magistrsko delo
Ana Brodnik (Avtor), Janez Košmrlj (Mentor), Iztok Turel (Član komisije za zagovor), Marjan Jereb (Član komisije za zagovor)

Povzetek

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.

Ključne besede

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

Podatki

Jezik: Slovenski jezik
Leto izida:
Tipologija: 2.09 - Magistrsko delo
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik: [A. Brodnik]
UDK: 547.1.057(043.2)
COBISS: 163000323 Povezava se bo odprla v novem oknu
Št. ogledov: 44
Št. prenosov: 21
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Angleški jezik
Sekundarni naslov: Synthesis of diphenylacetylene derivatives with interesting optical properties
Sekundarni povzetek: 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.
Sekundarne ključne besede: Alzheimer disease;fluorescent molecular probes;Sonogashira coupling;"push-pull" systems;solvatochromism;Univerzitetna in visokošolska dela;
Vrsta dela (COBISS): Magistrsko delo/naloga
Študijski program: 1000375
Konec prepovedi (OpenAIRE): 1970-01-01
Komentar na gradivo: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Strani: 93 str.
ID: 19833922