Oligonucleotide-Polyamide Hybrid Molecules Containing Multiple Pyrene Residues Exhibit Significant Excimer Fluorescence

Tong, Glenn; Lawlor, J. M.; Tregear, Geoffrey W.; Haralambidis, Jim

doi:10.1021/ja00154a015

Cited by 49 publications

(33 citation statements)

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“…[33][34][35] To understand the problem of intercalation, it would be desirable to discover a general rule that describes under which circumstances the dye is likely to intercalate.…”

Section: Introductionmentioning

confidence: 99%

2‐(1‐Ethynylpyrene)‐Adenosine as a Folding Probe for RNA—Pyrene in or out

et al. 2010

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A series of short RNA duplexes containing one or two 1-ethynylpyrene-modified adenine bases was synthesised. The melting behaviour of these duplexes was examined by monitoring temperature-dependent pyrene fluorescence. In the singly modified RNA duplexes, the bases flanking the ethynylpyrene-rA were varied to examine the sequence specificity of the fluorescence change of pyrene upon RNA hybridisation. Because an increase in pyrene fluorescence upon melting of the duplex can be correlated with intercalation of pyrene, and a decrease is usually associated with the position of pyrene outside the strand, a relationship between the flanking bases and the tendency of the dye to intercalate has been established. It was found that pyrene intercalation is less likely to take place if the modified base is flanked only by A-U base pairs. Flanking G-C base pairs, even only in the 5'-direction of the modified base, will favour intercalation. In addition, we examined a doubly modified compound that had a pyrene located on each strand. The spectra indicated that the two pyrenes were close enough for interaction. Upon melting of the strand, a fluorescence blue shift corresponding to the dissociation of the pyrene-pyrene complex could be observed in addition to the intensity effect already known from the singly modified compounds. Two melting curves based on the different properties of the fluorophore could be extracted, leading to different melting points corresponding to the global duplex melting and to the change of local pyrene environment, respectively.

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“…[33][34][35] To understand the problem of intercalation, it would be desirable to discover a general rule that describes under which circumstances the dye is likely to intercalate.…”

Section: Introductionmentioning

confidence: 99%

2‐(1‐Ethynylpyrene)‐Adenosine as a Folding Probe for RNA—Pyrene in or out

et al. 2010

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“…Excimer fluorescence of the pair of 5 0 -end and 3 0 -end pyrene labeled oligonucleotide, complementary to adjacent region within target DNA was successfully applied for detection of point mutation and quantification of DNA [17][18][19]23 . Oligonucleotide conjugates, exhibiting excimer fluorescence due to presence of two 20,21,23 or multiple pyrene residues in oligonucleotide conjugate 24 were developed. Some attempts to develop oligonucleotide probe, displaying excimer fluorescence have been complicated by multi-step synthesis of conjugates 21,24 .…”

Section: Introductionmentioning

confidence: 99%

5′-Bis-Pyrenylated Oligonucleotides Display Enhanced Excimer Fluorescence Upon Hybridization With Dna and Rna

Костенко¹,

Dobrikov²,

Комарова³

et al. 2001

Nucleosides, Nucleotides and Nucleic Acids

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A simple one-step procedure was applied for synthesis of oligonucleotide conjugates bearing two pyrene residues at the 5'-phosphate of oligonucleotide. Excimer fluorescence intensity of the conjugates is highly sensitive to duplex formation: binding of the bis-pyrenylated oligonucleotides to their DNA and RNA targets leads 10-fold increase of fluorescence. The data show that excimer fluorescence intensity of the conjugates depends linearly on the concentration of target DNA and permits quantification of DNA in solution.

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“…79 Significant excimer fluorescence from the DNA-b-polyamide was detected due to the close proximity of the chromophores. The multimerization of labels resulted in an increase of the emission intensity, proving the concept of a polylabel strategy.…”

confidence: 99%