Highly Activatable and Rapidly Releasable Caged Fluorescein Derivatives

Kobayashi, Tomonori; Urano, Yasuteru; Kamiya, Mako; Ueno, Takahiro; Kojima, Hirotatsu; Nagano, Tetsuo

doi:10.1021/ja070376d

Cited by 135 publications

(108 citation statements)

References 8 publications

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“…The absorption spectrum of 2a in neutral buffer reveals an intense band in the visible region for the heterocyclic chromophore [64]. Upon illumination at λ Ex of 490 nm, 2a changes its electronic configuration to populate S 1 .…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

“…This general design logic is extremely versatile and can easily be adapted to most of the main families of fluorescent probes with the aid of chemical synthesis. Indeed, photoactivatable acridinone [46], anthracene [47], benzofurazan [48], borondipyrromethene [49], chromone [50], coumarin [51][52][53][54][55][56], dihydrofuran [57][58][59], fluorescein [60][61][62][63][64][65][66][67], naphthalene [68], pyranine [69], pyrazolines [70], resorufin [71], rhodamine [66,[72][73][74][75][76], thioxanthone [77] and xanthone [78] derivatives have been developed on the basis of these operating principles. Furthermore, this general strategy has been adapted to activate also the luminescence of conjugated oligomers [79] and semiconductor quantum dots [80,81].…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

“…The behaviors of compounds 1a [57] and 2a [64] (Figure 4) are representative examples of the two main mechanisms for fluorescence photoactivation. The former has a photocleavable azide group attached to a dihydrofuran fluorophore.…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

“…The irreversible photolysis of the azide group of 1a and nitrobenzyl appendage of 2a releases an intact fluorescent fragment that can then emit upon excitation at an appropriate wavelength [57,64]. In some instances, however, the released fragment must associate with a supramolecular partner in order to discourage nonradiative decay and enable emission [67,68].…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

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Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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Photoactivatable fluorophores switch from a nonemissive to an emissive state upon illumination at an activating wavelength and then emit after irradiation at an exciting wavelength. The interplay of such activation and excitation events can be exploited to switch fluorescence on in a defined region of space at a given interval of time. In turn, the spatiotemporal control of fluorescence translates into the opportunity to implement imaging and spectroscopic schemes that are not possible with conventional fluorophores. Specifically, photoactivatable fluorophores permit the monitoring of dynamic processes in real time as well as the reconstruction of images with subdiffraction resolution. These promising applications can have a significant impact on the characterization of the structures and functions of biomolecular systems. As a result, strategies to implement mechanisms for fluorescence photoactivation with synthetic fluorophores are particularly valuable. In fact, a number of versatile operating principles have already been identified to activate the fluorescence of numerous members of the main families of synthetic dyes. These methods are based on either the irreversible cleavage of covalent bonds or the reversible opening and closing of rings. This paper overviews the fundamental mechanisms that govern the behavior of these photoresponsive systems, illustrates structural designs for fluorescence photoactivation, and provides representative examples of photoactivatable fluorophores in actions.

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Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

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Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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“…cis-and trans-APDOEGCG, and TokyoGreen (TG) were synthesized as described previously. [18][19][20] TG conjugation to (Ϯ)-cis-APDOEGCG was also described earlier, and the obtained EGCG-TG was purified by HPLC. 18) All other reagents used were of analytical grade.…”

mentioning

confidence: 99%

Anti-angiogenic Activity and Intracellular Distribution of Epigallocatechin-3-gallate Analogs

