Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

Baweja, Shefali; Panchagnula, Sanjana; Sanz, M. Eugenia; Pérez, Cristóbal; Evangelisti, Luca; Pate, Brooks H.

doi:10.1002/cphc.202000665

Cited by 11 publications

(7 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…19 ROS production leads to an oxidant-antioxidant imbalance or oxidative stress and can lead to irreversible biomolecules damage such as lipids, proteins, ribonucleic acid (RNA), and deoxyribonucleic acid (DNA), followed by cell death. 20,21 Other DNA damage mechanisms associated with quinone derivatives include DNA alkylating reaction and intercalation in the DNA double helix. 22 The quinone redox cycle may be influenced by adding electron-attracting or donating substituents to the quinoid system.…”

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Dias¹,

Campos²,

Moraes³

et al. 2023

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

The 1,4-naphthoquinones are an important group of compounds intensively studied because of their wide range of biological activities. Four 2-chloro-3-(substituted-phenylamino)- 1,4‑naphthoquinone derivatives were synthesized, and the vibrational modes of these molecules were assigned using Raman and Fourier transform infrared spectroscopy (FTIR) techniques. In addition, X-ray studies were performed for one of these derivatives. Density functional theory (DFT) calculations were also developed for these compounds and presented. In summary, the results obtained from these studies can assess chemical changes in the structures of functionalized quinones and the discovery of candidate biologically active compounds.

show abstract

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Dias¹,

Campos²,

Moraes³

et al. 2023

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…This chemical phenomenon takes place in (multi)‐substituted benzenes and in benzene rings fused to small saturated rings. Despite its interest, there are not many cases where it has been possible to observe this effect experimentally [30–33] …”

Section: Resultsmentioning

confidence: 99%

“…Despite its interest, there are not many cases where it has been possible to observe this effect experimentally. [30][31][32][33] As a result, it is interesting to assess in detail the structural changes induced by the addition of functional groups, a methoxy group (S), methyl group (MG) or vinyl group (VG), on the structures and bonding. For this purpose and due to the absence of experimental data on isotopologues, we used calculations at the B3LYP-GD3BJ/def2tzvp level which are the ones that best reproduce the experimental constants.…”

Section: Structural Analysismentioning

confidence: 99%

Bond Length Alternation and Internal Dynamics in Model Aromatic Substituents of Lignin

et al. 2022

View full text Add to dashboard Cite

Broadband microwave spectra were recorded over the 2‐18 GHz frequency range for a series of four model aromatic components of lignin; namely, guaiacol (ortho‐methoxy phenol, G), syringol (2,6‐dimethoxy phenol, S), 4‐methyl guaiacol (MG), and 4‐vinyl guaiacol (VG), under jet‐cooled conditions in the gas phase. Using a combination of 13C isotopic data and electronic structure calculations, distortions of the phenyl ring by the substituents on the ring are identified. In all four molecules, the rC(1)‐C(6) bond between the two substituted C‐atoms lengthens, leading to clear bond alternation that reflects an increase in the phenyl ring resonance structure with double bonds at rC(1)‐C(2), rC(3)‐C(4) and rC(5)‐C(6). Syringol, with its symmetric methoxy substituents, possesses a microwave spectrum with tunneling doublets in the a‐type transitions associated with H‐atom tunneling. These splittings were fit to determine a barrier to hindered rotation of the OH group of 1975 cm−1, a value nearly 50 % greater than that in phenol, due to the presence of the intramolecular OH⋅⋅⋅OCH3 H‐bonds at the two equivalent planar geometries. In 4‐methyl guaiacol, methyl rotor splittings are observed and used to confirm and refine an earlier measurement of the three‐fold barrier V3=67 cm−1. Finally, 4‐vinyl guaiacol shows transitions due to two conformers differing in the relative orientations of the vinyl and OH groups.

show abstract

“…The chemical composition of PAH-derived SOA is quite complex, with hundreds to thousands of compounds being present. To simplify our approach, and to allow a molecular approach to the toxic response of these particles, we investigated the impact of by-products mimicking naphthalene-derived aerosols [7][8][9][10]30].…”

Section: Naphthalene Soa By-productsmentioning

confidence: 99%

“…Once in the air, naphthalene undergoes atmospheric oxidation, mainly by reacting hydroxyl radicals (•OH), and thereby acts as a precursor of secondary organic aerosols (SOA). These ultrafine particles have a complex chemical composition and therefore possess chemical complexity and yield products such as 1,4-naphthoquinone (1,4-NQ), 2-hydroxy-1,4 naphthoquinone (2-OH-NQ), phthalic acid (PA), phthaldialdehyde (OPA) [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

Albuquerque

Berger

Tomaz

et al. 2021

Life

View full text Add to dashboard Cite

In 2018, seven million people died prematurely due to exposure to pollution. Polycyclic aromatic hydrocarbons (PAHs) are a significant source of secondary organic aerosol (SOA) in urban areas. We investigated the toxic effects of by-products of naphthalene SOA on lung cells. These by-products were 1,4-naphthoquinone (1,4-NQ), 2-hydroxy-1,4-naphthoquinone (2-OH-NQ), phthalic acid (PA) and phthaldialdehyde (OPA). Two different assessment methodologies were used to monitor the toxic effects: real-time cell analysis (RTCA) and the Holomonitor, a quantitative phase contrast microscope. The chemicals were tested in concentrations of 12.5 to 100 µM for 1,4-NQ and 1 to 10 mM for 2-OH-NQ, PA and OPA. We found that 1,4-NQ is toxic to cells from 25 to 100 µM (EC50: 38.7 µM ± 5.2); 2-OH-NQ is toxic from 1 to 10mM (EC50: 5.3 mM ± 0.6); PA is toxic from 5 to 10 mM (EC50: 5.2 mM ± 0.3) and OPA is toxic from 2.5 to 10 mM (EC50: 4.2 mM ± 0.5). Only 1,4-NQ and OPA affected cell parameters (migration, motility, motility speed and optical volume). Furthermore, 1,4-NQ is the most toxic by-product of naphthalene, with an EC50 value that was one hundred times higher than those of the other compounds. RTCA and Holomonitor analysis showed a complementarity when studying the toxicity induced by chemicals.

show abstract

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

Cited by 11 publications

References 62 publications

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Bond Length Alternation and Internal Dynamics in Model Aromatic Substituents of Lignin

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

Contact Info

Product

Resources

About