Styryl Conjugated Coumarin Caged Alcohol: Efficient Photorelease by Either One-Photon Long Wavelength or Two-Photon NIR Excitation

Bao, Chunyan; Fan, G.Y.; Lin, Qiuning; Li, Bo; Cheng, Shuiyu; Huang, Qi; Zhu, Linyong

doi:10.1021/ol203188h

Cited by 69 publications

(71 citation statements)

References 32 publications

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“…Thus, the high photolysis quantum yield and the significant molar absorption coefficient in the blue ( ϵΦ =2700 m −1 cm −1 at 390 nm), together with the very efficient release of 9‐aminodoxycycline, make 9‐(PEG7‐DEACMamino)doxycycline a very suitable caged doxycycline derivative for visible‐light photolysis at neutral pH. Moreover, from the previously reported two‐photon absorption cross‐section ( δ a ) for the DEACM chromophore of 2.3 GM at 800 nm and the calculated value of 19 GM at 740 nm (Supporting Information), the two‐photon uncaging action cross‐section ( δ u= δ a Φ ) of 9‐(PEG7‐DEACMamino)doxycycline is estimated to be 4.0 GM at 740 nm and 0.5 GM at 800 nm. This two‐photon uncaging action cross‐section of 9‐(PEG7‐DEACMamino)doxycycline is, to the best of our knowledge, not only the highest value reported for a caged doxycycline analogue but the highest for any transcriptionally active small‐molecule compound including caged derivatives of Tamoxifen and isopropyl β‐ d ‐1‐thiogalactopyranoside (IPTG).…”

Section: Resultsmentioning

confidence: 85%

Synthesis and Characterization of Photoactivatable Doxycycline Analogues Bearing Two‐Photon‐Sensitive Photoremovable Groups Suitable for Light‐Induced Gene Expression

et al. 2018

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We report the synthesis and photolytic properties of caged 9-aminodoxycycline derivatives modified with 2-{4'-bis-[2-(2methoxyethoxy)ethyl]-4-nitrobiphenyl-3-yl}prop-1-oxy (EANBP) and PEG7-ylated (7-diethylamino-2-oxo-2H-chromen-4-yl)methyl (PEG7-DEACM) groups. 9-Aminodoxycycline is a tetracycline analogue capable of activating transcription through the inducible TetOn transgene expression system and can be regioselectively coupled to two-photon-sensitive photo-removable protecting groups by carbamoylation. The EANBP-based caged 9-aminodoxycycline showed complex photochemical reactions but did release 10 % of 9-aminodoxycycline. However, 9-(PEG7-DEACMamino)doxycycline exhibited excellent photolysis efficiency at 405 nm with quantitative release of 9-aminodoxycycline and a 0.21 uncaging quantum yield. Thanks to the good two-photon sensitivity of the DEACM chromophore, 9-aminodoxycycline release by two-photon photolysis is possible, with calculated action cross-sections of up to 4.0 GM at 740 nm. Therefore, 9-(PEG7-DEACMamino)doxycycline represents a very attractive tool for the development of a light-induced gene expression method in living cells.

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Section: Resultsmentioning

confidence: 85%

Synthesis and Characterization of Photoactivatable Doxycycline Analogues Bearing Two‐Photon‐Sensitive Photoremovable Groups Suitable for Light‐Induced Gene Expression

et al. 2018

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“…[39] Various modifications of coumarin derivatives have been developed to shift their absorption to a biologically relevant range. [41] Recently, Winter and coworkers reported a family of borondipyrromethene (BODIPY) photocages cleaved by green light (>500 nm). [40] Zhu and coworkers developed a new series of coumarin derivatives with an elec tronrich styryl moiety at the 3position with excellent absorp tion in the light region between 430 and 515 nm (bluegreen), large twophoton absorption crosssections, and high uncaging quantum yields.…”

