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

Lješević, 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)-4-methylterephthalate, 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-chem...ical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 μg/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 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/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 μg/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:
PET dimer / PET trimer / PETase / Polyethylene terephthalate (PET) / ToxicitySource:
Chemosphere, 2021, 275, 130005-Publisher:
- Elsevier
Funding / projects:
- European Union’s Horizon 2020 research and innovation programme under grant agreement No 870292 (BioICEP)
Note:
- Peer-reviewed manuscript: https://cherry.chem.bg.ac.rs/handle/123456789/4411
- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4410
Related info:
- Version of
https://cherry.chem.bg.ac.rs/handle/123456789/4411 - Version of
https://doi.org/10.1016/j.chemosphere.2021.130005 - Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4410
DOI: 10.1016/j.chemosphere.2021.130005
ISSN: 0045-6535
WoS: 000647817200040
Scopus: 2-s2.0-85101382308
URI
https://www.sciencedirect.com/science/article/pii/S0045653521004744https://cherry.chem.bg.ac.rs/handle/123456789/4409
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Đapović, Milica AU - Milivojević, Dušan AU - Ilić-Tomić, Tatjana AU - Lješević, Marija AU - Nikolaivits, Efstratios AU - Topakas, Evangelos AU - Maslak, Veselin AU - Nikodinović-Runić, Jasmina PY - 2021 UR - https://www.sciencedirect.com/science/article/pii/S0045653521004744 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4409 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)-4-methylterephthalate, 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 μg/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 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/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 μg/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 - Elsevier T2 - Chemosphere T2 - ChemosphereChemosphere T1 - Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases VL - 275 SP - 130005 DO - 10.1016/j.chemosphere.2021.130005 ER -
@article{ author = "Đapović, Milica and Milivojević, Dušan and Ilić-Tomić, Tatjana and Lješević, 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)-4-methylterephthalate, 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 μg/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 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/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 μg/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 = "Elsevier", journal = "Chemosphere, ChemosphereChemosphere", title = "Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases", volume = "275", pages = "130005", doi = "10.1016/j.chemosphere.2021.130005" }
Đapović, M., Milivojević, D., Ilić-Tomić, T., Lješević, 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 Elsevier., 275, 130005. https://doi.org/10.1016/j.chemosphere.2021.130005
Đapović M, Milivojević D, Ilić-Tomić T, Lješević 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, Lješević, 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 . .