Nonnucleosidic Base Surrogates: The Effect of 1,2-Disubstituted Phenanthrenes on DNA Duplex Stability

Autor: Damian Ackermann, Robert Häner
Rok vydání: 2004
Předmět:
Zdroj: Helvetica Chimica Acta. 87:2790-2804
ISSN: 0018-019X
DOI: 10.1002/hlca.200490250
Popis: Phenanthrene-1,2-dimethanol was incorporated into oligodeoxynucleotides via formation of phosphodiester bonds (cf. Scheme 1). If placed at internal positions in a DNA duplex, a strong reduction of duplex stability is observed (Table 1). Terminal attachment of stretches of phenanthrene residues, however, leads to a substantial increase in stability. The stabilization is attributed to a cooperative interaction of the phenanthrene residues of the two strands rather than to dangling end effects. Chimeric oligomers containing a stretch of six phenanthrene residues show two separate transitions (Table 2): one arising from the denaturation of the DNA stem (observable by a hyperchromic effect at 260 nm) and a second one from the denaturation of the phenanthrene part (observable by temperature-dependant gel mobility assays). Based on these findings, a model of the chimeric hybrids is proposed, in which the phenanthrene residues stack in a zipper-like manner on top of the DNA base pairs without disrupting the B-form of the DNA stem (see Fig. 7).
Databáze: OpenAIRE