Crystal structure, molecular docking and protective activity on myocarditis of Co(II) coordination polymer based nanoparticles

Article abstract of DOI:10.1016/j.molstruc.2019.127038

This work presents the synthesis and characterization of a dicyanamide-bridged coordination polymer [Co(L)₂(dca)]_n (1) by using the bidentate NO donor Schiff base ligand (2-methoxy-6-((methylimino)methyl)phenol. Furthermore, the nanoparticles of complex 1 (denoted as nano 1) was prepared by a green grinding approach, which has good water dispersibility. The CVB3 infection mice model was built successfully, followed by nano 1 given for treatment. RT-PCR was used to detect the loading of CVB3 virus after nano 1 treatment. The left ventricular fractional shortening (LVFS) as well as left ventricular ejection fraction (LVEF) were assessed to evaluate the protective effect of cardiac functions after exposed to nano 1. The toxicities of nano 1 on H9C2 and HL-1 cardiomyocytes was evaluated by CCK-8 assay. The hypothesis originated from the experimental observations has been further confirmed by using molecular docking simulation.

Full text of DOI:10.1016/j.molstruc.2019.127038

Journal of Molecular Structure 1199 (2020) 127038
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: http://www.elsevier.com/locate/molstruc
Crystal structure, molecular docking and protective activity on
myocarditis of Co(II) coordination polymer based nanoparticles
a
a
a
,
b
,
**
, Qing-Shan Zhang a
, b, *
Dong-Song Bai , Li-Ying Bai , Ming Zhao
a
Inner Mongolia Key Laboratory of Mongolian Medicine Pharmacology for Cardio-Cerebral Vascular System, Tongliao, Inner Mongolia, 028000, China
Affiliated Hospital of Inner Mongolia University for Nationalities, Institute of Mongolia and Western Medicinal Treatment, Tongliao, Inner Mongolia,
28007, China
b
0
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 29 May 2019
Received in revised form
This work presents the synthesis and characterization of a dicyanamide-bridged coordination polymer
[
2 n
Co(L) (dca)] (1) by using the bidentate NO donor Schiff base ligand (2-methoxy-6-((methylimino)
methyl)phenol. Furthermore, the nanoparticles of complex 1 (denoted as nano 1) was prepared by a
green grinding approach, which has good water dispersibility. The CVB3 infection mice model was built
successfully, followed by nano 1 given for treatment. RT-PCR was used to detect the loading of CVB3 virus
after nano 1 treatment. The left ventricular fractional shortening (LVFS) as well as left ventricular ejection
fraction (LVEF) were assessed to evaluate the protective effect of cardiac functions after exposed to nano
29 August 2019
Accepted 4 September 2019
Available online 5 September 2019
Keywords:
Coordination polymer
Myocarditis
Left ventricular ejection fraction
Molecular docking
1. The toxicities of nano 1 on H9C2 and HL-1 cardiomyocytes was evaluated by CCK-8 assay. The hy-
pothesis originated from the experimental observations has been further confirmed by using molecular
docking simulation.
© 2019 Elsevier B.V. All rights reserved.
1. Introduction
crystal engineering are the focus of research in the field of coor-
dination chemistry supramolecular chemistry [6,7]. The more and
As we all know, myocarditis is an autoimmune disease that leads
to high death rate in the world every year [1]. It is a common heart
disease with severe inflammatory immune infiltration and necrosis
of myocardial cells. It can develop into chronic dilated cardiomy-
opathy (DCM) and cause sudden death [2,3]. Among different
myocarditis, the viral myocarditis is the most common one, which
is an inflammatory response usually resulted from the infection of
myocardial virus, and the coxsackievirus B3 (CVB3) is the most
familiar pathogen as reported [4]. Relying on the rearrangement of
intracellular membranes into double-membrane vesicles, the
replication of CVB3 explains the mechanism of viral myocarditis [5].
