Hybrid Oligonucleotides Containing Stilbene Units. Excimer Fluorescence and Photodimerization

Frederick D. Lewis*, Taifeng Wu, Eric L. Burch, Dario M. Bassani, Jye Shane Yang, Robert L. Letsinger, Siegfried Schneider, Wighard Jäger

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

94 Scopus citations

Abstract

Complementary pairs of oligonucleotides in which the stilbene chromophore is incorporated either in the middle or at the end of a 10 base pair sequence have been prepared and their spectroscopic and photochemical properties investigated. The individual oligonucleotides display fluorescence spectra and photoisomerization similar to that of a model 4,4’-stilbenedicarboxamide. Variations in fluorescence quantum yield and decay times are attributed to interactions with neighboring bases. One-to-one mixtures of complementary oligonucleotides form stable duplexes with melting temperatures of 40 and 46 °C, respectively, for the mid-strand and terminally labeled duplexes. Duplex formation results in hyperchromism of both the nucleotide and stilbene absorption bands and the appearance of broad, long-wavelength fluorescence attributed to an excited stilbene dimer. These duplexes provide a unique opportunity for the investigation of the here-to-for elusive stilbene excimer. The long wavelength absorption bands of both duplexes are efficiently bleached upon irradiation. Bleaching is a consequence of stereospecific stilbene [2+2] photodimerization and results in the formation of cross-linked duplexes of high thermal stability. Excimer and monomer fluorescence are found to provide a highly sensitive probe of duplex formation and dissociation.

Original languageEnglish (US)
Pages (from-to)8785-8792
Number of pages8
JournalJournal of the American Chemical Society
Volume117
Issue number34
DOIs
StatePublished - 1995

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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