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Isotope-LabeledCompounds
Tetrabenazine-d6
L-Leucine-15N
L-Leucine-18O2
D-Glucose-13C6
MCE
MasterofBioactiveMolecules
1
1H
1H2H3H
1
012
23
2H(D)
3H
2H 13C 15N 18O
1) 2)
[1][2][3]
Electronshell
e-
e-
e-
n
p+
p+
n
p+
n
Hydrogen-1 Hydrogen-2,deuterium Hydrogen-3,tritium
massnumber:1 massnumber:2 massnumber:3
Figure1.Isotopeofhydrogen
CONTENTS
2
MCE
4
10
MCE
12
www.MedChemE
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(PharmaceuticalResearch)
Deutetrabenazine
Tetrabenazine
[3]
4)
5)
1)
2)
3)
6)
PET
[4]
DeuterationinDrugDesign
C
H
C
D
Mayleadto:
PKImprovement
ReductionofToxicity
ReductionofEpimerization
MechanismofAction
denovoDrugDesign
O
ND
HO
O
F
NH2O
O
DD
N
D3CO
H
F
N
O
D
NN
N
H
N
*
N
NNN
ND
EtO
N
N
D3CO
N
N
N
N
D
H
Tetrabenazine-d6
JNJ38877605-d
Thalidomideanalogue-d
Linoleicacidanalogue-d2
VX-984
1stapproveddrug
Figure2.Deuterationindrugdesign[4]
(MetabolicResearch)
UPLC/QTOFMS
MS/MS
JixiaYang
13C15N
?6\QXFOHLQ
7
(?6\Q)
[5]
(Proteomics)
(Glycomics)
MichaelJ.Bowman TetraplexStable-IsotopeCodedTag
TetraplexStable-IsotopeCodedTag
[6]
2
MCE
MasterofBioactiveMolecules
(StandardsforEnvironmentalAnalysis)
PCBsPBDEs
ChenchenHuang
GC-qMS
Cl/Br
PCBs/PBDEs
[7]
(ClinicalResearch)
13C
(BiomolecularNMR)
13C
15N
(TraceElementAnalysis)
LinardsKlavins
?182?151?13C,‰
+
0
-
[8]
38.28
35.51
36.26
33.63
33.81
32.93
30.29
25.65
29.21
29.00
28.09
1.86
0.03
2.56
3.68
1.27
-0.20
-2.17
-6.24
-5.57
-9.89
-12.87
-23.89
-25.31
-25.14
-27.30
-26.98
-27.97
-26.27
-24.05
-24.77
-26.63
-28.60
Latvia
Poland
Germany
6SDLQ
Portugal
Morocco
China
Peru
Argentina
Chile
Uruguay
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MCE
6RUDIHQLE Donafenib
6RUDIHQLEG Donafenib(Sorafenibd3) Sorafenib
[9]
6RUDIHQLE 6RUDIHQLEG
Cl
F
FF
O O
NN
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O
N
Cl
N
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F
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NN
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N
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MCE
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1)
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MCE
2H(D)
2H(D) 1 1 1
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HY-B0590S
Tetrabenazine-d6
?DWRP'
D
D
D
O
D
O
D
H
D
N
CASNo.:1392826-25-3
HY-17357S
Nepafenac-d5
? DWRP ' D D D
DD
NH2
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CASNo.:1246814-53-8
HY-10065S1
HY-B0304AS1
Axitinib-d3
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Dapoxetine-d6hydrochloride
?DWRP'
