Photodimerisation of anthracenes using a DNA template and its analytical applications

Mukae, Motoko; Ihara, Toshihiro; Tabara, Miyuki; Arslan, Pelin; Jyo, Akinori

doi:10.1080/10610270802516625

Cited by 11 publications

(4 citation statements)

References 13 publications

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“…Photochemical, templated reactions are especially well suited for detection of nucleic acids in live cells, since they do not require any additives and the light dose and the illumination area can be easily controlled allowing spatial and temporal control of the reactions. Though UV-light-induced, templated, photochemical processes are most common, − their application in live cells and in vivo is problematic, since UV-light induces nucleobase transformations in the genomic DNA and activates intracellular photosensitizers, e.g., flavonoids . To avoid the damage of biomolecules, application of visible light in place of UV-light is desirable.…”

Section: Introductionmentioning

confidence: 99%

Fluorogenic, Catalytic, Photochemical Reaction for Amplified Detection of Nucleic Acids

2013

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Photochemical, nucleic acid-induced reactions, which are controlled by nontoxic red light, are well-suited for detection of nucleic acids in live cells, since they do not require any additives and can be spatially and temporally regulated. We have recently described the first reaction of this type, in which a phenylselenyl derivative of thymidine (5'-PhSeT-ODNa) is cleaved in the presence of singlet oxygen (Fülöp, A., Peng, X., Greenberg, M. M., Mokhir, A. (2010) A nucleic acid directed, red light-induced chemical reaction. Chem. Commun. 46, 5659-5661). The latter reagent is produced upon exposure of a photosensitizer 3'-PS-ODNb (PS = Indium(III)-pyropheophorbide-a-chloride: InPPa) to >630 nm light. In 2012 we reported on a fluorogenic version of this reaction (Dutta, S., Flottmann, B., Heilemann, M., Mokhir, A. (2012) Hybridization and reaction-based, fluorogenic nucleic acid probes. Chem. Commun. 47, 9664-9666), which is potentially applicable for the detection of nucleic acids in cells. Unfortunately, its yield does not exceed 25% and no catalytic turnover could be observed in the presence of substrate excess. This problem occurs due to the efficient, competing oxidation of the substrate containing an electron rich carbon-carbon double bonds (SCH═CHS) in the presence of singlet oxygen with formation of a noncleavable product (SCH═CHSO). Herein we describe a related, but substantially improved photochemical, catalytic transformation of a fluorogenic, organic substrate, which consists of 9,10-dialkoxyanthracene linked to fluorescein, with formation of a bright fluorescent dye. In highly dilute solution this reaction occurs only in the presence of a nucleic acid template. We developed three types of such a reaction and demonstrated that they are high yielding and generate over 7.7 catalytic turnovers, are sensitive to single mismatches in nucleic acid targets, and can be applied for determination of both the amount of nucleic acids and potentially their localization.

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Section: Introductionmentioning

confidence: 99%

Fluorogenic, Catalytic, Photochemical Reaction for Amplified Detection of Nucleic Acids

2013

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“…Using 10 cycles of irradiation and denaturation, a five-fold amplification was achieved, whereas no amplification was observed in the absence of thermal cycling. [85] The fast kinetics coupled to the potential amplification makes these methods an interesting alternative to enzymatic ligation strategies, in which efficiency can vary substantially. [86]…”

Section: Reactions Templated By Nucleic Acidsmentioning

confidence: 99%

Reactions Templated by Nucleic Acids: More Ways to Translate Oligonucleotide‐Based Instructions into Emerging Function

2013

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The programmability of oligonucleotide recognition offers an attractive platform to direct the assembly of reactive partners that can engage in chemical reactions. Recently, significant progress has been made in both the breadth of chemical transformations and in the functional output of the reaction. Herein we summarize these recent progresses and illustrate their applications to translate oligonucleotide instructions into functional materials and novel architectures (conductive polymers, nanopatterns, novel oligonucleotide junctions); into fluorescent or bioactive molecule using cellular RNA; to interrogate secondary structures or oligonucelic acids; or a synthetic oligomer.

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“…Die Templatreaktion läuft nach Bestrahlung 1 min lang nahezu vollständig ab, womit sie sich gut für eine schnelle Kreislaufführung eignet. Nach 10 Zyklen Bestrahlung und Denaturierung wurde eine fünffache Amplifizierung erreicht, während ohne Temperaturzyklen keine Vervielfältigung stattfand 85. Die schnelle Kinetik in Kombination mit der möglichen Amplifizierung macht diese Methode zu einer interessanten Alternative für enzymatische Ligationsstrategien, deren Effizienz erheblich schwanken kann 86…”

Section: Templat‐gestützte Strangligationunclassified

Reaktionen an Nucleinsäuretemplaten: mehr Methoden zur Übersetzung Oligonucleotid‐basierter Informationen in neue Funktionen

Górska

Winssinger

2013

Angewandte Chemie

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Die Programmierbarkeit der Oligonucleotid‐Erkennung bietet eine vielversprechende Plattform, um die Anordnung von Reaktanten zu steuern. Sowohl bei der Bandbreite chemischer Umwandlungen als auch beim funktionalen Ergebnis der Reaktion wurden kürzlich erhebliche Fortschritte erzielt. Hier fassen wir diese jüngsten Fortschritte zusammen und erläutern ihre Anwendungen, z. B. die Übersetzung von Oligonucleotid‐Informationen in Funktionsmaterialien und neuartige Architekturen (leitende Polymere, Nanomuster, neuartige Oligonucleotid‐Kreuzungen) oder – mithilfe zellulärer RNA – in fluoreszierende oder bioaktive Moleküle; zur Untersuchung von Sekundärstrukturen oder Oligonucleinsäuren; sowie in ein synthetisches Oligomer.

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Photodimerisation of anthracenes using a DNA template and its analytical applications

Cited by 11 publications

References 13 publications

Fluorogenic, Catalytic, Photochemical Reaction for Amplified Detection of Nucleic Acids

Fluorogenic, Catalytic, Photochemical Reaction for Amplified Detection of Nucleic Acids

Reactions Templated by Nucleic Acids: More Ways to Translate Oligonucleotide‐Based Instructions into Emerging Function

Reaktionen an Nucleinsäuretemplaten: mehr Methoden zur Übersetzung Oligonucleotid‐basierter Informationen in neue Funktionen

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