy of Sciences, Ufa, Russian Federation.
authors.forename: Yulia V
authors.initials: YV
authors.lastname: Vakhitova
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation. Electronic address: tom@ioc.ac.ru.
authors.forename: Yury V
authors.initials: YV
authors.lastname: Tomilov
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D057809:HEK293 Cells; D056945:Hep G2 Cells; D006801:Humans; D019169:Jurkat Cells; D053078:Membrane Potential, Mitochondrial / Q000187:drug effects; D009369:Neoplasms / Q000188:drug therapy / Q000378:metabolism; D014363:Tryptamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D014363:Tryptamines; C030820:tryptamine
keywords: Apoptosis; Cytotoxicity; Mitochondrial damage pathway; Tryptamine derivatives