Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties

Namba, Kosuke; Osawa, Ayumi; Nakayama, Akira; Mera, Akane; Tano, Fumi; Chuman, Yoshiro; Sakuda, Eri; Taketsugu, Tetsuya; Sakaguchi, Kazuyasu; Kitamura, Noboru; Tanino, Keiji

doi:10.1039/c4sc02780a

Cited by 33 publications

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“…To apply a fluorescent probe to cell biological applications, the fluorescent compound should be water soluble and small for cellular uptake and emit high fluorescence in an aqueous solvent. We have previously designed and synthesized fluorescent 1,3a,6a-triazapentalene derivatives ( Fig 1a ) that have a wide range of emission wavelengths [ 14 – 16 ]. Unlike other fluorescent probes with a relatively large molecular size, 1,3a,6a-triazapentalenes have a unique compact skeleton with a 10π-electron system and highly fluorescent chromophore.…”

Section: Resultsmentioning

confidence: 99%

Effective Cellular Morphology Analysis for Differentiation Processes by a Fluorescent 1,3a,6a-Triazapentalene Derivative Probe in Live Cells

et al. 2016

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Nuclear and cytoplasmic morphological changes provide important information about cell differentiation processes, cell functions, and signal responses. There is a strong desire to develop a rapid and simple method for visualizing cytoplasmic and nuclear morphology. Here, we developed a novel and rapid method for probing cellular morphological changes of live cell differentiation process by a fluorescent probe, TAP-4PH, a 1,3a,6a-triazapentalene derivative. TAP-4PH showed high fluorescence in cytoplasmic area, and visualized cytoplasmic and nuclear morphological changes of live cells during differentiation. We demonstrated that TAP-4PH visualized dendritic axon and spine formation in neuronal differentiation, and nuclear structural changes during neutrophilic differentiation. We also showed that the utility of TAP-4PH for visualization of cytoplasmic and nuclear morphologies of various type of live cells. Our visualizing method has no toxicity and no influence on the cellular differentiation and function. The cell morphology can be rapidly observed after addition of TAP-4PH and can continue to be observed in the presence of TAP-4PH in cell culture medium. Moreover, TAP-4PH can be easily removed after observation by washing for subsequent biological assay. Taken together, these results demonstrate that our visualization method is a powerful tool to probe differentiation processes before subsequent biological assay in live cells.

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Section: Resultsmentioning

confidence: 99%

Effective Cellular Morphology Analysis for Differentiation Processes by a Fluorescent 1,3a,6a-Triazapentalene Derivative Probe in Live Cells

et al. 2016

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“…18,19 To study the impact of the TAP substituents on spectroscopic properties, the development of specific synthetic pathways was required. [20][21][22][23][24][25][26] Although some improvements of this highly promising TAP scaffold were observed, further investigations towards fused ring chemical entities have not been considered so far as benzotriazapentalene 1 as a fused ring system were already reported as non-fluorescent ( Figure 1b). 17 Herein, we report the design, the synthesis, the fluorescent properties and the cellular imaging compatibility of a novel class of small nitrogen-containing tricyclic frameworks.…”

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An original class of small sized molecules as versatile fluorescent probes for cellular imaging

et al. 2019

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“…In particular, although a few 2,4-disubstituted-triazapentalenes have already been prepared in previous studies (vide infra), 23,25) the effect of a 4-substituent on fluorescence properties has not been investigated in detail. Therefore, we herein report the changes in fluorescence properties of 1,3a,6a-triazapentalenes by the introduction of a 4-substituent (Fig.…”

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“…On the basis of this effect, the fluorescence wavelength of 1,3a,6a-triazapentalenes has recently been extended to the red color region, and their molecules are smaller than the conventional yellow and red fluorescent molecules. 25) The yellow derivatives were proven to be useful fluorescent labeling reagents. On the other hand, the introduction of an electron-donating substituent at the C5-position substantially increased the fluorescence intensity, whereas the fluorescence wavelength remained nearly unaffected.…”