Piyaviriyakul

Shimizu

Asakawa

et al. 2011

Biological & Pharmaceutical Bulletin

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Tumor angiogenesis, a process of new blood vessel formation from pre-existing vessels, is crucial for the growth and development of tumors. It requires multiple interactions among endothelial cells, surrounding pericytes, and smooth muscle cells, extracellular matrix, and angiogenic cytokines/growth factors. [1][2][3] Since effective inhibition of tumor angiogenesis promises to provide crucial suppression of not only tumor growth but also tumor metastasis, the development of agents inhibiting angiogenic processes has become a matter of focus. (Ϫ)-Epigallocatechin-3-O-gallate (EGCG) is known as a major component of green tea extracts and to exhibit various biological activities including anti-viral, anti-microbial, and anti-oxidative ones. [4][5][6][7][8] Especially, the relationship between EGCG and anti-cancer activity is now the most notable, since cancer is the leading cause of human death in various countries. Previous studies demonstrated that EGCG suppresses tumor growth through the inhibition of tumor angiogenesis, and mechanistic studies on this anti-angiogenic effect of EGCG is now ongoing. Tang et al. demonstrated that EGCG inhibits vascular endothelial growth factor (VEGF)-induced Akt activation and VE-cadherin phosphorylation 9) ; and Rodriguez et al., that green tea catechin disrupts VEGF/VEGF receptor (VEGFR) complexes and subsequent signal transduction. 10) Also, Tachibana et al. directly identified the target molecule of EGCG as a 67-kDa laminin receptor by using surface plasmon resonance (SPR) assay, and they observed the suppression of tumor angiogenesis through the inhibition of the receptor-mediated signal transduction. 11,12) Our previous studies also demonstrated that EGCG suppresses tumor angiogenesis through the inhibition of membrane-type1 matrix metalloproteinase (MT1-MMP). 13,14) These findings indicate that EGCG, as a functional component of green tea, will become useful for cancer therapy and chemoprevention.Previous study demonstrated that 5,7-deoxyepigallocatechin gallate (DOEGCG), a synthetic EGCG derivative, possesses more potent anti-influenza infection activity than the original EGCG, suggesting that the phenolic hydroxyl groups on the A-ring in the flavan structure are not involved in the biological activity and that modification of A-ring of the EGCG structure does not abolish but rather enhances the functional ability of EGCG.15) Based on this and other structure-relationship studies, 16,17) we synthesized (Ϯ)-6-(5-aminopentyl)-5,7-deoxyepigallocatechin gallate (cis-APDOEGCG) and (Ϯ)-6-(5-aminopentyl)-5,7-deoxygallocatechin gallate (trans-APDOEGCG) as EGCG derivatives containing linkers and reactive amino groups added to the EGCG structure, as shown in Fig. 1. We compared their antiangiogenic activity with that of EGCG by examining the inhibitory effect on proliferation, migration, invasion, and tube formation by HUVECs. Then, we synthesized fluorescencelabeled EGCG by conjugating the fluorescent reagent TokyoGreen (TG) to (Ϯ)-cis-APDOEGCG (EGCG-TG) and examined the intracel...

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Photoactivatable Biomedical Materials Based on Luminogens with Aggregation‐Induced Emission (AIE) Characteristics

Sun

et al. 2021

Adv Healthcare Materials

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Fluorescence probes with aggregation-induced emission (AIE) property are fascinating and vital in biological fields due to their bright fluorescence in the solid state. In contrast, traditional AIE materials are obscured by the off-target effects and lack of spatial and temporal control. Photoactivatable materials with AIE characteristics, whose physicochemical behaviors can be remotely activated by light, provide great potential in biochemical information acquisition with high spatial and temporal resolution. By using AIE-featured photoactivatable fluorescence probes, accurate analysis of the targets of interest is possible. For example, where, when, and to what extent a process is started or stopped by manipulating the non-invasive light accurately. Thus, many researchers are enthusiastic about developing AIE-featured photoactivatable materials and mainly focus on developing novel molecules by rational molecular structure design, and exploring advanced applications by appropriate molecular functionalization. In this review, the recent achievements of photoactivatable materials with AIE characteristics from the aspects involving inherent mechanism of photoactivity, molecular design strategy, and the corresponding applications in biological fields, are summarized. The biological applications are highlighted and discussed, including photoactivatable bioimaging, diagnosis, and photo-controlled therapy. Finally, the challenges and prospects of the AIE-featured photoactivatable materials are also outlined and discussed.

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Highly Activatable and Rapidly Releasable Caged Fluorescein Derivatives

Cited by 135 publications

References 8 publications

Photoactivatable Fluorophores

Photoactivatable Fluorophores

Anti-angiogenic Activity and Intracellular Distribution of Epigallocatechin-3-gallate Analogs

Photoactivatable Biomedical Materials Based on Luminogens with Aggregation‐Induced Emission (AIE) Characteristics

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