Energy Barrier Reduction for the Double Proton-Transfer Reaction in Guanine–Cytosine DNA Base Pair on a Gold Surface

Freitas, Rafael; Rivelino, Roberto; Mota, F.; Gueorguiev, Gueorgui Kostov; Castilho, C.M.C. de

doi:10.1021/acs.jpcc.5b04149

Cited by 14 publications

(14 citation statements)

References 62 publications

(154 reference statements)

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“…In a theoretical study, Freitas et al suggested that the adsorption of a molecule (here, ADCL) on the surface of any abiogenic minerals (here, gold nanosurface) is governed by the weak van der Waals interaction between the adsorbed molecule and surface atom of the minerals which induces some changes in the electronic structure of the adsorbate . Considering the weak van der Waals interaction and SDPT mechanism, they obtained a high reduction (of around 31%) in the activation energy barrier of the GC → G*C* tautomeric process which actually triggers the occurrence of a spontaneous point mutation during DNA replication . Taking into account the above-mentioned fact, we can conclude that in our case also, the high activation energy barrier of the lactim* → lactam* tautomeric process through four-member intramolecular hydrogen-bonding unit of ADCL also decreases upon adsorption on the anisotropic gold surface by weak van der Waals interaction which results the faster ESIPT dynamics of the probe.…”

Section: Results and Discussionmentioning

confidence: 99%

“…16 Inspired by the aforesaid work by Vecchio et al, Freitas et al have investigated the impact of gold surface (Au(111)) on the simultaneous double-proton-transfer (SDPT) process of guanine−cytosine (GC) DNA base pairs by means of first-principles computational simulations. 17 They observed significant differences in the electronic structure, energetics, and kinetics of the tautomeric process of the GC pair during the contact with an inert gold surface which can influence the SDPT mechanism. 17 They have also determined a reduction of about 31% in the activation energy barrier of the protontransfer (PT) process in the GC/Au(111) system which points toward the faster PT process on the gold surface.…”

Section: Introductionmentioning

confidence: 99%

“…It is proposed that the tautomeric equilibrium, that is, lactim (enol)–lactam (keto) tautomerism (in thymine and guanine) and amine–imine tautomerism (in adenine and cytosine), occurring in the nitrogen bases of DNA is one of the main reasons behind spontaneous mutation . Inspired by the aforesaid work by Vecchio et al, Freitas et al have investigated the impact of gold surface (Au(111)) on the simultaneous double-proton-transfer (SDPT) process of guanine–cytosine (GC) DNA base pairs by means of first-principles computational simulations . They observed significant differences in the electronic structure, energetics, and kinetics of the tautomeric process of the GC pair during the contact with an inert gold surface which can influence the SDPT mechanism .…”

Section: Introductionmentioning

confidence: 99%

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Modulation of Excited-State Proton Transfer Dynamics in a Model Lactim–Lactam Tautomeric System by Anisotropic Gold Nanoparticles

et al. 2018

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The past few decades have witnessed significant advances in the development of functionalized gold nanoparticles (GNPs) for diverse applications in various fields such as chemistry, biology, pharmacy, and physics. However, a recent in vivo toxicity study of GNPs in Drosophila melanogaster demonstrated that GNPs are capable of inducing mutagenesis. Considering mutagenicity and tautomerism (lactim–lactam and amine–imine) of DNA base pairs are correlated with each other, a recent theoretical study reveal the modification of double-proton-transfer process of guanine–cytosine DNA base pairs upon interaction with the gold surface (Au(111)). However, there is a dearth of experimental data about the proton-transfer (PT) process in isolated base pairs on gold nanosurface. In this particular work, we have chosen a model lactim–lactam tautomeric system, namely, 1-(2-hydroxy-5-chloro-phenyl)-3,5-dioxo-1H-imidazo-[3,4-b] isoindole (ADCL), and carried out for the first time a comprehensive study of the modification of excited-state PT dynamics in the presence of synthesized isotropic (spherical) and anisotropic (trianglular, rod, and trigonal bipyramidal) GNPs by means of steady-state and time-resolved fluorescence spectroscopy. The PT process operative in ADCL was experimentally found to be accelerated on the anisotropic gold nanosurface, whereas spherical-shaped GNPs showed little impact on the dynamics of the above-mentioned photophysical phenomenon. Therefore, our experimental results regarding the modification of lactim–lactam tautomerism of a model compound on the gold nanosurface are an indirect evidence of mutation caused by GNPs.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Modulation of Excited-State Proton Transfer Dynamics in a Model Lactim–Lactam Tautomeric System by Anisotropic Gold Nanoparticles

et al. 2018

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“…A high- and low-temperature test box (KW-890, KOWINTEST, Dongguan, China) was used to conduct a rapid heat absorption and heat release performance test on the samples. Notably, the DFT theory developed by Rivelino et al [ 25 , 26 ], i.e., the synthetic growth method, is effective for the in-depth analysis of material stability and possible chemical reactions, and it has been applied to complex systems. In addition, although PW/EG/CF and SA–PA–LA/EG/CF CPCMs were involved in this study, the author has performed the application and material characterization of CPCM based on PW/EG many times in previous studies [ 27 , 28 , 29 ]; therefore, the characterization test materials involved in this study mainly included the SA–PA–LA ternary eutectic PCM and SA–PA–LA/EG/CF CPCM.…”

