Abstract
W ramach badań, opisanych w niniejszej rozprawie doktorskiej, zaprojektowano, otrzymano oraz scharakteryzowano połączenia tzw. parasoli molekularnych ze związkami o udowodnionej aktywności przeciwgrzybowej – FMDP i cis-pentacyny – będących inhibitorami enzymów grzybowych. Wspomniane cząsteczki aktywne wykazują dobre właściwości przeciwgrzybowe, jednak ze względu na swoją budowę chemiczną i polarny charakter, wykazują silnie ograniczoną zdolność do przenikania przez biwarstwę lipidową. Parasole molekularne stanowią grupę stosunkowo niedawno poznanych nanonośników, zdolnych do przenikania błon biologicznych na drodze dyfuzji prostej oraz zdolnych do transportu cząsteczek polarnych do wnętrza komórek. W efekcie badań eksperymentalnych otrzymano czternaście pochodnych – dziesięć połączeń parasoli molekularnych z cząsteczkami aktywnymi oraz cztery pochodne fluorescencyjne. W ramach pracy badawczej przetestowano możliwość tworzenia połączeń parasoli molekularnych z cząsteczkami transportowanymi połączonych za pośrednictwem różnych łączników. Zaproponowano także dwie alternatywne metody syntezy struktur parasolowych. Najprostsze otrzymane pochodne to bezpośrednie połączenia amidowe struktury nanonośnika z cząsteczką transportowaną. Pozostałe koniugaty zawierają w swojej strukturze labilny łącznik potencjalnie ulegający lizie w środowisku cytoplazmy patogennych komórek grzybowych. Jednymi z zastosowanych łączników są struktury dipeptydowe, w których cząsteczka ładunku połączona jest za pośrednictwem wiązania peptydowego, potencjalnie rozpoznawanego przez komórkowe amidazy. W innym podejściu zastosowano ideę tzw. układu ‘trimethyl lock’ labilnego w środowisku aktywności esteraz, w którym to cząsteczka ładunku tworzy wiązanie amidowe z jedną z grup karboksylowych wspomnianego układu. Podjęto także próbę syntezy koniugatów wyposażonych w łącznik o-ditiobenzoiloakrbamoilowy, zawierający w swojej konstytucji wiązanie disulfidowe, redukowane przez komórkowy glutation. Wszystkie końcowe oraz pośrednie struktury poddano analizie strukturalnej z wykorzystaniem technik spektroskopowych, m. in. spektroskopią 1H NMR i 13C NMR oraz spektrometrią mas. Ponadto, oznaczono ich czystość chemiczna przy pomocy wysokosprawnej chromatografii cieczowej (HPLC). Otrzymane pochodne przekazano do badań biologicznych mających na celu określenie aktywności przeciwgrzybowej, hemotoksyczności oraz cytotoksyczności.
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- Category:
- Thesis, nostrification
- Type:
- praca doktorska pracowników zatrudnionych w PG oraz studentów studium doktoranckiego
- Language:
- Polish
- Publication year:
- 2017
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- Konferencje naukowe Prezentacje ustne:
- Skwarecki, A. S. Synthesis of disubstituted 1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acids derivatives. BioTech 2013 (2013). open in new tab
- Artykuły konferencyjne:
- Skwarecki, A. S. Synthesis of disubstituted 1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acids derivatives. PhD Interdisciplinary Journal 1, 75-78 (2013). open in new tab
- Sesje posterowe: Skwarecki, A. S., Milewska, M. J. Parasole Molekularne -potencjalne transportery substancji aktywnych do komórek grzybowych. 58 Zjazd Polskiego Towarzystwa Chemicznego w Gdańsku. Gdańsk (2015). open in new tab
- Skwarecki, A. S., Milewska, M. J., Milewski, S., Wiśniewska, A., Schielmann, M., Kawczyński, M. T. Synteza dipeptydów o aktywności przeciwgrzybowej zawierających inhibitor dehydrogenazy homoserynowej. 58 Zjazd Polskiego Towarzystwa Chemicznego w Gdańsku. Gdańsk (2015). open in new tab
- Skwarecki, A. S., Skarbek, K., Koperkiewicz, D., Milewska, M. J. Koniugaty parasoli molekularnych z makrolidami polienowymi. 59 Zjazd Polskiego Towarzystwa Chemicznego w Poznaniu. Poznań (2016). open in new tab
- Verified by:
- Gdańsk University of Technology
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