Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

Zhang, Wenhui; Sun, Ruihao; Hou, Yilin; Qiu, Youli; Yu, Lushan

doi:10.1002/etc.4710

Cited by 8 publications

(3 citation statements)

References 37 publications

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“…Stability was used as an evaluation index for the molecular functionality of the DEP derivatives [ 34 ] with the frequency, total energy and energy gap as the parameters. The above parameters were calculated by Gaussian 2009 software (Gaussian Inc., Wallingford, CT, USA) based on density functional theory (DFT) at the unit level of b3pw91/6-31G* [ 35 ]; environmental friendliness was evaluated by the four persistent organic pollutants’ (POPs) characteristics of toxicity (LC 50 ), persistence (logt 1/2 ), bioconcentration (logBCF) and migration (−logPL) [ 36 ].…”

Section: Methodsmentioning

confidence: 99%

Enhanced Biodegradation of Phthalic Acid Esters’ Derivatives by Plasticizer-Degrading Bacteria (Burkholderia cepacia, Archaeoglobus fulgidus, Pseudomonas aeruginosa) Using a Correction 3D-QSAR Model

Zhang

Zhao

2020

IJERPH

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A phthalic acid ester’s (PAEs) comprehensive biodegradability three-dimensional structure-activity relationship (3D-QSAR) model was established, to design environmentally friendly PAE derivatives, which could be simultaneously degraded by plasticizer-degrading bacteria, such as Burkholderia cepacia, Archaeoglobus fulgidus, and Pseudomonas aeruginosa. Only three derivatives of diethyl phthalate (DEP (DEP-27, DEP-28 and DEP-29)) were suited for their functionality and environmental friendliness, which had an improved stability in the environment and improved the characteristics (bio-toxicity, bioaccumulation, persistence, and long-range migration) of the persistent organic pollutants (POPs). The simulation inference of the microbial degradation path before and after DEP modification and the calculation of the reaction energy barrier exhibited the energy barrier for degradation being reduced after DEP modification and was consistent with the increased ratio of comprehensive biodegradability. This confirmed the effectiveness of the comparative molecular similarity index analysis (CoMSIA) model of the PAE’s comprehensive biodegradability. In addition, a molecular dynamics simulation revealed that the binding of the DEP-29 derivative with the three plasticizer-degradation enzymes increased significantly. DEP-29 could be used as a methyl phthalate derivative that synergistically degrades with microplastics, providing directional selection and theoretical designing for plasticizer replacement.

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Section: Methodsmentioning

confidence: 99%

Enhanced Biodegradation of Phthalic Acid Esters’ Derivatives by Plasticizer-Degrading Bacteria (Burkholderia cepacia, Archaeoglobus fulgidus, Pseudomonas aeruginosa) Using a Correction 3D-QSAR Model

Zhang

Zhao

2020

IJERPH

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“…Phthalates are well-avowed plasticizers and additives that are commonly used in fabrics, food containers, pharmaceuticals, medical devices, polyvinyl chloride, detergents, and personal care items ( Zhang et al, 2020 ). However, because of their pervasiveness, they are classified as a high-risk group of emerging contaminants.…”

Section: Introductionmentioning

confidence: 99%

Uptake of a plasticizer (di-n-butyl phthalate) impacts the biochemical and physiological responses of barley

