magistrsko delo
Ana Brodnik (Author), Janez Košmrlj (Mentor), Iztok Turel (Thesis defence commission member), Marjan Jereb (Thesis defence commission member)

Abstract

Za potencialno fluorescenčno detekcijo proteinskih plakov amiloida ß, ki so eni izmed glavnih biomarkerjev Alzheimerjeve bolezni, smo pripravili šest difenilacetilenskih fluoroforov. S spajanjem po Sonogashiri smo iz komercialno dostopnega 4-etinil-N,N-dimetilanilina in 4'-bromoacetofenona sintetizirali keton, ki nam je služil kot substrat za vse nadaljnje pretvorbe. Z različnimi tipi kondenzacij in intramolekularnimi ciklizacijami z malononitrilom, DMF-DMA in cianoocetno kislino ter 2-ciano-3,3-bis(metiltio)akrilatom smo ga pretvorili v končne produkte. Pripravljene spojine smo popolnoma okarakterizirali z 1H in 13C NMR spektroskopijo, IR spektroskopijo in masno spektrometrijo visoke ločljivosti (HRMS), za trdne spojine pa smo določili tudi tališče. Čistost spojin smo preverili s tekočinsko kromatografijo visoke zmogljivosti (HPLC). Posneli smo absorpcijske, emisijske in eksitacijske spektre ter ugotovili, kako prisotnost različnih elektron-privlačnih skupin vpliva na optične lastnosti izbranih molekul. Izračunali smo tudi kvantni izkoristek in molarno absorptivnost. Rezultate optičnih meritev smo interpretirali v kontekstu uporabnosti novih spojin kot potencialnih molekulskih sond za diagnosticiranje Alzheimerjeve bolezni.

Keywords

Alzheimerjeva bolezen;fluorescenčne molekulske sonde;spajanje po Sonogashiri;"push-pull" sistemi;solvatokromizem;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [A. Brodnik]
UDC: 547.1.057(043.2)
COBISS: 163000323 Link will open in a new window
Views: 44
Downloads: 21
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Other data

Secondary language: English
Secondary title: Synthesis of diphenylacetylene derivatives with interesting optical properties
Secondary abstract: Six diphenylacetylene fluorophores were synthesized for potential fluorescence detection of amyloid ß protein plaques, which are one of the most important biomarkers of Alzheimer disease. From commercial 4-ethynyl-N,N-dimethylaniline and 4'-bromoacetophenone, ketone was obtained by Sonogashira coupling, which served as a substrate for all further transformations. The following compounds were prepared by various types of condensations and intramolecular cyclizations through reactions of the starting ketone with malononitrile, DMF-DMA, cyanoacetic acid, ethyl acetate and 2-cyano-3,3-bis(methylthio)acrylate. The prepared compounds were fully characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, high-resolution mass spectrometry (HRMS), and for solid compounds melting point was determined. The purity of the compound was verified by high performance liquid chromatography (HPLC). Absorption, emission, and excitation spectra were compared to determine how the presence of different electron-withdrawing groups affects the optical properties of the prepared molecules. The quantum yield and molar absorptivity were calculated. The results of the optical measurements were interpreted in the context of the applicability of the new compounds as potential molecular probes for the diagnosis of Alzheimer disease.
Secondary keywords: Alzheimer disease;fluorescent molecular probes;Sonogashira coupling;"push-pull" systems;solvatochromism;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: 93 str.
ID: 19833922