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Bio-inspired uracil building blocks as terminal functional groups for electronic materials
Krusberský, Vojtěch ; Ivanová, Lucia (referee) ; Richtár, Jan (advisor)
This bachelor thesis focuses on synthesis, purification and characterization of bio-inspired electron-accepting motifs based on N,N’-dialkylated barbituric acid derivatives for potential applications in the field of N-type organic semiconductors. The theoretical part deals with organic semiconductors and principles of their conductivity. Further covered topics are uracil, barbituric acid and its derivatives, synthetic approaches to target molecules and their analogues are also included. Within the experimental part two types of alkyl substituents were chosen – a flexible butyl and a bulky and rigid adamantylethyl. Both were incorporated into the structure via appropriate dialkylurea, which underwent condensation in the next phase. The final step of the synthetic route was the Knoevenagel condensation with a -conjugated trimer.
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Molecularly imprinted polymers as a tool for the isolation of key biologically active molecules
Vodová, Milada ; Jaroslava, Bezděková (referee) ; Nejdl, Lukáš (advisor)
This bachelor thesis is focused on preparation and optimization of molecularly imprinted polymers that are selective for the selected nucleobase(uracil). Molecularly imprinted polymers, which wereused for selective uracil isolation, have been prepared non-covalent imprinting technique. As a function monomer was used in this case dopamine. The detection ofisolated uracil was made by capillary electrophoresis with absorption detection (–260 nm). Conditions for preparation of molecularly imprinted polymers,their binding properties, adsorption kinetics, and selectivity wereinvestigatedin detail. Mentioned polymer materials were as well used for uracil selective isolation and detection from complexsamples. Tomato products were used as complex samples. Uracil in those samples was usedasanindicator ofbacterial contamination.
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Optimization of concentration determination of degrdation products of uracil via LC-MS
Kavale, Gustav ; Ševčík, Jan (advisor) ; Míšek, Jiří (referee)
In the Czech Republic, tens of thousands of oncology patients undergo treatment based on fluoropyrimidines every year. Many of these patients suffer from negative side effects that can even have a fatal impact. Currently, the best described factor in the cause of the toxicity of fluoropyrimidines is the activity of the pyrimidine catabolism enzyme - dihydropyrimidine dehydrogenase. Due to the high frequency of pathogenic mutations in the dihydropyrimidine dehydrogenase gene, the extreme risk of toxicity affects hundreds of patients in the Czech Republic every year. For this reason, the "European Medical Agency" has issued a recommendation to carry out investigations for the possible occurrence of toxic effects before starting treatment. One of the diagnostic options for determining sensitivity to fluorouracil is metabolomic analysis, based on the quantification of degradation products of uracil metabolism in plasma using liquid chromatography with mass spectrometry. The goal of this work is to perform basic optimization of mass spectrometer parameters for quantification of selected degradation products of uracil metabolism. Keywords: Uracil, Fluoruracil, Liquid Chromatography, Mass Spectrometry
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Bio-inspired uracil building blocks as terminal functional groups for electronic materials
Krusberský, Vojtěch ; Ivanová, Lucia (referee) ; Richtár, Jan (advisor)
This bachelor thesis focuses on synthesis, purification and characterization of bio-inspired electron-accepting motifs based on N,N’-dialkylated barbituric acid derivatives for potential applications in the field of N-type organic semiconductors. The theoretical part deals with organic semiconductors and principles of their conductivity. Further covered topics are uracil, barbituric acid and its derivatives, synthetic approaches to target molecules and their analogues are also included. Within the experimental part two types of alkyl substituents were chosen – a flexible butyl and a bulky and rigid adamantylethyl. Both were incorporated into the structure via appropriate dialkylurea, which underwent condensation in the next phase. The final step of the synthetic route was the Knoevenagel condensation with a -conjugated trimer.