However, up to now, there is still no available efficient therapeutic
agent against viral myocarditis.
more attention in this field is attributed to its valuable unit struc-
ture, as well as their latent applications in catalysis, biochemistry
and luminescence, and especially in contemporary medicinal
chemistry [8e12]. Because of its latent drug application value,
functional complexes have attracted wide attention in these pre-
pared complexes. And therefore, the selection of biocompatible li-
gands, safe and highly efficient has become a key element in the
field of clinical practice, the structural design as well as drug
treatment. Metal complexes containing oxygen and nitrogen li-
gands, such as Schiff base, have become more and more interest
and current in the coordination chemistry field, due to many
complexes have anticancer activity [13e16]. 4-chlorobenzaldhyde
and 2-aminophenol bidentate Schiff base ligand have many bio-
logical and clinical applications. On the other hand, Cobalt is a
necessary element of human body, indirectly regulates DNA syn-
thesis in the active site of vitamin B12. Because of its remarkable
biological activity, it attracts many organic metal chemists and bi-
ologists to study cobalt complexes with a view to their medical
applications [17]. Because cobalt complexes have the ability of
redox-dependent targeting malignant tissue of solid tumors and
systemic anti-cancer effects, there is a great interest in cobalt
complexes in the experimental research of malignant tumors
Metal supramolecular structures and their design on the basis of
*
Corresponding author. Inner Mongolia Key Laboratory of Mongolian Medicine
Pharmacology for Cardio-Cerebral Vascular System, Tongliao, Inner Mongolia,
28000, China.
* Corresponding author. Inner Mongolia Key Laboratory of Mongolian Medicine
Pharmacology for Cardio-Cerebral Vascular System, Tongliao, Inner Mongolia,
0
*
028000, China.
E-mail addresses: langzhe73@163.com (M. Zhao), qingshan_zhang666@163.com
(
Q.-S. Zhang).
https://doi.org/10.1016/j.molstruc.2019.127038
022-2860/© 2019 Elsevier B.V. All rights reserved.
0

2
D.-S. Bai et al. / Journal of Molecular Structure 1199 (2020) 127038
treatment [18]. This work presents the synthesis and character-
ization of a dicyanamide-bridged coordination polymer [Co(L) (d-
ca)] by using the bidentate NO donor Schiff base (2-methoxy-6-
(methylimino)methyl)phenol. Furthermore, the nanoparticles of
2.4. Real-time RT-PCR
2
n
The BALB/c male were affected by CVB3 virus, and then treated
with nano 1. On the 3rd and 7 days after infection, the loading of
CVB3 virus was detected by RT-PCR accordance to the producer's
plan [20]. In short, total RNA was separated by RNeasy Mini RNA
Isolation Kit (QIAGEN) and quantized the concentration of RNA,
followed by reverse transcript into cDNA with cDNA Synthesis Kit
(Takara). Real-time PCR was performed using the SYBR Green PCR
(
complex 1 (denoted as nano 1 hereafter) was prepared by a green
grinding approach, which has good water dispersibility. The virus
burden detected by RT-PCR showed that nano 1 could significantly
reduce the loading of the virus. And the values of LVEF and LVFS also
suggested the obviously protective effect of nano 1 on cardiac
functions. The CCK-8 assay of the nano 1 on H9C2 and HL-1 car-
diomyocytes showed that the nano 1 has no toxicities on normal
cells. The hypothesis that established upon the experimental ob-
servations has been examined by performing molecular docking
simulation.
0
Master Mix kit (Takara). The primers were CVB3 Forward: 5 -
ATCAAGTTGCGTGCTGTG-3 ;
0
0
CVB3
reverse:
5 -TGCGAAAT-
GAAAGGA. The relative expression levels of CVB3 were calculated
ꢁ
DDCt
by 2
method.
2.5. Echocardiography
2
. Experimental
After infected with CVB3 virus, the mice were treated with nano
at the dosage of 5 mg/kg. The heart functions indicators are left
ventricular fractional shortening (LVFS) and left ventricular ejection
fraction (LVEF), they were evaluated by an echocardiography
Vevo2100, Visual Sonics, Canada) at the 7th day after CVB3
contagion and nano 1 treatment [21].
1
2.1. Chemicals and measurements
The chemicals as well as reagents were purchased from Beijing
(
Bailingwei reagent company and Tianjin Guangfu chemical reagent
company, and they were utilized with no further depuration. We
utilized the elemental vario micro elemental analyzer to obtain
elemental results for the content of N, C, H elements content. SEM
was used for the sake of depicting the configuration and
morphology of the CP 1's nanostructures.
