The substituent effect on the antioxidant capacity of catechols and resorcinols

Ortega-Moo, Cristina; Garza, Jorge; Vargas, Rubicelia

doi:10.1007/s00214-016-1932-7

Cited by 20 publications

(17 citation statements)

References 45 publications

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“…For the catechol, this energy difference is of 4.1 kcal/mol [37] and for systems related with catechol also exhibit an energy difference of 4.1 kcal/mol. [20] Thus, estimations given in this work, deliver similar information to results reported in other studies. Some geometrical parameters obtained for DA 1 , DA 2 and DA wo are reported in Table 1.…”

Section: Geometry Analysissupporting

confidence: 89%

“…[36] In order to test one hypothesis proposed in this work, eight additional compounds were considered, with and without IHB. These compounds are based on the catechol moiety, which correspond to those studied by Ortega et al [20], these structures are represented in Fig. 2.…”

Section: Computational Detailsmentioning

confidence: 99%

“…This result agrees with results reported by Ortega-Moo et al, where it is remarkable that this IHB is not relevant for the antioxidant capacity in a family of catechols and resorcinols. [20] Global chemical predictors revised in Section 2 are reported in Table 2 for DA 1 , DA 2 and DA wo . From this table, it is evident that ω + exhibits small values, since the electron affinity has an important weight on this quantity and therefore the dopamine is not good electron acceptor, as it was mentioned above.…”

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

“…In particular, Ortega-Moo et al, have characterized this contact over some substituted catechols, by using three scalar fields, the non-covalent interaction index, the electron density through the atoms in molecules theory and the electron localization function. From their results, none of the scalar fields used ensures that an IHB is present in these kind of compounds, [20] giving important information about this possible contact. In addition, Ortega-Moo et al show that this contact is totally irrelevant to describe several chemical reactivity indicators.…”

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confidence: 99%

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Reactivity Sites in Dopamine Depend on its Intramolecular Hydrogen Bond

García‐Hernández

Garza

2017

J. Mex. Chem. Soc.

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In this work, three conformers of dopamine were theoretically analyzed, two of them forming an intramolecular hydrogen bond between OH groups in the catechol moiety, the third one without this interaction. The used theoretical method was based on the Kohn-Sham method within the hybrid exchange-correlation functionals without empirical parameters, PBE0. The molecular geometry obtained by this method was contrasted with that obtained from the second-order many-body perturbation theory (MP2) method and the 6-31+G(d), 6-311+G(d) and 6-311++G(d,p) basis sets. Global reactivity descriptors were predicted by using only the PBE0/6-311++G(d,p) method. This method revealed that dopamine is not a good acceptor of electrons. Thus, in one charge transfer process, this compound prefers donating electrons, as observed experimentally. All global chemical predictors do not show important changes regardless of the presence of an intramolecular hydrogen bond. However, in the case of local reactivity predictors, oxygen atoms of the catechol moiety exhibit changes when this contact is present. This conclusion was confirmed when 8 catechol derivatives were analyzed with the same procedure applied over the dopamine. Additionally, the carbon atoms opposite to the carbon atoms linked to oxygen atoms, in the catechol moiety, present the biggest changes when these systems donate one electron. Consequently, the electron involved during the charge transfer process of these systems will be detached from the region defined between these two carbon atoms.

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Section: Geometry Analysissupporting

confidence: 89%

Section: Computational Detailsmentioning

confidence: 99%

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

mentioning

confidence: 99%

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Reactivity Sites in Dopamine Depend on its Intramolecular Hydrogen Bond

García‐Hernández

Garza

2017

J. Mex. Chem. Soc.

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“…As a rule, antioxidants are produced in the organism or enter with food . It is worth to note that a lot of antioxidants have aromatic 1,2‐diols (catechols) structure, which accounts for their easy oxidation …”

Section: Introductionmentioning

confidence: 99%

Germanium Dioxide and the Antioxidant Properties of Catechols

et al. 2019

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Complexes of tetra-and hexa-coordinated germanium Adr Cat 2 Ge (1, Adr Cat = adrenaline catecholate), Ald Cat 2 Ge (2, Ald Cat = 4-formylcatecholate), Ald Cat 3 Ge(Et 3 NH) 2 (3) were synthesized by the reaction of germanium dioxide with adrenaline and 3,4-dihydroxybenzaldehyde in aqueous solution. The structures of the complexes were confirmed by 1 H and 13 C NMR and IR spectroscopy, HRMS, and elemental analysis. Cyclic voltammetry in phosphate buffer solutions (pH = 6.86) has shown the oxidation potentials E p of these complexes to be shifted by ca. 330-360 mV to more positive potentials compared to the parent aromatic diols, which means that their electron-releasing properties were diminished by about 7.6-8.3 kcal mol -1 . A study of the kinetics of the reaction of these complexes with 2,2diphenyl-1-picrylhydrazyl (DPPH) free radical in the presence of [a] N.

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A Sprayable Janus Hydrogel as an Effective Bioadhesive for Gastrointestinal Perforation Repair

Wang,

Xu,

et al. 2024

Adv Funct Materials

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Advancements in hydrogel bioadhesives for sealing gastrointestinal perforations (GP) face challenges due to weak mechanical properties, causing leakage, especially on uneven wound surfaces. Herein, a Janus hydrogel is introduced featuring a two‐step cross‐linking process, designed to serve as an efficient bioadhesive using a sprayable method. This Janus hydrogel formulation is achieved by modifying a photocurable hyaluronic acid hydrogel with dopamine (DA) and phenylboronic acid (PBA) groups, enabling reversible boronate ester bonds. These dynamic cross‐linking bonds facilitate shear‐thinning and self‐healing abilities, ensuring secure adhesion to complex wounds. A subsequent photocurable irreversible cross‐linking stage results in the formation of a hydrogel barrier with asymmetric adhesive properties, imparting inherent mechanical strength for postoperative anti‐adhesion. To enhance the clinical practicality of this hydrogel, an integrated sprayer device is further developed, enabling the efficient delivery of hydrogel at any angle and over long distances under minimally invasive conditions. Therefore, the HADP hydrogel, integrated with the sprayer device, successfully addressed the limitations associated with hydrogel bioadhesives in clinical applications concerning angles and terrains. This integrated approach presents a compelling solution for repairing gastrointestinal perforations in clinical settings. Moreover, it demonstrates significant potential for diverse applications in repairing complex wound surfaces.

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The substituent effect on the antioxidant capacity of catechols and resorcinols

Cited by 20 publications

References 45 publications

Reactivity Sites in Dopamine Depend on its Intramolecular Hydrogen Bond

Reactivity Sites in Dopamine Depend on its Intramolecular Hydrogen Bond

Germanium Dioxide and the Antioxidant Properties of Catechols

A Sprayable Janus Hydrogel as an Effective Bioadhesive for Gastrointestinal Perforation Repair

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