Semi-automatic synthesis, antiproliferative activity and DNA-binding properties of new netropsin and bis-netropsin analogues

Jakub Szerszenowicz; Danuta Drozdowska

doi:10.3390/molecules190811300

Semi-automatic synthesis, antiproliferative activity and DNA-binding properties of new netropsin and bis-netropsin analogues

Molecules. 2014 Jul 31;19(8):11300-15. doi: 10.3390/molecules190811300.

Authors

Jakub Szerszenowicz¹, Danuta Drozdowska²

Affiliations

¹ Saint Brunon Farmacy, Bohaterów Westerplatte 4 Str., 11-500 Giżycko, Poland. jakubszerszenowicz@o2.pl.
² Department of Organic Chemistry, Medical University, Mickiewicza 2A Str., 15-222 Białystok, Poland. danuta.drozdowska@umb.edu.pl.

Abstract

A general route for the semi-automatic synthesis of some new potential minor groove binders was established. Six four-numbered sub-libraries of new netropsin and bis-netropsin analogues have been synthesized using a Syncore Reactor. The structures of the all new substances prepared in this investigation were fully characterized by NMR ((1)H, (13)C), HPLC and LC-MS. The antiproliferative activity of the obtained compounds was tested on MCF-7 breast cancer cells. The ethidium displacement assay using pBR322 confirmed the DNA-binding properties of the new analogues of netropsin and bis-netropsin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / metabolism
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Cell Proliferation / drug effects
Chemistry Techniques, Synthetic
DNA / metabolism*
Humans
Inhibitory Concentration 50
Molecular Structure
Netropsin / analogs & derivatives*
Netropsin / chemical synthesis
Netropsin / metabolism*
Netropsin / pharmacology*

Substances

Antineoplastic Agents
Netropsin
bis-netropsin
DNA