2
.6. Toxicities detection
The toxicities of the nano 1 was detected by CCK-8 assay against
cardiomyocytes H9C2 and HL-1 according to the instructions as
previous introduced. In brief, the H9C2 and HL-1 cardiomyocytes
3
2.2. Preparation and characterization for coordination polymer
were planted in 96 well plates at the final destiny of 5 ꢂ 10 cells/
[Co(L) (dca)] (1)
2
n
well, and the cells were treated with serious dilutions of nano 1 (1,
2
, 4, 8, 10, 20, 40, 80
m
M) with Co(II) complex used as the parallel
ꢀ
We dissolved Cobalt acetate tetrahydrate which is 0.100 g and
.4 mmol, NaN(CN) (0.036 g, 0.4 mmol) as well as Schiff base (HL)
control. After 24 h incubation at 37 C, 5% CO
2
, 10
mL CCK8 reagent
0
2
(Sigma) in 100 mL medium without FBS was added into each well
which is 0.05 g and 0.3 mmol into methanol of 10 mL. And then, we
adjusted the pH numerical value of the reaction system to 5e6.
Transferring and sealing up the mixture into the stainless steel
for another 2 h culture. Finally, the absorbance at 450 nm was
detected for each sample. The cell viability rate was calculated ac-
cording to the OD450 value.
ꢀ
container which has 25 mL Teflon-lined, heating it for 12 h at 80 C,
and then we cooled the mixture to room temperature. We acquired
black single crystals suitable for X-ray diffraction analysis with
block-shape. The yield was 45% (in cobalt). Elemental findings
2.7. Molecular docking
In order to iterate over the conformational space of Co(II)
complex when interacting with active cites provider, the stochastic
5 4
resulted to C20H20CoN O : C, 22.99; H, 4.45; N, 15.45%. Found for N:
C, 23.06; H: 4.55; N: 15.72%.
The complex 1's X-ray data were obtained by utilizing the Ox-
ford Xcalibur E diffractometer. The intensity data was analyzed by
utilizing the CrysAlisPro software and converted to the HKL files.
The SHELXS program on the basis of direct approach was utilized to
create the complexes 1's initial structural models, the SHELXL-2014
program on the basis of the least-squares approach was modified
Table 1
Refinement details and crystallographic parameters for complex 1.
Empirical formula
C
20
H
20CoN
5 4
O
Formula weight
Temperature/K
Crystal system
Space group
a/Å
453.34
100.00(10)
monoclinic
C2/c
18.0260(12)
8.3690(5)
14.5540(6)
90
116.109(5)
90
1971.6(2)
4
[
19]. The 1's whole non-H atoms were mixed with anisotropic pa-
rameters. Then we utilized the AFIX commands to fix the whole H
atoms geometrically on the C atoms that they attached. Table 1
details complex 1's refinement details as well as crystallographic
parameters.
b/Å
c/Å
ꢀ
ꢀ
ꢀ
/
a
b
g
/
/
3
Volume/Å
Z
2.3. CVB3 infection mice model
3
r
calcg/cm
1.527
0.909
4192
ꢁ
1
BALB/c male BALB/c mice of 6e8 weeks and 18e20 g were
m
/mm
Reflections collected
Independent reflections
purchased from Model Animal Reaserch Center of Nanjing Uni-
versity (Nanjing, China) and preserved under standard laboratory
condition. This experiment was ratified by the Animal Protection
Ethics Committee of Nanjing University. For mice infection, intra-
1936 [Rint ¼ 0.0190, Rsigma ¼ 0.0289]
Data/restraints/parameters
1936/0/178
1.134
Goodness-of-fit on F2
Final R indexes [I ꢃ 2
s
(I)]
R1 ¼ 0.0416,
u
u
R2 ¼ 0.1199
¼ 0.1214
3
peritoneal injection (i.p.) was administered at a dose of 10 PFUs.
Final R indexes [all data]
Largest diff. peak/hole/e Å
CCDC
R
1
¼ 0.0442,
R
2
ꢁ
3
0.44/-0.86
1947499
CVB3 was subcultured in HeLa cells (ATCC, CCL-2). After infection,
the mice were further kept in the cage with free food and water.

