DNA-based electrochemical biosensors for monitoring of bis-indoles as potential antitumoral agents, chemistry, X-ray crystallography.
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.
Maciejewska
Dorota
D
Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02 097 Warsaw, Poland. domac@farm.amwaw.edu.pl
Szpakowska
Iwona
I
Wolska
Irena
I
Niemyjska
Maria
M
Mascini
Marco
M
Maj-Zurawska
Magdalena
M
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
C514678:5,5'-dimethoxy-3,3'-methanediyl-bis-indole; D000970:Antineoplastic Agents; D007211:Indoles; D004247:DNA