Fluorotelomer alcohols are efficiently biotransformed by Cunninghamella elegans.
Cytochrome P450
Fluorine
Fungus
LC–MS
Metabolite
PFAS
Journal
Environmental science and pollution research international
ISSN: 1614-7499
Titre abrégé: Environ Sci Pollut Res Int
Pays: Germany
ID NLM: 9441769
Informations de publication
Date de publication:
Feb 2023
Feb 2023
Historique:
received:
30
03
2022
accepted:
26
10
2022
pubmed:
4
11
2022
medline:
25
2
2023
entrez:
3
11
2022
Statut:
ppublish
Résumé
Cunninghamella elegans is a well-studied fungus that biotransforms a range of xenobiotics owing to impressive cytochrome P450 (CYP) activity. In this paper, we report the biotransformation of 6:2 fluorotelomer alcohol (6:2 FTOH) by the fungus, yielding a range of fluorinated products that were detectable by fluorine-19 nuclear magnetic resonance spectroscopy (
Identifiants
pubmed: 36327087
doi: 10.1007/s11356-022-23901-0
pii: 10.1007/s11356-022-23901-0
doi:
Substances chimiques
fluorotelomer alcohols
0
Fluorocarbons
0
Cytochrome P-450 Enzyme System
9035-51-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
23613-23623Subventions
Organisme : Irish Research Council
ID : IRC/GOI-PD/1064
Informations de copyright
© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
Références
Amadio J, Gordon K, Murphy CD (2010) Biotransformation of flurbiprofen by Cunninghamella species. Appl Environ Microbiol 76(18):6299–6303. https://doi.org/10.1128/aem.01027-10
Asha S, Vidyavathi M (2009) Cunninghamella – a microbial model for drug metabolism studies – a review. Biotechnol Adv 27(1):16–29. https://doi.org/10.1016/j.biotechadv.2008.07.005
Bhosale S, Saratale G, Govindwar S (2006) Biotransformation enzymes in Cunninghamella blakesleeana (NCIM-687). J Basic Microbiol 46(6):444–448. https://doi.org/10.1002/jobm.200510117
Buck RC, Franklin J, Berger U, Conder JM, Cousins IT, de Voogt P, Jensen AA, Kannan K, Mabury SA, van Leeuwen SP (2011) Perfluoroalkyl and polyfluoroalkyl substances in the environment: terminology, classification, and origins. Integr Environ Assess Manag 7(4):513–541. https://doi.org/10.1002/ieam.258
doi: 10.1002/ieam.258
Butt CM, Muir DCG, Mabury SA (2014) Biotransformation pathways of fluorotelomer-based polyfluoroalkyl substances: a review. Environ Toxicol Chem 33(2):243–267. https://doi.org/10.1002/etc.2407
doi: 10.1002/etc.2407
Camdzic D, Dickman RA, Aga DS (2021) Total and class-specific analysis of per- and polyfluoroalkyl substances in environmental samples using nuclear magnetic resonance spectroscopy. Journal of Hazardous Materials Letters 2:100023. https://doi.org/10.1016/j.hazl.2021.100023
doi: 10.1016/j.hazl.2021.100023
Che S, Jin BS, Liu ZK, Yu YC, Liu JY, Men YJ (2021) Structure-specific aerobic defluorination of short-chain fluorinated carboxylic acids by activated sludge communities. Environ Sci Technol Lett 8(8):668–674. https://doi.org/10.1021/acs.estlett.1c00511
doi: 10.1021/acs.estlett.1c00511
Daramola O, Rand AA (2021) Emerging investigator series: human CYP2A6 catalyzes the oxidation of 6:2 fluorotelomer alcohol. Environmental Science-Processes & Impacts 23(11):1688–1695. https://doi.org/10.1039/d1em00307k
doi: 10.1039/d1em00307k
Gluge J, Scheringer M, Cousins IT, DeWitt JC, Goldenman G, Herzke D, Lohmann R, Ng CA, Trier X, Wang ZY (2020) An overview of the uses of per- and polyfluoroalkyl substances (PFAS). Environmental Science-Processes & Impacts 22(12):2345–2373. https://doi.org/10.1039/d0em00291g
doi: 10.1039/d0em00291g
Goncalves MD, Tomiotto-Pellissier F, de Matos RLN, Assolini JP, Bortoleti BTD, Concato VM, Silva TF, Rafael JA, Pavanelli WR, Conchon-Costa I, Arakawa NS (2021) Recent advances in biotransformation by Cunninghamella species. Curr Drug Metab 22(13):1035–1064. https://doi.org/10.2174/1389200222666211126100023
Hogue C (2021) US House passes bill to control PFAS. C&EN Global Enterprise 99(27):6–7. https://doi.org/10.1021/cen-09927-leadcon
doi: 10.1021/cen-09927-leadcon
Khan MF, Murphy CD (2021a) Bacterial degradation of the anti-depressant drug fluoxetine produces trifluoroacetic acid and fluoride ion. Appl Microbiol Biotechnol 105(24):9359–9369. https://doi.org/10.1007/s00253-021-11675-3
doi: 10.1007/s00253-021-11675-3
Khan MF, Murphy CD (2021b) Cunninghamella spp. produce mammalian-equivalent metabolites from fluorinated pyrethroid pesticides. Amb Express 11 (1). https://doi.org/10.1186/s13568-021-01262-0
Khan MF, Murphy CD (2022) Cytochrome P450 5208A3 is a promiscuous xenobiotic biotransforming enzyme in Cunninghamella elegans. Enzyme Microb Technol 161:110102. https://doi.org/10.1016/j.enzmictec.2022.110102