D.-S. Bai et al. / Journal of Molecular Structure 1199 (2020) 127038
3
Fig. 1. (a) The basic repeating unit for 1. (b) The 1's 1D chain-like network. (c) The 3D packing diagram for the network of 1.
geometry searching approach has been used to sample through all
the possible binding interactions. To address such complicated task,
a modified version of autodock vina, Smina, has been used. The
initial configuration of Co(II) was taken from the experimental
crystal structure and used for molecular docking directly. A
maximum number of 25 binding modes have been used. Visuali-
zation has been done by using open source version of PyMOL v2.3.0.
along the b axis to afford a 1D layered network with the CoeCo
separation of 8.744 Å (Fig. 1b). Further research to the framework
shows that there are without p-p interreactions in the formed 1D
chain-like network. However, using the calcd H-bond manipulation
embedded in the software PLATON, there still exist the non-classic
H-bond interaction in the 1D chains, which is formed by the H atom
on the C8 and the O1 atom with the CeH$$$O distance of 2.858 Å.
The packing of the 1D chain-like structure via the Van der Waals
force affords a tightly packing 3D supramolecular framework with
no accessible solvent free volume (Fig. 1c). To check the phase
purity of the as-prepared 1, its PXRD patterns were collected using
the freshly as-prepared samples at room temperature. As shown in
Fig. S1, the PXRD pattern of the as-synthesized 1 is almost identical
to the calculated pattern, indicating the as-prepared 1 shows high
phase purity.
3
. Results and discussion
3.1. Molecular structure
The Schiff base ligand (2-methoxy-6-((methylimino)methyl)
phenol could be prepared by refluxing an excess MeNH with the 2-
2
hydroxy-3-methoxybenzaldehyde in the MeOH solution. After slow
evaporation of the reaction mixture, a bright yellow crystalline
solid of HL was obtained in a 60% yield. Reaction of cobalt acetate
2
tetrahydrate, HL and NaN(CN) in the MeOH solution under the
solvothermal condition results in forming the targeted complex 1
with a moderate high productivity. The refinement results as well
as structural solution on the basis of the crystal data collected at
100 K reflected that the black crystals of 1 is part of the monoclinic
crystal system that the space group is C2/c and demonstrates a 1D
chain-like network. Complex 1's asymmetric unit is shown in Fig. 1,
which indicates that the neutral network of 1 is composed of one
half Co(II) ion located on the 2-fold crystallographic axis, one
2
deprotonated L ligand along with a half HN(CN) molecule. Similar
2
þ
to the reported complex on the basis of the L ligand, the Co ion
ꢁ
takes up the N2O2 donor chamber of two L ligands. Two phenoxo
oxygen atoms (O1 and O1A) as well as two imine nitrogen atoms
2
þ
(
N1 and N1A) can coordinate the Co ion, and it forms the base of a
square pyramid, while N2 of 1,5-bidentate dca takes up the top
m
coordination. The CoeO bond distance is 1.854(2) Å and the bond
lengths of CoeN are in the region of 2.036(8) to 2.293(18), which
are comparable with those CoeO and CoeN bond distances in the
reported document [22]. The dca ligand, which adopts a
bidentate bridging mode, connects with the adjacent CoL
1,5
m -
units
2
Fig. 2. The SEM micrograph for the nanoparticles of 1.

4
D.-S. Bai et al. / Journal of Molecular Structure 1199 (2020) 127038
Fig. 3. Protective effect of nano 1 on mice infected with CVB3 virus. The infection of BALB/c with CVB3 virus and given nano 1 for treatment. the loads of CVB3 virus in mice was
measured by RT-PCR, p < 0.05 was considered as obvious difference. This experiment was in triplicate.
3
.2. Preparation of the nanostructure of 1
solution on the surface of a glass, and the thickness for the ball-like
nanoparticles is around 186 nm for nanostructure 1 (Fig. 2). The as-
prepared nanostructure has good dispersibility in the aqueous so-
lution (Fig. S2).