?DWRP'
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DD
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N
O
H
DN
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DDD
DDD
HCl
CASNo.:1126623-89-9
CASNo.:1246814-76-5
HY-16293S
HY-B0801S
Lurbinectedin-d3
O
D
Fexofenadine-d6
?DWRP'
HN
N
DD
?DWRP'
OH
SO
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OH
O
N
HHO
O
DD
NN
O
D
NH2
H
D
O
HH
HO
DDOOH
CASNo.:N/A
OH
O
CASNo.:548783-71-7
O
4
MCE
MasterofBioactiveMolecules
HY-14914S
Azilsartan-d5
?DWRP'
D
D
D
N
D
O
N
O
D
O
O
OH
HN
N
CASNo.:1346599-45-8
F
HY-131968
%06
N
N
?DWRP'
O
NH
O
D
D
N
D
H
HN
N
O
CASNo.:1771691-34-9
HY-110228
Metformin-d6hydrochloride?DWRP'
DD NH NH
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HY-50895S
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?DWRP'
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CASNo.:857091-32-8
HY-13562S
D
DD
Banoxantrone-d12
N
O
?DWRP'
D
OH
O
HNDD
OH
O
HN
DD
N
D
CASNo.:1562067-05-3
D
O
DD
HY-B0673S
Pirfenidone-d5
? DWRP ' D
D D
DN
DO
HY-10997S O
Ibrutinib-d5N
? DWRP 'N N
N
N
NH2
D
D
O
D
CASNo.:1553977-17-5
DD
HY-13631AS
Exatecan-d5mesylate
? DWRP ' H2N
O
N
O
N
O
OH
O
F
D
D
6
OH
DDD
O
CASNo.:N/A
HY-A0093S
Mexiletine-d6hydrochloride?DWRP'
D
DDD
D
O
DNH2
HCl
CASNo.:1185166-01-1
HY-15328
25-HydroxyVD2-d6
DD
?DWRP'
OHD
D
DD
H
HO
CASNo.:1020719-62-3
HY-15321S
Etoricoxib-d4
?DWRP'
OOD
6
D
D
N
D
Cl
N
CASNo.:1329835-60-0
HY-15777S
Ribociclib-d6
?DWRP'
H
NNNN
O
N
D
N
ND
D
HN
D
DD
CASNo.:1262843-46-8
HY-15330
VD2-d3
? DWRP '
D
H
D
D
HO
CASNo.:11217448-46-8
HY-19939S
9;
D
N
N
?DWRP'N
N
D
NH
N
ONH
CASNo.:1476074-39-1
CASNo.:1131345-14-6
HY-15285
Doxercalciferol-d3
? DWRP '
D
H
D
D
HOOH
CASNo.:N/A
HY-15332
Alfacalcidol-d6
DD
?DWRP'
D
D
DD
H
HO
OH
CASNo.:1641940-94-4
CASNo.:1328934-40-2
HY-W010388AS
Creatine-d3hydrate
?DWRP'
DD
D
O
H2N
N
OH
NHH2O
CASNo.:284664-86-4
HY-76814
Calcitriol-d6
HO
?DWRP'
D
H
OH
D
OH
D
D
D
D
CASNo.:78782-99-7
5
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HY-B0141S
HY-32351S
Estradiol-d3
Calcifediol-d3
OH
?DWRP'
HODD
?DWRP'
D
H
D
D
HD
H
H
HO
HO
H
HY-14654S
Aspirin-d3
? DWRP '
O
O
D
D
OOH
D
CASNo.:79037-37-9
CASNo.:140710-94-7
HY-17501S
HY-10201S
Bambuterol-d9hydrochloride
Sorafenib-d3
?DWRP'
D
D
DDD
?DWRP'
HN
D
D
Cl
HO
D
D
F
O
O
O
F
N
N
N
O
O
N
F
H
H
HCl
CASNo.:1794810-59-5
CASNo.:1130115-44-4
HY-N0570S1
HY-101392S
Hydroxytyrosol-d5
Harmane-d1
?DWRP'
D
?DWRP'
D
OH
HO
OH
DD
D
O DD
OND
N H
H
N
N
D
CASNo.:921943-73-9
HY-B0207AS
Pyridostigmine-d6bromide?DWRP'
DD
O
N+
D
N
O
Br-
DD
D
CASNo.:2375858-08-3
HY-15162A
00$(G
? DWRP 'O O OO
O
N
HN