Kumari

Kaur

2022

PeerJ

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Background DBP is one of the most commonly used plasticizers for imparting desirable properties to polymers. The introduction of phthalates is reported to have occurred in the late 1920s, and there has been a significant rise in their release into the environment in past decades due to a lack of covalent bonding with the parent matrix. Because of their numerous applications in day-to-day life, phthalates have become ubiquitous and also classified as endocrine disruptors. Hence, several studies have been conducted to investigate the phthalate-mediated toxicities in animals; however, plants have not been explored to the same amount. Methods Therefore, in the present study, the accumulation and translocation along with morpho-physiological perturbations in barley plants after 15, 30, 60, and 120 days of exposure to di-n-butyl phthalate (DBP) are investigated using standard protocols. Results The maximal accumulation and translocation of DBP in the roots and shoots of barley plants was observed after 60 days of exposure. The exposure of DBP from 15 to 120 days was recorded to decline all the morphological indices (i.e., dry weight, net primary productivity, seed number per spike, and seed weight) of barley plants. The pigments content declined under DBP treatment for all exposure durations except 120 days exposure. Carbohydrate content increased after 15–30 days of exposure afterward it was observed to be decreased under 60 and 120 days of exposure. The protein content was declined in DBP stressed plants for 15–120 days. Proline content was increased in all exposure durations and maximal percent increase was recorded in 120 days of exposure. MDA content showed an increase at earlier exposure durations then followed by a decline in long-term exposure. Hydrogen peroxide content increased at all exposure durations. There were significant alterations observed in the activities of all antioxidative enzymes in comparison to the control. Furthermore, DBP stressed plants after 60 days were analyzed for the macromolecular variations using Fourier transform infrared spectroscopy (FTIR). Conclusion Thus, the outcomes of the current work provide an appraisal of phthalates’ uptake and translocation mediated phytotoxic responses in barley plants. These observations can help in developing genetically modified edible plants that are resistant to phthalates uptake, thereby ensuring food security.

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“…To meet the challenges, quite a large number of studies have been conducted on various aspects of these plasticizers including microbial metabolism, toxicity, and so on. (Chatterjee and Dutta, 2003; Vamsee‐Krishna and Phale, 2008; Pant et al ., 2014; Giuliani et al ., 2020; Zhang et al ., 2020; Allotey et al ., 2021; González‐Mariño et al ., 2021; Sedha et al ., 2021).…”

Section: Introductionmentioning

confidence: 99%

Phthalate hydrolase: distribution, diversity and molecular evolution

Bhattacharyya

Basu

Dhar

et al. 2021

Environ Microbiol Rep

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The alpha/beta-fold superfamily of hydrolases is rapidly becoming one of the largest groups of structurally related enzymes with diverse catalytic functions. In this superfamily of enzymes, esterase deserves special attention because of their wide distribution in biological systems and importance towards environmental and industrial applications. Among various esterases, phthalate hydrolases are the key alpha/beta enzymes involved in the metabolism of structurally diverse estrogenic phthalic acid esters, ubiquitously distributed synthetic chemicals, used as plasticizer in plastic manufacturing processes. Although they vary both at the sequence and functional levels, these hydrolases use a similar acid-base-nucleophile catalytic mechanism to catalyse reactions on structurally different substrates. The current review attempts to present insights on phthalate hydrolases, describing their sources, structural diversities, phylogenetic affiliations and catalytically different types or classes of enzymes, categorized as diesterase, monoesterase and diesterase-monoesterase, capable of hydrolysing phthalate diester, phthalate monoester and both respectively. Furthermore, available information on in silico analyses and sitedirected mutagenesis studies revealing structurefunction integrity and altered enzyme kinetics have been highlighted along with the possible scenario of their evolution at the molecular level.

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Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

Cited by 8 publications

References 37 publications

Enhanced Biodegradation of Phthalic Acid Esters’ Derivatives by Plasticizer-Degrading Bacteria (Burkholderia cepacia, Archaeoglobus fulgidus, Pseudomonas aeruginosa) Using a Correction 3D-QSAR Model

Enhanced Biodegradation of Phthalic Acid Esters’ Derivatives by Plasticizer-Degrading Bacteria (Burkholderia cepacia, Archaeoglobus fulgidus, Pseudomonas aeruginosa) Using a Correction 3D-QSAR Model

Uptake of a plasticizer (di-n-butyl phthalate) impacts the biochemical and physiological responses of barley

Phthalate hydrolase: distribution, diversity and molecular evolution

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