No public access
master's thesis
Applications of peptide coupling to synthesis of selected 15^2-amino derivatives of chlorin eˇ6

Ana Cvitan (2016)
Sveučilište u Rijeci
Odjel za biotehnologiju
Metadata
TitlePrimjena peptidnog vezanja u sintezi odabranih 15^2-amino derivata klorina eˇ6
AuthorAna Cvitan
Mentor(s)Davor Margetić (thesis advisor)
Abstract
U svrhu korištenja porfirinskih derivata u fotodinamičkoj terapiji sintetski je pripravljen 152-konjugat klorina e6 i 2-(2-piridil)etilamina. U ovisnosti o reakcijskim uvjetima i reagensima korištenim za peptidno vezanje, nastaju različite smjese u kojima dominira 152-konjugat, u odnosu na 152,173-biskonjugat. Reakcijski mehanizam njihova nastanka i reaktivnosti klorina e6 su diskutirani. Optimizacija reakcije dobivanja 131,152-anhidrida klorina e6 nije dovela do njegove priprave u čistom obliku pogodnom za korištenje za konjugaciju s aminima. Nadalje je pokazano kako direktna 152-konjugacija klorina e6 i triptamina peptidnim vezanjem dovodi do djelomičnog stvaranja produkta. Peptidno vezanje je također korišteno za pripravu novog 131-konjugata klorina e6 i triptofana a korištenjem reagensa za peptidno vezanje. Struktura novopripravljenog spoja je okarakterizirana 1D i 2D NMR (COSY i NOESY), UV/VIS i IR spektroskopijom, te masenom spektrometrijom. Analogna reakcija sa nikotinskom kiselinom nije bila uspješna.
Keywordsporphyrins dimethyl pheophorbide a chlorin e6 photodynamic therapy
Parallel title (English)Applications of peptide coupling to synthesis of selected 15^2-amino derivatives of chlorin eˇ6
Committee MembersDavor Margetić (committee chairperson)
Jasminka Giacometti (committee member)
Mladenka Malenica Staver (committee member)
GranterSveučilište u Rijeci
Lower level organizational unitsOdjel za biotehnologiju
PlaceRijeka
StateCroatia
Scientific field, discipline, subdisciplineBIOTECHNICAL SCIENCES
Biotechnology
Study programme typeuniversity
Study levelgraduate
Study programmeMedicinal chemistry
Academic title abbreviationmag. med. chem.
Genremaster's thesis
Language Croatian
Defense date2016-09-16
Parallel abstract (English)
For the purpose of use of porphyrin derivatives in photodynamic therapy, new 152-conjugate of chlorin e6 and 2-(2-pyridyl)ethylamine was prepared. Depending on reaction conditions and reagents used in peptide coupling, different mixtures were synthesized, with major product the 152-conjugate. In this master thesis reaction mechanism and reactivity of chlorine e6 is discussed. Optimization of synthesis of 131,152-chlorine e6 anhydride did not lead to its pure state appropriate for amine conjugation. Furthermore is shown that direct conjugation of 152-chlorine e6 and tryptamine by peptide coupling leads to partial product synthesis. Peptide coupling was also used for the preparation of new 131-chlorine e6 conjugate and tryptophan with application of peptide coupling reagents. New compound structure was characterized by 1D and 2D NMR (COSY and NOESY), UV/VIS and IR spectroscopy and also by mass spectrometry. Analogous reaction with nicotic acid was not successful.
Parallel keywords (Croatian)porfirini dimetil feoforbid a klorin e6 fotodinamička terapija
Resource typetext
Access conditionNo public access
URN:NBNhttps://urn.nsk.hr/urn:nbn:hr:193:524352
CommitterLea Lazzarich