Novi derivati rezveratrola - sinteza i spektroskopska karakterizacija

undergraduate thesis

• Title (english): New carbamate derivatives of resveratrol - synthesis and spectroscopic characterization
• Author: Sara Milić
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Sanja Martinez (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-09-06, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Svrha je ovog rada sinteza novih rezveratrolnih derivata, prvenstveno radi ispitivanja mogućnosti njihove primjene kod liječenja Alzheimerove bolesti, kao inhibitora enzima kolinesteraza. Budući da je rezveratrol već prepoznat kao spoj s jakim antioksidacijskim svojstvima, cilj je ovog istraživanja poboljšanje njegovih bioloških karakteristika modificiranjem njegove kemijske strukture. Stoga su novi derivati sintetizirani postupkom Wittigove reakcije, uz odvajanje nastalih izomera kolonskom kromatografijom. Pritom su korišteni odgovarajući aldehid, sa željenim supstituentom u para-položaju u odnosu na hidroksilnu skupinu, te tiofenska sol, nesupstituirana ili 5-metil-2-supstituirana sol. Uspješno su dobiveni biološki aktivni trans-izomeri novih rezveratrolnih derivata, a njihove su ključne istraživane karakteristike antioksidacijska svojstva i sposobnost inhibicije enzima kolinesteraza. Uz to, spektroskopska karakterizacija sintetiziranih spojeva doprinosi boljem razumijevanju njihovih kemijskih svojstava. Na temelju rezultata mjerenja, spoj trans-7 pokazuje najznačajniju antioksidacijsku aktivnost, ostvarivši inhibiciju butirilkolinesteraze s vrijednosti IC50 od 24,8 μM te negativan in silico test na genotoksičnost.

Abstract (english)

The purpose of this study is the synthesis of new resveratrol derivatives, primarily to investigate their potential application in the treatment for Alzheimer's disease, as cholinesterase enzymes inhibitors. Since resveratrol is already recognized as a compound with strong antioxidant properties, the aim of this research is to enhance its biological characteristics by modifying its chemical structure. Therefore, the new derivatives were synthesized using the Wittig reaction, with separation of the resulting isomers by column chromatography. An aldehyde, with the desired substituent in para-position relative to the hydroxyl group, and a thiophene salt, either unsubstituted or 5-methyl-2-substituted, were used in the process. Biologically active trans-isomers were successfully obtained, and their key characteristics, such as antioxidant properties and the ability to inhibit cholinesterase enzymes, were examined. Additionally, the spectroscopic characterization of the synthesized compounds contributes to a better understanding of their chemical properties. Research results show that compound trans-7 demonstrates the most significant antioxidant activity, achieving butyrylcholinesterase inhibition with IC50 value of 24.8 μM and a negative in silico test for genotoxicity.

• Keywords: Alzheimerova bolest; antioksidacija; inhibicija; kolinesteraza; rezveratrol; Wittigova reakcija
• Keywords (english): Alzheimer's disease; antioxidation; inhibition; cholinesterase; resveratrol; Wittig reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:743105
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-11-06 09:35:14