Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases
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2021
Authors
Đapović, MilicaMilivojević, Dušan
Ilić-Tomić, Tatjana
Ljesević, Marija
Nikolaivits, Efstratios
Topakas, Evangelos
Maslak, Veselin
Nikodinović-Runić, Jasmina
Article (Published version)
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Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemi...cal properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 mg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 mg/mL with inhibiting concentration (IC50) values of 30 mg/mL and 50 mg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 mg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes.
Keywords:
Toxicity / Polyethylene terephthalate (PET) / PETase / PET trimer / PET dimerSource:
Chemosphere, 2021, 275, 130005-Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- European Union's Horizon 2020 research and innovation programme [870292]
Note:
- Related to Supplementary material: https://imagine.imgge.bg.ac.rs/handle/123456789/1733
- Related to accepted version: https://imagine.imgge.bg.ac.rs/handle/123456789/1732
Related info:
DOI: 10.1016/j.chemosphere.2021.130005
ISSN: 0045-6535
PubMed: 33640747
WoS: 000647817200040
Scopus: 2-s2.0-85101382308
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Đapović, Milica AU - Milivojević, Dušan AU - Ilić-Tomić, Tatjana AU - Ljesević, Marija AU - Nikolaivits, Efstratios AU - Topakas, Evangelos AU - Maslak, Veselin AU - Nikodinović-Runić, Jasmina PY - 2021 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/1415 AB - Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 mg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 mg/mL with inhibiting concentration (IC50) values of 30 mg/mL and 50 mg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 mg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Chemosphere T1 - Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases SP - 130005 VL - 275 DO - 10.1016/j.chemosphere.2021.130005 ER -
@article{ author = "Đapović, Milica and Milivojević, Dušan and Ilić-Tomić, Tatjana and Ljesević, Marija and Nikolaivits, Efstratios and Topakas, Evangelos and Maslak, Veselin and Nikodinović-Runić, Jasmina", year = "2021", abstract = "Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 mg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 mg/mL with inhibiting concentration (IC50) values of 30 mg/mL and 50 mg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 mg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Chemosphere", title = "Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases", pages = "130005", volume = "275", doi = "10.1016/j.chemosphere.2021.130005" }
Đapović, M., Milivojević, D., Ilić-Tomić, T., Ljesević, M., Nikolaivits, E., Topakas, E., Maslak, V.,& Nikodinović-Runić, J.. (2021). Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases. in Chemosphere Pergamon-Elsevier Science Ltd, Oxford., 275, 130005. https://doi.org/10.1016/j.chemosphere.2021.130005
Đapović M, Milivojević D, Ilić-Tomić T, Ljesević M, Nikolaivits E, Topakas E, Maslak V, Nikodinović-Runić J. Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases. in Chemosphere. 2021;275:130005. doi:10.1016/j.chemosphere.2021.130005 .
Đapović, Milica, Milivojević, Dušan, Ilić-Tomić, Tatjana, Ljesević, Marija, Nikolaivits, Efstratios, Topakas, Evangelos, Maslak, Veselin, Nikodinović-Runić, Jasmina, "Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases" in Chemosphere, 275 (2021):130005, https://doi.org/10.1016/j.chemosphere.2021.130005 . .