Section: Molecular Mechanismsmentioning

confidence: 99%

Design and Applications of Photoresponsive Hydrogels

2019

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materials with diverse applications in var ious fields due to their tunable chemistry structure and physical properties as well as excellent biocompatibility. [2][3][4][5] Hydrogel research has evolved from static mate rials to smart ones, whose structures and property show responsiveness to external stimuli, including temperature, pH, light, electric or magnetic fields, and the pres ence of enzymes or ion concentrations. [6][7][8][9][10][11] This unprecedented level of control over material properties has driven both med ical and industrial fields into the realm of possibility: controlled drug delivery, [12] chemical sensors, [13] soft actuators or robotics, [14][15][16] or scaffolds for dynamic 3D cell culture. [17] Photoresponsiveness is attractive due to the inherent advan tages of light as stimulus. Light is non invasive and allows remote manipulation of materials without requiring additional reagents, thus, with limited byproducts. Modulation of irradiation parameters, such as light intensity and irradiation time, permits the pre cise control of irradiation dosage, thereby, the degree of photo reactions. Spatial control can be achieved in both 2D and 3D, and temporal control is possible by simply turning the respec tive light source on or off. Wavelengthselective photo chemical reactions can be used for orthogonal photomediation of hydrogel properties. [18] Photoresponsive hydrogels, as externally tunable materials, strongly contribute to the field of soft smart materials in regard to the abovementioned applications. [19] In this review, we elaborate on the design and the emerging appli cations of photoresponsive hydrogels. A comprehensive review about utilizing light for the formation of hydrogels is given by Mi and coworkers. [20] First, we discuss responsive modes and photochemical mechanisms of photoresponsive hydrogels. Fol lowing this, we highlight their applications for dynamic cell environments, smart biointerfaces, controlled drug delivery, photodriven actuators, and lighthealing materials. The review concludes with an outlook on the challenges and potential future approaches for photo responsive hydrogels. Light as Stimulus for Hydrogels Macroscopic Hydrogel PhotoresponsesThe interaction of light with photoresponsive hydrogels can result in different responses, some of which are observable with the bare eye. Those include hydrogel formation or degradation, network contraction or expansion, and chemical modifications in the network, which then have an immediate consequence on Hydrogels are the most relevant biochemical scaffold due to their tunable properties, inherent biocompatibility, and similarity with tissue and cell environments. Over the past decade, hydrogels have developed from static materials to "smart" responsive materials adapting to various stimuli, such as pH, temperature, chemical, electrical, or light. Light stimulation is particularly interesting for many applications because of the capability of contact-free remote manipulation of biomaterial properties and inherent spatial and t...

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“…[55] Während hohe TPE-Querschnitte s 2 bei 800 nm erhalten wurden, ging das p-Ethoxyderivat 12 a keine Fragmentierung ein, und die Effizienz d u der p-Dimethylaminoderivate 12 b war doppelt so hoch (bis zu 0.26 GM im Vergleich zu 0.12 GM) als die des Stamm-Cumarinderivats 11 ohne Styrylgruppe (Abbildung 11).…”

Section: -Nitroindoline (Ni) Wurden Durch Amit Et Al Mitte Derunclassified

Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

et al. 2013

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Molekulare Systeme, die mit Licht “ferngesteuert” werden können, sind von wachsender Bedeutung in der Zellbiologie, der Physiologie und den Neurowissenschaften. Der entscheidende Aspekt hierbei ist die hohe räumliche und zeitliche Präzision, die mit Methoden der Lasermikroskopie erreicht werden kann. Das Verfahren der Zwei‐Photonen‐Anregung hat signifikante Vorzüge bei der Visualisierung biologischer Gewebe, allerdings ist der gezielte Entwurf intelligenter Sonden, die mit der Zellphysiologie kompatibel sind, nicht trivial. Dieser Aufsatz diskutiert die “chemischen” Herausforderungen bei der Entwicklung von Zwei‐Photonen‐Sonden.

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Styryl Conjugated Coumarin Caged Alcohol: Efficient Photorelease by Either One-Photon Long Wavelength or Two-Photon NIR Excitation

Cited by 69 publications

References 32 publications

Synthesis and Characterization of Photoactivatable Doxycycline Analogues Bearing Two‐Photon‐Sensitive Photoremovable Groups Suitable for Light‐Induced Gene Expression

Synthesis and Characterization of Photoactivatable Doxycycline Analogues Bearing Two‐Photon‐Sensitive Photoremovable Groups Suitable for Light‐Induced Gene Expression

Design and Applications of Photoresponsive Hydrogels

Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

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