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“…Although two 4-phenyl-1,3a,6a-triazapentalene derivatives were previously reported, 25) further 4-phenyl analogs were synthesized and investigated to ensure the generality and trend of the substituent effect of the 4-phenyl group on fluorescence properties ( Table 3). The click reaction of 2b with 3a afforded 4-phenyl-2-(4-cyanophenyl)-1,3a,6a-triazapentalene 4j in 70% yield (entry 1).…”

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Substituent Effect at the C4-Position of 1,3a,6a-Triazapentalene

Nakayama

Nishio

Otani

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Various 2,4-disubstituted-1,3a,6a-triazapentalenes possessing methyl and phenyl groups at the C4-position were synthesized. Fluorescence observation of the synthetic 4-methyl-and 4-phenyl-1,3a,6a-triazapentalenes revealed that the introduction of a substituent at the C4-position allowed a long-wavelength shift of the fluorescence maximum. Furthermore, the phenyl group at the C4-position was found to induce a substantial increase in the extinction coefficient value.Key words 1,3a,6a-triazapentalene; substituent effect; longer-wavelength shift; 4-methyl-1,3a,6a-triazapentalene; 4-phenyl-1,3a,6a-triazapentalene Fluorescent organic molecules are an important class of compounds in modern science and technology, and are widely used in biological imaging probes, sensors, lasers, and lightemitting devices.1-3) Thus, the development of useful fluorescent organic molecules is crucial for the advancement of many industries, and has been a subject of intensive research. [4][5][6][7][8][9][10][11][12][13][14][15] In particular, fluorescent organic molecules have received a great deal of attention in a pharmacology field, because the visualization of biologically active small compounds by introducing fluorophores is one of the most useful methods in mechanistic studies. [16][17][18][19][20][21][22] However, the introductions of fluorescent organic molecules sometimes induces a loss of biological activities because the physical properties of fluorescent molecules affect the biological activities of the original compound. Furthermore, highly fluorescent organic molecules are usually larger than small biologically active compounds, and the fluorescent labeling reagent disturbs the original interactions of the parent compounds with target proteins such as receptors. To overcome these problems, there is strong demand for the development of small fluorophores. We recently discovered that 1,3a,6a-triazapentalene 1 is a compact and highly fluorescent chromophore 23) (Fig. 1). Since the disclosure of the fluorescence properties of 1,3a,6a-triazapentalenes, the 1,3a,6a-triazapentalene system has attracted a great deal of interest as a novel fluorophores, and another group has also reported the alternative synthesis of 1,3a,6a-triazapentalenes.24) 1,3a,6a-Triazapentalenes exhibit various useful fluorescence properties such as intense fluorescence, a large Stokes shift, and a positive fluorescence solvatochromism. More interestingly, the fluorescence wavelengths of 1,3a,6a-triazapentalenes vary widely with 2-substituents. For example, the fluorescence maxima shifts to longer wavelengths as the inductive effect of the 2-substituents increases. On the basis of this effect, the fluorescence wavelength of 1,3a,6a-triazapentalenes has recently been extended to the red color region, and their molecules are smaller than the conventional yellow and red fluorescent molecules.25) The yellow derivatives were proven to be useful fluorescent labeling reagents. On the other hand, the introduction of an electron-donating substituent at the C5-position ...

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Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties

Abstract: To expand the function of the fluorescent 1,3a,6a-triazapentalenes as labelling reagents, their fluorescence wavelength was extended to the red color region.

Cited by 33 publications

References 59 publications

Effective Cellular Morphology Analysis for Differentiation Processes by a Fluorescent 1,3a,6a-Triazapentalene Derivative Probe in Live Cells

Effective Cellular Morphology Analysis for Differentiation Processes by a Fluorescent 1,3a,6a-Triazapentalene Derivative Probe in Live Cells

An original class of small sized molecules as versatile fluorescent probes for cellular imaging

Substituent Effect at the C4-Position of 1,3a,6a-Triazapentalene

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