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• W2322862564 abstract "To expand the arsenal of fluorescent cytidine analogues for the detection of genetic material, we synthesized para-substituted phenyl-imidazolo-cytidine (PhImC) analogues 5a–g and established a relationship between their structure and fluorescence properties. These analogues were more emissive than cytidine (λem 398–420 nm, Φ 0.009–0.687), and excellent correlation was found between Φ of 5a–g and σp– of the substituent on the phenyl-imidazolo moiety (R2 = 0.94). Calculations suggested that the dominant tautomer of PhImC in methanol solution is identical to that of cytidine. DFT calculations of the stable tautomer of selected PhImC analogues suggested a relationship between the HOMO–LUMO gap and Φ and explained the loss of fluorescence in the nitro analogue. Incorporation of the CF3-PhImdC analogue into a DNA probe resulted in 6-fold fluorescence quenching of the former. A 17-fold reduction of fluorescence was observed for the G-matched duplex vs ODN(CF3-PhImdC), while for A-mismatched duplex, only a 2-fold decrease was observed. Furthermore, since the quantum yield of ODN(CF3-PhImdC):ODN(G) was reduced 17-fold vs that of a single strand, whereas that of ODN(CF3-PhImdC):ORN(G) was reduced only 3.8-fold, ODN(CF3-PhImdC) appears to be a DNA-selective probe. We conclude that the ODN(CF3-PhImdC) probe, exhibiting emission sensitivity upon single nucleotide replacement, may be potentially useful for DNA single nucleotide polymorphism (SNP) typing." @default.
• W2322862564 created "2016-06-24" @default.
• W2322862564 creator A5022009203 @default.
• W2322862564 creator A5073414709 @default.
• W2322862564 creator A5079440580 @default.
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• W2322862564 date "2014-07-14" @default.
• W2322862564 modified "2023-09-27" @default.
• W2322862564 title "Phenyl-imidazolo-cytidine Analogues: Structure–Photophysical Activity Relationship and Ability To Detect Single DNA Mismatch" @default.
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• W2322862564 doi "https://doi.org/10.1021/jo5011944" @default.
• W2322862564 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24992467" @default.
• W2322862564 hasPublicationYear "2014" @default.
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