Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol

Engesser, Karl‐Heinrich; Rubio, Miguel A.; Knackmuss, Hans‐Joachim

doi:10.1007/bf00173734

Cited by 23 publications

(9 citation statements)

References 27 publications

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“…5. In general, 2-fluoromuconate was-nearly as a dogma-recognized to be the principal and final dead-end metabolite (Schreiber et al 1980;Schmidt and Knackmuss 1984;Engesser et al 1990b;Boersma et al 2004).…”

Section: Halogenated Catechol Derivatives: 3-fluorocatecholmentioning

confidence: 98%

The biodegradation vs. biotransformation of fluorosubstituted aromatics

Kiel

Engesser

2015

Appl Microbiol Biotechnol

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Fluoroaromatics are widely and--in recent years--increasingly used as agrochemicals, starting materials for chemical syntheses and especially pharmaceuticals. This originates from the special properties the carbon-fluorine bond is imposing on organic molecules. Hence, fluoro-substituted compounds more and more are considered to be important potential environmental contaminants. On the other hand, the microbial potentials for their transformation and mineralization have received less attention in comparison to other haloaromatics. Due to the high electronegativity of the fluorine atom, its small size, and the extraordinary strength of the C-F bond, enzymes and mechanisms known to facilitate the degradation of chloro- or bromoarenes are not necessarily equally active with fluoroaromatics. Here, we review the literature on the microbial degradation of ring and side-chain fluorinated aromatic compounds under aerobic and anaerobic conditions, with particular emphasis being placed on the mechanisms of defluorination reactions.

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Section: Halogenated Catechol Derivatives: 3-fluorocatecholmentioning

confidence: 98%

The biodegradation vs. biotransformation of fluorosubstituted aromatics

Kiel

Engesser

2015

Appl Microbiol Biotechnol

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“…In fact, some fluorinated drugs require advanced photo-oxidation treatment for degradation [81]. This is because the position of fluorine on the fluorinated drug impacts its catabolism, and the position of fluorine might result in the formation of non-biodegradable dead-end metabolites [82].…”

Section: Fungal and Bacterial Biodegradation Of Anpsmentioning

confidence: 99%

Environmental Remediation of Antineoplastic Drugs: Present Status, Challenges, and Future Directions

et al. 2020

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The global burden of cancer is on the rise, and as a result, the number of therapeutics administered for chemotherapy is increasing. The occupational exposure, recalcitrant nature and ecotoxicological toxicity of these therapeutics, referred to as antineoplastic (ANP) drugs, have raised concerns about their safe remediation. This review provides an overview of the environmental source of ANPs agents, with emphasis on the currently used remediation approaches. Outpatient excreta, hospital effluents, and waste from pharmaceutical industries are the primary source of ANP waste. The current review describes various biotic and abiotic methods used in the remediation of ANP drugs in the environment. Abiotic methods often generate transformation products (TPs) of unknown toxicity. In this light, obtaining data on the environmental toxicity of ANPs and its TPs is crucial to determine their toxic effect on the ecosystem. We also discuss the biodegradation of ANP drugs using monoculture of fungal and bacterial species, and microbial consortia in sewage treatment plants. The current review effort further explores a safe and sustainable approach for ANP waste treatment to replace existing chemical and oxidation intensive treatment approaches. To conclude, we assess the possibility of integrating biotic and abiotic methods of ANP drug degradation.

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“…A small number of reports describe investigations on the bacterial transformation of benzoate and catechol substituted with a trifluoromethyl group, which the most widely used fluorinated moiety in pharmaceuticals and agrochemicals (Engesser et al 1988;Engesser et al 1990).…”

Section: Fluoroaromaticsmentioning

confidence: 99%

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Murphy

Clark

Amadio

2009

Appl Microbiol Biotechnol

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Publication information Applied Microbiology and Biotechnology, 84 (4): 617-629Publisher Springer Item record/more information http://hdl.handle.net/10197/5314 Publisher's statementThe final publication is available at www.springerlink.com can lead to the generation of toxic compounds that are of environmental concern, yet similar biotransformations can yield difficult-to-synthesise products and intermediates, in particular derivatives of biologically active secondary metabolites. In this paper we review the historical and recent developments of organofluorine biotransformation in microorganisms, and highlight the possibility of using microbes as models of fluorinated drug metabolism in mammals.3

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Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol

Cited by 23 publications

References 27 publications

The biodegradation vs. biotransformation of fluorosubstituted aromatics

The biodegradation vs. biotransformation of fluorosubstituted aromatics

Environmental Remediation of Antineoplastic Drugs: Present Status, Challenges, and Future Directions

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

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