Biotransformation of sulfonamide antibiotics by ammonia ...
Transcript of Biotransformation of sulfonamide antibiotics by ammonia ...
Biotransformation of sulfonamide antibiotics
by ammonia oxidizers
Presenter: Yaochun Yu
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5/21/2019
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University of Illinois at Urbana-Champaign
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Introduction
Objectives
Results
Summary
Outline
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SAs as one of the biggest families of antibiotics are widely used as human and
animal drugs.
Introduction Objectives Results Summary
Sulfonamide (SA) antibiotics
Why do we care about sulfonamides?
Adverse effects on ecosystem and public health.
- Induce the antibiotic resistance
Sulfonamides functional group
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Introduction Objectives Results Summary
How do SAs enter into the ecosystem?
https://environmicrobe.weebly.com/research.html
SAs &Unknown transformation products
WWTPs
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Introduction Objectives Results Summary
Biotransformation of SAs by activated sludge.
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Activated sludge
Heterotrophs
Introduction Objectives Results Summary
Biotransformation of SAs by activated sludge.
Ammonia oxidizers
Nitrifiers
Nitrite oxidizers
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Activated sludge
Heterotrophs
Introduction Objectives Results Summary
Biotransformation of SAs by activated sludge.
Ammonia oxidizersAOB
Nitrifiers
Nitrite oxidizer
Yu Y, et al. 2018
Mia
nser
in
Indo
met
hacin
Ran
itidi
ne
Asula
m
Furos
emid
e
Fenhe
xam
id
Ruf
inam
ide
Bezaf
ibra
te
Isop
rotu
ron
Car
bend
azim
Trimet
hopr
im
Mon
uron
Clo
maz
one
Aceta
mip
rid
Leve
tirac
etam
Irgar
ol
Tebuf
enoz
ide
-40
-20
0
20
40
60
80
100 *
16
8h
re
moval (%
)
AOB/NOB co-culture
NOB pure culture
Fresh medium ctrl
Heat-inactivaed ctrl
* *
**
* *
*
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Activated sludge
Heterotrophs
Introduction Objectives Results Summary
Biotransformation of SAs by activated sludge.
Ammonia oxidizers
AOB AOA Comammox
Nitrifiers
Nitrite oxidizer
Ammonia
Oxidizing
Bacteria
Ammonia
Oxidizing
Archaea
Complete
Ammonia
Oxidizers
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Introduction Objectives Results Summary
Investigate the roles of 3 ammonia oxidizers in SAs biotransformation.
Q1: Can ammonia oxidizers biotransform any SAs?
Q2: What are the transformation mechanisms?
Q3: What are the transformation products?
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AOB: Nitrosomonas nitrosa Nm90
AOA: Nitrososphara gargensis
COMAMMOX: Nitrospira inopinataBatch reactor, triplicates
Introduction Objectives Results Summary
Seven sulfonamides:
Sulfadiazine, sulfadoxine, sulfamethazine, sulfamethoxazole,
sulfamonomethoxine, sulfamerazine, sulfathiazole.
Q1: Can ammonia oxidizers biotransform selected SAs?
AOAAOB
COMAMMOX
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Q1: Can ammonia oxidizers biotransform selected SAs?
A1: Yes, sulfonamides can be biotransformed by ammonia oxidizers.
Introduction Objectives Results Summary
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AOA:N. gargensis
0 100 200 300 400 500
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Time (h)
w/ 0.2 uM ammonia
w/ unlimited ammonia
Sulfadiazine
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Sulfamethazine0 100 200 300 400 500
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Time (h)
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Sulfadiazine
AOB: N. nitrosa Nm90
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Sulfamethazine0 20 40 60 80 100 120 140 160 180
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Time (h)0 50 100 150 200 250 300
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Time (h)
0.2
0.4
0.6
0.8
1.0
0
C/C
0
Sulfamethazine
0.2
0.4
0.6
0.8
1.0
1.2
1.4
1.6
0
C/C
0
Sulfadiazine
COMAMMOX:N. inopinata
Q2: What are the transformation mechanisms?
Introduction Objectives Results Summary
A2: Cometabolism with ammonia oxidation.
(Take sulfadiazine & sulfamethazine as examples)
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Introduction Objectives Results Summary
Q3: What are the transformation products?
A3: Suspect and non-target screening.
TPs of SAs formed activated sludge
Achermann S, et al. 2018
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Introduction Objectives Results Summary
Q3: What are the transformation products?
A3: Suspect and non-target screening.
Deamination (-NH)Sulfadiazine TP236
Pterin conjugation
Pe
ak a
rea
Pe
ak a
rea
Pea
k a
rea
AOA AOB COMAMMOX
For AOB
Pterin-SDZ
TP280
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Introduction Objectives Results Summary
Q3: What are the transformation products?
A3: Suspect and non-target screening.
Pe
ak a
rea
Pe
ak a
rea
Pe
ak a
rea
AOA AOB COMAMMOX
Sulfamethazine
TP264
TP325Pterin-SMZ (AOB)
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Introduction Objectives Results Summary
Ammonia oxidizers
AOB AOA Comammox
Yu Y, et al. 2018
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Introduction Objectives Results Summary
Sulfa
diaz
ine
Sulfa
doxine
Sulfa
met
hazine
Sulfa
met
hoxa
zole
Sulfa
mon
omet
hoxine
Sulfa
mer
azine
Sulfa
thiazo
le0
20
40
60
80
1001
68
h R
em
ova
l (%
)
Abiotic: sulfonamides + hydroxylamine (5μM/12h)
All selected SAs can react with hydroxylamine.
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Introduction Objectives Results Summary
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Introduction Objectives Results Summary
https://doi.org/10.1016/j.watres.2019.05.031
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We thank Dr. Zhong (Lucas) Li form Roy J.
Carver Biotechnology Center.
Dr. Yujie Men
Dr. Michael Wagner
Dr. Ping Han
Dr. Li-Jun Zhou
Acknowledgements
Dr. Baozhan Wang
Dr. Qinglong Wu
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Thanks!
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SAs as one of the biggest families of antibiotics are widely used as human and
animal drugs.
Introduction Objectives Results Summary
Sulfonamide (SA) antibiotics
Sulfonamides functional group
Dihydropteroate
Synthase
(enzyme DHPS)
Folate/
Vitamin B9
Cell growth
How does SA work?