A double branched photosensitive prodrug: synthesis and characterization of light triggered drug release

Liu, Wei; Liang, Li; Lo, Pik Kwan; Gou, Xiao Jun; Sun, Xiaoqian

doi:10.1016/j.tetlet.2016.01.064

Cited by 3 publications

(1 citation statement)

References 35 publications

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“… 163 These chromophores had λ max abs values of 336–371 nm but were photolyzed inefficiently to release a carboxylic acid (Φ r = 0.001), in keeping with the previously mentioned inverse correlation between shifts in λ max abs and Φ r . 163 Derivatives of biphenyl 10a exhibited a bathochromic shift in λ max abs of ∼70 nm relative to 5a , 163 , 185 , 186 and an additional ∼60 nm shift was achieved by using a dialkylamine EDG ( 10b ; Figure 1 ). 187 , 188 The release of a carboxylic acid 187 and the fragmentation of the selective Ca 2+ -chelator ethylene glycol tetraacetic acid 27 (EGTA) with subsequent Ca 2+ release were achieved at λ irr = 400–405 nm using PPGs of this type.…”

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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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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Synthesis and characterization of a photoresponsive doxorubicin/combretastatin A4 hybrid prodrug

Liu

Liang

Zhao

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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Application of TNB in dual photo‐controlled release of phenamacril, imidacloprid, and imidacloprid synergist

Yin,

Fu,

et al. 2024

Photochem & Photobiology

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Pesticides can improve crops' yield and quality, but unreasonable applications of pesticides lead to waste of pesticides which are further accumulated in the environment and threaten human health. Developing the release of controlled drugs can improve the utilization rate of pesticides. Among these methods, light‐controlled release is a new technology of controlled release, which can realize spatiotemporal delivery of drugs by light. Four compounds, named Imidacloprid‐Thioacetal o‐nitrobenzyl‐Phenamacril (IMI‐TNB‐PHE), Imidacloprid‐Thioacetal o‐nitrobenzyl‐ Imidacloprid (IMI‐TNB‐IMI), Phenamacril‐Thioacetal o‐nitrobenzyl‐Phenamacril (PHE‐TNB‐PHE), and Imidacloprid‐Thioacetal o‐nitrobenzyl‐Imidacloprid Synergist (IMI‐TNB‐IMISYN), were designed and synthesized by connecting thioacetal o‐nitrobenzyl (TNB) with pesticides TNB displaying simple and efficient optical properties in this work. Dual photo‐controlled release of pesticides including two molecules of IMI or PHE, both IMI and PHE, as well as IMI and IMISYN were, respectively, studied in this paper. Insecticidal/fungicidal activities of the photosensitive pesticides showed 2–4 times increments if they were exposed to light. In addition, a synergistic effect was observed after the light‐controlled release of IMI‐TNB‐IMISYN, which was consistent with the effect of IMISYN. The results demonstrated whether dual photo‐controlled release of the same or different pesticide molecules could be achieved with a TNB linker with spatiotemporal precision. We envisioned that TNB will be an innovative photosensitive protective group for light‐dependent application of agrochemicals in the future.

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A double branched photosensitive prodrug: synthesis and characterization of light triggered drug release

Cited by 3 publications

References 35 publications

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

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

Synthesis and characterization of a photoresponsive doxorubicin/combretastatin A4 hybrid prodrug

Application of TNB in dual photo‐controlled release of phenamacril, imidacloprid, and imidacloprid synergist

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