N
HO
O
D
DD
HN
N
D
D
H
DDD
CASNo.:N/A
HY-13609S
Deflazacort-d5
O
?DWRP'
O
O
D
D
D
ND
HO
D
O
H
H
H
H
O
CASNo.:N/A
HY-B0273S
Sulfadiazine-d4
?DWRP'
D
O
H
D
6
N
N
H2N
D
O
N
D
CASNo.:N/A
HY-B0510S2
Trimethoprim-d3
? DWRP ' D
ODD
H2NNNH2
O
NO
CASNo.:1189923-38-3
HY-14914S
Azilsartan-d5
DD
?DWRP'
ND
D
O
O
D
O
N
O
OH
HN
N
CASNo.:2070009-72-0
HY-N0324S
Cholicacid-d4
?DWRP'
OH
H
OH
D
H
O
D
H
H
HO
OH
DDH
CASNo.:116380-66-6
HY-B0801S
Fexofenadine-d6
DDO
?DWRP'
DD
OH
D
HO
D
N
OH
CASNo.:1020719-78-1
CASNo.:1346599-45-8
HY-113468AS
HY-16060S
3-O-Methyldopa-d3
Apalutamide-d4
?DWRP'
?DWRP'
F
F
O
F
6
O
D
O
OH
N
N
D
NN
H
D
NH2
N
DF
HO
D
OD
CASNo.:586954-09-8
CASNo.:1638885-65-0
D
CASNo.:548783-71-7
HY-B0469S
Medroxyprogesterone-acetate-d3
? DWRP '
O
D
D
O
D
H
O
H
H
O
CASNo.:N/A
6
MCE
MasterofBioactiveMolecules
13C
13C13C
(12C)
HY-50896S1
Erlotinib-13C6 H
?DWRP13C H13C13C13CH
HN13C13C13C
OONH
OON
CASNo.:1211107-68-4
HY-N0437S1
Progesterone-13C5
?DWRP13C O 13CH
13C 3
H
H213C
HH
13C
O
13C
H
CASNo.:2687960-32-1
HY-14605BS
Rasagiline-13C3mesylateracemic
?DWRP13C
H2
HN
13C
13C
O
13CH
6
OH
CASNo.:1216757-55-9
O
HY-Y0252S
L-Proline-13C5
?DWRP13C
H2 O
13CH13C
H213C13C OH
H213CNH
CASNo.:201740-83-2
HY-Y0479S3
L-Lacticacid-2-13C1
?DWRP13C
O
H
13C OH
OH
CASNo.:740788-63-0
6 7
HY-B1732S1
DL-3-Phenylalanine-13C
?DWRP13C
H2
O
13C
OH
NH2
CASNo.:286425-42-1
HY-N0683S
?9LWDPLQ( &
?DWRP13C
13C OH
13C13C
O13C13C13C
CASNo.:2140857-08-3
HY-17598S
Rafoxanide-13C6
?DWRP13C
O
O
I
C
13
N
Cl
Cl
13
C
13
C
H
13
C
C
13
OH
13
C
I
CASNo.:1353867-98-7
HY-W010407S
Cyanuricacid-13C3
?DWRP13C
O
HN13CNH
O13CN13CO
H
CASNo.:201996-37-4
HY-N0486S1
L-Leucine-13C
?DWRP13C
O
13COH
NH2
CASNo.:74292-94-7
13
HY-N0216S1
Benzoicacid-13C6
?DWRP13C
H
O
H13C
13C
OH
13C
H13C
13
13CH
HC
CASNo.:125945-98-4
HY-15306S
(E/Z)-Eltrombopag-13C4
?DWRP13C
13CH3
N13C
H
OH
N13C
N
OH
13C
N
O
O
CASNo.:1217230-31-3
HY-B0289S
Erdosteine-13C4
?DWRP13C
6
O
O
O
13C
613C
OH
N
13
13
H
H2C
H2C
CASNo.:N/A
HY-115584S
Lufenuron-13C6
?DWRP13C
H
F
Cl
13C
O
F
FO
O13C
13C
F
13C
13CF
F
F
N
N
13C
Cl
FH
H
H
CASNo.:N/A
HY-15407AS
Sacubitril-13C4hemicalciumsalt?DWRP13C
H2
O
O
13C
13C
0.5Ca2+
13C
13C
N
O-H2
H
O
CASNo.:N/A
O
7
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15N
15N (14N)7815N
HY-41877S
HY-N0390S
Succinimide-15N
L-Glutamine-15N
?DWRP15N
?DWRP15N
H
O
O
15N
O
O
H2N
15
OH
CASNo.:80143-57-3
NH2
CASNo.:32807-36-6
HY-W008371S
HY-Z0283S
Fmoc-Met-OH-15N
Benzamide-15N
?DWRP15N
?DWRP15N
O
H
15NH2
O
15N
6
OO
OH
CASNo.:934183-50-3
CASNo.:31656-62-9
HY-Y0271S
HY-19821S
Urea-15N2
Fmoc-Ile-OH-15N
?DWRP15N
?DWRP15N
O
H
H215N