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Synthesis, reactivity and biological activity of C5 substituted uracil analogues
Brulíková, Lucie ; Holý, Antonín (advisor) ; Rosenberg, Ivan (referee) ; Moravcová, Jitka (referee)
Bibliographical identification: Author's first name and surname: RNDr. Lucie Brulíková (nee Spáčilová) Title: Synthesis, reactivity and biological activity of C-5 substituted uracil analogues Type of thesis: Ph.D. thesis Department: Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc Advisor: prof. RNDr. Antonín Holý, Dr.Sc., Dr.hc. mult. Advisor-consultant: doc. RNDr. Jan Hlaváč, Ph.D. The year of presentation: 2011 Abstract: The presented thesis is focused on the synthesis of various C-5 modified uracil analogues, the study of their reactivity and biological activity, especially cytotoxic activity. In the first part, the brief survey of described results for selected 5-alkoxymethyluracil analogues is performed. The second part of the presented thesis deals with the synthesis of novel uracil analogues modified at the C-5 position, the development and optimizing of procedure leading to the desired compounds, the study of biological activity and the evaluation of structure- activity relationship (SAR). This part presents the synthesis of a series of 5-[alkoxy(4- nitrophenyl)methyl)]uracil and 5-alkoxymethyluracil analogues and extended SAR studies depending on a substitution of metylene bridge directly attached at the C-5 position as well as alkoxy chain length. The last part of...
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Molecularly imprinted polymers as a tool for the isolation of key biologically active molecules
Vodová, Milada ; Jaroslava, Bezděková (referee) ; Nejdl, Lukáš (advisor)
This bachelor thesis is focused on preparation and optimization of molecularly imprinted polymers that are selective for the selected nucleobase(uracil). Molecularly imprinted polymers, which wereused for selective uracil isolation, have been prepared non-covalent imprinting technique. As a function monomer was used in this case dopamine. The detection ofisolated uracil was made by capillary electrophoresis with absorption detection (–260 nm). Conditions for preparation of molecularly imprinted polymers,their binding properties, adsorption kinetics, and selectivity wereinvestigatedin detail. Mentioned polymer materials were as well used for uracil selective isolation and detection from complexsamples. Tomato products were used as complex samples. Uracil in those samples was usedasanindicator ofbacterial contamination.
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Synthesis, reactivity and biological activity of C5 substituted uracil analogues
Brulíková, Lucie ; Holý, Antonín (advisor) ; Rosenberg, Ivan (referee) ; Moravcová, Jitka (referee)
Bibliographical identification: Author's first name and surname: RNDr. Lucie Brulíková (nee Spáčilová) Title: Synthesis, reactivity and biological activity of C-5 substituted uracil analogues Type of thesis: Ph.D. thesis Department: Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc Advisor: prof. RNDr. Antonín Holý, Dr.Sc., Dr.hc. mult. Advisor-consultant: doc. RNDr. Jan Hlaváč, Ph.D. The year of presentation: 2011 Abstract: The presented thesis is focused on the synthesis of various C-5 modified uracil analogues, the study of their reactivity and biological activity, especially cytotoxic activity. In the first part, the brief survey of described results for selected 5-alkoxymethyluracil analogues is performed. The second part of the presented thesis deals with the synthesis of novel uracil analogues modified at the C-5 position, the development and optimizing of procedure leading to the desired compounds, the study of biological activity and the evaluation of structure- activity relationship (SAR). This part presents the synthesis of a series of 5-[alkoxy(4- nitrophenyl)methyl)]uracil and 5-alkoxymethyluracil analogues and extended SAR studies depending on a substitution of metylene bridge directly attached at the C-5 position as well as alkoxy chain length. The last part of...
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Theoretical Study of Tautomeric Forms of Uracil and Their Interactions with Mg\hindex{2+}
ROMANCOVÁ, Ingrid
This bachelor thesis is focused on theoretical study of uracil tautomers and their interactions with bare and hydrated Mg2+ cation in the gas phase. The main aim was to find the most stable comlexes of Mg2+ ion with different uracil tautomers and compare their relative and interaction energies. A comparison with analogous Mg2+ complexes with thymine tautomers was also done and influence of the the metal ion hydration on the relative stability of the tautomers was evaluated.
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