title: Synthesis, fluorescence properties and the promising cytotoxicity of pyrene-derived aminophosphonates.
abstract: A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20-97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (ΦF = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC50 = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC50 = 230.8 µM).
authors: Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors: Jarosław
authors: J
authors: Lewkowski
authors: Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors: Maria
authors: M
authors: Rodriguez Moya
authors: Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors: Anna
authors: A
authors: Wrona-Piotrowicz
authors: Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
authors: Janusz
authors: J
authors: Zakrzewski
authors: Laboratory of Cytogenetics, Faculty of Biology and Environmental Protection, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland.
authors: Renata
authors: R
authors: Kontek
authors: Laboratory of Cytogenetics, Faculty of Biology and Environmental Protection, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland.
authors: Gabriela
authors: G
authors: Gajek
keywords: MTT test; aminophosphonic derivatives; cytotoxicity; fluorescence properties; pyrene-1-carboxaldehyde