Theoretical study of hydrogen bond interactions of felodipine with polyvinylpyrrolidone and polyethyleneglycol

Teberekidis, Vasilios I.; Sigalas, Michael P.

doi:10.1016/j.theochem.2006.09.016

Cited by 42 publications

(22 citation statements)

References 37 publications

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“…In the urea monomer, the proton donor N-H bond lengths are both 0.101267 nm, and the N-H symmetrical stretching vibration frequencies are 3,562.6 and 3,567.8 cm -1 before hydrogen bonding interaction. The corresponding N-H bond lengths are both lengthened to 0.101365 nm, and the symmetrical stretching vibration frequencies are lowered to 3,556.5 and 3,564.6 cm -1 after the formation of [25][26][27][28][29][30]. The same phenomena can be observed in thiourea-HNO 2 formation.…”

Section: Structuresmentioning

confidence: 62%

Hydrogen bonding interaction between ureas or thioureas and nitro-compounds

Zheng

Huang

et al. 2010

Res Chem Intermed

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The hydrogen bonding interactions between ureas or thioureas and different nitro-compounds were studied using the MP2 method. After comparing four possible conformations, the most stable one was found, which has the typical hydrogen bonding feature of red-shift effect. Based on it, the substituent effects on both nitro-compounds and (thio) urea were researched. The results indicated that electron-withdrawing groups on ureas or thioureas and electron-donating groups on nitro-compounds can both facilitate the hydrogen bonding formation. The NBO analysis further disclosed the essence of the hydrogen bonding interaction. We also studied the cis-trans isomerization of the complexes of (thio) urea with nitroalkenes, which revealed that, for hydrogen-bonding complexes, it is necessary to take both cis and trans isomers into consideration, especially for nitroalkenes with little steric effect substituents.

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Section: Structuresmentioning

confidence: 62%

Hydrogen bonding interaction between ureas or thioureas and nitro-compounds

Zheng

Huang

et al. 2010

Res Chem Intermed

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“…To properly predict the most thermodynamically stable structure, oB97X-D functional and 6-31G* basis set were used to approximate the electron density and molecular interactions of the self-assembled structure composed of large numbers of atoms 32 . Figure 3 depicts an optimized trimer obtained with a simplified molecular structure, suggesting that 1 self-assembles into helical stacks via hydrogen bonding of the amides (see Methods and Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Induction and control of supramolecular chirality by light in self-assembled helical nanostructures

et al. 2015

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Evolution of supramolecular chirality from self-assembly of achiral compounds and control over its handedness is closely related to the evolution of life and development of supramolecular materials with desired handedness. Here we report a system where the entire process of induction, control and locking of supramolecular chirality can be manipulated by light. Combination of triphenylamine and diacetylene moieties in the molecular structure allows photoinduced self-assembly of the molecule into helical aggregates in a chlorinated solvent by visible light and covalent fixation of the aggregate via photopolymerization by ultraviolet light, respectively. By using visible circularly polarized light, the supramolecular chirality of the resulting aggregates is selectively and reversibly controlled by its rotational direction, and the desired supramolecular chirality can be arrested by irradiation with ultraviolet circularly polarized light. This methodology opens a route to ward the formation of supramolecular chiral conducting nanostructures from the self-assembly of achiral molecules.

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“…It is chemically described as ethylmethyl-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylate [USP (United States Pharmacopoeia 29). FL is a calcium antagonist used commonly for its excellent antihypertension and antianginal effects (Teberekidis et al, 2007). FL is a poorly water soluble drug belonging to the category of BCS class II (Yasir et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Design and optimization of self-microemulsifying drug delivery system (SMEDDS) of felodipine for chronotherapeutic application

Storti-Filho

Damke

Carrara

et al. 2014

Braz. J. Pharm. Sci.

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The objective of this research work was to design, develop and optimize the self micro-emulsifying drug delivery system (SMEDDS) of Felodipine (FL) filled in hard gelatine capsule coated with polymer in order to achieve rapid drug release after a desired time lag in the management of hypertension. Microemulsion is composed of a FL, Lauroglycol FCC, Transcutol P and Cremophor EL. The optimum surfactant to co-surfactant ratio was found to be 2:1. The resultant microemulsions have a particle size in the range of 65-85 nm and zeta potential value of -13.71 mV. FL release was adequately adjusted by using pH independent polymer i.e. ethyl cellulose along with dibutyl phthalate as plasticizer. Influence of formulation variables like viscosity of polymer, type of plasticizer and percent coating weight gain was investigated to characterize the time lag. The developed formulation of FL SMEDDS capsules coated with ethyl cellulose showed time lag of 5-7 h which is desirable for chronotherapeutic application.Uniterms: Felodipine/self-microemulsifying delivery. Felodipine/chronotherapeutic application. Selfmicroemulsifying drug delivery system/development. Drugs/controlled release. Ethyl cellulose/drugs coated. Hypertension/treatment. Chronotherapeutics/hypertension treatment.O objetivo desse trabalho de pesquisa foi planejar, desenvolver e otimizar sistema de liberação de fármaco auto-microemulsificante(SMEDDS) de felodipino (FL) em cápsulas de gelatina dura revestidas com polímero, a fim de obter liberação rápida após tempo desejado no manejo da hipertensão. A microemulsão é composta de FL, lauroglilcol FCC, Transcutol P e Cremophor EL. A proporção ótima de tensoativo e de co-tensoativo foi de 2:1. As microemulsões resultantes têm tamanho de partícula na faixa de 65-85 nm com potencial zeta de -13,71 mV. A liberação de FL foi ajustada adequadamente, utilizando-se polímero independente de pH, como etilcelulose com ftalato de dibutila como plastificante. A influência das variáveis da formulação, como viscosidade do polímero, tipo de plastificante e ganho percentual de peso do revestimento foi investigada para caracterizar o intervalo de tempo de liberação. A formulação de cápsulas de FL SMEDDS revestidas com etilcelulose mostrou intervalo de tempo de liberação de 5 a 7 horas, o que é desejável para uma aplicação cronoterapêutica.Uniterms: Felodipino/liberação de fármaco auto-emulsificante. Felodipino/aplicação cronoterapêutica. Sistema de liberação de fármaco auto-emulsificante/desenvolvimento. Fármacos/liberação controlada. Etilcelulose/revestimento de fármacos. Hipertensão/tratamento. Cronoterapia/tratamento da hipertensão.

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Theoretical study of hydrogen bond interactions of felodipine with polyvinylpyrrolidone and polyethyleneglycol

Cited by 42 publications

References 37 publications

Hydrogen bonding interaction between ureas or thioureas and nitro-compounds

Hydrogen bonding interaction between ureas or thioureas and nitro-compounds

Induction and control of supramolecular chirality by light in self-assembled helical nanostructures

Design and optimization of self-microemulsifying drug delivery system (SMEDDS) of felodipine for chronotherapeutic application

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