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Synthesis of isoprenoid naringenin derivatives
Kernal, Jakub ; Zimčík, Petr (advisor) ; Demuth, Jiří (referee)
5 Abstract Charles University, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Candidate Jakub Kernal Supervisor prof. PharmDr. Consultant Hubert Chapuis, Ph.D. Title of Thesis Synthesis of Isoprenoid Naringenin Derivatives Naringenin as a member of flavanone subclass of flavonoids and its derivatives have been subjects of intensive study for their antibacterial, antifungal, and antineoplastic properties. Recent development in current methods of synthetic chemistry allows us to satisfy the increasing demand for these molecules by providing an alternative source of these naturally occurring substances in the means of chemical synthesis. The aim of this work was synthesis and characterization of naringenin derivatives with increased lipophilic profile which will serve in future research as potential cytotoxic agents. Two major approaches have been developed in the process of obtaining lipophilic derivatives of naringenin (Fig. 2) where the lipophilic moiety consists of terpene or terpenoid part, which is believed to increase the uptake of the desired product by cells. In the first approach, we focused on the modification of the B phenolic ring by esterification of the hydroxyl group on the 4 carbon or on the modification of both A and B...
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Synthesis of isoprenoid naringenin derivatives
Kernal, Jakub ; Zimčík, Petr (advisor) ; Demuth, Jiří (referee)
5 Abstract Charles University, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Candidate Jakub Kernal Supervisor prof. PharmDr. Consultant Hubert Chapuis, Ph.D. Title of Thesis Synthesis of Isoprenoid Naringenin Derivatives Naringenin as a member of flavanone subclass of flavonoids and its derivatives have been subjects of intensive study for their antibacterial, antifungal, and antineoplastic properties. Recent development in current methods of synthetic chemistry allows us to satisfy the increasing demand for these molecules by providing an alternative source of these naturally occurring substances in the means of chemical synthesis. The aim of this work was synthesis and characterization of naringenin derivatives with increased lipophilic profile which will serve in future research as potential cytotoxic agents. Two major approaches have been developed in the process of obtaining lipophilic derivatives of naringenin (Fig. 2) where the lipophilic moiety consists of terpene or terpenoid part, which is believed to increase the uptake of the desired product by cells. In the first approach, we focused on the modification of the B phenolic ring by esterification of the hydroxyl group on the 4 carbon or on the modification of both A and B...
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Synthesis of isoprenoid naringenin derivatives
Kernal, Jakub ; Zimčík, Petr (advisor) ; Demuth, Jiří (referee)
5 Abstract Charles University, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Candidate Jakub Kernal Supervisor prof. PharmDr. Consultant Hubert Chapuis, Ph.D. Title of Thesis Synthesis of Isoprenoid Naringenin Derivatives Naringenin as a member of flavanone subclass of flavonoids and its derivatives have been subjects of intensive study for their antibacterial, antifungal, and antineoplastic properties. Recent development in current methods of synthetic chemistry allows us to satisfy the increasing demand for these molecules by providing an alternative source of these naturally occurring substances in the means of chemical synthesis. The aim of this work was synthesis and characterization of naringenin derivatives with increased lipophilic profile which will serve in future research as potential cytotoxic agents. Two major approaches have been developed in the process of obtaining lipophilic derivatives of naringenin (Fig. 2) where the lipophilic moiety consists of terpene or terpenoid part, which is believed to increase the uptake of the desired product by cells. In the first approach, we focused on the modification of the B phenolic ring by esterification of the hydroxyl group on the 4 carbon or on the modification of both A and B...
