pH-sensitive fluorescent deoxyuridines labeled with 2-aminofluorene derivatives

Lee, Ji Won; Son, Ye-Seul; Lee, Jung-Yean; Kim, Mi Hyun; Woo, Sang-Keun; Lee, Kyo Chul; Lee, Yong Jin; Hwang, Gil Tae

doi:10.1016/j.tet.2016.07.049

Cited by 7 publications

(6 citation statements)

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“…The suitability of BBDMAF as a starting material for cross-coupling reactions was evaluated against the Suzuki and Sonogashira couplings, and the desired products 2 and 3 were obtained in 50% and 66% yield, respectively ( Scheme 3 ) [ 21 , 22 ]. Therefore, it is assumed that BBDMAF can be employed in various cross-coupling reactions if the appropriate reaction conditions are used.…”

Section: Resultsmentioning

confidence: 99%

5-Bromo-4′,5′-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies

et al. 2018

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In this study, three new fluorescein derivatives—5-bromo-4′,5′-dinitrofluorescein (BDNF), 5-bromo-4′,5′-diaminofluorescein (BDAF), and 5-bromo-4′,5′-bis(dimethylamino)fluorescein (BBDMAF)—were synthesized and their pH-dependent protolytic equilibria were investigated. In particular, BBDMAF exhibited pH-dependent fluorescence, showing strong emission only at pH 3–6. BBDMAF bears a bromine moiety and thus, can be used in various cross-coupling reactions to prepare derivatives and take advantage of its unique emission properties. To confirm this, the Suzuki and Sonogashira reactions of BBDMAF with phenylboronic acid and phenylacetylene, respectively, were performed, and the desired products were successfully obtained.

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Section: Resultsmentioning

confidence: 99%

5-Bromo-4′,5′-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies

et al. 2018

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“…The 2'‐deoxyuridine derivative labeled with 2‐dimethylaminofluorene ( U DAF ) undergoes an increase in fluorescence, a result of inhibited photoinduced intramolecular charge transfer (ICT), when acidified (Figure S1) [9,10] . Therefore, we expected that incorporating a U DAF residue into the hTel sequence would not significantly affect the stability of its iM structure, but the fluorescence would increase upon iM formation.…”

Section: Figurementioning

confidence: 99%

“…We synthesized U DAF and its corresponding phosphoramidite according to reported protocols [9,10] . We then synthesized the four modified hTel iM DNA strands DNA( U 4 DAF ), DNA( U 10 DAF ), DNA( U 16 DAF ), and DNA( U 22 DAF ), in which a U DAF residue replaced the T 4 , T 10 , T 16 , and T 22 residues, respectively, of hTel iM (Figure 1).…”

Section: Figurementioning

confidence: 99%

“…Similar to the method for obtaining the values of pH T from the CD spectra, Figure S6 presents a plot of the change in the emission intensity of the modified hTel iM according to pH; the changes in fluorescence in the pH range 5.0–7.6 did not, however, result in a sigmoidal curve similar to that from the CD data. For reference, the value of p K a of the free nucleoside U DAF , measured from the emission intensities at pH 3.1–9.3, is 4.66 [9] . U DAF also exhibited an increase in fluorescence, a result of inhibition of ICT, upon decreasing the pH, but the fluorescence intensity changed more rapidly near the value of pH T when U DAF was included in the iM sequence (Figure S6).…”

Section: Figurementioning

confidence: 99%

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2‐Dimethylaminofluorene‐Labeled 2'‐Deoxyuridine as a Turn‐On Fluorescent Probe for i‐Motif DNA

Hong

Hwang

2021

ChemistrySelect

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i‐Motif (iM) DNA, a cytosine‐rich sequence having a four‐stranded structure, is believed to play an important role in regulating gene expression. In this study, we replaced each of the four thymidine units of the human telomeric iM sequence individually with a 2‐dimethylaminofluorene–substituted 2'‐deoxyuridine derivative (UDAF), then evaluated the formation of the iM structures with respect to pH through melting temperature measurements and circular dichroism, fluorescence, and UV‐Vis spectra. Introduction of the UDAF residue did not adversely affect the formation or stability of the iM structure; one of these strands functioned as an efficient fluorescent probe for iM formation.

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“…We synthesized 2′-deoxyuridine derivatives U AF and U DAF labeled with 2-aminofluorene and 2-dimethylaminofluorene, respectively ( Figure 17 c) [ 89 ]. The p K a values of U AF and U DAF were 4.27 and 4.66, respectively, and their fluorescence increased under acidic conditions.…”

Section: Microenvironment-sensitive Probesmentioning

confidence: 99%

Single-Labeled Oligonucleotides Showing Fluorescence Changes upon Hybridization with Target Nucleic Acids

Hwang

2018

Molecules

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Sequence-specific detection of nucleic acids has been intensively studied in the field of molecular diagnostics. In particular, the detection and analysis of single-nucleotide polymorphisms (SNPs) is crucial for the identification of disease-causing genes and diagnosis of diseases. Sequence-specific hybridization probes, such as molecular beacons bearing the fluorophore and quencher at both ends of the stem, have been developed to enable DNA mutation detection. Interestingly, DNA mutations can be detected using fluorescently labeled oligonucleotide probes with only one fluorophore. This review summarizes recent research on single-labeled oligonucleotide probes that exhibit fluorescence changes after encountering target nucleic acids, such as guanine-quenching probes, cyanine-containing probes, probes containing a fluorophore-labeled base, and microenvironment-sensitive probes.

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pH-sensitive fluorescent deoxyuridines labeled with 2-aminofluorene derivatives

Cited by 7 publications

References 40 publications

5-Bromo-4′,5′-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies

5-Bromo-4′,5′-bis(dimethylamino)fluorescein: Synthesis and Photophysical Studies

2‐Dimethylaminofluorene‐Labeled 2'‐Deoxyuridine as a Turn‐On Fluorescent Probe for i‐Motif DNA

Single-Labeled Oligonucleotides Showing Fluorescence Changes upon Hybridization with Target Nucleic Acids

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