Collect. Czech. Chem. Commun. 1999, 64, 1419-1432

Linear Heptapeptides Containing DNA-Intercalators. Synthesis and Interaction with DNA

Zbyněk Matušinaa, Radomíra Olbřímkováb, Hana Votavovác, Josef Neumannc, Martin Hradilekc, Milan Součekc, Petr Maloňc, Milan Kodíčekb and Ivan Stibora,*

a Department of Organic Chemistry, Prague Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic
b Department of Biochemistry, Prague Institute of Chemical Technology, Technická 3, 166 28 Prague 6, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


Five peptides of general structure X-Ser-Pro-Thr-Ser-Pro-Ser-Y (X = Tyr, quinoxaline- 2-carbonyl, acridine-9-carbonyl, Y = Tyr, (quinoxalin-2-yl)amino) were prepared using standard solid-phase peptide synthesis technique. Their interaction with DNA (calf thymus DNA and plasmids pUC9, p∆NS and pGEMEX) was studied using UV and CD spectroscopy, sedimentation analysis and agarose gel electrophoresis after treatment with topoisomerase I. In contrast to earlier findings (Suzuki M.: Nature 1990, 344, 562) intercalation into DNA structure has not been proved for any compound studied.

Keywords: Intercalation; Peptides; DNA; Topoisomerase I; UV spectroscopy; CD spectroscopy; Sedimentation analysis; Acridines; Quinoxalines.