Disulfide chemistry in responsive aggregation of amphiphilic systems

Bej, Raju; Dey, Pradip; Ghosh, Suhrit

doi:10.1039/c9sm01960j

Cited by 45 publications

(31 citation statements)

References 166 publications

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“…In fact, the strategy described in this paper could be applied to retinoids in general to achieve an accelerated release. Even if those studies are not directly comparable, the GSH-enhanced release of hydrophobic content is consistent with the supposed mechanism of the NC degradation via disulfide bonds cleavage [ 57 , 58 ]. The more plausible explanation according to the literature is that the PEG hydrophilic chains are then detached from the hydrophobic PLA core causing the destabilization of the NCs leading to the higher release of the contents [ 6 ].…”

Section: Resultsmentioning

confidence: 80%

Three-Step Synthesis of a Redox-Responsive Blend of PEG–block–PLA and PLA and Application to the Nanoencapsulation of Retinol

Gheluwe

Buchy²,

Chourpa

et al. 2020

Polymers

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Smart polymeric nanocarriers have been developed to deliver therapeutic agents directly to the intended site of action, with superior efficacy. Herein, a mixture of poly(lactide) (PLA) and redox-responsive poly(ethylene glycol)–block–poly(lactide) (PEG–block–PLA) containing a disulfide bond was synthesized in three steps. The nanoprecipitation method was used to prepare an aqueous suspension of polymeric nanocarriers with a hydrodynamic diameter close to 100 nm. Retinol, an anti-aging agent very common in cosmetics, was loaded into these smart nanocarriers as a model to measure their capacity to encapsulate and to protect a lipophilic active molecule. Retinol was encapsulated with a high efficiency with final loading close to 10% w/w. The stimuli-responsive behavior of these nanocarriers was demonstrated in vitro, in the presence of l-Glutathione, susceptible to break of disulfide bond. The toxicity was low on human keratinocytes in vitro and was mainly related to the active molecule. Those results show that it is not necessary to use 100% of smart copolymer in a nanosystem to obtain a triggered release of their content.

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Section: Resultsmentioning

confidence: 80%

Three-Step Synthesis of a Redox-Responsive Blend of PEG–block–PLA and PLA and Application to the Nanoencapsulation of Retinol

Gheluwe

Buchy²,

Chourpa

et al. 2020

Polymers

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“…219,220 Especially, the degradation of disulfide crosslinkers as response to intracellular GSH has been used to design new nanogel carriers for drugs and biomolecules. 221 In contrast to such labile crosslinks, the reduction of disulfides can also be exploited to introduce hydrophilicity due to the generated thiol groups in a hydrophobic nanogel. Using this strategy, Lowry and colleagues reported amphiphilic nanogels containing hydrophilic thiols for mercury removal applications.…”

Section: Deprotection Of Masked Hydrophilic Moietiesmentioning

confidence: 99%

Amphiphilic micro‐ and nanogels: Combining properties from internal hydrogel networks, solid particles, and micellar aggregates

Biglione

Neumann-Tran

Kanwal

et al. 2021

Journal of Polymer Science

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Polymeric micro-and nanogels are defined by their water-swollen hydrophilic networks that can often impart outstanding biocompatibility and highcolloidal stability. Unfortunately, this highly hydrophilic nature limits their potential in areas where hydrophobic or amphiphilic interactions are required, for example, the delivery of hydrophobic cargoes or tailored interactions with amphipathic (bio-)surfaces. To overcome this limitation, amphiphilic microÀ/nanogels are emerging as new colloidal materials that combine properties from hydrogel networks with hydrophobic segments, known from solid hydrophobic polymer particles or micellar cores. The ability to accurately adjust the balance of hydrophobic and hydrophilic components in such amphiphilic colloidal systems enables new tailored properties. This opens up new applications ranging from the