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Study of azaphthalocyanines as fluorescence quenchers in oligodeoxynucleotide probes
Demuth, Jiří ; Nováková, Veronika (advisor) ; Hocek, Michal (referee) ; Vávrová, Kateřina (referee)
Charles University, Faculty of Pharmacy in Hradec Kralove Department: Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Author: Mgr. Jiří Demuth Supervisor: doc. PharmDr. Veronika Nováková, Ph.D. Consultant: prof. PharmDr. Petr Zimčík, Ph.D. Doctoral Thesis: Study of azaphthalocyanines suitable for quenching of fluorescence in oligodeoxynucleotide probes Phthalocyanines (Pcs) and azaphthalocyanines (AzaPcs) are planar macrocyclic compounds. These synthetic compounds are derived from naturally occurring dyes - porphyrins. Pcs and AzaPcs have very interesting photophysical properties due to their extensive 18 -electron conjugated system. They are used in electrotechnics, material industry or in medicinal applications. Octaalkylamino substituted tetrapyrazinoporphyrazines (TPyzPzs), which belong to AzaPc family, can quench fluorescence of other molecules due to the ultrafast intramolecular charge transfer. This thesis studies this quenching ability of TPyzPzs with the aim to develop efficient fluorescence probes. Such probes could find application in a variety of experiments across scientific disciplines i.e. - biochemistry, forensic or genetic analysis. Synthetic part of dissertation thesis is a continuation of previous investigation of TPyzPzs in our research group. It describes...
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Study of azaphthalocyanines as fluorescence quenchers in oligodeoxynucleotide probes
Demuth, Jiří ; Nováková, Veronika (advisor) ; Hocek, Michal (referee) ; Vávrová, Kateřina (referee)
Charles University, Faculty of Pharmacy in Hradec Kralove Department: Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Author: Mgr. Jiří Demuth Supervisor: doc. PharmDr. Veronika Nováková, Ph.D. Consultant: prof. PharmDr. Petr Zimčík, Ph.D. Doctoral Thesis: Study of azaphthalocyanines suitable for quenching of fluorescence in oligodeoxynucleotide probes Phthalocyanines (Pcs) and azaphthalocyanines (AzaPcs) are planar macrocyclic compounds. These synthetic compounds are derived from naturally occurring dyes - porphyrins. Pcs and AzaPcs have very interesting photophysical properties due to their extensive 18 -electron conjugated system. They are used in electrotechnics, material industry or in medicinal applications. Octaalkylamino substituted tetrapyrazinoporphyrazines (TPyzPzs), which belong to AzaPc family, can quench fluorescence of other molecules due to the ultrafast intramolecular charge transfer. This thesis studies this quenching ability of TPyzPzs with the aim to develop efficient fluorescence probes. Such probes could find application in a variety of experiments across scientific disciplines i.e. - biochemistry, forensic or genetic analysis. Synthetic part of dissertation thesis is a continuation of previous investigation of TPyzPzs in our research group. It describes...
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Synthesis and photophysical study of hydrophilic tetrapyridoporphyrazines bearing charged substituents on the periphery
Demuth, Jiří ; Nováková, Veronika (advisor) ; Vávrová, Kateřina (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Biophysics and Physical Chemistry Candidate Jiří Demuth Supervisor Assoc. Prof. Veronika Nováková, PhD. Title of Thesis Synthesis and photophysical study of hydrophilic tetrapyridoporphyrazines bearing charged substituents on the periphery Phthalocyanines are planar organic molecules, which have a metal cation coordinated in their centre. This work deals with their aza-analogues - tetra-3,4-pyridoporphyrazines (TPyPz). TPyPz can absorb light in red part spectrum and then produce singlet oxygen. Due to this ability, they may be used in photodynamic therapy (PDT) of cancer. PDT's mechanism is based on three components: photosensitizer, light and singlet oxygen. Photosensitizer transfers energy of absorbed light to oxygen making, thus, cytotoxic singlet oxygen. The goal of this thesis was to synthesize water soluble TPyPzs absorbing in red part of absorption spectrum. TPyPzs bearing different charged substituents will be compared within the series. The synthesis consisted of preparation of 2-chloro-5,6-dimethylpyridine-3,4-dicarbonitrile (1), which was the starting precursor for other reactions. Nucleophilic substitution of 1 was used for the introducing of various hydrophilic substituents. Prepared precursors...
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