Dual-wavelength efficient two-photon photorelease of glycine by π-extended dipolar coumarins

Klausen, Maxime; Dubois, Victor; Clermont, Guillaume; Tonnelé, Claire; Castet, Frédéric; Blanchard‐Desce, Mireille

doi:10.1039/c9sc00148d

Cited by 63 publications

(66 citation statements)

References 52 publications

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“…Prompted by the above considerations, we turned our attention to coumarin-based photocages 13 , 23 , 24 , 28 , 45 and tetrazine quenched fluorogenic probes. 38 , 40 , 46 , 47 We assumed that both the fluorescence and the light-induced bond dissociation originate from the same excited state, thus, we hypothesized that similarly to fluorescence, the photoresponsivity of photocages can also be modulated by the bioorthogonal and quencher tetrazine moiety.…”

Section: Resultsmentioning

confidence: 99%

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Conditionally Activatable Visible-Light Photocages

et al. 2020

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The proof of concept for conditionally activatable photocages is demonstrated on a new vinyltetrazine-derivatized coumarin. The tetrazine form is disabled in terms of light-induced cargo release, however, bioorthogonal transformation of the modulating tetrazine moiety results in fully restored photoresponsivity. Irradiation of such a “click-armed” photocage with blue light leads to fast and efficient release of a set of caged model species, conjugated via various linkages. Live-cell applicability of the concept was also demonstrated by the conditional release of a fluorogenic probe using mitochondrial pretargeting.

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Section: Resultsmentioning

confidence: 99%

“… 20 , 29 − 31 In addition to the impact on chemical biology, photocaging-based drug delivery systems, especially photoactivated chemoterapy (PACT) could also benefit from the development of such improved photocages possessing specific targeting elements. 23 , 32 …”

Section: Introductionmentioning

confidence: 99%

Conditionally Activatable Visible-Light Photocages

et al. 2020

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“…Blanchard-Desce, Kele, and co-workers independently developed a series of 3-π-extended 7-(diethylamino)coumarinylmethyl derivatives bearing electron-withdrawing end-groups ( 55a – i , Table 10 ). 295 , 470 Coumarins 55a – f had absorption maxima at 457–472 nm, and the charged pyridinium and benzothiazolium derivatives 55g – i exhibited even more pronounced bathochromic shifts in λ max abs . 295 , 470 The 66 nm difference in λ max abs between 55c and 55i (472 and 538 nm, respectively; Figure 3 ) can be attributed to the effect of the N -alkyl moiety on the benzothiazolyl end-group.…”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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“…The fluorescence intensity in a.u. is related to the ability to absorb two photons [33] . As we know, a high fluorescence signal is an indicator for few ultrafast decay pathways, which are the main photolysis competitors.…”

Section: Resultsmentioning

confidence: 99%

Selective Modification for Red‐Shifted Excitability: A Small Change in Structure, a Huge Change in Photochemistry

Becker

Roth

Scheurer³

et al. 2020

Chemistry A European J

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We developed three bathochromic, green‐light activatable, photolabile protecting groups based on a nitrodibenzofuran (NDBF) core with D‐π‐A push–pull structures. Variation of donor substituents (D) at the favored ring position enabled us to observe their impact on the photolysis quantum yields. Comparing our new azetidinyl‐NDBF (Az‐NDBF) photolabile protecting group with our earlier published DMA‐NDBF, we obtained insight into its excitation‐specific photochemistry. While the “two‐photon‐only” cage DMA‐NDBF was inert against one‐photon excitation (1PE) in the visible spectral range, we were able to efficiently release glutamic acid from azetidinyl‐NDBF with irradiation at 420 and 530 nm. Thus, a minimal change (a cyclization adding only one carbon atom) resulted in a drastically changed photochemical behavior, which enables photolysis in the green part of the spectrum.

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Dual-wavelength efficient two-photon photorelease of glycine by π-extended dipolar coumarins

Abstract: Efficient photolabile protecting groups: how to achieve exceptional photo-triggered amino-acid delivery upon irradiation in the NIR.

Cited by 63 publications

References 52 publications

Conditionally Activatable Visible-Light Photocages

Conditionally Activatable Visible-Light Photocages

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Selective Modification for Red‐Shifted Excitability: A Small Change in Structure, a Huge Change in Photochemistry

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