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“…We envisaged it would be even better for delivery applications if a supramolecular assembly could ensure that the protein was not accessible unless it was intentionally released in response to an external stimulus. With this objective, we synthesized NDI-28 (Figure a) in which BSA was conjugated with an amide-containing SSDU (similar to NDI-25, Figure ) by a glutathione-responsive disulfide linker . We assumed that NDI-28 would produce bundles of fibers, similar to NDI-25, which would help to locate the protein in the protected interior of the fibrillar network and provide the desired stability.…”

Section: Ssdu-regulated Assembly Of Proteinsmentioning

confidence: 99%

Molecular Recognition Driven Bioinspired Directional Supramolecular Assembly of Amphiphilic (Macro)molecules and Proteins

et al. 2021

Self Cite

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Metrics & MoreArticle Recommendations CONSPECTUS: Bioinspired self-assembly has been explored with diverse synthetic scaffolds, among which amphiphiles are perhaps the most extensively studied systems. Classical surfactants or amphiphilic block copolymers, depending on the hydrophobic− hydrophilic balance, produce distinct nanostructures, which hold promise for applications ranging from biology to materials sciences. Nevertheless, their immiscibility-driven aggregation does not provide the opportunity to precisely regulate the internal order, morphology, or functional group display, which is highly desirable, especially in the context of biological applications.A new class of amphiphiles have emerged in the recent past in which the hydrophilic segment(s) is appended with a hydrophobic supramolecular-structure-directing-unit (SSDU), consisting of a π-conjugated chromophore and a H-bonding group. Selfrecognition of the SSDU by attractive directional interactions governs the supramolecular assembly, which is fundamentally different than the repulsive solvent-immiscibility driven aggregation of traditional amphiphiles. Such SSDU-appended hydrophilic polymers exhibit entropy-driven highly stable self-assembly producing distinct nanostructures depending on the H-bonding functional group. For example, polymers with the hydrazide-functionalized SSDU attached form a polymersome, while in a sharp contrast, the same polymers when connected to an amide containing SSDU produce a cylindrical micelle via a spherical-micelle intermediate. This relationship holds true for a series of SSDU-attached hydrophilic polymers irrespective of the hydrophobic/hydrophilic balance or chemical structure, indicating that the supramolecular-assembly is primarily controlled by the specific molecular-recognition motif of the SSDU, instead of the packing parameter-based norms. Beyond synthetic polymers, SSDU-attached proteins also exhibit similar molecular-recognition driven self-assembly as well as coassembly with SSDU-attached polymers or hydrophilic wedges, producing multi-stimuli-responsive nanostructures in which the protein gains remarkable protection from thermal denaturation or enzymatic hydrolysis and exhibits redox-responsive enzymatic activity. Furthermore, SSDU-derived bola-shape π-amphiphiles have been recognized as a useful scaffold for the synthesis of unsymmetric polymersomes, rarely reported in the literature. The building block consists of a hydrophobic naphthalene-diimide (NDI) π-system attached to a hydrophilic functional group (ionic or nonionic) and a nonionic wedge on its two opposite arms. Extended H-bonding among the hydrazide groups, placed only on one side of the central chromophore by design, ensures stacking of the NDIs with parallel orientation and induces a preferred direction of curvature so that the H-bonded chain and consequently the functional groups attached to the same side remain at the inner-wall of the supramolecular polymersome. Automatically, the functional groups, located on the other side, are displayed ...

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Disulfide chemistry in responsive aggregation of amphiphilic systems

Abstract: We highlight the nanostructure assemblies containing disulfide linkages, dynamics, GSH triggered disassembly and implications in biological applications.

Cited by 45 publications

References 166 publications

Three-Step Synthesis of a Redox-Responsive Blend of PEG–block–PLA and PLA and Application to the Nanoencapsulation of Retinol

Three-Step Synthesis of a Redox-Responsive Blend of PEG–block–PLA and PLA and Application to the Nanoencapsulation of Retinol

Amphiphilic micro‐ and nanogels: Combining properties from internal hydrogel networks, solid particles, and micellar aggregates

Molecular Recognition Driven Bioinspired Directional Supramolecular Assembly of Amphiphilic (Macro)molecules and Proteins

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