Origin of iodine preferential attack at sulfur in phosphorothioate and subsequent P-O or P-S bond dissociation

Huang, Qiang; Lee, Ga Young; Li, Jiayi; Wang, Chuan; Zhao, Rosalinda; Deng, Zixin; Houk, K. N.; Zhao, Yi‐Lei

doi:10.1073/pnas.2119032119

Cited by 11 publications

(16 citation statements)

References 52 publications

(64 reference statements)

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“…A recent study found that Tri-HCl buffer takes an active role in DNA cleavage ( Huang et al, 2022b ), so Tri-HCl buffer was selected to provide a positive reaction environment for DTAFP. Since Tris-HCl was a neutral and weakly basic buffer, the prepared aptasensor were tested in Tris-HCl buffer ranging from pH 7 to pH 9.5, Figure 5C observed that the DPV response signal reached a maximum at pH 7.…”

Section: Resultsmentioning

confidence: 99%

Dual-Target Electrochemical Sensor Based on 3D MoS2-rGO and Aptamer Functionalized Probes for Simultaneous Detection of Mycotoxins

Han

Yin

et al. 2022

Front. Chem.

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A dual-target aptamer functionalized probes (DTAFP) was applied for the detection of aflatoxin B1 (AFB1) and zearalenone (ZEN) simultaneously, which has not been reported. Meanwhile, two functional materials for signal amplification of the DTAFP were synthesized: 1) a three-dimensional molybdenum disulfide-reduced graphene oxide (MoS2-rGO) as a favorable loading interface; 2) a double-probes gold nanoparticles (AuNPs) modified by Thionin (Thi) and 6-(Ferrocenyl) hexanethiol (FC6S) as distinguishable and non-interfering signals. Mycotoxins on the electrode surface release into solution under the function of the DTAFP, leading a reduction of the differential peak impulse in signal response. Under the optimum conditions, the aptasensor exhibited a detection range of 1.0 pg mL−1–100 ng mL−1 for AFB1 and ZEN, with no observable cross reactivity. In addition, the aptasensor performed excellent stability, reproducibility, specificity, and favorable recovery in the detection of edible oil. This work demonstrated a novel method for the construction of a simple, rapid, and sensitive aptasensor in the detection of multiple mycotoxins simultaneously.

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Section: Resultsmentioning

confidence: 99%

Dual-Target Electrochemical Sensor Based on 3D MoS2-rGO and Aptamer Functionalized Probes for Simultaneous Detection of Mycotoxins

Han

Yin

et al. 2022

Front. Chem.

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“…Low-energy conformers were optimized with the dispersion-included ωB97X-D functional in Gaussian 16 with the 6–31+G(d,p) basis set. , The prediction of reactive sites between the nucleophile and electrophile was studied by Hirshfeld charges, frontier molecular orbital (FMO) analysis, and Fukui functions (FFs). The details have been provided in previous works. − The isosurface maps were produced according to the outputs from Multiwfn calculations . We used the SMD solvation model to optimize the structure and calculate the frequency, obtaining the Gibbs free energy at 298 K via the GoodVibes program , Intrinsic reaction coordinate (IRC) calculations were conducted to determine the transition states.…”

Section: Methodsmentioning

confidence: 99%

High-Molecular-Weight and Light-Colored Disulfide-Bond-Embedded Polyesters: Accelerated Hydrolysis Triggered by Redox Responsiveness

