title: DNA-based electrochemical biosensors for monitoring of bis-indoles as potential antitumoral agents, chemistry, X-ray crystallography.
abstract: Facile and practical electrochemical DNA bioassay, X-ray diffraction analysis, synthesis and 1H and 13C NMR data of the 5,5'-disubstituted-3,3'-methanediyl-bis-indoles are reported. On the basis of electrochemical measurements we have hypothesized that the analyzed bis-indoles have an effect on human tumor cells due to DNA binding at adenine-thymidine deoxynucleotides rich region in a concentration/substituent dependent manner. Interesting N-H...pi and hydrogen-bonding intermolecular interactions were observed which may differentiate their biological features. The 5,5'-dimethoxy-3,3'-methanediyl-bis-indole (2) was found to reduce considerably the growth of cancer cell lines HOP-92 (lung), A498 (renal) and MDA-MB-231/1TCC (breast). The results indicate that title compounds could be interesting as potential antitumoral chemotherapeutics.
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02 097 Warsaw, Poland. domac@farm.amwaw.edu.pl
authors.forename: Dorota
authors.initials: D
authors.lastname: Maciejewska
authors.forename: Iwona
authors.initials: I
authors.lastname: Szpakowska
authors.forename: Irena
authors.initials: I
authors.lastname: Wolska
authors.forename: Maria
authors.initials: M
authors.lastname: Niemyjska
authors.forename: Marco
authors.initials: M
authors.lastname: Mascini
authors.forename: Magdalena
authors.initials: M
authors.lastname: Maj-Zurawska
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015374:Biosensing Techniques / Q000379:methods*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004563:Electrochemistry; D006801:Humans; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012680:Sensitivity and Specificity; D014961:X-Ray Diffraction
chemical_list: C514678:5,5'-dimethoxy-3,3'-methanediyl-bis-indole; D000970:Antineoplastic Agents; D007211:Indoles; D004247:DNA