ArticleChemphyschem : a European journal of chemical physics and physical chemistry2012
Modified 6-aza uridines: highly emissive pH-sensitive fluorescent nucleosides.
Article in Chemphyschem : a European journal of chemical physics and physical chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 37 citations in OpenAlex.
- Isomorphic Fluorescent Nucleosides.Accounts of chemical research · 2024Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Pentacyclic adenine: a versatile and exceptionally bright fluorescent DNA base analogue.Chemical science · 2018Article
- Enzymatic incorporation and utilization of an emissive 6-azauridine.Organic & biomolecular chemistry · 2017Article
- Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions.Chemical science · 2016Article
- Chromophoric Nucleoside Analogues: Synthesis and Characterization of 6-Aminouracil-Based Nucleodyes.The Journal of organic chemistry · 2016Article
- Visibly emissive and responsive extended 6-aza-uridines.Organic letters · 2014Article
- Two-photon-induced fluorescence of isomorphic nucleobase analogs.Chemphyschem : a European journal of chemical physics and physical chemistry · 2014Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Optimized facile syntheses and highly desirable spectroscopic properties of two isomorphic fluorescent pyrimidines, comprising a 1,2,4-triazine motif conjugated to a thiophene (1 a) or a furan (1 b), are described. Although structurally related to their 5-modified uridine counterparts, these modified 6-aza-uridines reveal dramatically improved fluorescence properties and a remarkable sensitivity to polarity and pH changes. The thiophene derivative 1 a has an absorption maximum around 335 nm, which upon excitation yields visible emission with a polarity-sensitive maximum and fluorescence quantum yield ranging from 415 nm (Φ=0.8) to 455 nm (Φ=0.2) in dioxane and water, respectively. Nucleoside 1 a also displays susceptibility to acidity. Correlating emission intensity and solution pH yields a pK(a) value of 6.7-6.9, reasonably close to physiological pH values. The results illustrate that highly sought-after fluorescence features (brightness and responsiveness) are not necessarily the trait of large fluorophores alone, but can be observed with probes that meet stringent isomorphic design criteria.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.