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The dynamic disulfide linkage plays a vital role in various biological processes as well as drugs and biomaterials. Oxidation of thiols is a widely utilized approach for disulfide synthesis; however, achieving both optimal reactivity and selectivity continues to pose a significant challenge. Here, we report the redox-click chemistry for disulfide f...
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... Text: In nature, disulfide bonds are crucial for protein folding and stability (1), as well as a prevalent moiety in drugs and biomaterials (Fig.1). The dynamic nature of disulfide bonds makes them an attractive reversible linkage for on-demand drug delivery (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). ...
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... in drugs and biomaterials (Fig.1). The dynamic nature of disulfide bonds makes them an attractive reversible linkage for on-demand drug delivery (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). Recently, biodegradable cell-penetrating poly(disulfide)s have been employed to deliver drugs, nucleic acids, and proteins into cells via thiol-mediated uptake pathways (Fig. 1B) (4,5). Moreover, antibody-drug conjugates 5 (ADCs) emerged as a significant class of cancer therapeutics, with disulfides used as the predominant chemically cleavable motifs in ADC linkers (Fig. 1C) (6). Disulfide-containing polymers, owing to their inherent biodegradability and biocompatibility, also serve as biomaterials and are ...
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... cell-penetrating poly(disulfide)s have been employed to deliver drugs, nucleic acids, and proteins into cells via thiol-mediated uptake pathways (Fig. 1B) (4,5). Moreover, antibody-drug conjugates 5 (ADCs) emerged as a significant class of cancer therapeutics, with disulfides used as the predominant chemically cleavable motifs in ADC linkers (Fig. 1C) (6). Disulfide-containing polymers, owing to their inherent biodegradability and biocompatibility, also serve as biomaterials and are extensively utilized in tissue engineering and wound healing applications (Fig. 1D) (7)(8)(9)(10)(11). Considering the importance of disulfide linkages in drugs, natural products, and biomaterials, it ...
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... as a significant class of cancer therapeutics, with disulfides used as the predominant chemically cleavable motifs in ADC linkers (Fig. 1C) (6). Disulfide-containing polymers, owing to their inherent biodegradability and biocompatibility, also serve as biomaterials and are extensively utilized in tissue engineering and wound healing applications (Fig. 1D) (7)(8)(9)(10)(11). Considering the importance of disulfide linkages in drugs, natural products, and biomaterials, it is 10 imperative to develop highly efficient, selective, and biocompatible synthetic methodologies. Thiol-disulfide exchange serves as the basis for most in vivo enzyme-catalyzed disulfide linkage formation process ...
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... reaction between the same amount of 1g and 1ad gave 76% of the crosscoupling product with only <15% symmetrical disulfide formed from the competitive homocoupling reaction. By increasing the amount of the aliphatic thiols to 2 equiv., good yields can be 10 obtained for a range of aromatic thiols (1g, 1i-1l, 1p, 1t, 1x) and aliphatic thiols (1ab, 1ad). To explain the unusual selectivity of this cross-coupling reaction, a series of controlled reaction were conducted (see SI 13 for details). ...
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... modified chitosan, was selected for investigation. The results showed that rapid hydrogel formation could be achieved by mixing an aqueous solution of N-acetyl-L-cysteine modified chitosan and Et3N, and a solution of SO2F2 in 15 CH3CN (Fig. 6A). The dynamic time sweep rheological experiment revealed an immediate crossover of G′ and G″ (Fig. S11), signifying the swift formation of a 3D network through disulfide cross-linkers. When the freshly mixed in-situ gel was applied to porcine skin, a tissue adhesive strength of 42.5 kPa was observed after 16 h, which was comparable to that of other in-situ hydrogels cured by UV radiation (Table S11). In a separate experiment, a colored ...
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... 98% at the hydrogel concentration of 25000 ug/mL after 24 h incubation period. Furthermore, to test the performance of this redox-click reaction in vivo, the in-situ gel was administered on a tissue defect model. This model entailed the generation of a dorsal wound, measuring 1.5 cm in length and 3 mm in depth, on Sprague Dawley rat dorsal skin (Fig. S13). The hydrogel exhibited rapid curing upon application to the wound, thus indicating the effectiveness of the redox-click reaction as a cross-linking method for in-situ gelling. Subsequent histological 5 analysis conducted after seven days revealed favorable biocompatibility for the hydrogel crosslinked by redox-click reaction (Fig. ...
