PMID- 28521164
OWN - NLM
STAT- MEDLINE
DCOM- 20170921
LR  - 20181202
IS  - 1879-1298 (Electronic)
IS  - 0045-6535 (Linking)
VI  - 182
DP  - 2017 Sep
TI  - Biotransformation of hexabromocyclododecanes with 
      hexachlorocyclohexane-transforming Sphingobium chinhatense strain IP26.
PG  - 491-500
LID - S0045-6535(17)30749-X [pii]
LID - 10.1016/j.chemosphere.2017.05.047 [doi]
AB  - Bacterial evolution has resulted in the appearance of several Sphingomonadacea 
      strains that gained the ability to metabolize hexachlorocyclohexanes (HCHs). HCHs 
      have been widely used as pesticides but were banned under the Stockholm 
      Convention on persistent organic pollutants (POPs) in 2009. Here we present 
      evidence for bacterial transformation reactions of hexabromocyclododecanes 
      (HBCDs), which are structurally related to HCHs. HBCDs were used as flame 
      retardants. They are now also considered as POPs and their production and use is 
      restricted since 2013. Racemic alpha-, beta-, and gamma-HBCDs and their mixture were exposed 
      to Sphingobium chinhatense IP26 in resting cell assays in parallel to beta-HCH. All 
      HBCD stereoisomers were converted with (-)beta-HBCD being the best and both alpha-HBCD 
      enantiomers the poorest substrates. HBCD conversion rates were 27-430 times 
      slower than that of beta-HCH. Three generations of hydroxylated transformation 
      products were observed, 7 pentabromocyclododecanol isomers (PeBCD-ols), 11 
      tetrabromocyclododecadiols (TeBCD-diols) and 3 tribromocyclododecatriols 
      (TrBCD-triols). The conversion of (+)alpha-, (-)beta- and (-)gamma-HBCD was faster than 
      those of their enantiomers. Therefore the respective enantiomeric excess 
      increased to 3 +/- 1%, 36 +/- 1% and 6 +/- 2% during 48 h of bacterial exposure. 
      PeBCD-ols appeared first, followed by TeBCD-diols and TrBCD-triols indicating 
      stepwise hydrolytic dehalogenation reactions. In conclusion, severe HCH pollution 
      at geographically distinct dumpsites triggered bacterial evolution to express 
      enzymes transforming such compounds. We used S. chinhatense IP26 bacteria to 
      transform structurally related HBCDs, also regulated under the Stockholm 
      Convention. Such bacteria might be useful for bioremediation but the toxicity of 
      the numerous transformation products observed must be assessed in advance.
CI  - Copyright (c) 2017 Elsevier Ltd. All rights reserved.
FAU - Heeb, Norbert V
AU  - Heeb NV
AD  - Empa, Swiss Federal Laboratories for Materials Testing and Research, Laboratory 
      for Advanced Analytical Technologies, Uberlandstrasse 129, CH-8600, Dubendorf, 
      Switzerland. Electronic address: norbert.heeb@empa.ch.
FAU - Grubelnik, Andreas
AU  - Grubelnik A
AD  - Empa, Swiss Federal Laboratories for Materials Testing and Research, Laboratory 
      for Advanced Analytical Technologies, Uberlandstrasse 129, CH-8600, Dubendorf, 
      Switzerland.
FAU - Geueke, Birgit
AU  - Geueke B
AD  - Eawag, Swiss Federal Institute of Aquatic Science and Technology, Uberlandstrasse 
      133, CH-8600, Dubendorf, Switzerland.
FAU - Kohler, Hans-Peter E
AU  - Kohler HE
AD  - Eawag, Swiss Federal Institute of Aquatic Science and Technology, Uberlandstrasse 
      133, CH-8600, Dubendorf, Switzerland.
FAU - Lienemann, Peter
AU  - Lienemann P
AD  - ZHAW, Zurich University of Applied Sciences, Institute of Chemistry and 
      Biological Chemistry, Reidbach, CH-8820, Wadenswil, Switzerland.
LA  - eng
PT  - Journal Article
DEP - 20170511
PL  - England
TA  - Chemosphere
JT  - Chemosphere
JID - 0320657
RN  - 0 (Environmental Pollutants)
RN  - 0 (Flame Retardants)
RN  - 0 (Hydrocarbons, Brominated)
RN  - 59NEE7PCAB (Hexachlorocyclohexane)
RN  - 5I9835JO3M (hexabromocyclododecane)
RN  - YM80ODM9PD (beta-hexachlorocyclohexane)
SB  - IM
MH  - Biodegradation, Environmental
MH  - Biotransformation
MH  - Environmental Pollutants/analysis/*metabolism
MH  - Flame Retardants/analysis/*metabolism
MH  - Halogenation
MH  - Hexachlorocyclohexane/analysis/*metabolism
MH  - Hydrocarbons, Brominated/analysis/*metabolism
MH  - Sphingomonadaceae/*metabolism
MH  - Stereoisomerism
OTO - NOTNLM
OT  - Bacterial HBCD transformation
OT  - Dehalohydroxylation
OT  - HCH biotransformation
OT  - Persistent organic pollutants
OT  - Sphingobium chinhatense
EDAT- 2017/05/19 06:00
MHDA- 2017/09/22 06:00
CRDT- 2017/05/19 06:00
PHST- 2016/11/30 00:00 [received]
PHST- 2017/05/05 00:00 [revised]
PHST- 2017/05/08 00:00 [accepted]
PHST- 2017/05/19 06:00 [pubmed]
PHST- 2017/09/22 06:00 [medline]
PHST- 2017/05/19 06:00 [entrez]
AID - S0045-6535(17)30749-X [pii]
AID - 10.1016/j.chemosphere.2017.05.047 [doi]
PST - ppublish
SO  - Chemosphere. 2017 Sep;182:491-500. doi: 10.1016/j.chemosphere.2017.05.047. Epub 
      2017 May 11.