NMR studija utjecaja UV svjetla na reakciju kloriranja ifosfamida

master's thesis

• Title (english): NMR study of the effect of UV light on the chlorination reaction of ifosfamide
• Author: Edi Vuljanković
• Mentor: Valerije Vrček (mentor)
• Committee member: Valerije Vrček (predsjednik povjerenstva)
• Committee member: Davor Šakić (član povjerenstva)
• Committee member: Viktor Pilepić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of organic chemistry); Zagreb
• Defense date and country: 2025-03-10, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Ifosfamid se nalazi u grupi citotoksičnih lijekova kojeg je JRC Europske komisije svrstala u
zabrinjavajuće spojeve obzirom da još uvijek nije razvijena učinkovita metoda njegovog uklanjanja
iz otpadnih voda. Najvećim dijelom se izlučuje urinom nepromijenjen i kao takav dolazi u sustav
otpadnih voda. U ovom radu je proučavana reakcija kloriranja ifosfamida u tami i pod utjecajem
različitih tipova elektromagnetskog zračenja (bijelo svjetlo, UV svjetlo), s ciljem utvrđivanja
učinkovitosti najčešće korištenih metoda obrade otpadnih voda u uklanjanju navedenog onečišćivala
iz otpadnih voda. Identificiran je glavni produkt reakcije kloriranja i razmotrena njegova stabilnost
u mraku i pod svjetlom, kako bi se utvrdila njegova relevantnost za ekotoksikološka ispitivanja. Iz
dobivenih 1H, 13C, 31P NMR spektara, može se zaključiti da dolazi do kloriranja egzocikličkog
dušika iz N-(2-kloroetil) skupine ifosfamida. Klorirani produkt je fotolabilan u prisutnosti UV
svjetla i njegova razgradnja je jako ovisna o intenzitetu zračenja, dok je sam ifosfamid stabilan.
Obzirom da se pregradnja kloriranog ifosfamida u ifosfamid vjerojatno odvija putem homolitičkog
cijepanja, ali i zbog same toksičnosti ifosfamida, potrebno je provesti daljnja istraživanja
ekotoksičnosti kloriranih produkata.

Abstract (english)

Ifosfamide is in the group of cytotoxic drugs classified by the JRC of the European Commission as
a compound of concern, since an effective method of its removal from wastewater has not yet been
developed. It is mostly excreted in the urine unchanged and as such enters the wastewater system.
In this paper, the chlorination reaction of ifosfamide in the dark and under the influence of different
types of electromagnetic radiation (white light, UV light) was studied, with the aim of determining
the effectiveness of the most commonly used wastewater treatment methods in removing this
pollutant from wastewater. The main product of the chlorination reaction was identified and its
stability in the dark and under light was considered, in order to determine its relevance for
ecotoxicological studies. From the obtained 1H, 13C, 31P NMR spectra, it can be concluded that
chlorination of exocyclic nitrogen from the N-(2-chloroethyl) group of ifosfamide occurs. The
chlorinated product is photolabile in the presence of UV light and its degradation is highly dependent
on the intensity of radiation, while ifosfamide itself is stable. Given that the conversion of
chlorinated ifosfamide to ifosfamide probably occurs by homolytic cleavage, but also due to the
toxicity of ifosfamide itself, further research on the ecotoxicity of chlorinated products needs to be
conducted.

• Keywords: ifosfamid; NMR; klorirani ifosfamid; reakcija N-kloriranja
• Keywords (english): ifosfamide; NMR; chlorinated ifosfamide; N-chlorination reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:163:587332
• Study programme: Title: Pharmacy - integrated undergraduate and graduate - university study; Study programme type: university; Study level: integrated undergraduate and graduate; Academic / professional title: sveučilišni magistar farmacije (sveučilišni magistar farmacije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2025-04-11 11:38:43