ArticleTetrahedron2007
Furan Decorated Nucleoside Analogues as Fluorescent Probes: synthesis, photophysical evaluation and site-specific incorporation.
Article in Tetrahedron, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
31 citing papers in PubMed, 125 citations in OpenAlex.
- Increased brightness of fluorescent uridine, qU, inside single- and double-stranded RNA.Scientific reports · 2026Article
- Furan Dissociation Induced by Collisions with HMolecules (Basel, Switzerland) · 2025Article
- Microwave-assisted synthesis of base-modified fluorescent 1,4-dihydropyridine nucleosides: photophysical characterization and insights.RSC advances · 2024Article
- Isomorphic Fluorescent Nucleosides.Accounts of chemical research · 2024Article
- Caging of a Strongly Pairing Fluorescent Thymidine Analog with Soft Nucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- 8-Furylimidazolo-2'-deoxycytidine: crystal structure, packing, atropisomerism and fluorescence.Acta crystallographica. Section C, Structural chemistry · 2022Article
- 7-Iodo-5-aza-7-deazaguanine ribonucleoside: crystal structure, physical properties, base-pair stability and functionalization.Acta crystallographica. Section C, Structural chemistry · 2020Article
- Fluorescent Biaryl Uracils with C5-Dihydro- and Quinazolinone Heterocyclic Appendages in PNA.Molecules (Basel, Switzerland) · 2020Article
- A Novel NAD-RNA Decapping Pathway Discovered by Synthetic Light-Up NAD-RNAs.Biomolecules · 2020Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines.Beilstein journal of organic chemistry · 2019Article
- Fluorescent nucleobases as tools for studying DNA and RNA.Nature chemistry · 2017Review
- Crystal structure of 5-(dibenzo-furan-4-yl)-2'-deoxy-uridine.Acta crystallographica. Section E, Crystallographic communications · 2017Article
- Excitation-dependent fluorescence from atomic/molecular layer deposited sodium-uracil thin films.Scientific reports · 2017Article
- Enzymatic incorporation and utilization of an emissive 6-azauridine.Organic & biomolecular chemistry · 2017Article
- Stimuli Responsive Furan and Thiophene Substituted Difluoroboron β-Diketonate Materials.Materials chemistry frontiers · 2017Article
- Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions.Chemical science · 2016Article
- Discovery of New Acid Ceramidase-Targeted Acyclic 5-Alkynyl and 5-Heteroaryl Uracil Nucleosides.ACS medicinal chemistry letters · 2015Article
- New class of 8-aryl-7-deazaguanine cell permeable fluorescent probes.Bioorganic & medicinal chemistry letters · 2015Article
- Versatile synthesis and biological evaluation of novel 3'-fluorinated purine nucleosides.Beilstein journal of organic chemistry · 2015Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis and photophysical evaluation of modified nucleoside analogues in which a five-membered heterocycle (furan, thiophene, oxazole and thiazole) is attached to the 5 position of 2'-deoxyuridine are reported. The furan containing derivative is identified as the most promising responsive nucleoside of this family due to its emission quantum efficiency and degree of sensitivity to its microenvironment. The furan moiety was then attached to the 5 position of 2'-deoxycytidine as well as the 8 position of adenosine and guanosine. Photophysical evaluation of these four furan containing nucleoside analogues reveal distinct differences in the absorption, emission and quantum efficiency depending upon the class of nucleoside (pyrimidine or purine). Comparing the photophysical properties of all furan containing nucleosides, identifies the furan thymidine analogue, 5-(fur-2-yl)-2'-deoxyuridine, as the best candidate for use as a responsive fluorescent probe in nucleic acids. 5-(fur-2-yl)-2'-deoxyuridine was then converted to the corresponding phosphoramidite and site specifically incorporated into DNA oligonucleotides with greater than 88% coupling efficiency. Such furan-modified oligonucleotides form stable duplexes upon hybridization to their complementary DNA strands and display favorable fluorescent features.
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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.