Section: Experiments Methodologymentioning

confidence: 99%

Preparation of SA–PA–LA/EG/CF CPCM and Its Application in Battery Thermal Management

et al. 2021

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To improve the heat dissipation efficiency of batteries, the eutectic mass ratios of each component in the ternary low-melting phase change material (PCM), consisting of stearic acid (SA), palmitic acid (PA), and lauric acid (LA), was explored in this study. Subsequently, based on the principle of high thermal conductivity and low leakage, SA–PA–LA/expanded graphite (EG)/carbon fiber (CF) composite phase change material (CPCM) was prepared. A novel double-layer CPCM, with different melting points, was designed for the battery-temperature control test. Lastly, the thermal management performance of non-CPCM, single-layer CPCM, and double-layer CPCM was compared via multi-condition charge and discharge experiments. When the mass ratio of SA to PA is close to 8:2, better eutectic state is achieved, whereas the eutectic mass ratio of the components of SA–PA–LA in ternary PCM is 29.6:7.4:63. SA–PA–LA/EG/CF CPCM formed by physical adsorption has better mechanical properties, thermal stability, and faster heat storage and heat release rate than PCM. When the CF content in SA–PA–LA/EG/CF CPCM is 5%, and the mass ratio of SA–PA–LA to EG is 91:9, the resulting SA–PA–LA/EG/CF CPCM has lower leakage rate and better thermal conductivity. The temperature control effect of single-layer paraffin wax (PW)/EG/CF CPCM is evident when compared to the no-CPCM condition. However, the double-layer CPCM (PW/EG/CF and SA–PA–LA/EG/CF CPCM) can further reduce the temperature rise of the battery, effectively control the temperature and temperature difference, and primarily maintain the battery in a lower temperature range during usage. After adding an aluminum honeycomb to the double-layer CPCM, the double-layer CPCM exhibited better thermal conductivity and mechanical properties. Moreover, the structure showed better battery temperature control performance, while meeting the temperature control requirements during the charging and discharging cycles of the battery.

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“…The DNA base pair, (A–B), is composed of two or three hydrogen bonds between two bases. The proton or hydrogen atom is easily transferred in the base pairs at the excited and ion radical states. − It is known that the transfer of proton or hydrogen atom takes place very fast within 100–200 fs. The transfer is also one of the energy relaxation processes of (A–B)* at the excited state or ion radical state. − The DNA base pair is possibility utilized as a proton ON–OFF switching element.…”

Section: Introductionmentioning

confidence: 99%

Molecular Design of Ionization-Induced Proton Switching Element Based on Fluorinated DNA Base Pair

Tachikawa

Kawabata

2016

J. Phys. Chem. A

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To design theoretically the high-performance proton switching element based on DNA base pair, the effects of fluorine substitution on the rate of proton transfer (PT) in the DNA model base pair have been investigated by means of direct ab initio molecular dynamics (AIMD) method. The 2-aminopyridine dimer, (AP)2, was used as the model of the DNA base pair. One of the hydrogen atoms of the AP molecule in the dimer was substituted by a fluorine (F) atom, and the structures of the dimer, expressed by F-(AP)2, were fully optimized at the MP2/6-311++G(d,p) level. The direct AIMD calculations showed that the proton is transferred within the base pair after the vertical ionization. The rates of PT in F-(AP)2(+) were calculated and compared with that of (AP)2(+) without an F atom. It was found that PT rate is accelerated by the F-substitution. Also, the direction of PT between F-AP and AP molecules can be clearly controlled by the position of F-substitution (AP)2 in the dimer.

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Energy Barrier Reduction for the Double Proton-Transfer Reaction in Guanine–Cytosine DNA Base Pair on a Gold Surface

Cited by 14 publications

References 62 publications

Modulation of Excited-State Proton Transfer Dynamics in a Model Lactim–Lactam Tautomeric System by Anisotropic Gold Nanoparticles

Modulation of Excited-State Proton Transfer Dynamics in a Model Lactim–Lactam Tautomeric System by Anisotropic Gold Nanoparticles

Preparation of SA–PA–LA/EG/CF CPCM and Its Application in Battery Thermal Management

Molecular Design of Ionization-Induced Proton Switching Element Based on Fluorinated DNA Base Pair

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