Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment

Pugachev, A. D.; Ozhogin, Ilya V.; Lukyanova, M. B.; Lukyanov, B. S.; Ростовцева, Ирина А.; Дороган, И. В.; Макарова, Н. И.; Ткачев, В. В.; Metelitsa, Anatoly V.; Алдошин, С. М.

doi:10.1016/j.saa.2020.118041

Cited by 24 publications

(13 citation statements)

References 72 publications

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“…Spectroscopic and spectroelectrochemical studies indicate the involvement of cobalt hydride in initiating the visible light‐driven isomerization of terminal alkenes. Recently, other visible light‐driven molecular switches, like spiropyrans and nitrile‐rich photochromes, have been designed, synthesized and studied [163,164] …”

Section: Different Classes Of Visible Light‐driven Molecular Switches...mentioning

confidence: 99%

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Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Wang

Bisoyi

Zhang

et al. 2022

Chemistry A European J

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Inspired by human vision, a diverse range of light‐driven molecular switches and motors have been developed for fundamental understanding and application in material science and biology. Recently, the design and synthesis of visible light‐driven molecular switches and motors have been actively pursued. This emerging trend is partly motivated to avoid the harmful effects of ultraviolet light, which was necessary to drive the classical molecular switches and motors at least in one direction, impeding their employment in biomedical and photopharmacology applications. Moreover, visible light‐driven molecular switches and motors are demonstrated to enable benign optical materials for advanced photonic devices. Therefore, during the past several years, visible light‐driven molecular switches based on azobenzene derivatives, diarylethenes, 1,2‐dicyanodithienylethenes, hemithioindigo derivatives, iminothioindoxyls, donor‐acceptor Stenhouse adducts, and overcrowded alkene based molecular motors have been judiciously designed, synthesized, and used in the development of functional materials and systems for a wide range of applications. In this Review, we present the recent developments toward the design of visible light‐driven molecular switches and motors, with their applications in the fabrication of functional materials and systems in material science, bioscience, pharmacology, etc. The visible light‐driven molecular switches and motors realized so far undoubtedly widen the scope of these interesting compounds for technological and biological applications. We hope this Review article could provide additional impetus and inspire further research interests for future exploration of visible light‐driven advanced materials, systems, and devices.

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Section: Different Classes Of Visible Light‐driven Molecular Switches...mentioning

confidence: 99%

“…Recently, other visible light-driven molecular switches, like spiropyrans and nitrile-rich photochromes, have been designed, synthesized and studied. [163,164]…”

Section: Other Visible-light-driven Molecular Switchesmentioning

confidence: 99%

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Wang

Bisoyi

Zhang

et al. 2022

Chemistry A European J

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“…Recently, the development of photoPROTACs has been the focus of several researchers and has been receiving increasing interest ( Graupner et al, 2018 ; Heindl and Wegner, 2020 ; Pugachev et al, 2020 ). After retrieval of comprehensive information, we found that photochromic and photocleavable functional groups are most extensively used in photoPROTAC development.…”

Section: Progress Of Photoprotac Developmentmentioning

confidence: 99%

Photopharmacology of Proteolysis-Targeting Chimeras: A New Frontier for Drug Discovery

et al. 2021

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Photopharmacology is an emerging field that uses light to precisely control drug activity. This strategy promises to improve drug specificity for reducing off-target effects. Proteolysis-targeting chimeras (PROTACs) are an advanced technology engineered to degrade pathogenic proteins through the ubiquitin-proteasome system for disease treatment. This approach has the potential to target the undruggable proteome via event-driven pharmacology. Recently, the combination strategy of photopharmacology and PROTACs has gained tremendous momentum for its use in the discovery and development of new therapies. This review systematically focuses on PROTAC-based photopharmacology. Herein, we provide an overview of the new and vibrant research on photoPROTACs, discuss the advantages and disadvantages of this approach as a biological tool, and outline the challenges it faces in a clinical setting.

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“…These amphiphilic structures selfassemble into micelles in which the drug is encapsulated. UV light irradiation induces the isomerization of hydrophobic SP units to hydrophilic zwitterionic MC units, leading to the shift of the hydrophilic-hydrophobic balance, which consequently disassembles and disrupts the micellar structure and the encapsulated drug is released 23,24,30 . The second strategy uses SP as a gate molecule on the surface of drugloaded mesoporous silica [31][32][33][34] .…”

Section: Introductionmentioning

confidence: 99%

“…One is introducing SP into amphiphilic block copolymers in which SP represents the hydrophobic segment. − These amphiphilic structures self-assemble into micelles in which the drug is encapsulated. UV light irradiation induces the isomerization of hydrophobic SP units to hydrophilic zwitterionic MC units, leading to the shift of the hydrophilic–hydrophobic balance, which consequently disassembles and disrupts the micellar structure and releases the encapsulated drug. ,, The second strategy uses SP as a gate molecule on the surface of drug-loaded mesoporous silica. − Exploiting the hydrophobicity–hydrophilicity switch between the closed (SP) and open (MC) isomers allows control and adjustment of the wetting behavior of the surface and release of the drug.…”

Section: Introductionmentioning

confidence: 99%

Molecular-Gated Drug Delivery Systems Using Light-Triggered Hydrophobic-to-Hydrophilic Switches

Ghani¹,

Heiskanen²,

Thomsen³

et al. 2021

ACS Appl. Bio Mater.

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A photo-responsive molecule-gated drug delivery system (DDS) based on silicone-hydrogel (poly(HEMA-co-PEGMEA)) interpenetrating polymer networks (IPN) functionalized with carboxylated spiropyran (SPCOOH) was designed and demonstrated as an on-demand DDS. The triggered release mechanism relies on controlling the wetting behaviour of the surface by light, exploiting different hydrophobicity between the "closed" and "open" isomers of spiropyran as the photo-switchable molecular gate on the surface of IPN (SP-photogated IPN). The light-triggered release of doxycycline (DOX) as the model drug indicated that the spiropyran (SP) molecules provide a hydrophobic layer around the drug carrier and have a good gate-closing efficiency for IPNs with 20-30 % hydrogel content. Upon UV light irradiation the SP convert to the open hydrophilic merocyanine state, which triggers the release of DOX. These results were compared with a previously developed SP-bulk modified IPN using the same hydrogel as a control, proving the efficiency of the gated IPN system. The covalent attachment of SPCOOH to the alcohol groups of the hydrogel and the structural change caused by UV light was indicated with FTIR analysis. XPS results also confirms the presence of SP by indicating the atomic percentage of nitrogen with respect to the hydrogel content.

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Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment

Cited by 24 publications

References 72 publications

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

Photopharmacology of Proteolysis-Targeting Chimeras: A New Frontier for Drug Discovery

Molecular-Gated Drug Delivery Systems Using Light-Triggered Hydrophobic-to-Hydrophilic Switches

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