From One‐Photon to Two‐Photon Probes: “Caged” Compounds, Actuators, and Photoswitches

Bort, Guillaume; Gallavardin, Thibault; Ogden, David; Dalko, Peter I.

doi:10.1002/anie.201204203

Cited by 244 publications

(186 citation statements)

References 141 publications

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“…In addition, the reported probes for imaging of intracellular sulfite/bisulfite levels have been evaluated using one-photon microscopy (OPM) with relatively short excitation wavelengths. Two-photon microscopy (TPM) is becoming a powerful tool in molecular imaging of cells and tissues [22][23][24][25][26]. The advantages of two-photon excitation include reduced out-of-focus photobleaching, reduced autofluorescence, non-invasive excitation, deeper tissue penetration and intrinsically high three-dimensional resolution.…”

Section: Introductionmentioning

confidence: 99%

“…Higher values of ' enable detection of lower probe concentrations at reduced laser powers, suppress autofluorescence, reduce phototoxic effects on the sample and facilitate higher resolution images of living cells and deep tissues. Many practical two-photon fluorescent dyes exhibit ' values larger than 10 [22][23][24][25][26]. To achieve such values, a high luminescent efficiency and/or large TPA cross-section value is essential.…”

Section: Introductionmentioning

confidence: 99%

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Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe

Chen

Wang

et al. 2015

Biomaterials

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Sulfur dioxide (SO2) and its derivatives sulfite and bisulfite play important roles in biological systems. However, in vivo detection of sulfite/bisulfite remains challenging.In this study, we developed a dinuclear Ir(III) complex (Ir4) as a two-photon phosphorescent probe for sulfite and bisulfite. Ir4 selectively and rapidly responded, with high sensitivity, to sulfite/bisulfite over other bio-related ions and molecules.One-photon and two-photon microscopy images revealed that Ir4 preferentially targeted mitochondria and was capable of imaging biological sulfite/bisulfite levels in vitro and in vivo. In situ sulfite generation in C. elegans was visualized by two-photon excitation real-time imaging. Finally, Ir4 was employed to monitor sulfite distribution in rat brain and other tissues. This study is the first report of the direct visualization of SO2 derivatives in vivo. These results provide new insights into the biological importance of SO2.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe

Chen

Wang

et al. 2015

Biomaterials

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“…[10][11][12] Two-photon (TP) excitation processes using light in the near-infrared (NIR) region, 650-1050 nm, are advantageous for physiological studies, because deep penetration and a high spatial resolution can be achieved. [13][14][15][16] The development of new NIR-TP-responsive chromophores is currently a state-ofthe-art challenge. Several π-extended coumarin derivatives with TP absorption (TPA) character have been synthesized.…”

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confidence: 99%

Design and Synthesis of a Caged Carboxylic Acid with a Donor−π–Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

et al. 2017

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A caged carboxylic acid with a novel two-photon (TP)-responsive donor−π–donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ε ≈ 29000 cm–1 M–1) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.

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“…Caged compounds with TPA character enable greater spatial control of the release of bioactive substances. 13 For practical applications, a higher uncaging efficiency is necessary to conduct biological studies. The uncaging efficiency for OP excitation is defined as the uncaging quantum yield (Φ u ) multiplied by the excitation probability (¾: molar extinction coefficient).…”

mentioning

confidence: 99%

Design, Synthesis, and Reaction of π-Extended Coumarin-based New Caged Compounds with Two-photon Absorption Character in the Near-IR Region

Chitose¹,

Abe²,

Furukawa³

et al. 2016

Chem. Lett.

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Novel π-extended coumarin-based chromophores were designed with two-photon absorption (TPA) character in the near-IR region. Caged benzoates with a TP-responsive chromophore were synthesized, and their TP-uncaging reactions were conducted under near-IR light. The 6,7-dimethoxy-substituted derivative had a high TPA cross-section of 69 GM at 740 nm. The 7-methoxysubstituted derivative showed a high TPA uncaging efficiency with a TPA efficiency of 3.4 GM at 710 nm.Keywords: Caged compounds | Two-photon absorption | Donor-π-AcceptorCaged compounds, 1 the inactive forms of bioactive molecules formed using a photolabile protecting group (PPG), 2 are now used to elucidate the mechanism of bioactivity of substances in various life processes and phenomena. For instance, caged compounds contribute to the development of new medicines. The PPG is removed photochemically under neutral conditions without chemical reagents, thus rapidly releasing the bioactive compound. This efficient uncaging is biologically useful because the timing, location, and amplitude of photoirradiation can be controlled. Thus, the photoinduced release of bioactive molecules has been utilized in various fields such as neuroscience, cell patterning, or biomedical science. 35 Coumarin derivatives have been used to study various functions of biomolecules and for cellular imaging.6 The advantages of coumarin as a chromophore include its inherent fast response to photolysis, thermal stability, high molar extinction coefficient, and good fluorescent property for monitoring its reactions in vivo.7 However, the recent concern for physiological application of coumarin-based compounds is mainly its short absorption wavelength. Coumarin itself possesses an absorption wavelength maximum of 274 nm in methanol.8 Due to this short wavelength, cell damages cannot be avoided using one-photon absorption (OPA).9 But better penetration to the deeper part of cells 10 can be afforded using chromophores having significant twophoton absorption (TPA) character in the near-IR region. 11,12Chromophores with TPA character have attracted much attention because of their application in physiology. Caged compounds with TPA character enable greater spatial control of the release of bioactive substances. 13 For practical applications, a higher uncaging efficiency is necessary to conduct biological studies. The uncaging efficiency for OP excitation is defined as the uncaging quantum yield (Φ u ) multiplied by the excitation probability (¾: molar extinction coefficient). Similarly, the efficiency ¤ u of a TP excitation process is expressed using the TPA cross-section (· 2 ): ¤ u = Φ u · 2 . The minimum threshold value of TP efficiency for in vivo studies was reported as 3 GM.14 In 1999, Furuta et al. In this study, a coumarin containing a stilbene skeleton (12 GM at 514 nm) 18 with a p-nitrophenyl group as the electronwithdrawing group was designed to increase the TPA crosssections due to its dipolar character (Figure 1). 19 The cyclic structure should prevent cistrans isomerization ...

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From One‐Photon to Two‐Photon Probes: “Caged” Compounds, Actuators, and Photoswitches

Cited by 244 publications

References 141 publications

Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe

Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe

Design and Synthesis of a Caged Carboxylic Acid with a Donor−π–Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

Design, Synthesis, and Reaction of π-Extended Coumarin-based New Caged Compounds with Two-photon Absorption Character in the Near-IR Region

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