Anthracene–DNA conjugates as building blocks of designed DNA structures constructed by photochemical reactions

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

doi:10.1039/b821869b

Cited by 34 publications

(25 citation statements)

References 38 publications

(2 reference statements)

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“…To construct the system for artificial (non-enzymatic or chemical) splicing of DNA, we can choose appropriate clipping reactions from many bioorthogonal chemistries including click reactions 48,49 and photochemical reactions 37,[44][45][46]50 . The techniques could be applied for signal amplification in bioanalyses through DNA circuits based on autonomous succession of strand exchange 26,51 .…”

Section: Discussionmentioning

confidence: 99%

Metal ion-directed dynamic splicing of DNA through global conformational change by intramolecular complexation

et al. 2015

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Chemically engineered DNAs-in which global conformation can be modulated in response to specific stimuli-could be allosteric functional DNAs themselves or work as a modulator of the functional nucleic acids such as DNAzymes and aptamers. Here, we show that two terpyridines built in the DNA backbone form a stable intramolecular 1:2 complex, [M(terpy) 2 ] 2 þ , with divalent transition metal ions. Upon complexation, the DNA conjugates adopt a O-shape structure, in which two distal sequences located outside the terpyridines connect with each other to form a continuous segment with a specific structure or sequence. Such a DNA structure is globally controlled by local metal complexation events that can be rationally designed based on general coordination chemistry. This method is regarded as metal ion-directed dynamic sequence edition or DNA splicing. DNAzymes with peroxidaselike activity can thus be regulated by several transition metal ions through sequence edition techniques based on the O-motif.

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Section: Discussionmentioning

confidence: 99%

Metal ion-directed dynamic splicing of DNA through global conformational change by intramolecular complexation

et al. 2015

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“…This strategy will also provide new tools for photocrosslinking and photoligation that will be used in biotechnology. [19][20][21][22][23][24][25][26] …”

Section: Introductionmentioning

confidence: 99%

Efficiency of [2 + 2] photodimerization of various stilbene derivatives within the DNA duplex scaffold

2015

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A DNA duplex was used as a scaffold to evaluate the intrinsic reactivity of [2 + 2] photodimerization between stilbene derivatives; the duplex pre-organizes the substrates avoiding the need for an association step. Unmodified stilbenes were first introduced at base-pairing positions on complementary DNA strands. The duplex was then irradiated with 340 nm UV light. HPLC analyses revealed that [2 + 2] photodimerization proceeded rapidly without side reactions. Thus, it was confirmed that the DNA duplex could be used as an ideal scaffold for [2 + 2] photodimerization of stilbenes. Next, we examined homo-photodimerization abilities of various stilbene derivatives. Homo-photodimerization of p-cyanostilbene, p-methylstilbazolium, and p-stilbazole occurred efficiently, whereas homo-photodimerization of p-dimethylaminostilbene and p-nitrostilbene did not proceed at all, probably because the reaction was quenched by dimethylamino and nitro groups. Time-dependent density functional theory calculations revealed that excitation energy was correlated with quantum yield. We further investigated hetero-photodimerization. These reactions were made possible by the use of two complementary oligodeoxyribonucleotides tethering different stilbene derivatives. Reactivities in hetero-photodimerization were highly dependent on the combination of derivatives. A high correlation was observed between the quantum yields and energy gaps of HOMO and LUMO between reactive derivatives. Unexpectedly, nitrostilbene, which was non-reactive in homo-photodimerization, cross-reacted with p-methylstilbazolium and p-stilbazole, both of which had close HOMO or LUMO with nitrostilbene. Evaluation of the intrinsic reactivity of homo- and hetero-photodimerization of stilbene derivatives was made possible by the use of DNA as a scaffold.

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“…An anthroquinone-containing nucleotide has also been incorporated into DNA to facilitate the study of duplexes by electrochemical DNA methods (M. F. . Knowledge of the photochemistry of anthracene has enabled the templated synthesis of a bespoke DNA structure (Mukae et al, 2009). A carefully designed system enabled two DNA-conjugated anthracene units to be in sufficiently close proximity that a light-induced dimerisation reaction could occur.…”

Section: The Chemical Biology Of Nucleic Acidsmentioning

confidence: 99%

Chemical Biology: What is Its Role in Drug Discovery?

Pirrie¹,

Westwood²

2011

Drug Discovery and Development - Present and Future

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Anthracene–DNA conjugates as building blocks of designed DNA structures constructed by photochemical reactions

Cited by 34 publications

References 38 publications

Metal ion-directed dynamic splicing of DNA through global conformational change by intramolecular complexation

Metal ion-directed dynamic splicing of DNA through global conformational change by intramolecular complexation

Efficiency of [2 + 2] photodimerization of various stilbene derivatives within the DNA duplex scaffold

Chemical Biology: What is Its Role in Drug Discovery?

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