Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes

Chang, Chaokang; Song, Meng; Ma, Minglin; Song, Jihong; Cao, Fengyi; Qin, Qi

doi:10.3390/molecules28030955

Cited by 20 publications

(7 citation statements)

References 36 publications

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“…In addition to the binding energy ( E binding ), the solubility parameter can be used to evaluate the compatibility of the antioxidant and NR, where the latter could not only dictate the permeability rate of O 2 inflowing the NR matrix but also ensure the reactivity among oxygen and the NR chain. − Therefore, suitable dispersibility becomes essential for screening antioxidant molecules. The solubility parameters could be computed using a semiempirical approach as follows. Δδ = | δ antioxidant − δ NR | …”

Section: Resultsmentioning

confidence: 99%

“…External stimuli, including light, heat, ozone, and oxygen, could significantly deteriorate the physical or chemical properties of NR products. − Thus, enhancing the NR’s oxidative aging resistance is of primary importance for physical or chemical property enhancement and for economic reasons. N -phenyl- N ′-(1,3-dimethyl butyl)- p -phenylenediamine (6-PPD) is a worldwide antioxidant commonly added to delay the thermo-oxidative degradation of tire rubbers. − 6-PPD functions by forming a protective layer on the tire surface and thus preferentially reacts with atmospheric ozone and oxygen, resulting in various transformation products (TPs). Moreover, 6-PPD migrates easily from the NR matrix at higher temperatures due to its low molecular weight , and loses its antiaging efficiency.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Insights into Antioxidant Efficiency of Melanin: A Sustainable Antioxidant for Natural Rubber Formulations

Abdul Sattar,

Patnaik

2023

J. Phys. Chem. B

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N-(1,3-Dimethyl butyl)-N′-phenyl-p-phenylenediamine (6-PPD) is a worldwide antioxidant commonly added to delay the thermo-oxidative degradation of tire rubbers. Unfortunately, 6PPD and its transformation product 6PPD-quinone are toxic to aquatic organisms (e.g., coho salmon). Herein, we explore the free radical scavenging activity and protective mechanism of melanin (MLN) on natural rubber's (NR's) oxidative resistance using molecular dynamics (MD) and quantum mechanical (QM) calculations. The relationship between the molecular structure and the chemical nature of the antioxidant molecules via transition state calculations is explored to unravel the reaction mechanisms of antioxidants interacting with peroxy radicals (ROO • ) of NR with the estimation of reaction barriers. Following this, the radical scavenging activity of antioxidants was quantified via a hydrogen atom transfer mechanism and bond dissociation energy calculations. Parallel MD simulations were considered to study the interfacial interactions of antioxidant molecules with polymer chains and fillers with a quantifiable structure−property correlation. Given these results, the nanocomposite (NR-MLN-SiO 2 ) with natural antioxidant melanin manifested outstanding antioxidant properties by preferentially bagging the ROO • radicals, thus improving NR's thermal-oxidative aging relative to 6-PPD. The MD results revealed that the intermolecular interactions at the NR/antioxidant interface benefited the antioxidant MLN to bind tightly to the NR in NR-MLN-SiO 2 composite, thus exhibiting improved dispersion, O 2 barrier properties, and thermo-oxidative stability, which could extend the service life of NR products (e.g., tires). In addition, as a sustainable antioxidant, MLN could replace toxic antioxidants like 6-PPD. More importantly, the QM/MD simulations provided a fundamental understanding of the mechanistic pathways of antioxidant molecules in NR composites, which are conducive to designing highperformance and sustainable green elastomers.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Molecular Insights into Antioxidant Efficiency of Melanin: A Sustainable Antioxidant for Natural Rubber Formulations

Abdul Sattar,

Patnaik

2023

J. Phys. Chem. B

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“…Crystal structures of CD-MOFs and β-CD were extracted from the reported single-crystal structure. ,,, To prepare the I 2 molecule model, molecular minimization simulations were conducted using NAMD 2.6 parallel software package and the general amber force field (gaff). The docking program AutoDock Vina 1.1.2 was employed to perform the automated molecular docking calculation .…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Structure of the β-Cyclodextrin Metal–Organic Framework Optimizes Iodine Stability and Its Co-delivery with l-Menthol for Antibacterial Applications

