The Mechanochemical Release of Naphthalimide Fluorophores from β-Carbonate and β-Carbamate Disulfide-Centered Polymers

Shi, Zhiyuan; Song, Qingchuan; Göstl, Robert; Herrmann, Andreas

doi:10.31635/ccschem.021.202101147

Cited by 25 publications

(23 citation statements)

References 50 publications

(65 reference statements)

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“…36 A more recent investigation comparing the mechanically triggered release of NAP (X = OH) and the amine analogue Nalkyl-4-amino-1,8-naphthalimide (X = NH 2 ) revealed significantly diminished release efficiency for the amine payload conjugated to the disulfide mechanophore via carbamate linkers (Scheme 7). 126 While ∼50% release of the hydroxylfunctional payload was released after 240 min of sonication, <3% release of the amine cargo was observed after being subjected to the same ultrasonication conditions. As for the 2furylcarbinol platform discussed above, these results highlight the importance of the leaving group on molecular release.…”

Section: ■ Mechanically Gated Reactivitymentioning

confidence: 97%

Harnessing the Power of Force: Development of Mechanophores for Molecular Release

Versaw

Zeng

et al. 2021

J. Am. Chem. Soc.

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Polymers that release small molecules in response to mechanical force are promising materials for a variety of applications ranging from sensing and catalysis to targeted drug delivery. Within the rapidly growing field of polymer mechanochemistry, stress-sensitive molecules known as mechanophores are particularly attractive for enabling the release of covalently bound payloads with excellent selectivity and control. Here, we review recent progress in the development of mechanophore-based molecular release platforms and provide an optimistic, yet critical perspective on the fundamental and technological advancements that are still required for this promising research area to achieve significant impact.

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Section: ■ Mechanically Gated Reactivitymentioning

confidence: 97%

Harnessing the Power of Force: Development of Mechanophores for Molecular Release

Versaw

Zeng

et al. 2021

J. Am. Chem. Soc.

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“…This was performed by firstly treating a solution of M1 with BME, subsequent centrifugation for three times at 5000 rpm for 30 min, and eventually the kinetic observation of the release process by fluorescence spectroscopy (Figure S25). As we had expected that the generation of thiols would not be the rate determining step of the reaction, 15 the downstream release step by the retro DA reaction ultimately governed the timescale and conversion of the process. We found that by BME reduction ca.…”

Section: Release Of Fluorophore 1 From Microgels M1mentioning

confidence: 99%

“…The mechanochemical activity of a carrier‐payload construct can be tailored by the properties of the bound drug, 15,22 the force‐response of the mechanophore, 12,35 as well as power, frequency, and duration of US application 36,37 . In addition, polymer topology has a remarkable effect on the mechanochemical activity 38 and represents an important parameter to be investigated in the context of mechanochemical drug activation.…”

Section: Introductionmentioning

confidence: 99%

“…Several approaches are being used where stimuli‐responsive systems addressed by, for example, light, 6,7 electromagnetic fields, 8 pH, 9 or redox, 10 allow to control the delivery and release of therapeutic agents. Recently, concepts in polymer mechanochemistry were exploited to activate or release drugs 11–16 and other molecules 17–27 by ultrasound (US) 28,29 . Therefore, shear force is exerted on polymer chains to activate a mechanochemically latent site (the mechanophore) at a higher rate compared to the remaining bonds in the polymer 30–34 …”

Section: Introductionmentioning

confidence: 99%

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Microgels as drug carriers for sonopharmacology

Zou

Zhao

Fan

et al. 2022

Journal of Polymer Science

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The ultrasound‐induced cleavage of covalent and non‐covalent bonds to activate drugs (sonopharmacology) is a promising concept to gain control over the action of active pharmaceutical ingredients by an external trigger. Previously, linear polymer architectures bearing drug payloads were exploited for drug release by using the principles of polymer mechanochemistry. In this work, the carrier design is altered by the polymer topology to improve the ultrasound‐triggered release of covalently anchored drugs from polymer scaffolds. We use microgels crosslinked by mechanoresponsive disulfides and copolymerized with Diels‐Alder adducts of furylated payload molecules and acetylenedicarboxylate. Force‐induced thiol formation induces a Michael‐type addition liberating the payload from the microgels. The use of microgels significantly reduces sonication times compared to linear polymer chains and shields the cargo efficiently from non‐triggered activation using ultrasound that produces inertial cavitation at a frequency of 20 kHz as model condition.

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“…As a nucleoside analogue, 30 a replaces cytidine during DNA replication, which results in cell death [46] . This strategy was then adapted from hydroxy‐bearing cargo molecules to amine‐functionalities, further expanding the drug and fluorophore scope, although the release of amines from their carbamate derivatives was considerably slower and occasionally less efficient after mechanochemical disulfide scission compared to the carbonate counterparts [47] …”

Section: Molecular Release Systemsmentioning

confidence: 99%

Release of Molecular Cargo from Polymer Systems by Mechanochemistry

Küng

Göstl

Schmidt

2022

Chemistry A European J

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The design and manipulation of (multi)functional materials at the nanoscale holds the promise of fuelling tomorrow's major technological advances. In the realm of macromolecular nanosystems, the incorporation of force‐responsive groups, so called mechanophores, has resulted in unprecedented access to responsive behaviours and enabled sophisticated functions of the resulting structures and advanced materials. Among the diverse force‐activated motifs, the on‐demand release or activation of compounds, such as catalysts, drugs, or monomers for self‐healing, are sought‐after since they enable triggering pristine small molecule function from macromolecular frameworks. Here, we highlight examples of molecular cargo release systems from polymer‐based architectures in solution by means of sonochemical activation by ultrasound (ultrasound‐induced mechanochemistry). Important design concepts of these advanced materials are discussed, as well as their syntheses and applications.

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The Mechanochemical Release of Naphthalimide Fluorophores from β-Carbonate and β-Carbamate Disulfide-Centered Polymers

Cited by 25 publications

References 50 publications

Harnessing the Power of Force: Development of Mechanophores for Molecular Release

Harnessing the Power of Force: Development of Mechanophores for Molecular Release

Microgels as drug carriers for sonopharmacology

Release of Molecular Cargo from Polymer Systems by Mechanochemistry

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