Hu,

Luan,

et al. 2023

Biomacromolecules

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Disulfide bonds have attracted considerable attention due to their reduction responsiveness, but it is crucial and challenging to prepare disulfide-bond-based polyesters by melt polycondensation. Herein, the inherently poor thermal stability of the S–S bond in melting polycondensation was overcome. Moreover, poly(butylene succinate-co-dithiodipropionate) (PBSDi) with a light color and high molecular weights (Mn values up to 84.7 kg/mol) was obtained. These polyesters can be applied via melt processing with T d,5% > 318 °C. PBSDi10-PBSDi40 shows good crystallizability (crystallinity 56–38%) and compact lamellar thickness (2.9–3.2 nm). Compared with commercial poly(butylene adipate-co-terephthalate) (PBAT), the elevated mechanical and barrier performances of PBSDi make them better packaging materials. For the degradation behavior, the disulfide monomer obviously accelerates the enzyme degradation but has a weaker effect on hydrolysis. In 0.1 mol/L or higher concentrations of H2O2 solutions, the oxidation of disulfide bonds to sulfoxide and sulfone groups can be realized. This process results in a stronger nucleophilic attack, as confirmed by the Fukui function and DFT calculations. Additionally, the greater polarity and hydrophilicity of oxidation products, proved by noncovalent interaction analysis, accelerate the hydrolysis of polyesters. Moreover, glutathione-responsive breakage, from polymers to oligomers, is confirmed by an accelerated decline in molecular weight. Our research offers fresh perspectives on the effective synthesis of the disulfide polyester and lays a solid basis for the creation of high-performance biodegradable polyesters that degrade on demand.

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“…Then, we built PBXI–CALB systems and carried out MD simulations to study the enzymatic degradation mechanisms. The prereaction state analysis , and noncovalent interaction (NCI) analysis , of PBXI–CALB were performed to reveal the origin of substrate preference (details of MD simulations and subsequent analyses are given in the Supporting Information). Isosurface maps were produced using the VMD 1.9.3 program and Multiwfn 3.7 software package …”

Section: Methodsmentioning

confidence: 99%

Efficient Synthesis of Itaconate Polyesters with Amine-Triggered Rapid Degradation and Outstanding Mechanical Properties: An Experimental and Theoretical Study on Degradation Mechanisms

Wang

et al. 2022

Macromolecules

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A range of degradable polyesters have been developed as sustainable alternatives for commercial plastics; however, limitations of composting facilities and uncontrolled degradation in the environment hindered their viability. In this study, biobased itaconic acid was selected as an active site to control the degradation of polyesters. A series of PBXI copolyesters with M w 's ranging from 4.86 to 8.31 × 10 4 g/mol and high intrinsic viscosities of more than 1.15 dL/g were successfully synthesized without any crosslinking by selecting appropriate reaction conditions, including condensation temperature and vacuum, effective inhibitor, and catalyst. The obtained copolyesters were semicrystalline, and their T m 's could be regulated from 42.5 to 179.5 °C. They exhibited outstanding elastic modulus (120−598 MPa) and tensile strength (17.9−51.4 MPa) among degradable polymers. Degradation experiments demonstrated that the incorporation of itaconate segments could facilitate both the hydrolysis and enzymatic degradation of polyesters. The state-of-the-art computation and analysis via molecular dynamics (MD) simulations of PBXI−CALB complexes elucidated the enzymatic degradation mechanism. Experimental results proved that, at room temperature, the degradation could be stimulated and regulated by amines without a catalyst and the M n 's of lactamization products rapidly decreased to less than 5000 g/mol within 24 h. Moreover, the copolymerized structure of copolyesters and solvent factors could influence the aza-Michael addition between amines and itaconate units. This work provides a strategy to synthesize biodegradable copolymers with the potential to undergo controlled and rapid in vivo degradation with outstanding mechanical properties.

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Origin of iodine preferential attack at sulfur in phosphorothioate and subsequent P-O or P-S bond dissociation

Cited by 11 publications

References 52 publications

Dual-Target Electrochemical Sensor Based on 3D MoS2-rGO and Aptamer Functionalized Probes for Simultaneous Detection of Mycotoxins

Dual-Target Electrochemical Sensor Based on 3D MoS2-rGO and Aptamer Functionalized Probes for Simultaneous Detection of Mycotoxins

High-Molecular-Weight and Light-Colored Disulfide-Bond-Embedded Polyesters: Accelerated Hydrolysis Triggered by Redox Responsiveness

Efficient Synthesis of Itaconate Polyesters with Amine-Triggered Rapid Degradation and Outstanding Mechanical Properties: An Experimental and Theoretical Study on Degradation Mechanisms

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