Fluorescence switching of photochromic vinylpyrene-substituted 2′-deoxyguanosine

Saitō, Yoshio; Matsumoto, Katsuhiko; Takeuchi, Yoshiki; Bag, Subhendu Sekhar; Kodate, Satoshi; Morii, Takashi; Saito, Isao

doi:10.1016/j.tetlet.2009.01.029

Cited by 18 publications

(9 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8-Pyrenylvinyl deoxyguanosine, 8PV G, was chosen as the PCN for in vivo use because it can be isomerized by nontoxic UV-A light. 28,29 The details of 8PV G synthesis were previously reported. 28,29 8PV G was incorporated into the oligonucleotides shown in Table 1 using standard automated DNA synthesis protocols.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Moreover, since introducing PCNs into G-quadruplex increases its stability, we predicted that PCN-modified G-quadruplex indicates hyperstability and can effectively regulate transcription in reversible manner with light. 8-Pyrenylvinyl deoxyguanosine, 8PV G, was chosen as the PCN for in vivo use because it can be isomerized by nontoxic UV-A light. , The details of 8PV G synthesis were previously reported. , 8PV G was incorporated into the oligonucleotides shown in Table using standard automated DNA synthesis protocols.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Transcription Driven by Reversible Photocontrol of Hyperstable G-Quadruplexes

Ogasawara

2018

ACS Synth. Biol.

View full text Add to dashboard Cite

G-quadruplexes occur in promoter regions, 5′-untranslated regions of mRNA and telomeric regions, and they function as regulatory elements for various key biological events, such as transcription, translation, and telomere elongation. As the stability of G-quadruplexes dramatically impacts these biological processes, controlling G-quadruplex stability via external stimuli such as light enables regulation of important biological phenomena with high spatial and temporal resolution. Here, we report a method for reversible photoregulation of transcription by controlling the stability of Gquadruplexes via cis−trans photoisomerization of photochromic nucleobase (PCN). Transcription was effectively inhibited when the PCN-modified G-quadruplex was in a hyperstable state, whereas transcription activity recovered markedly when the G-quadruplex changed to an unstable state induced by trans to cis PCN photoisomerization. Moreover, a reversibly photoactivatable plasmid was constructed by introducing PCN-modified Gquadruplexes downstream of the cytomegalovirus promoter of the pCS2 plasmid, which was used to demonstrate photoregulation of gene expression in zebrafish embryos.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Transcription Driven by Reversible Photocontrol of Hyperstable G-Quadruplexes

Ogasawara

2018

ACS Synth. Biol.

View full text Add to dashboard Cite

show abstract

“…Derivatives of 8-vinyl guanosine, including 8-(2-phenylethenyl)-2′-deoxyguanosine ( 3 ), were recently reported to be cis–trans photoisomerizable switches capable of influencing DNA conformation ( 39 , 42–44 ) Nucleoside 3 photoisomerizes upon irradiation at 370 nm to reach a photostationary E:Z ratio of 6:94, while irradiation at 254 nm caused the reverse photoisomerization and reached a E:Z ratio of 80:20. According to HPLC and NMR analysis, we were able to reproduce these results with nucleoside 3 in our laboratory ( 42 ).…”

Section: Resultsmentioning

confidence: 99%

Highly fluorescent guanosine mimics for folding and energy transfer studies

Dumas

Luedtke

2011

Nucleic Acids Research

View full text Add to dashboard Cite

Guanosines with substituents at the 8-position can provide useful fluorescent probes that effectively mimic guanine residues even in highly demanding model systems such as polymorphic G-quadruplexes and duplex DNA. Here, we report the synthesis and photophysical properties of a small family of 8-substituted-2′-deoxyguanosines that have been incorporated into the human telomeric repeat sequence using phosphoramidite chemistry. These include 8-(2-pyridyl)-2′-deoxyguanosine (2PyG), 8-(2-phenylethenyl)-2′-deoxyguanosine (StG) and 8-[2-(pyrid-4-yl)-ethenyl]-2′-deoxyguanosine (4PVG). On DNA folding and stability, 8-substituted guanosines can exhibit context-dependent effects but were better tolerated by G-quadruplex and duplex structures than pyrimidine mismatches. In contrast to previously reported fluorescent guanine analogs, 8-substituted guanosines exhibit similar or even higher quantum yields upon their incorporation into nucleic acids (Φ = 0.02–0.45). We have used these highly emissive probes to quantify energy transfer efficiencies from unmodified DNA nucleobases to 8-substituted guanosines. The resulting DNA-to-probe energy transfer efficiencies (ηt) are highly structure selective, with ηt(duplex) < ηt(single-strand) < ηt(G-quadruplex). These trends were independent of the exact structural features and thermal stabilities of the G-quadruplexes or duplexes containing them. The combination of efficient energy transfer, high probe quantum yield, and high molar extinction coefficient of the DNA provides a highly sensitive and reliable readout of G-quadruplex formation even in highly diluted sample solutions of 0.25 nM.

show abstract

“…Especially, various guanine/guanosine and adenine/adenosine derivatives bearing C 8 -sp 2 -carbon substituents have been prepared and studied as fluorescent/photosensitive [1][2][3][4][5] and electrochemical 6,7 marks in order to found a tool for the analysis of DNA or RNAs sequences. In addition, self-assebly of 8-aryl-2′-deoxyguanosine induced by the complexation of metal cations such as K + or Na + to dendrimers and oligomers was described 8 .…”

mentioning

confidence: 99%

“…The first experiments with 5 mole % Pd(PPh 3 ) 4 and PdCl 2 (PPh 3 ) 4 catalysts at ambient temperature, turned out to be a successful choice furnishing the desired substitution products 3a and 4a as a mixture of Z-and E-stereoisomers in high isolated yields (Table I, Entries 1,2). When Pd 2 dba 3 ·CHCl 3 was used, single (E)-alkenylpurine 4a has been obtained ( (Table I, Entry 5).…”

mentioning

confidence: 99%

Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines

Tobrmanová

Tobrman

Dvořák

2011

Collect. Czech. Chem. Commun.

View full text Add to dashboard Cite

Dedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.C 8 -Alkenylpurines were synthesized starting from purin-8-yl(allyl) acetates using Pdcatalyzed allylic substitution. The described protocol allows, by reaction of purin-8-yl(allyl) acetates with stabilized nucleophiles, an access to novel (E)-8-alkenylpurine derivatives under Pd 2 dba 3 ·CHCl 3 catalysis in dry THF in yields ranging from 31 to 76%. A wide range of nucleophiles showed exclusive E-alkene formation, however, ethyl nitroacetate gave mixture of E/Z-alkenes. On contrary, purin-2-yl(allyl) acetates reacted smoothly only with dimethyl malonate.

show abstract

Fluorescence switching of photochromic vinylpyrene-substituted 2′-deoxyguanosine

Cited by 18 publications

References 20 publications

Transcription Driven by Reversible Photocontrol of Hyperstable G-Quadruplexes

Transcription Driven by Reversible Photocontrol of Hyperstable G-Quadruplexes

Highly fluorescent guanosine mimics for folding and energy transfer studies

Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines

Contact Info

Product

Resources

About