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Fluorotelomer alcohols are efficiently biotransformed by Cunninghamella elegans

Khan, Mohd Faheem, Murphy, Cormac D.·2022·Environmental Science and Pollution Research
DOI 10.1007/s11356-022-23901-0
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Abstract

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 ( 19 F NMR), gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS). Upon incubation with the pre-grown cultures, the substrate (100 mg/L) was completely consumed within 48 h, which is faster biotransformation than other fungi that have hitherto been studied. The main metabolite formed was the 5:3 fluorotelomer carboxylic acid (5:3 FTCA), which accumulated in the culture supernatant. When the cytochrome P450 inhibitor 1-aminobenzotriazole was included in the culture flasks, there was no biotransformation of 6:2 FTOH, indicating that these enzymes are key to the catalysis. Furthermore, when exogenous 5:3 FTCA was added to the fungus, the standard biotransformation of the drug flurbiprofen was inhibited, strongly suggesting that the main fluorotelomer alcohol biotransformation product inhibits CYP activity and accounts for its accumulation.

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  1. 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 · DOI
  2. 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 · DOI
  3. 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 · DOI
  4. 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 · Paper page
  5. 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 · Paper page
  6. 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
  7. 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 · Paper page
  8. 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
  9. 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 · DOI
  10. 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
  11. 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 · Paper page
  12. 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 · DOI
  13. 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 · DOI · Paper page
  14. 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 · Paper page
  15. 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 · Paper page
  16. 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
  17. Lim X (2019) The fluorine detectives. Nature 566(7742):26–29. https://doi.org/10.1038/d41586-019-00441-1 · DOI
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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 · DOI
  23. 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 · DOI
  24. 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 · DOI
  25. 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
  26. 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 · DOI
  27. 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 · DOI
  28. 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 · Paper page
  29. Wackett LP (2022b) Strategies for the biodegradation of polyfluorinated compounds. Microorganisms 10 (8). https://doi.org/10.3390/microorganisms10081664 · DOI
  30. 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 · DOI
  31. 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 · Paper page

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Metadata

Authors
Khan, M. F., & Murphy, C. D.
ORCID
Venue
Environmental Science and Pollution Research
Publisher
Springer Science and Business Media LLC
Published
2022-11-03
Volume
30
Issue
9
Pages
23613-23623
ISSN
1614-7499
DOI
10.1007/s11356-022-23901-0
Cited by
36
References
2
Language
en
Licence
Funders
Irish Research Council (IRC/GOI-PD/1064)

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