Highly fluorescent conjugated pyrenes in nucleic acid probes: (Phenylethynyl)pyrenecarbonyl-functionalized locked nucleic acids

Irina Astakhova, Vladimir A. Korshun, Jesper Wengel

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

In recent years, fluorescently labeled oligonucleotides have become a widely used tool in diagnostics, DNA sequencing, and nanotechnology. The recently developed (phenylethynyl)pyrenes are attractive dyes for nucleic acid labeling, with the advantages of long‐wave emission relative to the parent pyrene, high fluorescence quantum yields, and the ability to form excimers. Herein, the synthesis of six (phenylethynyl)pyrene‐functionalized locked nucleic acid (LNA) monomers M1–M6 and their incorporation into DNA oligomers is described. Multilabeled duplexes display higher thermal stabilities than singly modified analogues. An increase in the number of phenylethynyl substituents attached to the pyrene results in decreased binding affinity towards complementary DNA and RNA and remarkable bathochromic shifts of absorption/emission maxima relative to the parent pyrene fluorochrome. This bathochromic shift leads to the bright fluorescence colors of the probes, which differ drastically from the blue emission of unsubstituted pyrene. The formation of intra‐ and interstrand excimers was observed for duplexes that have monomers M1–M6 in both complementary strands and in numerous single‐stranded probes. If more phenylethynyl groups are inserted, the detected excimer signals become more intense. In addition, (phenylethynyl)pyrenecarbonyl–LNA monomers M4, M5, and M6 proved highly useful for the detection of single mismatches in DNA/RNA targets.

OriginalsprogEngelsk
TidsskriftChemistry: A European Journal
Vol/bind14
Udgave nummer35
Sider (fra-til)11010-11026
Antal sider16
ISSN0947-6539
DOI
StatusUdgivet - 2008

Fingeraftryk

Nucleic acids
Pyrene
DNA
Monomers
RNA
Fluorescence
Oligonucleotides
Quantum yield
Nanotechnology
Oligomers
Labeling
Thermodynamic stability
Dyes
Color

Citer dette

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title = "Highly fluorescent conjugated pyrenes in nucleic acid probes: (Phenylethynyl)pyrenecarbonyl-functionalized locked nucleic acids",
abstract = "In recent years, fluorescently labeled oligonucleotides have become a widely used tool in diagnostics, DNA sequencing, and nanotechnology. The recently developed (phenylethynyl)pyrenes are attractive dyes for nucleic acid labeling, with the advantages of long‐wave emission relative to the parent pyrene, high fluorescence quantum yields, and the ability to form excimers. Herein, the synthesis of six (phenylethynyl)pyrene‐functionalized locked nucleic acid (LNA) monomers M1–M6 and their incorporation into DNA oligomers is described. Multilabeled duplexes display higher thermal stabilities than singly modified analogues. An increase in the number of phenylethynyl substituents attached to the pyrene results in decreased binding affinity towards complementary DNA and RNA and remarkable bathochromic shifts of absorption/emission maxima relative to the parent pyrene fluorochrome. This bathochromic shift leads to the bright fluorescence colors of the probes, which differ drastically from the blue emission of unsubstituted pyrene. The formation of intra‐ and interstrand excimers was observed for duplexes that have monomers M1–M6 in both complementary strands and in numerous single‐stranded probes. If more phenylethynyl groups are inserted, the detected excimer signals become more intense. In addition, (phenylethynyl)pyrenecarbonyl–LNA monomers M4, M5, and M6 proved highly useful for the detection of single mismatches in DNA/RNA targets.",
author = "Irina Astakhova and Korshun, {Vladimir A.} and Jesper Wengel",
year = "2008",
doi = "10.1002/chem.200801077",
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Highly fluorescent conjugated pyrenes in nucleic acid probes: (Phenylethynyl)pyrenecarbonyl-functionalized locked nucleic acids. / Astakhova, Irina; Korshun, Vladimir A.; Wengel, Jesper.

I: Chemistry: A European Journal, Bind 14, Nr. 35, 2008, s. 11010-11026.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Highly fluorescent conjugated pyrenes in nucleic acid probes: (Phenylethynyl)pyrenecarbonyl-functionalized locked nucleic acids

AU - Astakhova, Irina

AU - Korshun, Vladimir A.

AU - Wengel, Jesper

PY - 2008

Y1 - 2008

N2 - In recent years, fluorescently labeled oligonucleotides have become a widely used tool in diagnostics, DNA sequencing, and nanotechnology. The recently developed (phenylethynyl)pyrenes are attractive dyes for nucleic acid labeling, with the advantages of long‐wave emission relative to the parent pyrene, high fluorescence quantum yields, and the ability to form excimers. Herein, the synthesis of six (phenylethynyl)pyrene‐functionalized locked nucleic acid (LNA) monomers M1–M6 and their incorporation into DNA oligomers is described. Multilabeled duplexes display higher thermal stabilities than singly modified analogues. An increase in the number of phenylethynyl substituents attached to the pyrene results in decreased binding affinity towards complementary DNA and RNA and remarkable bathochromic shifts of absorption/emission maxima relative to the parent pyrene fluorochrome. This bathochromic shift leads to the bright fluorescence colors of the probes, which differ drastically from the blue emission of unsubstituted pyrene. The formation of intra‐ and interstrand excimers was observed for duplexes that have monomers M1–M6 in both complementary strands and in numerous single‐stranded probes. If more phenylethynyl groups are inserted, the detected excimer signals become more intense. In addition, (phenylethynyl)pyrenecarbonyl–LNA monomers M4, M5, and M6 proved highly useful for the detection of single mismatches in DNA/RNA targets.

AB - In recent years, fluorescently labeled oligonucleotides have become a widely used tool in diagnostics, DNA sequencing, and nanotechnology. The recently developed (phenylethynyl)pyrenes are attractive dyes for nucleic acid labeling, with the advantages of long‐wave emission relative to the parent pyrene, high fluorescence quantum yields, and the ability to form excimers. Herein, the synthesis of six (phenylethynyl)pyrene‐functionalized locked nucleic acid (LNA) monomers M1–M6 and their incorporation into DNA oligomers is described. Multilabeled duplexes display higher thermal stabilities than singly modified analogues. An increase in the number of phenylethynyl substituents attached to the pyrene results in decreased binding affinity towards complementary DNA and RNA and remarkable bathochromic shifts of absorption/emission maxima relative to the parent pyrene fluorochrome. This bathochromic shift leads to the bright fluorescence colors of the probes, which differ drastically from the blue emission of unsubstituted pyrene. The formation of intra‐ and interstrand excimers was observed for duplexes that have monomers M1–M6 in both complementary strands and in numerous single‐stranded probes. If more phenylethynyl groups are inserted, the detected excimer signals become more intense. In addition, (phenylethynyl)pyrenecarbonyl–LNA monomers M4, M5, and M6 proved highly useful for the detection of single mismatches in DNA/RNA targets.

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DO - 10.1002/chem.200801077

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JO - Chemistry: A European Journal

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