90429-09-7

Usage

InChI:InChI=1/C10H9NO7/c1-17-8-2-6(4-12)7(11(15)16)3-9(8)18-5-10(13)14/h2-4H,5H2,1H3,(H,13,14)

Upstream product

• 1660-19-1 (4-formyl-2-methoxyphenoxy)acetic acid 
• 121-33-5 vanillin 
• 51264-70-1 ethyl 2-(4-formyl-2-methoxyphenoxy)acetate 
• 179002-91-6 tert-butyl 2-(4-formyl-2-methoxyphenoxy)acetate 

Downstream Products

• 188891-14-7 N-benzyl-(4-formyl-2-methoxy-5-nitrophenoxy)acetamide 
• 1227683-25-1 2-(4-formyl-2-methoxy-5-nitrophenoxy)-N-(2-(N-tert-butoxycarbonylamino)ethylamine)acetamide 
• 1227683-22-8 2-(4-hydroxymethyl-2-methoxy-5-nitrophenoxy)-N-(2-(N-tert-butoxycarbonylamino)ethylamine)acetamide 

Relevant academic research and scientific papers

Janus Gold Nanostars–Mesoporous Silica Nanoparticles for NIR-Light-Triggered Drug Delivery

Janus gold nanostar–mesoporous silica nanoparticle (AuNSt–MSNP) nanodevices able to release an entrapped payload upon irradiation with near infrared (NIR) light were prepared and characterized. The AuNSt surface was functionalized with a thiolated photolabile molecule (5), whereas the mesoporous silica face was loaded with a model drug (doxorubicin) and capped with proton-responsive benzimidazole-β-cyclodextrin supramolecular gatekeepers (N 1). Upon irradiation with NIR-light, the photolabile compound 5 photodissociated, resulting in the formation of succinic acid, which induced the opening of the gatekeeper and cargo delivery. In the overall mechanism, the gold surface acts as a photochemical transducer capable of transforming the NIR-light input into a chemical messenger (succinic acid) that opens the supramolecular nanovalve. The prepared hybrid nanoparticles were non-cytotoxic to HeLa cells, until they were irradiated with a NIR laser, which led to intracellular doxorubicin release and hyperthermia. This induced a remarkable reduction in HeLa cells viability.

A NIR light-triggered drug delivery system using core-shell gold nanostars-mesoporous silica nanoparticles based on multiphoton absorption photo-dissociation of 2-nitrobenzyl PEG

Gold nanostars coated with a mesoporous silica shell and functionalized with poly(ethylene glycol) containing photolabile 2-nitrobenzyl moieties are able to release doxorubicin after NIR light irradiation at low power irradiance via a multiphoton absorpti

Synthesis of a photocaged tamoxifen for light-dependent activation of Cre-ER recombinase-driven gene modification

We report the design of a water-soluble, quaternized tamoxifen photoprobe and demonstrate its application in light-controlled induction of green fluorescent protein expression via a Cre-ER recombinase system. The Royal Society of Chemistry.

Light-controlled release of caged doxorubicin from folate receptor-targeting PAMAM dendrimer nanoconjugate

We report the synthesis and in vitro evaluation of folate receptor-targeted nanoconjugate that releases its therapeutic payload via a photochemical mechanism.

Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage

Both a model phenacyl and o-nitrobenzyl photolabile linker from the literature along with four new o-nitrobenzyl linkers were prepared and the kinetics of their photolytic cleavage examined in solution. The linkers were prepared by amidation of the carboxylic acid anchoring tether with benzylamine, and the cleavable benzylic substituent was chosen to be either acetic acid or acetamide. Irradiation of the linkers in four solvents (methanol, p-dioxane, and aqueous buffer ± dithiothreitol) at 365 nm and analysis via HPLC afforded kinetic rates of cleavage suitable for comparative purposes. The phenacyl linker was found to cleave slowly under aqueous conditions with no detectable cleavage being observed in the organic solvents. Known o-nitrobenzyl linker 4 showed modest rates of cleavage in aqueous and organic solvents. Incorporation of two alkoxy groups in the benzene ring to generate the veratryl-based linker 13a increased the rate of cleavage dramatically, and introduction of an additional benzylic methyl group (13b) increased the rate of cleavage by an additional 5 fold. Increasing the length of the anchoring carboxylic acid tether from acetic to butyric acid (19) improved the cleavage kinetics modestly in organic media and slightly diminished the rates in water. The amide model linker 21 cleaved from 3 to 7 times faster than the corresponding ester linkage 19. An amide-generating linker 26 was prepared, and its performance to generate photolabile solid supports was briefly examined. The stability of the linker and subsequent cleavage upon photolysis from the support of an isotopically enriched 4-thiazolidinone was demonstrated by gel phase 13C NMR.

Acidic o-nitroaromatics as photoinhibitors of polymerization in positive working films

A photopolymerizable coating composition comprising (1) a nongaseous, ethylenically unsaturated, polymerizable compound, (2) a specified acidic o-nitroaromatic compound, and (3) an organic, radiation-sensitive, free-radical generating system which is useful for making a positive or negative polymeric image on a substrate.