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

Chitose, Youhei; Abe, Manabu; Furukawa, Ko; Lin, Jhe Yi; Lin, Tzu Chau; Katan, Claudine

doi:10.1021/acs.orglett.7b00957

Cited by 42 publications

(42 citation statements)

References 35 publications

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“…In the development of new PPGs, they are expected to have long‐wavelength absorption that leads to deeper tissue penetration and matches the common laser wavelengths . Many efforts have been made to develop visible and near‐IR light‐induced uncaging groups based on o ‐nitrobenzyl, coumarin, BODIPY, cyanine, and quinone derivatives either by one‐ or two‐photon excitation. Among them, the coumarin‐based photocaging groups attract much attention because of the rapid photolysis and large two‐photon (TP) absorption cross‐section.…”

Section: Figurementioning

confidence: 99%

Coumarin Photocaging Groups Modified with an Electron‐Rich Styryl Moiety at the 3‐Position: Long‐Wavelength Excitation, Rapid Photolysis, and Photobleaching

et al. 2018

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A new class of coumarin photocaging groups modified with an electron-rich styryl moiety at the 3-position was constructed. The large π-conjugated structure and stabilization of the carbocation intermediates by electron donors endowed the new photocaging groups with excellent long-wavelength absorption, large two-photon absorption cross-sections, and high uncaging quantum yields. Moreover, the new photocaging groups displayed unique photobleaching properties after photocleavage as a result of the intramolecular cyclization rearrangement of a carbocation intermediate to form five-membered ring byproducts and block the styryl conjugation at the 3-position. These superior properties of the new photocaging groups are extremely beneficial for high-concentration samples and thick specimens, thus extending the application of photocaging groups in many fields.

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Section: Figurementioning

confidence: 99%

Coumarin Photocaging Groups Modified with an Electron‐Rich Styryl Moiety at the 3‐Position: Long‐Wavelength Excitation, Rapid Photolysis, and Photobleaching

et al. 2018

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“…The UV light locally converted allows photoresponsive reaction, resulting in effective drug release controlled by remote NIR light. The conversion of lower energy NIR photons to higher energy UV and/or Vis photons generally encompasses the processes of two‐photon absorption and upconverting using upconversion nanoparticles (UCNPs) . Different with two‐photon absorption based nanomaterials which the high‐power femtosecond laser excitation is needed, upconversion luminescence (UCL) from UCNPs can be obtained under low power light irradiation, such as continuous‐wave (CW) lasers.…”

Section: Introductionmentioning

confidence: 99%

Remote Light‐Responsive Nanocarriers for Controlled Drug Delivery: Advances and Perspectives

Zhao

Wang

et al. 2019

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Engineering of smart photoactivated nanomaterials for targeted drug delivery systems (DDS) has recently attracted considerable research interest as light enables precise and accurate controlled release of drug molecules in specific diseased cells and/or tissues in a highly spatial and temporal manner. In general, the development of appropriate light‐triggered DDS relies on processes of photolysis, photoisomerization, photo‐cross‐linking/un‐cross‐linking, and photoreduction, which are normally sensitive to ultraviolet (UV) or visible (Vis) light irradiation. Considering the issues of poor tissue penetration and high phototoxicity of these high‐energy photons of UV/Vis light, recently nanocarriers have been developed based on light‐response to low‐energy photon irradiation, in particular for the light wavelengths located in the near infrared (NIR) range. NIR light‐triggered drug release systems are normally achieved by using two‐photon absorption and photon upconversion processes. Herein, recent advances of light‐responsive nanoplatforms for controlled drug release are reviewed, covering the mechanism of light responsive small molecules and polymers, UV and Vis light responsive nanocarriers, and NIR light responsive nanocarriers. NIR‐light triggered drug delivery by two‐photon excitation and upconversion luminescence strategies is also included. In addition, the challenges and future perspectives for the development of light triggered DDS are highlighted.

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“…In the last decade, we developed a TP-responsive photo-labile protecting group [56–58] with simple cyclic stilbene structures such as 2-(4-nitrophenyl)benzofuran (NPBF) that absorb in the NIR region of 710–760 nm for the uncaging of bioactive substances such as glutamate and Ca 2+ [59–64]. Herein, we report the synthesis of new caged nitroxides (nitroxide donors) 2a and 2b having the TP-responsive NPBF chromophore and the NIR TP-triggered generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical under atmospheric conditions using these species (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

Yamada¹,

Abe²,

Nishimura³

et al. 2019

Beilstein J. Org. Chem.

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Novel caged nitroxides (nitroxide donors) with near-infrared two-photon (TP) responsive character, 2,2,6,6-tetramethyl-1-(1-(2-(4-nitrophenyl)benzofuran-6-yl)ethoxy)piperidine (2a) and its regioisomer 2b, were designed and synthesized. The one-photon (OP) (365 ± 10 nm) and TP (710–760 nm) triggered release (i.e., uncaging) of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical under air atmosphere were discovered. The quantum yields for the release of the TEMPO radical were 2.5% (2a) and 0.8% (2b) in benzene at ≈1% conversion of 2, and 13.1% (2a) and 12.8% (2b) in DMSO at ≈1% conversion of 2. The TP uncaging efficiencies were determined to be 1.1 GM at 740 nm for 2a and 0.22 GM at 730 nm for 2b in benzene. The cytocidal effect of compound 2a on lung cancer cells under photolysis conditions was also assessed to test the efficacy as anticancer agents. In a medium containing 100 μg mL−1 of 2a exposed to light, the number of living cells decreased significantly compared to the unexposed counterparts (65.8% vs 85.5%).

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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

Cited by 42 publications

References 35 publications

Coumarin Photocaging Groups Modified with an Electron‐Rich Styryl Moiety at the 3‐Position: Long‐Wavelength Excitation, Rapid Photolysis, and Photobleaching

Coumarin Photocaging Groups Modified with an Electron‐Rich Styryl Moiety at the 3‐Position: Long‐Wavelength Excitation, Rapid Photolysis, and Photobleaching

Remote Light‐Responsive Nanocarriers for Controlled Drug Delivery: Advances and Perspectives

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

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