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Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases

Authorized Users Only
2021
Authors
Đapović, Milica
Milivojević, Dušan
Ilić-Tomić, Tatjana
Lješević, Marija
Nikolaivits, Efstratios
Topakas, Evangelos
Maslak, Veselin
Nikodinović-Runić, Jasmina
Article (Published version)
Metadata
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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-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) / Toxicity
Source:
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
[ Google Scholar ]
34
13
URI
https://www.sciencedirect.com/science/article/pii/S0045653521004744
https://cherry.chem.bg.ac.rs/handle/123456789/4409
Collections
  • Publikacije / Publications
Institution/Community
Hemijski fakultet / Faculty of Chemistry
TY  - 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 . .

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