1. ENDOCRINE
DISRUPTING
ORGANIC
POLLUTANTS
Denise Williamson
June 8, 2014
1

2. 2
Introduction: Persistent Organic
Pollutants (POPs)
 Phthalate and organophosphate esters, alkylphenols,
polychlorinated biphenyls (PCBs)
 BPA [2,2-Bis(4-hydroxyphenyl)propane], polycyclic
aromatic hydrocarbons (PAHs) such as benzo[]pyrene,
nitropyrenes
 Ubiquitous chemicals (plasticizers, flame retardants,
pesticides, fuel combustion by-products, etc.)
 Hydrophobic and lipophilic; found to bioaccumulate
primarily in adipose tissue of organisms.1

3. 3
a. 17--estradiol
(Estrogen)
b. Benzo[]pyrene
c. Bisphenol A
Images:
a) http://www.sigmaaldrich.com/catalog/product/sigma/e8875
b) http://www.sigmaaldrich.com/catalog/product/sigma/b1760
c) http://www.sigmaaldrich.com/catalog/product/aldrich/239658

4. 4
Overview :
POPs as Endocrine Disruptors
 Absorbed, inhaled or ingested to enter the bloodstream
and circulate like natural, endogenous hormones
 Act as agonists or antagonists at hormone receptors and
disrupt endocrine signaling pathways, especially
reproductive cycles.2
Image: http://www.mdpi.com/1660-4601/9/9

5. 5
Human Estrogen-Related Receptor (ERR-)
ligand-binding domain complex with BPA
Image: http://www.rcsb.org/pdb/explore/images.do?structureId=2E2R

6. 6
Receptor Binding:
Nitropyrenes as Endocrine Disruptors
 The estrogenic activities of 3-, 6- and 8-hydroxy-1-
nitropyrene were assayed in yeast cells expressing human
estrogen receptor (hER)
 All three isomers demonstrated greater estrogenic
activity than BPA, a well-known endocrine disruptor.3
 Supported a previous finding that 4 rings in rectangular
configuration and substituents must be coplanar for strong
ER binding:
Structure of Hydroxy-1-Nitropyrenes2

7. 7
Quantification of
POPs in Automobile Exhaust
 Soluble organic fractions of gas and diesel exhaust,
obtained by Soxhlet extraction, recovered from particulate
matter collected with air monitoring filters
 Samples were concentrated using a Kuderna-Danish
evaporative concentrator, dissolved in CH2Cl2 and
analyzed by GC-MS
 21 endocrine disrupting chemicals (EDCs) identified,
with p-n-pentylphenol and benzo[]pyrene found in
highest concentration (0.5-17 and 0.1-0.8g/mL).4

8. 8
Removal of BPA by
Recyclable Magnetic Photocatalyst
 Remediation of 2,2-bis(hydroxyphenyl)propane from
water with BiOBr/SiO2/Fe3O4 nanoparticles by
photocatalytic oxidation has been reported
 Nanoparticles used to oxidize and degrade BPA in the
presence of visible light can be removed after treatment
by applying an external magnetic field
 After 50 min., 87.0% of the BPA in a test solution was
degraded by BiOBr/SiO2/Fe3O4 nanoparticles, compared
to 27.2% using a commercial TiO2 photocatalyst.5

9. 9
Photooxidation of BPA by
BiOBr/SiO2/Fe3O4 Nanoparticles5

10. REFERENCES
1. Hassan, A. A.; Rylander, C.; Brustad, M.; Sandanger, T. M. Persistent Organic Pollutants in Meat,
Liver, Tallow and Bone Marrow from Semi-domesticated Reindeer (Rangifer tarandus L.) in Northern
Norway. Acta Vet. Scand. 2013, 55, 57.
2. Tartu, S.; Angelier, F.; Herzke, D.; Moe, B.; Bech, C.; Gabrielsen, G.W.; Bustnes, J.O.; Chastel, O.
The Stress of Being Contaminated? Adrenocortical Function and Reproduction in Relation to
Persistent Organic Pollutants in Female Black Legged Kittiwakes. Sci. Total Environ. 2014, 476, 553-
560.
3. Kameda, T.; Akiyama, A.; Toriba, A.; Tachikawa, C.; Yoshita, M.; Tang, N.; Hayakawa, K. Evaluation of
Endocrine Disrupting Activities of Mono Hydroxylated Derivatives of 1-nitropyrene by Yeast Two-
hybrid Assay. J. Health Sci. 2008, 54,118-122.
4. Murahashi, T.; Sasaki, S.; Nakajima, T. Determination of Endocrine Disruptors in Automobile Exhaust
Particulate Matter. J. Health Sci. 2003, 49, 72-75.
5. Zhang, L.; Wang, W. Z.; Sun, S. M.; Sun, Y. Y.; Gao, E. P.; Zhang, Z. J. Elimination of BPA Endocrine
Disruptor by Magnetic BiOBr@SiO2@Fe3O4 Photocatalyst. Appl. Catal. B, 2014,148,164-169.
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