magistrsko delo
Uroš Vezonik (Author), Janez Košmrlj (Mentor), Helena Prosen (Thesis defence commission member), Martin Gazvoda (Thesis defence commission member)

Abstract

V magistrskem delu smo se ukvarjali s pripravo novih “pametnih” molekulskih sond, ki bi lahko bile uporabljene za zgodnjo detekcijo Alzheimerjeve bolezni. Spojine smo zasnovali tako, da so ustrezale ''push-pull" arhitekturi – gre za π-sistem, ki je na eni strani zaključen z elektrondonorsko skupino in na drugi strani z elektronakceptorsko skupino, vmes pa je konjugiran π-sistem (D–π–A). Da bi omogočili čim hitrejšo in enostavnejšo spreminjanje elektrondonorskega dela molekule, smo se ukvarjali tudi z optimizacijo reakcijskih pogojev za s paladijem katalizirano tvorbo C-N vezi v zadnjem koraku sinteze. S preučevanjem reakcijskih pogojev na modelni reakciji med 8 in pirolidinom smo pokazali, da je aminiranje v zadnjem koraku mogoče kljub prisotnosti 4-metil-2-okso-2H-piran-3-karbonitrilne skupine in reakcijo uspešno izvedli še z uporabo dimetilamina. Pripravljene produkte smo okarakterizirali z 1H in 13C NMR ter IR spektroskopijo, masno spektrometrijo visoke ločljivosti, meritvijo tališča ter čistost določili s HPLC analizo. Izbranim spojinam smo posneli optične lastnosti in jim določili absorpcijske, emisijske in ekscitacijske maksimume ter za dane molekule izračunali molarne absorptivnosti in kvantne izkoristke. S strani partnerjev na projektu so bili na izbranih spojinah že narejeni preliminarni in vitro ter ex vivo biološki testi, ki so dali zelo spodbudne rezultate.

Keywords

Alzheimerjeva bolezen;biomarkerji;pametne molekulske sonde;organska sinteza;Buchwald-Hartwig aminiranje;naftalen;optične lastnosti;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [U. Vezonik]
UDC: 547.652(043.2)
COBISS: 116926979 Link will open in a new window
Views: 155
Downloads: 69
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Other data

Secondary language: English
Secondary title: Synthesis of Novel Naphthalene-Based Fluorescent Molecules
Secondary abstract: In this thesis, we are describing a preparation of new smart molecular probes which could be used for an early detection of the Alzheimer’s disease. Compounds were designed based on the “push-pull” architecture – this is a π-system on one side end-capped with an electron-donating group and on the other side with the electron-accepting group (D–π–A). To allow for a fast and straight-forward diversification of the electron-donating part of the molecule, we were also working on developing optimized reaction conditions for a palladium catalysed late-stage C-N coupling. With methodical screening of the reaction conditions on a model reaction between 8 and pyrrolidine, we have shown that amination in the last step is possible despite presence of 4-methyl-2-oxo-2H-pyran-3-carbonitrile group and have also demonstrated this transformation using dimethylamine as an amine source. We have characterized synthesized compounds with a 1H and 13C NMR and IR spectroscopy, high-resolution mass spectrometry, recorded their melting point and determined their purity with HPLC analysis. For chosen compounds, we have also recorded their optical properties and determined their absorption, emission and excitation maximums. For those compounds we have also calculated their molar absorptivity and quantum yields. Partners on the project have also performed preliminary in vitro and ex vivo biological tests using selected compounds, which gave very promising results.
Secondary keywords: Alzheimer's disease;Buchwald-Hartwig amination;optical properties;organic synthesis;smart molecular probes;Univerzitetna in visokošolska dela;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 122 str.
ID: 15841046