Predicting the biodegradation products of perfluorinated chemicals using CATABOL

Dimitrov, S.; Kamenska, Verginia; Walker, John D.; Windle, Wiletta M.; Purdy, Rich; Lewis, Michael A.; Mekenyan, Ovanes G.

doi:10.1080/1062936032000169688

Cited by 66 publications

(35 citation statements)

References 47 publications

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“…Finally, BCF predictions based on a hybrid deterministic and probabilistic approach are provided by the commercial expert system, CATABOL [90,91]. A detailed description of these computer-based expert systems is outside the scope of this review.…”

Section: Expert Systemsmentioning

confidence: 99%

Review of Literature‐Based Quantitative Structure–Activity Relationship Models for Bioconcentration

2008

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This paper reviews the state of the art of in silico methods for assessing the tendency of a substance to bioconcentrate in aquatic organisms usually expressed as its Bioconcentration Factor (BCF). It is based on an in-depth review performed by the European Chemicals Bureau of the European Commissions Joint Research Centre in support of the development of technical guidance for the implementation of the REACH legislation, and is one of a series of minireviews in this journal. The most widely used in silico approaches to estimate BCF are described, with emphasis on literature-based (Quantitative) Structure-Activity Relationship [(Q)SAR] models: (1) linear relationships that correlate the BCF with octanol -water partition coefficient; (2) (Q)SAR models based on experimentally derived descriptors and (3) new (Q)SAR models aimed to evaluate the potential of other descriptors. Recommendations for further research are also provided.

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Section: Expert Systemsmentioning

confidence: 99%

Review of Literature‐Based Quantitative Structure–Activity Relationship Models for Bioconcentration

2008

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“…Different from UM-PPS, metabolism rules in CATALOGIC are hierarchically ranked by occurrence probabilities judged by expert knowledge and documented metabolic maps [60,62]. Metabolic trees could be generated with quantitative distributions of the precursor and subsequent transformation products.…”

Section: Computer-aided Prediction Of Biotransformation Pathwaysmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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A B S T R A C TBiotransformation of polyfluoroalkyl precursors contributes in part to the perfluoroalkyl carboxylates and sulfonates detected in the global environment and biota. Robust sample preparation and sensitive analytical techniques for maximum analyte recovery are essential to identify and to quantify biotransformation products often present at low levels in environmental matrices and experimental systems. This critical review covers current sample-preparation and analytical methods, including extraction, concentration, clean-up and derivatization, mass spectrometry coupled to gas or liquid chromatography, and radioisotope labeling and tracking techniques. We also critically review methodologies for molecular structural elucidation and in-silico prediction of potential transformation products. We describe current knowledge gaps and challenges in studying novel alternative polyfluoroalkyl substances. We discuss future trends on utilizing advanced analytical techniques.

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“…Unfortunately, these processes continue to require the use of fluorinated ligands to disperse the nanoparticles. These CO 2 soluble fluorinated compounds suffer from the disadvantages of being both expensive and environmentally unfriendly [116,117].…”

Section: Non-fluorous Thiols Resultsmentioning

confidence: 99%

Synthesis and Evaluation of CO2 Thickeners Designed with Molecular Modeling

Enick¹,

Beckman²,

Johnson³

2009

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The objective of this research was to use molecular modeling techniques, coupled with our prior experimental results, to design, synthesize and evaluate inexpensive, non-fluorous carbon dioxide thickening agents.The first type of thickener that was considered was associating polymers. Typically, these thickeners are copolymers that contain a highly CO 2 -philic monomer, and a small concentration of a CO 2 -phobic associating monomer.Yale University was solely responsible for the synthesis of a second type of thickener; small, hydrogen bonding compounds. These molecules have a core that contains one or more hydrogen-bonding groups, such as urea or amide groups. Non-fluorous, CO 2 -philic functional groups were attached to the hydrogen bonding core of the compound to impart CO 2 stability and macromolecular stability to the linear "stack" of these compounds.The third type of compound initially considered for this investigation was CO 2 -soluble surfactants. These surfactants contain conventional ionic head groups and composed of CO 2 -philic oligomers (short polymers) or small compounds (sugar acetates) previously identified by our research team. Mobility reduction could occur as these surfactant solutions contacted reservoir brine and formed mobility control foams in-situ.The vast majority of the work conducted in this study was devoted to the copolymeric thickeners and the small hydrogen-bonding thickeners; these thickeners were intended to dissolve completely in CO 2 and increase the fluid viscosity. A small but important amount of work was done establishing the groundwork for CO 2 -soluble surfactants that reduced mobility by generating foams in-situ as the CO 2 +surfactant solution mixed with in-situ brine. PolymersIn this final report, we review our entire co-polymeric thickener effort and detail, for the first time, the phase behavior and viscosity results of the first non-fluorous, oxygenated hydrocarbon-based, associating polymer CO 2 thickener, poly(vinyl acetate -co -benzoyl 5% ). The CO 2 -philic monomer was vinyl acetate, and the associative thickener monomer was vinyl benzoate. Poly(vinyl acetate -co -benzoyl 5% ), Mw ~ 12000, is capable of increasing the viscosity of CO 2 by 70% at a concentration of 2wt%, a shear rate of ~5000s -1 , 298K and 9500 psia. Unfortunately, poly(vinyl acetate -co -benzoyl 5% ) is not capable of dissolving in CO 2 at pressures close to the MMP, roughly 1200 psia at 298 K. In fact, we are now convinced that a non-fluorous, hydrocarbon-based copolymeric thickener cannot be designed that will dissolve in CO 2 at typical reservoir conditions. Why? Every polymer that we designed using molecular modeling tools was indeed CO 2 soluble, a somewhat remarkable achievement given the small number of CO 2 soluble surfactants that have ever been identified, but each one was less soluble in CO 2 than poly(vinyl acetate). Therefore co-polymeric thickeners based on any CO 2 soluble polymer will undoubtedly be less soluble in CO 2 (i.e. require even greater pressures than 9500 psia)...

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Predicting the biodegradation products of perfluorinated chemicals using CATABOL

Cited by 66 publications

References 47 publications

Review of Literature‐Based Quantitative Structure–Activity Relationship Models for Bioconcentration

Review of Literature‐Based Quantitative Structure–Activity Relationship Models for Bioconcentration

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Synthesis and Evaluation of CO2 Thickeners Designed with Molecular Modeling

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