Izdelava ekotoksikološkega profila bisfenolov in njihovih razgradnih produktov in silico

Jašovič, Vita (avtor), Jakopin, Žiga (mentor)

Bisfenoli so široko uporabljane industrijske kemikalije, prisotne v številnih potrošniških izdelkih, ki zaradi njihove obstojnosti in potencialne ekotoksičnosti vzbujajo vse večjo skrb tudi glede vpliva na vodne ekosisteme. V magistrskem delu smo z uporabo pristopov in silico ocenili ekotoksikološke lastnosti izbranih predstavnikov bisfenolov ter raziskali njihovo okoljsko usodo. Osredotočili smo se na lastnosti, kot so biorazgradljivost, bioakumulacija, obstojnost v sedimentu in toksičnost za vodne organizme. Raziskave smo izvedli s pomočjo treh računalniških programov, in sicer VEGA QSAR, ECOSAR in T.E.S.T. Modeli so omogočili primerjalno oceno tveganj za ribe, rake in alge, pa tudi napoved fizikalno-kemijskih lastnosti, kot so lipofilnost, organski sorpcijski koeficient in topnost v vodi. Napovedi so pokazale, da ima večina analiziranih bisfenolov nizko biorazgradljivost, visoko lipofilnost in znaten bioakumulacijski potencial. Najbolj ekotoksični so bili bisfenol A, bisfenol AF in bisfenol S. Posebej zaskrbljujoča je prisotnost teh spojin v rekah in podzemnih vodah, saj so bile v različnih državah ugotovljene koncentracije, ki presegajo varnostni prag. Tudi v Sloveniji so bile izmerjene koncentracije bisfenola A, ki se približujejo potencialno škodljivim vrednostim. Poleg osnovnih bisfenolov smo obravnavali tudi vpliv razgradnje, in sicer halogenacije, ki lahko poveča toksičnost in okoljsko obstojnost tovrstnih spojin, pri čemer se intenziteta teh lastnosti, do neke mere, povečuje s stopnjo substitucije. Med ocenjenimi spojinami sta bila kot najverjetneje obstojna, bioakumulativna in toksična, prepoznana derivata Br3-BPA in Cl4-BPA. Kljub uporabnosti metod in silico kot hitrega orodja za oceno nevarnosti kemikalij, smo ugotovili, da pomanjkanje eksperimentalnih podatkov omejuje zanesljivost končnih ocen tveganja. Rezultati magistrskega dela prispevajo k boljšemu razumevanju usode bisfenolov in njihovih razgradnih produktov v okolju ter poudarjajo nujnost njihovega zakonodajnega nadzora ter nesmiselnosti uporabe analogov bisfenola A, kot ustreznejših alternativ, saj so le-ti lahko še bolj toksični kot osnovna spojina.

• Jezik: Slovenski jezik
• Ključne besede: bisfenoli, ekotoksikološki profil, metode in silico, halogeniranje, vodni ekosistem, razgradni produkti
• Vrsta gradiva: Magistrsko delo/naloga
• Organizacija: FFA - Fakulteta za farmacijo
• Leto izida: 2025
• PID: 20.500.12556/RUL-173715
• Datum objave v RUL: 20.09.2025

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: In silico ecotoxicological profiling of bisphenols and their degradation products

Izvleček

Bisphenols are widely used industrial chemicals, present in many consumer products, which, due to their persistence and potential ecotoxicity, are of increasing concern regarding their impact on aquatic ecosystems. In this Master's thesis, we used in silico approaches to assess the ecotoxicological properties of selected bisphenols and also investigated their environmental fate. We focused on properties such as biodegradability, bioaccumulation, persistence in sediment and toxicity to aquatic organisms. The research was carried out using three different softwares: VEGA QSAR, ECOSAR and T.E.S.T. The models enabled a comparative assessment of risks to fish, crustaceans and algae, as well as the prediction of physicochemical properties such as lipophilicity, organic carbon sorption coefficient and water solubility. The software predictions showed that most of the analyzed bisphenols have low biodegradability, high lipophilicity and a significant bioaccumulation potential. The highest ecotoxicity was observed for bisphenol A, bisphenol AF and bisphenol S. The presence of these compounds in rivers and groundwater is of particular concern, as concentrations exceeding the safety threshold were found in various countries. Concentrations of bisphenol A approaching potentially harmful values were also measured in Slovenia. In addition to the basic bisphenols, we also considered the impact of transformations, specifically halogenation, which can increase the toxicity and environmental persistence of these compounds, with the intensity of these properties increasing to some extent with the number of substitutions. Despite the usefulness of in silico methods as a rapid tool for chemical hazard assessment, we found that the lack of experimental data limits the reliability of final risk assessments. The results of this Master's thesis contribute to a better understanding of the fate of bisphenols and their degradation products in the environment and emphasize the necessity of their regulatory control, as well as the futility of using bisphenol A analogues as more suitable alternatives, as they can be even more toxic than the basic compound.

• Ključne besede: bisphenols, ecotoxicological profile, in silico methods, halogenation, aquatic ecosystem, degradation products