Menacher, Florian and Rubner, Moritz and Berndl, Sina and Wagenknecht, Hans-Achim (2008) Thiazole orange and Cy3: Improvement of fluorescent DNA probes with use of short range electron transfer. JOURNAL OF ORGANIC CHEMISTRY, 73 (11). pp. 4263-4266. ISSN 0022-3263,
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Thiazole orange was synthetically incorporated into oligo-nucleotides by using the corresponding phosphoramidite as the building block for automated DNA synthesis. Due to the covalent fixation of the TO dye as a DNA base surrogate, the TO-modified oligonucleotides do not exhibit a significant increase of fluorescence upon hybridization with the counterstrand. However, if 5-nitroindole (NI) is present as a second artificial DNA base (two base pairs away from the TO dye) a fluorescence increase upon DNA hybridization can be observed. That suggests that a short-range photoin-duced electron transfer causes the fluorescence quenching in the single strand. The latter result represents a concept that can be transferred to the commercially available Cy3 label. It. enables the Cy3 fluorophore to display the DNA hybridization by a fluorescence increase that is normally not observed with this dye.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PEPTIDE NUCLEIC-ACIDS; RESONANCE ENERGY-TRANSFER; MOLECULAR BEACONS; ARTIFICIAL BASE; CHARGE-TRANSFER; OLIGONUCLEOTIDES; DYE; PHENANTHRIDINIUM; HYBRIDIZATION; MISMATCHES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Prof. Dr. Hans-Achim Wagenknecht Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Oct 2020 10:18 |
| Last Modified: | 29 Oct 2020 10:18 |
| URI: | https://pred.uni-regensburg.de/id/eprint/30746 |
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