15NH2
O
15N
CASNo.:2067-80-3
CASNo.:204633-89-6
OO
OH
HY-Y1117S
HY-Y0978S
Melamine-15N3
Boc-Glycine-15N
?DWRP15N
15NH2
?DWRP15N
H
O
15
HY-N0473S1
L-Tyrosine-15N
?DWRP15N
O
OH
HO15NH2
CASNo.:35424-81-8
HY-N0667S2
L-Asparagine-15N2monohydrate?DWRP15N
O
H215NOH
O 15NH2
HOH
CASNo.:287484-32-6
HY-N0455AS
L-Arginine-15N2hydrochloride?DWRP15N
15NH O
H215NNOH
H NH2HCl
CASNo.:204633-92-1
HY-101037S
Sarcosine-15N
?DWRP15N
H O
N
N
O
15N
OH
H215N
N
15NH2
O
CASNo.:287476-11-3
CASNo.:106665-75-2
HY-N0326S
HY-W017443S1
15N
CASNo.:N/A
HY-N0470S
OH
L-Methionine-15N1
L-Asparagine-amide-15N
?DWRP15N
?DWRP15N
O
O
6
OH
H215N
OH
ONH2
15NH2
HOH
CASNo.:82572-25-6
CASNo.:204451-47-8
L-Lysine-15N2hydrochloride?DWRP15N
O
H215NOH
15NH2
HCl
CASNo.:1217460-44-0
8
MCE
MasterofBioactiveMolecules
2H 13C 15N
HY-B1640S
Ethacrynicacid-13C2,d5
HY-90001S1
Ritonavir-13C,d3
HY-B0495S
Lamotrigine-13C3,d3
?DWRP'?DWRP13C
DD
O
D
DD
Cl
CASNo.:N/A
Cl
HY-70050AS1
Alosetron-13C,d3
?DWRP'D?DWRP13CDD
13C
N
H2
13C OH
O13C
O
? DWRP '
? DWRP 13C
6
D
D
D
O
OH
N
C
13
H
H
O
N
N
N
N
N
6
O
H
O
CASNo.:N/A
HY-12651AS
Primaquine-13C,d3
? DWRP '
? DWRP 13C
D
N
? DWRP '
? DWRP 13CD D D
Cl13CNN
Cl 13C 13C
H2NN NH2
CASNo.:1246815-13-3
HY-B0373S
Tiopronin-13C,d3
?DWRP'
?DWRP13C
6H
H
O
D
N
N N
ONH
CASNo.:N/A
HY-B0421S1
Mycophenolicacid-13C,d3
? DWRP ' D
? DWRP 13C D13CD
OO O
OH
O OH
CASNo.:2455553-76-9
HY-16637S2
Folicacid-13C5,15N1
? DWRP 13C
?DWRP
15
N
O
O
C
OH
13
13
H2
C
OH
O
13
C
N
15
N
H
13
C
13
C
HN
N
H
H
O
2
H2
N
N
N
H
CASNo.:N/A
HY-B0389S
D-Glucose-13C6,d7
? DWRP '
? DWRP13CDOHDOHOHO13C13C13C13C13C13CD
D DHODHOD
CASNo.:201417-01-8
D
NH2
D13CO
N
H
CASNo.:N/A
HY-135330
Lamivudine-13C,15N2
?DWRP13C
?DWRP15N
O
6
OH
13C
O
O
15N
15N
H2N
CASNo.:1391052-30-4
HY-W017443S
L-Asparagine-13C4,15N2
? DWRP 13C
? DWRP 15N H2 O
H215N13C13C13CH13COH
O 15NH2
HOH
CASNo.:202406-87-9
HY-I0626S
Cytosine-13C2,15N2
?DWRP13C
?DWRP15N
H
H215N13
15N
O
C
13C
15N
CASNo.:285978-06-5
D
13C
OH
DOH
H
CASNo.:1189695-13-3
HY-107372S
Uridinetriphosphate-13C9,15N2
?DWRP13C
?DWRP15N
H2
O
O
O
OH
O
H13C
O
P
O
P
O
P
OH
15
N
13C
13
13
C
H
15
C13
OH
OH
OH
13C
N13
CH
13
CH
O
13C
CHHO
OH
H
CASNo.:285978-18-9
HY-N0667S
/$VSDUDJLQH&1G
?DWRP13C
?DWRP15N
O
D
15N
D
?DWRP'
D
13C
13C
13C
O
D
15N
D13C
D
D
D
O
CASNo.:1217464-18-0
HY-N0666S1
L-Asparticacid-13C4,15N
?DWRP13C
?DWRP15N
O
H2
13CH13C
OH
HO
13C13C
15NH2
O
CASNo.:202468-27-7
9
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(MFA)
13C 15N
[10]
Metabolite
extraction
BiofluidsCellsandmedia
Tissues
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Glucose
Acetyl-CoA
Oxaloacetate