Kiel M, Engesser KH (2015) The biodegradation vs. biotransformation of fluorosubstituted aromatics. Appl Microbiol Biotechnol 99(18):7433–7464. https://doi.org/10.1007/s00253-015-6817-5
doi: 10.1007/s00253-015-6817-5
Kim MH, Wang N, Chu KH (2014) 6:2 Fluorotelomer alcohol (6:2 FTOH) biodegradation by multiple microbial species under different physiological conditions. Appl Microbiol Biotechnol 98(4):1831–1840. https://doi.org/10.1007/s00253-013-5131-3
doi: 10.1007/s00253-013-5131-3
Li ZM, Guo LH, Ren XM (2016) Biotransformation of 8:2 fluorotelomer alcohol by recombinant human cytochrome P450s, human liver microsomes and human liver cytosol. Environmental Science-Processes & Impacts 18(5):538–546. https://doi.org/10.1039/c6em00071a
doi: 10.1039/c6em00071a
Lim X (2019) The fluorine detectives. Nature 566(7742):26–29. https://doi.org/10.1038/d41586-019-00441-1
doi: 10.1038/d41586-019-00441-1
Liu JX, Wang N, Szostek B, Buck RC, Panciroli PK, Folsom PW, Sulecki LM, Bellin CA (2010) 6–2 Fluorotelomer alcohol aerobic biodegradation in soil and mixed bacterial culture. Chemosphere 78(4):437–444. https://doi.org/10.1016/j.chemosphere.2009.10.044
doi: 10.1016/j.chemosphere.2009.10.044
Merino N, Wang M, Ambrocio R, Mak K, O’Connor E, Gao A, Hawley EL, Deeb RA, Tseng LY, Mahendra S (2018) Fungal biotransformation of 6:2 fluorotelomer alcohol. Remediation 28(2):59–70. https://doi.org/10.1002/rem.21550
doi: 10.1002/rem.21550
Murphy CD (2016) Microbial degradation of fluorinated drugs: biochemical pathways, impacts on the environment and potential applications. Appl Microbiol Biotechnol 100(6):2617–2627. https://doi.org/10.1007/s00253-016-7304-3
doi: 10.1007/s00253-016-7304-3
Murphy CD, Sandford G (2015) Recent advances in fluorination techniques and their anticipated impact on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol 11(4):589–599. https://doi.org/10.1517/17425255.2015.1020295
doi: 10.1517/17425255.2015.1020295
Nakayama N, Takemae A, Shoun H (1996) Cytochrome P450foxy, a catalytically self-sufficient fatty acid hydroxylase of the fungus Fusarium oxysporum. J Biochem 119(3):435–440
Palmer-Brown W, Miranda-CasoLuengo R, Wolfe KH, Byrne KP, Murphy CD (2019) The CYPome of the model xenobiotic-biotransforming fungus Cunninghamella elegans. Sci Rep 9:1–9. https://doi.org/10.1038/s41598-019-45706-x
Piska K, Zelaszczyk D, Jamrozik M, Kubowicz-Kwasny P, Pekala E (2016) Cunninghamella biotransformation – similarities to human drug metabolism and its relevance for the drug discovery process. Curr Drug Metab 17(2):107–117. https://doi.org/10.2174/1389200216666151103115817
Rodil A, Slawin AMZ, Al-Maharik N, Tomita R, O’Hagan D (2019) Fluorine-containing substituents: metabolism of the alpha, alpha-difluoroethyl thioether motif. Beilstein J Org Chem 15:1441–1447. https://doi.org/10.3762/bjoc.15.144
doi: 10.3762/bjoc.15.144
Sakai K, Matsuzaki F, Wise L, Sakai Y, Jindou S, Ichinose H, Takaya N, Kato M, Wariishi H, Shimizu M (2018) Biochemical characterization of CYP505D6, a self-sufficient cytochrome P450 from the white-rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol 84(22). https://doi.org/10.1128/aem.01091-18
Sloczynska K, Wojcik-Pszczola K, Canale V, Zmudzki P, Zajdel P, Pekala E (2018) Biotransformation of 4-fluoro-N-(1-{2- (propan-2-yl)phenoxy ethyl}-8-azabicyclo 3.2.1 octan-3 -yl)-benzenesulfonamide, a novel potent 5-HT7 receptor antagonist with antidepressant-like and anxiolytic properties: in vitro and in silico approach. J Biochem Mol Toxicol 32(5). https://doi.org/10.1002/jbt.22048
Tseng N, Wang N, Szostek B, Mahendra S (2014) Biotransformation of 6:2 fluorotelomer alcohol (6:2 FTOH) by a wood-rotting fungus. Environ Sci Technol 48(7):4012–4020. https://doi.org/10.1021/es4057483
doi: 10.1021/es4057483
Wackett LP (2022a) Nothing lasts forever: understanding microbial biodegradation of polyfluorinated compounds and perfluorinated alkyl substances. Microb Biotechnol 15(3):773–792. https://doi.org/10.1111/1751-7915.13928
doi: 10.1111/1751-7915.13928
Wackett LP (2022b) Strategies for the biodegradation of polyfluorinated compounds. Microorganisms 10 (8). https://doi.org/10.3390/microorganisms10081664
Wan X, Liang Z, Gong YM, Zhang YB, Jiang ML (2013) Characterization of three delta 9-fatty acid desaturases with distinct substrate specificity from an oleaginous fungus Cunninghamella echinulata. Mol Biol Rep 40(7):4483–4489. https://doi.org/10.1007/s11033-013-2540-4
Zhang ZM, Sarkar D, Biswas JK, Datta R (2022) Biodegradation of per- and polyfluoroalkyl substances (PFAS): a review. Biores Technol 344:126223. https://doi.org/10.1016/j.biortech.2021.126223
doi: 10.1016/j.biortech.2021.126223