Synthesis and photophysical properties of novel cyclonucleosides—substituent effects on fluorescence emission

O’Mahony, Gavin; Ehrman, Eleonor; Grøtli, Morten

doi:10.1016/j.tet.2008.05.098

Cited by 19 publications

(11 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…19,77,78 While the 8-azido- arabino -adenosine 2 has no fluorescence, the click adduct 7 with triazole ring attached directly to the imidazolyl ring of purine via a nitrogen atom emits at 300–500 nm with the maximum emission at 376 nm (Φ em = 0.6%, B = 0.13 M −1 cm −1 ). Similarly, 5-azidouridine 21 exhibits no noticeable fluorescence, whereas the triazole product 23 shows moderate emission between 285 nm and 550 nm with two emission peaks at 320 nm and 450 nm (Φ em = 1.1%, B = 0.12 M −1 cm −1 ).…”

Section: Resultsmentioning

confidence: 99%

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Zayas¹,

Annoual²,

Das³

et al. 2015

Bioconjugate Chem.

View full text Add to dashboard Cite

Strain-promoted click chemistry of nucleosides and nucleotides with an azido group directly attached to the purine and pyrimidine rings with various cyclooctynes in aqueous solution at ambient temperature resulted in efficient formation (3 min - 3 h) of fluorescent, light-up, triazole products. The 2- and 8-azidoadenine nucleosides reacted with fused cyclopropyl cyclooctyne, dibenzylcyclooctyne or monofluorocyclooctyne to produce click products functionalized with hydroxyl, amino, N-hydroxysuccinimide, or biotin moieties. The 5-azidouridine and 5-azido-2′-deoxyuridine were similarly converted to the analogous triazole products in quantitative yields in less than 5 minutes. The 8-azido-ATP quantitatively afforded the triazole product with fused cyclopropyl cyclooctyne in aqueous acetonitrile (3 h). The novel triazole adducts at the 2 or 8 position of adenine or 5-position of uracil rings induce fluorescence properties which were used for direct imaging in MCF-7 cancer cells without the need for traditional fluorogenic reporters. FLIM of the triazole click adducts demonstrated their potential utility for dynamic measuring and tracking of signaling events inside single living cancer cells.

show abstract

Section: Resultsmentioning

confidence: 99%

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Zayas¹,

Annoual²,

Das³

et al. 2015

Bioconjugate Chem.

View full text Add to dashboard Cite

show abstract

“…They possessed useful fluorescent properties (Table 10). [49] www.eurjoc.org Table 10. Photophysical characterization of compounds 106, with the 1,2,3-triazole moiety between the purine base and the ribose.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

2015

View full text Add to dashboard Cite

Azolylpurines and azolylpurine nucleosides have important medicinal and biological applications. They are used as adenosine receptor agonists and antagonists and also as antivirals. Several compounds of this class exhibit fluorescent properties that can be applied in biological chemistry. This review summarizes and classifies all reported classes of purine‐azole conjugates, strategies for their syntheses, and suggestions of compound classes yet to be synthesized. Synthetic methodologies directed towards purine–azole conjugates, including SNAr reactions, cyclizations of amino‐ or hydrazinylpurines, and transition‐metal‐catalyzed cross‐coupling reactions, are discussed, as well as the use of selected azolylpurine derivatives as synthetic intermediates.

show abstract

“…O'Mahony et al performed a Sonogashira coupling reaction to introduce a substituted alkyne at the C-8 position of adenine derivatives 34 [20]. This step was promoted by microwave irradiation in 12 min to afford the expected analogs 35 from 34 to 88% yield.…”

Section: Sonogashira Reactionmentioning

confidence: 99%

Development of nucleoside analogs under microwave irradiation

Niemiec

Bessières

Roy

et al. 2014

Microwaves in Drug Discovery and Development: Recent Advances

View full text Add to dashboard Cite

Synthesis and photophysical properties of novel cyclonucleosides—substituent effects on fluorescence emission

Cited by 19 publications

References 15 publications

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging

Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

Development of nucleoside analogs under microwave irradiation

Contact Info

Product

Resources

About