PMID- 29180039
OWN - NLM
STAT- MEDLINE
DCOM- 20180918
LR  - 20180918
IS  - 1879-3177 (Electronic)
IS  - 0887-2333 (Linking)
VI  - 47
DP  - 2018 Mar
TI  - Regioselective ester cleavage of di-(2-ethylhexyl) trimellitates by porcine liver 
      esterase.
PG  - 178-185
LID - S0887-2333(17)30365-X [pii]
LID - 10.1016/j.tiv.2017.11.015 [doi]
AB  - In a comparative study the ester hydrolysis of the plasticizers di-(2-ethylhexyl) 
      phthalate (DEHP) and tri-(2-ethylhexyl) trimellitate (TEHTM) as well as of the 
      diester isomers 1,2-di-(2-ethylhexyl) trimellitate (1,2-DEHTM), 
      1,4-di-(2-ethylhexyl) trimellitate (1,4-DEHTM) and 2,4-di-(2-ethylhexyl) 
      trimellitate (2,4-DEHTM) was investigated by a newly developed in vitro 
      experimental design using porcine liver esterase (PLE). The substrates were 
      incubated with PLE for 48h at 25 degrees C in borate buffer and samples were taken at 
      predetermined intervals during the experiment. The samples were processed using 
      liquid-liquid extraction and analyzed using LC-MS/MS. The results demonstrated a 
      rapid and extensive hydrolysis of the diester DEHP to the monoester 
      mono-(2-ethylhexyl) phthalate (MEHP) during the incubation with PLE. The isomers 
      of DEHTM were also hydrolyzed by PLE to a high extent, whereas TEHTM showed a 
      high stability against enzymatic hydrolysis. The regioselective analysis revealed 
      that the monoester isomers 1-MEHTM and 2-MEHTM were predominantly produced during 
      the degradation of DEHTM isomers, indicating a preferred hydrolysis at the 
      para-position. These findings are eminent for planning further investigations on 
      the human TEHTM metabolism, as the extent, rate and route of metabolism are of 
      crucial importance for a toxicological assessment.
CI  - Copyright (c) 2017 Elsevier Ltd. All rights reserved.
FAU - Hollerer, Christine
AU  - Hollerer C
AD  - Institute and Outpatient Clinic of Occupational, Social and Environmental 
      Medicine, Friedrich-Alexander-Universitat Erlangen-Nurnberg, Schillerstrasse 
      25/29, 91054 Erlangen, Germany.
FAU - Becker, Gunther
AU  - Becker G
AD  - OXEA GmbH, Rheinpromenade 4a, 40789 Monheim, Germany.
FAU - Goen, Thomas
AU  - Goen T
AD  - Institute and Outpatient Clinic of Occupational, Social and Environmental 
      Medicine, Friedrich-Alexander-Universitat Erlangen-Nurnberg, Schillerstrasse 
      25/29, 91054 Erlangen, Germany. Electronic address: thomas.goeen@fau.de.
FAU - Eckert, Elisabeth
AU  - Eckert E
AD  - Institute and Outpatient Clinic of Occupational, Social and Environmental 
      Medicine, Friedrich-Alexander-Universitat Erlangen-Nurnberg, Schillerstrasse 
      25/29, 91054 Erlangen, Germany.
LA  - eng
PT  - Journal Article
DEP - 20171124
PL  - England
TA  - Toxicol In Vitro
JT  - Toxicology in vitro : an international journal published in association with 
      BIBRA
JID - 8712158
RN  - 0 (Benzoates)
RN  - 0 (Plasticizers)
RN  - 3319-31-1 (tri-(2-ethylhexyl)trimellitate)
RN  - C42K0PH13C (Diethylhexyl Phthalate)
RN  - EC 3.1.1.- (Carboxylic Ester Hydrolases)
SB  - IM
MH  - Animals
MH  - Benzoates/chemistry/*metabolism
MH  - Biotransformation
MH  - Carboxylic Ester Hydrolases/*metabolism
MH  - Chromatography, High Pressure Liquid
MH  - Diethylhexyl Phthalate/chemistry/*metabolism
MH  - Hydrolysis
MH  - Kinetics
MH  - Molecular Structure
MH  - Plasticizers/chemistry/*metabolism
MH  - Stereoisomerism
MH  - Substrate Specificity
MH  - Sus scrofa
MH  - Tandem Mass Spectrometry
OTO - NOTNLM
OT  - Di-(2-ethylhexyl) phthalate
OT  - Metabolism
OT  - Porcine liver esterase
OT  - Tri-(2-ethylhexyl) trimellitate
EDAT- 2017/11/29 06:00
MHDA- 2018/09/19 06:00
CRDT- 2017/11/29 06:00
PHST- 2017/08/22 00:00 [received]
PHST- 2017/11/15 00:00 [revised]
PHST- 2017/11/22 00:00 [accepted]
PHST- 2017/11/29 06:00 [pubmed]
PHST- 2018/09/19 06:00 [medline]
PHST- 2017/11/29 06:00 [entrez]
AID - S0887-2333(17)30365-X [pii]
AID - 10.1016/j.tiv.2017.11.015 [doi]
PST - ppublish
SO  - Toxicol In Vitro. 2018 Mar;47:178-185. doi: 10.1016/j.tiv.2017.11.015. Epub 2017 
      Nov 24.