Theoretical studies on hydrogen bonding in caffeine–theophylline complexes

Karthika, M.; Senthilkumar, L.; Kanakaraju, R.

doi:10.1016/j.comptc.2011.10.015

Cited by 28 publications

(12 citation statements)

References 26 publications

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“…the greatest difference is observed for the extracyclic n-c bonds and the angles between these bonds and the corresponding intra-cyclic bonds. this deviation may be due to the fact that the theoretical calculations apply to a single molecule in a gas phase, whereas the experimental results apply to a molecule in a solid state (10). the lengths of the methyl c-h bonds vary from 1.087 Å to 1.094 Å. however, the calculated values were found to be in a good agreement with those reported by Poltev (19) (obtained by MP2/6-31G(d,p) calculations) and egawa (5) (obtained by MP2/6-31G** and B3lYP/6-31G** calculations).…”

Section: Resultsmentioning

confidence: 93%

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts

Stanchev

Mitkov

Georgieva

et al. 2012

Biotechnology & Biotechnological Equipment

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Section: Resultsmentioning

confidence: 93%

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts

Stanchev

Mitkov

Georgieva

et al. 2012

Biotechnology & Biotechnological Equipment

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“…A média dos comprimentos de ligação e dos ângulos de ligação são apresentadas, respectivamente, nas Tabelas 1 e 2. Valores teóricos obtidos por cálculos ab-initio DFT com conjunto de bases 6-311G++(d,p), Hartree-Fock (HF) com conjunto de bases 6-31G++(d,p) com funcional de troca e correlação B3LYP e dados experimentais de difração de raios-X também foram incluídos na tabela para efeito de comparação 16,17 .…”

Section: Resultsunclassified

Estudo Teórico dos Parâmetros Estruturais da Cafeína no Vácuo Usando Dinâmica Molecular de Car-Parrinello

et al. 2017

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A cafeína é uma das substâncias mais utilizadas no mundo. É classificada como um alcaloide que pertence ao grupo das metilxantinas (1,3,7 -timetilxantina). Está presente em várias plantas, é também encontrada nos chás, cacau, café, guaraná e refrigerantes. Quando consumida, afeta quase todos os sistemas, com seus efeitos mais perceptíveis no sistema nervoso central (SNC). Com essas propriedades biológicas observadas, o presente trabalho tem como objetivo estudar os comprimentos e ângulos de ligação da cafeína no vácuo, utilizando o método de Dinâmica Molecular de Car-Parrinello (DMCP). Para os cálculos, a molécula foi disposta em uma caixa cúbica, com aresta de 16 Å. O funcional de energia de troca e correlação foi modelado usando o funcional do gradiente corrigido PBE. Os elétrons do núcleo foram tratados com pseudopotenciais ultrasolf de Vanderbilt, e os de valência foram representados pelo conjunto de funções de base de ondas planas, truncadas em energia cinética de corte de 25 Ry. As simulações de DMCP foram realizadas a uma temperatura de 300 K, com um passo de integração de 5,0 a.t.u. (unidade atômica de tempo) e massa fictícia de 400 a.u. (unidade atômica). Os resultados obtidos para cálculos das propriedades estruturais utilizando DMCP mostram boa concordância com resultados obtidos por outros métodos teóricos e com dados experimentais. Este estudo contribui para a compreensão inicial das propriedades estruturais e da metodologia utilizada que é bastante promissora em estudos de planejamento de fármacos. Palavras chave: Car-Parrinello; cafeína; dinâmica molecular.Caffeine is the most widely used drugs in the world. It classed as an alkaloid which belongs to the group of methylxanthines (1,3,7-timetilxantina). It is present in various plants, it is also found in tea, cocoa, coffee, guarana and sodas. When consumed, it affects almost every system, with its most noticeable effects on the central nervous system (CNS). With these diverse biological properties observed, this work is aimed at the study of lengths and vacuum caffeine bond angles, using the molecular dynamics method of Car-Parrinello. For the calculations, the molecule was arranged in a cubic box, with dimensions of 16 Å. The functional exchange energy and correlation was modeled using the functional gradient corrected PBE. The core electrons were treated with ultrasolf Vanderbilt pseudopotentials, and valence were represented by the set of basis functions in plane waves, truncated into kinetic energy cut of 25 Ry. DMCP The simulations were performed at a temperature of 300 K with an integration step of 5.0 cur (atomic unit of time) and fictitious mass of 400 au (atomic unit). The results of calculations for the structural properties using DMCP in good agreement with results obtained by other methods theoretical and experimental data. This study adds to the initial understanding of the structural properties and the methodology used, which is very promising in drug design studies.

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“…S4b and S4b 0 , ESI †) confirms the presence of six C-HÁ Á ÁO and C-HÁ Á ÁN intermolecular hydrogen bonds between the two caffeine molecules. [69][70][71][72] Although the difference in electronegativity between C and H is small, the weak hydrogen bonds between caffeine molecules play an important role, together with the p-p stacking of the aromatic rings, in controlling the selfassociation process. 73 To evaluate all possible interactions, a computational approach based on probing the potential energy surface of caffeine dimers was applied.…”

Section: Caffeine Dimersmentioning

confidence: 99%

Prediction of self-assembly of adenosine analogues in solution: a computational approach validated by isothermal titration calorimetry

Redivo

Anastasiadi

Pividori

et al. 2019

Phys. Chem. Chem. Phys.

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Theoretical studies on hydrogen bonding in caffeine–theophylline complexes

Cited by 28 publications

References 26 publications

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts

Estudo Teórico dos Parâmetros Estruturais da Cafeína no Vácuo Usando Dinâmica Molecular de Car-Parrinello

Prediction of self-assembly of adenosine analogues in solution: a computational approach validated by isothermal titration calorimetry

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Theoretical studies on hydrogen bonding in caffeine–theophylline complexes

Cited by 28 publications

References 26 publications

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental1H Chemical Shifts

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental1H Chemical Shifts

Estudo Teórico dos Parâmetros Estruturais da Cafeína no Vácuo Usando Dinâmica Molecular de Car-Parrinello

Prediction of self-assembly of adenosine analogues in solution: a computational approach validated by isothermal titration calorimetry

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GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts

GIAO NMR Calculations of Some Novel 8-Thio-Substituted 1,3,7-Trimethylxanthines: Comparison of Theoretical and Experimental¹H Chemical Shifts