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Polythiolactone-based redox-responsive layers for the reversible release of functional molecules

(2014) ACS APPLIED MATERIALS & INTERFACES. 6(24). p.22457-22466
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Abstract
The development of thin macromolecular layers with incorporated disulfide bonds that can be disrupted and formed again under redox stimulation is of general interest for drug release applications, because such layers can provide rapid and reversible responses to specific biological systems and signals. However, the preparation of such layers from polythiols remains difficult, because of the fast oxidation of thiol groups in ambient conditions. Here we propose water-soluble thiolactone-containing copolymers as stable precursors containing protected thiol groups, allowing us to produce on demand polythiol layers on gold substrates in the presence of amine derivatives. Electrochemical, water contact angle, X-ray photoelectron spectroscopy, and X-ray reflectometry measurements evidence the formation of uniform copolymer layers containing both anchored and free thiol groups. The number of free thiols increases with the content of thiolactone units in the copolymers. In a second step, a thiolated dye, used as a model drug, was successfully grafted on the free thiol groups through disulfide bonds using mild oxidizing conditions, as proved by fluorescence and quartz crystal microbalance measurements. Finally, the reversible release/regrafting of the dye under redox stimulation is demonstrated.
Keywords
polythiol, disulfide link, thiolactone aminolysis, stimuli-responsive polymer, gold surface modification, responsive surface, drug release, SELF-ASSEMBLED MONOLAYERS, DRUG-DELIVERY, ONE-POT, IMPEDANCE SPECTROSCOPY, POLYMER CAPSULES, GOLD SURFACES, SYSTEMS, THIOL, CARRIER, NANOPARTICLE

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Citation

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MLA
Belbekhouche, Sabrina, Stefan Reinicke, Pieter Espeel, et al. “Polythiolactone-based Redox-responsive Layers for the Reversible Release of Functional Molecules.” ACS APPLIED MATERIALS & INTERFACES 6.24 (2014): 22457–22466. Print.
APA
Belbekhouche, S., Reinicke, S., Espeel, P., Du Prez, F., Eloy, P., Dupont-Gillain, C., Jonas, A. M., et al. (2014). Polythiolactone-based redox-responsive layers for the reversible release of functional molecules. ACS APPLIED MATERIALS & INTERFACES, 6(24), 22457–22466.
Chicago author-date
Belbekhouche, Sabrina, Stefan Reinicke, Pieter Espeel, Filip Du Prez, Pierre Eloy, Christine Dupont-Gillain, Alain M Jonas, Sophie Demoustier-Champagne, and Karine Glinel. 2014. “Polythiolactone-based Redox-responsive Layers for the Reversible Release of Functional Molecules.” Acs Applied Materials & Interfaces 6 (24): 22457–22466.
Chicago author-date (all authors)
Belbekhouche, Sabrina, Stefan Reinicke, Pieter Espeel, Filip Du Prez, Pierre Eloy, Christine Dupont-Gillain, Alain M Jonas, Sophie Demoustier-Champagne, and Karine Glinel. 2014. “Polythiolactone-based Redox-responsive Layers for the Reversible Release of Functional Molecules.” Acs Applied Materials & Interfaces 6 (24): 22457–22466.
Vancouver
1.
Belbekhouche S, Reinicke S, Espeel P, Du Prez F, Eloy P, Dupont-Gillain C, et al. Polythiolactone-based redox-responsive layers for the reversible release of functional molecules. ACS APPLIED MATERIALS & INTERFACES. 2014;6(24):22457–66.
IEEE
[1]
S. Belbekhouche et al., “Polythiolactone-based redox-responsive layers for the reversible release of functional molecules,” ACS APPLIED MATERIALS & INTERFACES, vol. 6, no. 24, pp. 22457–22466, 2014.
@article{5802582,
  abstract     = {The development of thin macromolecular layers with incorporated disulfide bonds that can be disrupted and formed again under redox stimulation is of general interest for drug release applications, because such layers can provide rapid and reversible responses to specific biological systems and signals. However, the preparation of such layers from polythiols remains difficult, because of the fast oxidation of thiol groups in ambient conditions. Here we propose water-soluble thiolactone-containing copolymers as stable precursors containing protected thiol groups, allowing us to produce on demand polythiol layers on gold substrates in the presence of amine derivatives. Electrochemical, water contact angle, X-ray photoelectron spectroscopy, and X-ray reflectometry measurements evidence the formation of uniform copolymer layers containing both anchored and free thiol groups. The number of free thiols increases with the content of thiolactone units in the copolymers. In a second step, a thiolated dye, used as a model drug, was successfully grafted on the free thiol groups through disulfide bonds using mild oxidizing conditions, as proved by fluorescence and quartz crystal microbalance measurements. Finally, the reversible release/regrafting of the dye under redox stimulation is demonstrated.},
  author       = {Belbekhouche, Sabrina and Reinicke, Stefan and Espeel, Pieter and Du Prez, Filip and Eloy, Pierre and Dupont-Gillain, Christine and Jonas, Alain M and Demoustier-Champagne, Sophie and Glinel, Karine},
  issn         = {1944-8244},
  journal      = {ACS APPLIED MATERIALS & INTERFACES},
  keywords     = {polythiol,disulfide link,thiolactone aminolysis,stimuli-responsive polymer,gold surface modification,responsive surface,drug release,SELF-ASSEMBLED MONOLAYERS,DRUG-DELIVERY,ONE-POT,IMPEDANCE SPECTROSCOPY,POLYMER CAPSULES,GOLD SURFACES,SYSTEMS,THIOL,CARRIER,NANOPARTICLE},
  language     = {eng},
  number       = {24},
  pages        = {22457--22466},
  title        = {Polythiolactone-based redox-responsive layers for the reversible release of functional molecules},
  url          = {http://dx.doi.org/10.1021/am506489j},
  volume       = {6},
  year         = {2014},
}

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