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The influence of experimental conditions on chiral separation of borane clusters in capillary electrophoresis
Bodi, Adrián ; Kučera, Radim (advisor) ; Pilařová, Pavla (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of pharmaceutical chemistry and pharmaceutical analysis Candidate: Adrián Bodi Thesis supervisor: doc. PharmDr. Radim Kučera, Ph.D. Consultant: Mgr. Ondřej Horáček Title of thesis: The influence of experimental conditions on chiral separation of borane clusters in capillary electrophoresis Keywords: chiral separation, borane clusters, capillary electrophoresis, cyclodextrins Abstract: Boron compounds also include borane clusters, in which boron atoms form triangular configuration and 30 such sides are presented as a so-called cage. These clusters can be synthetically modified into various forms (open or closed) and can be substitued, for example by carbon atoms. This substitution can lead to the asymmetry of these molecules and thus to their chirality. Currently, their potential is also being studied in medicinal chemistry, where they could contribute to the design of new drugs. For instance, while they are been tested as HIV inhibitors, for boron neutron capture therapy, as CA IX inhibitors, they have also been suitable as part of hydrophobic pharmacophores in the design of drugs targetting the binding sites of various receptors. The task of this thesis is to test the influence of experimental conditions on the chiral separation of...
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The uset of HPLC in the field of chiral separations VII.
Štilcová, Kristýna ; Kučera, Radim (advisor) ; Pilařová, Pavla (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Student: Kristýna Štilcová Supervisor: doc. PharmDr. Radim Kučera, Ph.D. Consultant: Mgr. Ondřej Horáček Title of Thesis: The employment of HPLC in the field of chiral separations VII. Boron clusters are inorganic, synthetically prepared, three-dimensional, cage-like structures. Boron cluster compounds which are made only of boron and hydrogen atoms are completely symmetrical. Their symmetry can be disrupted by endo- or exoskeletal substitution resulting in chiral compounds. Carboranes, subgroup of the boron cluster compounds, contain at least one carbon atom in their structure and usually include exoskeletal substitution. Therefore, the metallacarboranes containing cobalt bis(dicarbollides) and 7,8-dicarba-nido-undecaborates that have been studied can be found among these chiral structures. Thanks to the specific properties such as high lipophilicity, metabolic stability and delocalized negative charge, the studied compounds can be used as isosteric substitution of phenyl ring in pharmacophores. Due to the growing interest in cobalt bis(dicarbollides) and 7,8-dicarba-nido-undecaborates and the importance of chirality in pharmacy, suitable conditions for chiral...
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The uset of HPLC in the field of chiral separations VII.
Štilcová, Kristýna ; Kučera, Radim (advisor) ; Pilařová, Pavla (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Student: Kristýna Štilcová Supervisor: doc. PharmDr. Radim Kučera, Ph.D. Consultant: Mgr. Ondřej Horáček Title of Thesis: The employment of HPLC in the field of chiral separations VII. Boron clusters are inorganic, synthetically prepared, three-dimensional, cage-like structures. Boron cluster compounds which are made only of boron and hydrogen atoms are completely symmetrical. Their symmetry can be disrupted by endo- or exoskeletal substitution resulting in chiral compounds. Carboranes, subgroup of the boron cluster compounds, contain at least one carbon atom in their structure and usually include exoskeletal substitution. Therefore, the metallacarboranes containing cobalt bis(dicarbollides) and 7,8-dicarba-nido-undecaborates that have been studied can be found among these chiral structures. Thanks to the specific properties such as high lipophilicity, metabolic stability and delocalized negative charge, the studied compounds can be used as isosteric substitution of phenyl ring in pharmacophores. Due to the growing interest in cobalt bis(dicarbollides) and 7,8-dicarba-nido-undecaborates and the importance of chirality in pharmacy, suitable conditions for chiral...
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Chiral separation of boron cluster compounds
Linková, Kristýna ; Kučera, Radim (advisor) ; Lochman, Lukáš (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Candidate: Kristýna Linková Supervisor: doc. PharmDr. Radim Kučera, Ph.D. Consultant: Mgr. Ondřej Horáček Title of thesis: Chiral separation of boron cluster compounds The boron atom has the ability to form electro-deficientient bonds, when only two electrons participate in the three bonds. Significant delocalization of electrons over the three- center bond is responsible for the formation of three-dimensional clusters. Boron cluster compounds have an abiotic character. They are characterized by their specific properties, such as thermal and metabolic stability, high lipophilicity and delocalized negative charge. These compounds are investigated as isosteric to phenyl group in the field of medicinal chemistry. They have anti-cancer activity, the ability to inhibit HIV-proteases and anti-rheumatoid activity. Furthermore, boron cluster compounds have been used in neutron capture therapy in the treatment of cancer. Some boron cluster compounds studied as new potential drugs are chiral, therefore it is necessary to get enantiomerically pure substances to further expand their use in pharmacy and medicine. The recent investigations in our research group have been focused on the...
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The uset of HPLC in the field of chiral separations VI.
Marvalová, Jana ; Kučera, Radim (advisor) ; Pilařová, Pavla (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical chemistry and Pharmaceutical analysis Candidate: Jana Marvalová Supervisor: doc. PharmDr. Radim Kučera, PhD. Title of Thesis: The employment of HPLC in field of chiral separations VI. Boron clusters are synthetically prepared substances that are being intensively studied in connection with Boron Neutron Capture Therapy, the substitution of phenyl rings of molecules of already known drugs and as potential inhibitors of HIV protease. Boron clusters are symmetric molecules, however, by endo- or exo-skeletal substitution, the symmetry of the cluster is disrupted and enantiomers are formed. This diploma thesis is focused on the investigation of chromatographic conditions for chiral separations of cosanes (bis(dicarbollides) and 7,8-dicarb-nido-undecaborates derivatives using high performance liquid chromatography and chiral selectors based on cellulose and amylose in reverse-phase liquid chromatography. For this purpose, columns Lux Cellulose-1 and Lux Amylose-1 were selected with chiral selectors cellulose tris(3,5-dimethylphenylcarbamate) and amylose tris(3,5-dimethylphenylcarbamate), respectively. The mobile phases were mixtures of methanol or acetonitrile with sodium perchlorate or sodium chloride...
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