Bifunctional Aryloxylate Esters as potential oxidatively cleavable linkers

Czarnecki, Paweł; Kampert, Anna; Barbe, Sophie; Tiller, Joerg C.

doi:10.1016/j.tetlet.2011.04.083

Cited by 5 publications

(5 citation statements)

References 34 publications

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“…Its spectroscopic properties were in agreement with those reported in the literature. 2 N,N'-Bis-((dimethylamino)ethylamino)-2-((4-hydroxyphenyl) 2; 163.8; 163.1; 157.7; 153.2; 138.8; 134.4; 131.6; 131.1; 130.6; 130.0; 128.5; 124.4, 122.2; 121.2; 117.0; 100.5; 79.2; 57.6; 57.2; 46.2; 44.5; 37.6; 37.0; 35.8 ,4.93;Br,11.49;Cl,10.20;N,10.07;O,11.50. Found C,51.84;H,5.00;Br,11.46;Cl,10.28;N,10.12.…”

Section: Synthesis Of Intermediates and Final Ligandsmentioning

confidence: 99%

Hybrid ligand–alkylating agents targeting telomeric G-quadruplex structures

Doria

Nadai²,

Folini

et al. 2012

Org. Biomol. Chem.

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The synthesis, physico-chemical properties and biological effects of a new class of naphthalene diimides (NDIs) capable of reversibly binding telomeric DNA and alkylate it through an electrophilic quinone methide moiety (QM), are reported. FRET and circular dichroism assays showed a marked stabilization and selectivity towards telomeric G4 DNA folded in a hybrid topology. NDI-QMs' alkylating properties revealed a good reactivity on single nucleosides and selectivity towards telomeric G4. A selected NDI was able to significantly impair the growth of melanoma cells by causing telomere dysfunction and down-regulation of telomerase expression. These findings points to our hybrid ligand-alkylating NDIs as possible tools for the development of novel targeted anticancer therapies.

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Section: Synthesis Of Intermediates and Final Ligandsmentioning

confidence: 99%

Hybrid ligand–alkylating agents targeting telomeric G-quadruplex structures

Doria

Nadai²,

Folini

et al. 2012

Org. Biomol. Chem.

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“…Peroxalate ester can undergo a reaction with H 2 O 2 , leading to the formation of 1,2dioxetanediones. 176 These 1,2-dioxetanediones are wellknown for their ability to rapidly decompose into carbon dioxide. Therefore, peroxalate ester bonds can be triggered by reactive oxygen species (ROS) to undergo degradation, facilitating the release of drugs (Scheme 7, left).…”

Section: Peroxalate Estermentioning

confidence: 99%

“…Peroxalate ester can undergo a reaction with H 2 O 2 , leading to the formation of 1,2-dioxetanediones . These 1,2-dioxetanediones are well-known for their ability to rapidly decompose into carbon dioxide.…”

Section: Cleavage Chemistry In Ros-responsive Materialsmentioning

confidence: 99%

Cleavage and Noncleavage Chemistry in Reactive Oxygen Species (ROS)-Responsive Materials for Smart Drug Delivery

Chi,

Sang,

Wang

et al. 2023

Bioconjugate Chem.

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The design and development of advanced drug delivery systems targeting reactive oxygen species (ROS) have gained significant interest in recent years for treating various diseases, including cancer, psychiatric diseases, cardiovascular diseases, neurological diseases, metabolic diseases, and chronic inflammations. Integrating specific chemical bonds capable of effectively responding to ROS and triggering drug release into the delivery system is crucial. In this Review, we discuss commonly used conjugation linkers (chemical bonds) and categorize them into two groups: cleavable linkers and noncleavable linkers. Our goal is to clarify their unique drug release mechanisms from a chemical perspective and provide practical organic synthesis approaches for their efficient production. We showcase numerous significant examples to demonstrate their synthesis routes and diverse applications. Ultimately, we strive to present a comprehensive overview of cleavage and noncleavage chemistry, offering insights into the development of smart drug delivery systems that respond to ROS.

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“…For example, the rate of oxidation of an aryl oxalate was greatly accelerated in NaHCO 3 solution compared to that in pure water, while the reaction hardly proceeded at all in acidic solution. 56 Additionally, aryl oxalates with electronegative groups at the 2-or 4-position of the aryl ring, not aliphatic oxalates, are preferred to increase the chemiluminescence efficacy. 5f,54b The aryl oxalate/H 2 O 2 -based chemiluminescence system is very promising for in vitro or in vivo H 2 O 2 detection because of its versatile performance.…”

Section: Aryl Oxalate-containing Polymersmentioning

confidence: 99%