Zhao,

Li,

Guo

et al. 2024

ACS Appl. Mater. Interfaces

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The spread of upper respiratory tract (URT) infections harms people's health and causes social burdens. Developing targeted treatment strategies for URT infections that exhibit good biocompatibility, stability, and strong antimicrobial effects remains challenging. The dual antimicrobial and antiviral effects of iodine (I 2 ) in combination with the cooling sensation of L-menthol in the respiratory tract can simultaneously alleviate URT inflammation symptoms. However, as both I 2 and L-menthol are volatile, addressing stability issues is crucial. In this study, a potassium iodide β-cyclodextrin metal−organic framework [β-CD-POF(I)] with appropriate particle size was used to coload and deliver I 2 and L-menthol. Primarily, β-CD-POF(I) was employed as the most efficient carrier to significantly enhance the stability of I 2 , surpassing any other known protection strategies in the pharmaceutical field (CD complexations, PVP conjugations, and cadexomer iodine). The mechanism underlying the improvement in stability of I 2 by β-CD-POF(I) was investigated through scanning electron microscopy with energy-dispersive X-ray spectroscopy, Xray photoelectron spectroscopy, Raman spectroscopy, and molecular docking. The results revealed that the key processes involved in improving stability were the inclusion of I 2 by β-CD cavities in β-CD-POF(I) and the formation of polyiodide anion between iodine ions and I 2 . Furthermore, the potential of β-CD-POF(I) to load and deliver drugs was validated, and coloading of L-menthol and I 2 demonstrated reliable stability. β-CD-POF(I) achieved a rate of URT deposition ≥95% in vitro, and the combined antibacterial effects of coloaded I 2 and L-menthol was better than I 2 or PVP-I alone, with no irritation noted following URT administration in rabbits. Therefore, the stable coloading of drugs by β-CD-POF(I), leading to enhanced antimicrobial effects, provides a new strategy for treating URT infections.

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“…due to its exceptional entropy-elasticity. The NR molecular chains contain cis -1,4-polyisoprene units with numerous active allylic hydrogen atoms and CC bonds, which makes NR highly vulnerable to thermo-oxidative degradation caused by heat, oxygen, ultraviolet (UV), etc. − As an indispensable antioxidant globally, 6PPD ( N -(1,3-dimethyl butyl)- N ′′-phenyl- p -phenylenediamine) is employed to retard the thermo-oxidative aging of tires. − The thin layer of 6PPD on the tire surface shields the tire from atmospheric ozone and oxygen, thus acting as an antiozonant, resulting in various transformation products. , However, 6PPD and 6PPD-quinone (6PPD-Q), an oxidative product of 6PPD are harmful to aquatic and human life. − Although the increasing demand for automobiles resulted in a worldwide tire market, the reduction in the longevity of rubber products results in waste accumulation and causes environmental and health problems. , Specifically, the tire wear particles formed via abrasion loss of rubber products contained 6PPD and 6PPD-Q. They were found to be significant contaminants of roadway runoff that would eventually be released into the ecosystem.…”

Section: Introductionmentioning

confidence: 99%

Curcuma Longa-Based Green and Sustainable Antioxidants for Biopolymers

Abdul Sattar

2024

ACS Sustainable Chem. Eng.

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Unsaturated biopolymers (e.g., natural rubber (NR)) are highly vulnerable to thermo-oxidative degradation, which causes premature failure of NR products. As an indispensable antioxidant globally, 6PPD (N-(1,3-dimethyl butyl)-N′-phenyl-p-phenylenediamine) is employed to retard the thermo-oxidative aging of NR. Unluckily, 6PPD and 6PPD-quinone (an oxidative product of 6PPD) are highly harmful to aquatic and human life and, thus, obviously merit their replacement with sustainable and safer antioxidants for environmental protection. This study explored the use of natural antioxidant curcumin for NR-based polymer nanocomposites (PNCs). The combined experimental, molecular dynamics (MD), and quantum mechanics (QM) simulations are implemented to analyze the effect of isomeric forms of curcumin on the protective mechanism, oxidative stability, solubility, dispersibility, and diffusion in the NR matrix. The results revealed that both 6PPD and curcumin scavenged the free radical preferentially via a hydrogen atom transfer mechanism. The computed transition state energies show that curcumin's enolic form (i.e., Curcumin (E)) interacts preferentially with ROO. (peroxy) radicals of NR with the lower barrier energy compared to 6PPD and could protect the NR from thermo-oxidative aging. The MD simulations have shown that the interfacial interactions at the NRcurcumin interface resulted in stronger binding energies, thus improving solubility and dispersibility with lower mean square displacement than 6PPD. While the migration of antioxidants is necessary to replenish their concentrations at the tire surface, the higher diffusion rate may cause the physical loss of antioxidants and thus decrease the service life of NR-PNCs. Overall, the NR-PNCs loaded with natural antioxidant curcumin exhibited improved oxidative resistance and viscoelastic performance compared to PNCs made with 6PPD. Thus, as a sustainable and safe antioxidant, curcumin could open an essential avenue toward the substantial pollution abatement from accumulated waste NR products in making "Greener NR-PNCs.″

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Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes

Cited by 20 publications

References 36 publications

Molecular Insights into Antioxidant Efficiency of Melanin: A Sustainable Antioxidant for Natural Rubber Formulations

Molecular Insights into Antioxidant Efficiency of Melanin: A Sustainable Antioxidant for Natural Rubber Formulations

Supramolecular Structure of the β-Cyclodextrin Metal–Organic Framework Optimizes Iodine Stability and Its Co-delivery with l-Menthol for Antibacterial Applications

Curcuma Longa-Based Green and Sustainable Antioxidants for Biopolymers

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