Poly(disulfide)s: From Synthesis to Drug Delivery

Zhang, Ruhe; Nie, Tianqi; Ying, Fang; Huang, Hai; Wu, Jun

doi:10.1021/acs.biomac.1c01210

Cited by 54 publications

(38 citation statements)

References 180 publications

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“…[24][25][26][27] It was reported that dynamic disulfide bonds were labile (e.g., disulfide exchange, thiol-disulfide exchange, reduction-oxidation, and radical-mediated disulfide fragmentation) under heat, photoirradiation, and mechanical stress. [28] The responsivity may enable a self-healing property at high temperatures or under photo-irradiation. When characterizing by the tensile strain at break (Figure S7C, Supporting Information), the elastomer showed a healing efficiency of 90% after healing at 60 °C for 4 h (Figure 1F).…”

Section: Resultsmentioning

confidence: 99%

Reversible Wet‐Adhesive and Self‐Healing Conductive Composite Elastomer of Liquid Metal

Pei

Liu

et al. 2022

Adv Funct Materials

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Stretchable conductors with the combination of high elasticity and electric conductivity have long been pursued in soft electronics. Liquid metals (LMs), whose mechanical properties match well with the elastomeric matrix, have been successfully applied in soft robotics, electronic skins and wearable devices. But it remains challenging to develop conductive composite elastomers of LMs with reversible adhesion and self-healing. Herein, EGaIn droplets are uniformly dispersed into elastomer, which contain dynamic disulfide to endow the composite elastomer with thermal processability, recyclability, reversible wet adhesion, and self-healing. With the EGaIn content of ≥40 vol.%, the resultant composite elastomer shows the electric conductivity of 1.3 × 104 S m −1 , self-healing in 8.0 h, and reversible wet adhesion strength up to 670 kPa after curing for 2.0 h. When serving as conductive adhesive, it can easily adhere to the metal electrode to light up the LED even when stretched to 50%. When serving as self-adhesive bioelectrode, it can also detect human electromyography signals. Thus, not only may this study provide a new platform of designing self-adhesive, self-healing, and conductive composite elastomers of liquid metals, but their reversible wet adhesion and self-healing also promise the facileness of building damage-endurable soft electronics and applying to human-machine interfaces.

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Section: Resultsmentioning

confidence: 99%

Reversible Wet‐Adhesive and Self‐Healing Conductive Composite Elastomer of Liquid Metal

Pei

Liu

et al. 2022

Adv Funct Materials

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“…The ring-opening polymerization (ROP) of 1,2-dithiolanes affords polydisulfides (PDS) with fascinating self-adaptive, highly dynamic, and stimuli-responsive properties. − Lipoic acid (LPA) and its derivatives, for example, are the most frequently studied 1,2-dithiolane monomers for their biogenesis source, intrinsic biocompatibility, and ease of modification. Although the polymerization of LPA can be traced back to as early as the 1940s, the PDS were not explicitly explored until the past decade. , A series of pioneering works were accomplished by Matile and co-workers, who reported LPA-derived PDS with unusual thiol–disulfide exchange-mediated cellular penetration ability. − Yao et al have coupled various LPA-derived PDS to nanoparticles and proteins, achieving efficient cytosolic delivery of the cargos. − Waymouth and Moore et al have carefully studied the polymerizability of various 1,2-dithiolanes and the topology control of PDS in organic solvents, respectively. , Moreover, Qu and Feringa et al have together fabricated various fascinating self-healing and recyclable bulk PDS-based materials. − Taking advantage of their unique properties of PDS, numerous new applications have been demonstrated including hydrogels, catalysis, gene delivery, etc. ,− …”

Section: Introductionmentioning

confidence: 99%

Room-Temperature Grafting from Synthesis of Protein–Polydisulfide Conjugates via Aggregation-Induced Polymerization

et al. 2022

J. Am. Chem. Soc.

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The reversible modification of proteins with lipoic acid (LPA)-derived polydisulfides (PDS) is an important approach toward the transient regulation and on-demand recovery of protein functions. The in situ growth of PDS from the cysteine (Cys) residue of a protein, however, has been challenging due to the nearequilibrium thermodynamics of the ring-opening polymerization of LPA. Here, we report the protein-mediated, aggregation-induced polymerization (AIP) of amphiphilic LPA-derived monomers at room temperature, which can be performed at a concentration as low as ∼2% of the equilibrium monomer concentration normally needed. The aggregation of monomers increases the effective monomer concentration in aqueous solutions to the degree that the polymerizations behave similarly to those in bulk. The PDS conjugation enhances the thermostability, protease resistance, and tolerance to freeze−thaw treatments of the target proteins. Moreover, the PDS conjugation allows rapid and convenient purification of Cys-bearing proteins by taking advantage of the liquid− liquid phase separation of the protein−PDS conjugates and the full recovery of native proteins under mild reducing conditions. This AIP effect may shed light on facilitating other polymerizations with a similar near-equilibrium character. The PDS conjugation can open up new avenues to protein delivery, dynamic and reversible protein engineering, enzyme preservation, and recycling.

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“…The thiol–maleimide linkage is considerably robust in nature and only upon exposure to excess competitive thiol undergoes a relatively slow degradation . In this regard, the disulfide bond is unique for its rapid cleavage upon exposure to moderate amounts of thiol, an attribute that has been widely exploited in the fabrication of stimuli-responsive polymeric materials. − The advantage of the approach outlined here is that the complementary reactive groups used allow the formation of a disulfide-containing near-well-defined network structure. During gelation, there is no small-molecule byproduct formation; thus, gels can be used as prepared.…”

Section: Introductionmentioning

confidence: 99%

Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry

et al. 2022

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Fast-forming yet easily dissolvable hydrogels (HGs) have potential applications in wound healing, burn incidences, and delivery of therapeutic agents. Herein, a combination of a thiol–maleimide conjugation and thiol–disulfide exchange reaction is employed to fabricate fast-forming HGs which rapidly dissolve upon exposure to dithiothreitol (DTT), a nontoxic thiol-containing hydrophilic molecule. In particular, maleimide disulfide-terminated telechelic linear poly(ethylene glycol) (PEG) polymer and PEG-based tetrathiol macromonomers are employed as gel precursors, which upon mixing yield HGs within a minute. The selectivity of the thiol–maleimide conjugation in the presence of a disulfide linkage was established through 1 H NMR spectroscopy and Ellman’s test. Rapid degradation of HGs in the presence of thiol-containing solution was evident from the reduction in storage modulus. HGs encapsulated with fluorescent dye-labeled dextran polymers and bovine serum albumin were fabricated, and their cargo release was investigated under passive and active conditions upon exposure to DTT. One can envision that the rapid gelation and fast on-demand dissolution under relatively benign conditions would make these polymeric materials attractive for a range of biomedical applications.

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Poly(disulfide)s: From Synthesis to Drug Delivery

Cited by 54 publications

References 180 publications

Reversible Wet‐Adhesive and Self‐Healing Conductive Composite Elastomer of Liquid Metal

Reversible Wet‐Adhesive and Self‐Healing Conductive Composite Elastomer of Liquid Metal

Room-Temperature Grafting from Synthesis of Protein–Polydisulfide Conjugates via Aggregation-Induced Polymerization

Fast-Forming Dissolvable Redox-Responsive Hydrogels: Exploiting the Orthogonality of Thiol–Maleimide and Thiol–Disulfide Exchange Chemistry

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