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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5710_Библиотеки_им_академика_М_И_Перельмана
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108 Oxadiazole in Material and Medicinal Chemistry
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CHAPTER 6
Oxadiazole-Based
Heterocyclic Compounds
as Chemical Probes in
Live Cell Imaging
1. Introduction
Oxadiazoles are five-membered heterocyclic compounds that belong to the aromatic
azole family. Out of four different isomers of oxadiazole, 1,2,4-oxadiazole,
and 1,3,4-oxadiazole exhibit a diverse range of chemical as well as biological
characteristics. These heterocyclic scaffolds (1,3,4-oxadiazole) are used as primary
synthons during drug manufacturing (Siwach and Verma 2020). Additionally,
1,3,4-oxadiazole-based probes exhibit high fluorescence quantum yield and good
thermal and chemical stability (Hughes and Bryce 2005). These electron-deficient
heterocyclic compounds can unravel remarkable biological phenomena when linked
with suitable functional moieties. For example, (i) attachment of
18
F ligand to the
basic oxadiazole derivative could potentially map abnormal tissues in the body,
and (ii) modification of oxadiazole-based structure with
123/125
I could map the exact
location of cholinergic nerve loss in case of dementia.
Two of its positions on the ring can be substituted with different groups to
yield a range of useful compounds (Maan et al. 2021). The covalent attachment
of oxadiazole with fluorophores provides a brighter fluorescence response. These
fluorescent probes could be utilized for cell function labeling, pH indicators, and
intracellular metal ion quantification. Oxadiazole derivatives are also being explored
as chelating motifs owing to their rich coordination characteristics. Potential metal
ions such as Zn
2+
and Fe
3+
/Fe
2+
might be suitable for binding with the oxadiazole
precursor in the presence of a suitable functional group such as hydroxyl moiety.
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N
O
N
COOH
N
N
OH
O
18
F
N
N
N
N
O
18
F
O
F
3
C
1
CF
3
2
Structures 1 and 2
N
N
O
O
OH
OH
O
N
N
F
F
O
O
CF
3
3
CF
3
4
OH
N
N
O
O
O
CF
3
F
5
O
Structures 3–5
110 Oxadiazole in Material and Medicinal Chemistry
2. Oxadiazole-Based Probes in PET Imaging
Positron emission tomography (PET) is one of the advanced non-invasive imaging
tools to investigate the biochemical nature of tissues and organs. During the PET
scanning process, a radioactive drug called “tracer” is normally used in order to
visualize the bright signals. This type of imaging is more suitable for abnormal tissue
detection; therefore, it is more frequently used in cancer detection. Applications
of oxadiazole-based synthetic probes as radiotracers in PET imaging are
explained below.
The subtype sphingosine 1-phosphate receptor 1 (S1PR1) exhibits inflammatory
importance among G-protein-coupled receptors. Rosenberg et al. developed fluorine
(
18
F) tagged S1P probe 1 in a multi-step synthetic process (Rosenberg et al. 2016).
The synthetic ligand that contains centrally positioned 1,2,4-oxadiazole moiety
exhibited high selectivity (> 100-fold) as well as high potency (2.63 nM) toward
S1P
1
and accumulated in the mouse liver during in vivo evaluation. Studies like
microPET imaging, in vitro autoradiography, and biodistribution confirmed
18
F
tagged ligand 1 as a positron emission tomography (PET) radiotracer for S1P
1
and
could be used for LPS-induced liver injury with increased expression of S1P
1
. Luo
et al. developed triazole functionalized probe 2 by modifying the earlier version of
azetidine-3-carboxylic acid-based ligand with hydroxymethyl capped triazole moiety
with around 14.1% radiochemical yield and 54.1 GBq/ȝ mol specific activity (Luo
et al. 2018). The biodistribution analysis found interesting results where the
fluorinated probe can enter the blood-brain barrier with 0.71% ID/g brain uptake
following 1 h of injection (Figure 1). Additionally, the uptake was shortened by
a specific S1PR1 ligand called SEW2871, confirmed by in vitro autoradiography
analysis. The
18
F labeled probe might be useful for inflammatory evaluation as a PET
radiotracer.
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Oxadiazole-Based Heterocyclic Compounds as Chemical Probes in Live Cell Imaging 111
Figure 1. A bar chart showing regional brain uptake distribution of probe 2 in female Lewis rats. Animals
were euthanized after 5, 30, 60, and 120 min injections. %ID/gram values (mean ± SD) with 4 rats per
group. Reprinted with permission from Elsevier (Luo et al. 2018).
In 2018, The same group (Luo et al.) also developed a series of
fluorine-substituted S1PR1 probes 3–5 (Luo et al. 2018). The compounds 3–5
displayed strong binding tendencies toward the S1PR1 ligand with IC
50
values
of 6.7 ± 0.7, 14.0 ± 0.4, and 15.4 ± 3.3 nM, respectively. Radiolabelling these
compounds with F-18 resulted in high-yield compounds with more than 98% purity.
The synthesized radiolabelled probes could penetrate the blood-brain barrier, which
might be useful for in vivo response in inflammatory models in the future.
Visualization of type 2 cannabinoid receptor (CB2) has significant advantages
in quantification of neuro-inflammation and clinical settings. The CB2 receptor is
mainly expressed in immune cells (Gazzi et al. 2022). Ahamed et al. developed
N-arylamide functionalized oxadiazole derivatives labeled with
11
C and
18
F (Ahamed
et al. 2016). The binding affinity for the human CB2 receptor was found to be
87 nM and 0.8 nM with probes 6 and 8, respectively. The EC
50
values for probes
6 and 8 were estimated to be 3 and 0.1 nM, respectively, which were confirmed as
potent CB2 receptor agonists. The synthesized probes 7 and 9 exhibited good brain
uptake along with appropriate clearance from blood, which suggested that these
probes could be useful for PET in vivo imaging of CB2 receptors. In another study,
probe 9 exhibited a longer half-life (109.8 min) and greater affinity toward CB2
receptor agonist (K
i
~ 0.8 nM) (Attili et al. 2019).
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kinase enzyme that is a tumor suppressor (Mishra 2010). Kumata et al. developed
11
C labeled radiotracers 10–12 using thiol-based synthetic precursor (Kumata
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112 Oxadiazole in Material and Medicinal Chemistry
F
F
Cl
Cl
N
N
H
N
11
CO
N
H
N
MeO
N
H
3
O
O
N
N
6
7
F
F
Cl
Cl
N
N
H
N
H
N
N
O
18
F
N
O
O
O
F
N
9
N
8
Structures 6–9
11
CH
3
11
CH
3
11
CH
3
O
O
S
S
S
O
H
3
C
H
3
C
H
3
C
O
O
O
N
N
N
N
N
N
O
O
O
10
11
12
Structures 10–12
et al. 2015). Both the methylsulfanyl (10) and methylsulfonyl (12) probes exhibited
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inhibitors.
The histone deacetylase (HDAC) enzyme eliminates acetyl moiety from the
lysine part of histone protein through the deacetylation process. This catalytic
method regulates oncogene expression and cell-cycle progression (Ropero and
Esteller 2007). HDAC is known as a promising target for chemotherapy. The
trifluoromethyloxadiazolyl (TFMO) is a unique class-IIa HDAC pharmacophore
that coordinates with the Zn
2+
ion in the catalytic pocket. Therefore, Turkman et al.
developed an
18
F labeled oxadiazole scaffold (> 98% radiochemical purity) through
radiofluorination from bromodifluoromethyl attached oxadiazole (Turkman et al.
2021). The probe worked as a class-IIa HDAC inhibitor.
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