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master's thesis
Derivati harmina kao potencijalni inhibitori bakterijskog biofilma
Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry, 2020. urn:nbn:hr:163:916342
Kapović, Katja
University of Zagreb
Faculty of Pharmacy and Biochemistry
Department of medicinal chemistry

Institutional repository: Repository of Faculty of Pharmacy and Biochemistry University of Zagreb

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Kapović, K. (2020). Derivati harmina kao potencijalni inhibitori bakterijskog biofilma (Master's thesis). Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry. Retrieved from https://urn.nsk.hr/urn:nbn:hr:163:916342

Kapović, Katja. "Derivati harmina kao potencijalni inhibitori bakterijskog biofilma." Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, 2020. https://urn.nsk.hr/urn:nbn:hr:163:916342

Kapović, Katja. "Derivati harmina kao potencijalni inhibitori bakterijskog biofilma." Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, 2020. https://urn.nsk.hr/urn:nbn:hr:163:916342

Kapović, K. (2020). 'Derivati harmina kao potencijalni inhibitori bakterijskog biofilma', Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, accessed 27 May 2024, https://urn.nsk.hr/urn:nbn:hr:163:916342

Kapović K. Derivati harmina kao potencijalni inhibitori bakterijskog biofilma [Master's thesis]. Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry; 2020 [cited 2024 May 27] Available at: https://urn.nsk.hr/urn:nbn:hr:163:916342

K. Kapović, "Derivati harmina kao potencijalni inhibitori bakterijskog biofilma", Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:163:916342

Metadata
TitleDerivati harmina kao potencijalni inhibitori bakterijskog biofilma
Title (english)Harmine derivatives as potential biofilm inhibitors
AuthorKatja Kapović
MentorZrinka Rajić (mentor)
Committee memberZrinka Rajić (predsjednik povjerenstva)
Committee memberIvana Perković (član povjerenstva)
Committee memberAna Mornar Turk (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Pharmacy and Biochemistry
(Department of medicinal chemistry)
Zagreb
Defense date and country2020-10-05, Croatia
Scientific / art field,
discipline and subdiscipline		BIOMEDICINE AND HEALTHCARE
Pharmacy
Pharmacy
Abstract
Biofilm je zajednica različitih vrsta mikroorganizama koji su uklopljeni u matriks. Matriks predstavlja fizičku barijeru koja otežava penetraciju antibiotika do ciljnih stanica, a s druge strane, zbog viskoelastičnosti otežano je mehaničko uklanjanje. Navedeno čini biofilm kako zdravstvenim, tako i industrijskim problemom s obzirom da se može formirati na bilo kojoj metalnoj ili plastičnoj površini. U ovom radu sintetizirana su tri potencijalna inhibitora biofilma (6-8). Sinteza se odvijala u četiri koraka, a kao početni spoj uzet je harmin. U prvom koraku sinteze Michaelovom adicijom dobiven je ester 1. U idućem koraku u reakciji hidrolize dobivena je kiselina 2. U trećem koraku sinteze reakcijom couplinga između kiseline 2 i odgovarajućeg amina (4-amino-1-Boc-piperidina, 4-(NBoc- amino)piperidina ili N-Bocetilendiamina), uz HATU/DIEA dobiveni su N-Boc zaštićeni amidi (3-5). Boc zaštitna skupina uklonjena je u kiselim uvjetima, uz TFA, te su dobiveni odgovarajući amidi (6-8). Spojevima su određena su tališta, a njihove strukture potvrđene su standardnim spektroskopskim i spektrometrijskim tehnikama (IR, 1H i 13C NMR, MS). U daljnjim istraživanjima, bit će ispitano njihovo inhibitorno djelovanje na bakterijski biofilm.
Abstract (english)
Biofilm is a community consisting of various types of microorganisms embedded in extracellular matrix, which represents a physical barrier that complicates antibiotic penetration to target bacteria. Furthermore, mechanical removal is complicated due to viscoelastic properties of biofilm. Aforementioned makes biofilm a major healthcare, as well as industrial problem, due to the fact that it can be formed on any metal or plastic surface. Three potential biofilm inhibitors have been synthetized (6-8). Synthesis was done in a four step procedure using harmine as a starting compound. The first step included Michael reaction resulting in esther 1, which was subsequently hydrolised to give acid 2. The third step included coupling reaction between acid 2 and corresponding amine (4- amino-1-Boc-piperidine, 4-(N-Boc-amino)piperidine or N-Boc-ethylenediamine), in the presence of HATU/DIEA, resulting in N-Boc protected amides (3-5). Boc protective group was removed under acid conditions, (TFA), to yield final compounds, amides (6-8). Melting points of new compounds were determined and their structures were confirmed using standard spectroscopic and spectrometric techniques (IR, 1H and 13C NMR, MS). Their inhibitory activity on bacterial biofilm will be tested in further studies.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:163:916342
Study programmeTitle: Pharmacy
Study programme type: university
Study level: integrated undergraduate and graduate
Academic / professional title: magistar/magistra farmacije (magistar/magistra farmacije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2022-10-05
Terms of useLicence In copyright icon
Created on2022-03-02 13:55:37