Redox‐Responsive Polymer with Self‐Immolative Linkers for the Release of Payloads

Iamsaard, Supitchaya; Seidi, Farzad; Dararatana, Naruphorn; Crespy, Daniel

doi:10.1002/marc.201800071

Cited by 26 publications

(19 citation statements)

References 34 publications

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“…[147,148] The second step was an esterification, following a modified version of procedures that were previously reported. [71,148] MBTS 2 OH (2.00 g, 8.23 mmol), MAAn (3.68 mL, 24.7 mmol), and HQ (0.027 g, 0.25 mmol) were dissolved in DCM (70 mL) under nitrogen atmosphere. The mixture was stirred in an icewater bath, followed by a dropwise addition of Et 3 N (3.44 mL, 24.7 mmol).…”

Section: Methodsmentioning

confidence: 99%

“…[6] To overcome this problem, corrosion inhibitors were conjugated to polymers with linkages that can be cleaved by stimuli, which are consequences of the corrosion process. [65] These stimuli include a local change of pH value [66][67][68][69][70] or a variation of the electrochemical potential near the metal, [71][72][73] and induced the release of corrosion inhibitors. The latter stimulus relies on the fact that the corrosion process involves redox reactions than can be used to trigger reduction of disulfide linkages, and hence the release of inhibitors.…”

Section: Introductionmentioning

confidence: 99%

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Adaptive Coatings with Anticorrosion and Antibiofouling Properties

Yimyai

Thiramanas

Phakkeeree

et al. 2021

Adv Funct Materials

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Biofouling on surfaces immersed in aquatic environment induces catastrophic corrosion of metallic materials in petrochemical infrastructures, maritime facilities, and power plants. To combat the synergistic effect of biofouling and corrosion on the deterioration of metallic materials, smart coatings possessing a dual function of antibiofouling and anticorrosion properties are needed. Herein, redox‐responsive copolymer conjugates are synthesized and employed as coatings with the dual function of biofouling and corrosion mitigation. The dual function of copolymers is attributed to fluorinated units and the corrosion inhibitor 2‐mercaptobenzothiazole (MBT) conjugated via disulfide linkages. Indeed, the disulfide linkages can be cleaved in a reducing environment, yielding controlled release of the corrosion inhibitor MBT during corrosion process. The antibiofouling action against protein adsorption and algal attachment is enabled by cooperation of the repellent characteristic of fluorinated moieties and the biocidal effect of conjugated MBT.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Adaptive Coatings with Anticorrosion and Antibiofouling Properties

Yimyai

Thiramanas

Phakkeeree

et al. 2021

Adv Funct Materials

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“…Corrosion inhibitors can be incorporated in active layers by directly mixing inhibitors with coating components, encapsulation of corrosion inhibitors in nanoparticles, micro/nanocapsules, nanofibers, and conjugation of corrosion inhibitor via labile or non‐labile bonds to polymers coatings . Conjugation of corrosion inhibitors to polymer structures via stimuli‐cleavable linkages allow sustained release of corrosion inhibitors upon changes of environments due to corrosion, such as change of pH value or electrochemical potential.…”

Section: Introductionmentioning

confidence: 99%

“…Conjugation of corrosion inhibitors to polymer structures via stimuli‐cleavable linkages allow sustained release of corrosion inhibitors upon changes of environments due to corrosion, such as change of pH value or electrochemical potential. Acid‐labile hemiaminal ether and β‐thiopropionate linkages and redox‐responsive disulfide bond were used for conjugating corrosion inhibitors to polymers to achieve controllable release of inhibitors in response to lowering of pH value or reduction.…”

Section: Introductionmentioning

confidence: 99%

Controlling Release Kinetics of Payloads from Polymer Conjugates by Hydrophobicity

Seidi

Couffon

Prawatborisut

et al. 2019

Macro Chemistry & Physics

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Polymers conjugated with active molecules are useful for controlled delivery of corrosion inhibitors, phytosanitary products, and drugs. To avoid detrimental side effects, active molecules need to be selectively released upon specific external stimuli. Imine groups are highly acid‐labile linkages that are usually hydrolyzed in a few hours even in neutral medium, which can be detrimental when slow release of payloads is needed. Herein, release kinetics are adjusted by controlling hydrophobicity of pH‐responsive polymers. 5‐(Aminomethyl)‐8‐hydroxyquinoline (AM8HQ), an effective corrosion inhibitor, is conjugated via imine linkage to aldehyde pendant groups in three different copolymers. Release kinetics of AM8HQ from polymer nanoparticles are investigated in acidic and neutral media. Very fast release from polymethacrylate‐based and slow release from polystyrene‐based polymer conjugates clearly show that adjusting the hydrophobicity of the polymer backbone is an effective synthetic strategy to control the cleavage rate of highly labile imine bonds.

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“…GSH is expected to reduce the backbone disulfide bond − to generate a thiol which then intramolecularly attacks the carbonate/urethane linkage to release the active therapeutic agent (Scheme ). − To test these possibilities, we have studied a chemotherapeutic agent Camptothecin (CPT)-conjugated amphiphilic polymeric prodrug P1 (Scheme ). CPT is a naturally occurring alkaloid which exhibits high toxicity against various cell lines and has been examined extensively in context of the cancer treatment .…”

Section: Introductionmentioning

confidence: 99%

Glutathione Triggered Cascade Degradation of an Amphiphilic Poly(disulfide)–Drug Conjugate and Targeted Release

Bej

Ghosh

2018

Bioconjugate Chem.

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A bioreducible poly(disulfide)-derived amphiphilic block copolymer–drug conjugate (loading content 31%) was synthesized by post-polymerization modification. It shows redox-responsive polymersome assembly in water with aggregation induced emission property arising from the appended Camptothecin (CPT) drug. Glutathione (GSH), a tripeptide overexpressed in cancer cells, triggers a cascade reaction resulting in simultaneous degradation of the polymer backbone (consisting of disulfide linkage) and the release of the pendant drug. The cascade reaction involves GSH trigger cleavage of the backbone disulfide bond producing free thiol followed by its intrachain nucleophilic attack to the adjacent carbonate group that links the appended drug molecule. The polymeric pro-drug exhibits killing efficiency to a cancer cell with remarkably low IC50 value of 3.1 μg/mL (based on the CPT concentration) while it shows negligible toxicity to a normal cell up to polymer concentration 300 μg/mL.

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Redox‐Responsive Polymer with Self‐Immolative Linkers for the Release of Payloads

Cited by 26 publications

References 34 publications

Adaptive Coatings with Anticorrosion and Antibiofouling Properties

Adaptive Coatings with Anticorrosion and Antibiofouling Properties

Controlling Release Kinetics of Payloads from Polymer Conjugates by Hydrophobicity

Glutathione Triggered Cascade Degradation of an Amphiphilic Poly(disulfide)–Drug Conjugate and Targeted Release

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