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value
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10
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log
-
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Functionalandmechanisticvaildation
Metabolicfluxanalysis
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Heatmap
20
Group1
15
10
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5
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4
6
8
10
Metabolites
Metabolomicdataanalysis
5
Pyrimidinemetabolism
-log103value
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1
TCAcycle
2
3
3
4
5
2
Impact
0.1
1
0.3
0.5
0 0.2 0.4
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Metabolicpathwayanalysis
Figure4.WorkflowofLC-MSbasedmetabolomics[10]
10
MCE
MasterofBioactiveMolecules
NADPH
(OxPPP)THF
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(MEI)
NADPH
NADPH
DNA
(OxPPP)
(Non-OxPPP)
M
(<1-13C>glucose
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OxPPP
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Non-OxPPP
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M+2
5[11][12]
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Oxidative
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%
C1
[1,2-13C]glucosefeeding
C2
D-Glucose
Oxidative
C1
C1
C1
6PGC2
PPP
G6P
C2
C2
G-1,5--6P
C1
C1
C1C2
C1
G3P
C2
Non-xidativeF6PC2
Ru5P
Ribose
PPP
TK
C1
C1
C4C5C6
C2
C2
C
Xu5P
R5P
Histidine
E4P
G3P
TK
C1C2C3C4
TA
63
Legends
OxPPP
None-OxPPP
1.0
[12C]
[13C]
Absenceofgene
ProportionalMIDs
0.8
0.6
0.4
0.2
0
m0
m1
m2
m3
m4
+LVP]
[C1-6]
Legends
OxPPP
None-OxPPP
[12C]
1.0
[13C]
ProportionalMIDs
Absenceofgene
0.8
0.6
0.4
0.2
0
m0
m1
m2
m3
m4
+LVP]
[C1-6]
Figure5.Movementof13ClabelthroughOxPPPandnon-OxPPPinR.solanacearumF1C1[11]
11
www.MedChemE
,QKLELWRUV?6FUHHQLQJ/LEUDULHV?3URWHLQV
MCE
MCE
2HD1313C
1515N
MCE
MCE
MCE
MCE
D 13C
15N 18O
(
13C )
(AA)
20
(TCA)
?
(EMP)
6
A
B?
37
(C2-C6)
(C7-C12)
(>C14)
VAVB VCVDVE
16
(C16-C19)
MCE
12
MCE
MasterofBioactiveMolecules
HY-32349S
25-hydroxyVitaminD2-d3
?DWRP'
D
OH
D
HD
HO
H
CASNo.:1217467-39-4
HY-Y0966S
Glycine-15N
? DWRP 15N
O
H215NOH
CASNo.:7299-33-4
HY-B0350S
Butyricacid-d7
? DWRP '
DD O
D OH
DDDD
CASNo.:73607-83-7
HY-B0389A
D-Glucose-13C6
?DWRP13C
OH
OH
H2
13
13
O
13CH
HC
H
HC
13
HO
13C
13C
C
H
OH
OH
CASNo.:110187-42-3
HY-B0141S
Estradiol-d3
?DWRP'
HO
DD
H
D
HY-32351S
Calcifediol-d3
?DWRP'
D
OH
D
HD
HO
H
CASNo.:140710-94-7
HY-N0486S3
L-Leucine-15N
? DWRP 15N
O
OH
15NH2
CASNo.:59935-31-8
HY-N0420S
Succinicacid-d6
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