Bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol: a new and efficient photolabile protecting group for aldehydes and ketones

Kantevari, Srinivas; Narasimhaji, Ch. Venkata; Mereyala, Hari Babu

doi:10.1016/j.tet.2005.04.007

Cited by 27 publications

(8 citation statements)

References 31 publications

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“…216 The substituted version 109 with a red-shifted absorption was proposed later. 217 On the other hand, for the release of simple aldehydes, it is not necessary to consume two aromatic-releasing units, and α-acetyl acetals have been shown to release aldehydes efficiently upon irradiation (Scheme 39). 218 …”

Section: Nitroaryl Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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Section: Nitroaryl Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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“…To maximize the Zn 2+ offloading capability with concurrent preservation of pre-photolysis metal ion buffering capacity, we envisioned introducing a second o -nitrobenzyl photocaging group. Utilization of two photolabile groups in photocages has precedent in organic synthesis as well as in small molecule photocages . In the first Ca 2+ photocage utilizing two photolabile groups Nitr-8, the affinity of the Ca 2+ -selective chelator decreases 1600-fold upon uncaging; however, Nitr-8 was reported in a review that lacked extensive characterization data .…”

Section: Introductionmentioning

confidence: 99%

Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺ Photocages Using Multiple Nitrobenzyl Groups

et al. 2013

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Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn(2+) chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal-bound aniline ligands, which decreases the Zn(2+) affinity 190-fold. The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14-fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,N'-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn(2+)-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn(2+) complexes, and photolysis of two photolabile groups increases the Zn(2+) affinity changes to 480-fold. The Zn(2+), Cu(2+), and Cd(2+) binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn(2+)-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.

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“…[28][29][30] This accelerates the boron-alcohol self-binding of iminoboronic acid and BNPE to form the target triplesensitive polymer of PEG-INEC and finally allows the selfassembly that can respond to stimulation by UV light, pH, and redox potential in aqueous solution. Under 365 nm light irradiation, the hydrophobic INEC tails undergo a photo-cleavage reaction to cleave nitroso derivates; [9,36,37] upon acidification, PEG-INEC is reverted back to the original subcomponents via the hydrolysis of CN and BO bonds. [29,[31][32][33]38] In response to aqueous H 2 O 2 , the iminoboronate esters are expected to be oxidized to salicylic aldehydes.…”

Section: Resultsmentioning

confidence: 99%

Fabricating Triple-Sensitive Polymer Nano-Aggregates via an Aqueous Iminoboronate Multicomponent Reaction

Liu

Chen

et al. 2017

Macromol. Rapid Commun.

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A triple-sensitive polymer of poly(ethylene glycol)-iminoboronate nitrobenzyl ethanediol chelate (PEG-INEC) is efficiently fabricated via the convenient aqueous iminoboronate multi-component reaction (MCR) of methoxypolyethylene glycol amine (mPEG-NH ), 2-formylphenylboronic acid (FPBA), and bis(2-nitrophenyl) ethanediol (BNPE, a photo-cleavable nitrobenzyl alcohol derivate). The aqueous MCR synthetic procedure is followed using H NMR and turbidity analysis. It is shown that polymer nano-aggregates of PEG-INEC in aqueous solution can be dissociated through the stimuli responsive reactions of the hydrophobic iminoboronate nitrobenzyl ethanediol chelates (INECs) when exposed to UV light, acid, and H O , respectively. Furthermore, upon the stimulation of combined triggers, the dissociation of polymer nano-aggregates can be accelerated to different extents, resulting in the synergistic release of encapsulated hydrophobic molecules in water. The proposed facile and general method is quite desirable and of great importance in practical applications like drug and gene delivery.

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Bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol: a new and efficient photolabile protecting group for aldehydes and ketones

Cited by 27 publications

References 31 publications

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺ Photocages Using Multiple Nitrobenzyl Groups

Fabricating Triple-Sensitive Polymer Nano-Aggregates via an Aqueous Iminoboronate Multicomponent Reaction

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Bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol: a new and efficient photolabile protecting group for aldehydes and ketones

Cited by 27 publications

References 31 publications

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn2+ Photocages Using Multiple Nitrobenzyl Groups

Fabricating Triple-Sensitive Polymer Nano-Aggregates via an Aqueous Iminoboronate Multicomponent Reaction

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Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺ Photocages Using Multiple Nitrobenzyl Groups