title: Synthesis of chloro-substituted analogs of Thiazole orange - Fluorophores for flow cytometric analyses.
abstract: Synthesis, absorption and fluorescence properties of a series of asymmetrical monomethine cyanine dyes, chloro-containing analogs of Thiazole orange, are reported. Their staining ability was studied by flow cytometry. The saturating concentrations of each dye that gives a stable staining intensity have been determined. The ability of dyes B9, B11, B13 to stain live macrophages and apoptotic splenocytes was investigated. Positive signal in nucleus of adherent macrophages detected by fluorescent microscopy showed good specificity of B9, B11 and B13 dyes for DNA. In apoptotic assay cells positive for Annexin V were stained more brightly with the dyes B9, B11 and B13 than with propidium iodide. Despite that B13 showed high DNA selectivity it induces apoptosis of splenocytes and it is not suitable for detection of dead cells. The other synthesized chloro-containing analogs of Thiazole orange B9 and B11 can be successfully used for flow cytometric analyses of DNA content in live cells and for analyses of cell apoptosis.
authors.affiliation: Department of Applied Organic Chemistry, Faculty of Chemistry, University of Sofia, 1164 Sofia, Bulgaria. ohtsk@chem.uni-sofia.bg
authors.forename: S
authors.initials: S
authors.lastname: Kaloyanova
authors.forename: I
authors.initials: I
authors.lastname: Ivanova
authors.forename: A
authors.initials: A
authors.lastname: Tchorbanov
authors.forename: P
authors.initials: P
authors.lastname: Dimitrova
authors.forename: T
authors.initials: T
authors.lastname: Deligeorgiev
mesh_terms: D000818:Animals; D017209:Apoptosis / Q000187:drug effects*; D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000032:analysis / Q000378:metabolism; D005434:Flow Cytometry / Q000379:methods*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008813:Mice, Inbred ICR; D008856:Microscopy, Fluorescence / Q000379:methods*; D011419:Propidium / Q000737:chemistry / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013154:Spleen / Q000166:cytology / Q000378:metabolism
chemical_list: D052160:Benzothiazoles; D005456:Fluorescent Dyes; D006843:Hydrocarbons, Chlorinated; D011804:Quinolines; C051000:thiazole orange; D011419:Propidium; D004247:DNA