Considering the following bioactivity tests, it is essentially
reducing the particle size of 1 to the nanometer scale, which can
motivate the drug to be discharged into the whole body and then
can be absorbed by specific tissues through the intravenous
administration. In the previous studies, it has been shown that the
mechanical grinding technology is a green and valid approach to
establish coordination polymer nanostructures that are simple to
be operate. Intriguingly, f or the complex 1's single crystals, the
crystalline nanoscale complex 1 were acquired when the single
crystals were mechanically ground in a pestle and mortar for
approximately 30 min. The crystalline nature of the nanoscale
materials is confirmed by PXRD studies, and it is also noticed that
the PXRD pattern of the nanoscale compound matched perfectly
well with the simulated and bulk PXRD patterns of the complex 1,
indicating complex 1 could maintain the integrity after the for-
mation of the nanoparticles (Fig. S1) [23,24]. The nanostructures'
formation was further identified by utilized SEM studies, which
were acquired by dropping the nanostructures' DMSO dispersion
3.3. Nano 1 reduces the CVB3 virus burden in mice
Coxsackie virus B3 (CVB3) is a globally prevalent virus, which is
frequently associated with myocarditis. As reported, most
myocarditis diseases were caused by CVB3 virus infection. So, to
further explore the protective effect nano 1 in the CVB3 infected
animal model, the animal model was constructed firstly followed
by the nano 1 treatment. Then, the virus burden was measured by
RT-PCR assay. As the results showed in Fig. 3, the virus loads on the
3
rd and 7th day after treatment was significantly reduced in a time-
dependent manner. The nano 1 could reduce the loads to 20% and
5%, compared to the infection model group (p < 0.005). This result
2
suggested the nano 1 could significantly reduce the virus in the
infected animal, and exert an excellent protective effect in vivo.
Fig. 4. Increased cardiac functions of CVB3 virus infected mice after nano 1 treatment. The CVB3 virus infected mice were given complexes for 7 days treatment, the cardiac
functions were evaluated by LVEF and LVFS. p < 0.05 was considered as obvious difference, this study was repeated at least three times. Nano 1 showed no toxicities on H9C2 and
HL-1 cardiomyocytes.

D.-S. Bai et al. / Journal of Molecular Structure 1199 (2020) 127038
5
Fig. 5. No toxicities of nano 1 on H9C2 and HL-1 cardiomyocytes. The H9C2 and HL-1 cardiomyocytes were treated with serious dilutions of nano 1 for 24 h, the toxicities of nano 1
on H9C2 and HL-1 cardiomyocytes was evaluated by CCK-8 assay. This experiment was conducted at least three times.
3
mice
.4. Nano 1 improve the cardiac functions of CVB3 virus infected
cover the entire docking pocking, and 25 docking trials were used
for the screening of the possible binding interactions. The Co(II)
complex can be used as protective activity with strong confidence
due to the activity to interact with both DNA and protein, as shown
in Fig. 6a, which depicts the summary view of Co(II) complex
wrapping into the binding pocket that was provided by 4QJU. The
molecular docking results show that 8 different binding modes has
been found above the 25 searches, the binding energies are
increasing from ꢁ6.2 to ꢁ3.4 kcal/mol. In Fig. 6b and c we show two
energy favorable binding modes in which the chain structures of
nitrogen are interacting with double helix structure on the one
hand and with protein on the other hand. While the energy unfa-
vorable binding mode is showing that the stability of the binding is
weak when oxygen-containing functional groups are interacting
with the receptor. Such result has qualitative agreement to the
observations in experiment.
Myocarditis is combined with LVEF and LVFS systolic dysfunc-
tion, which are applied in the diagnosis, management and prog-
nostication of myocarditis. During the procession of myocarditis,
there is usually a reduced level of LVEF and LVFS compared with the
normal people. As the important marker of cardiac functions, the
LVEF and LVFS of CVB3 virus infected mice was evaluated at the end
of the nano 1 treatment period. We can see, the CVB3 virus infec-
tion caused a weaker left ventricular systolic function, the per-
centage of LVEF was reduced to about 30%, but this damage could
be reversed by nano 1 to almost 80% obviously (Fig. 4). This result
suggested the excellent protective effect of nano 1 on the cardiac
functions of CVB3 virus infected mice.
Considering the necessary of nano 1 willing to become a drug,
the toxicities of the nano 1 on H9C2 and HL-1 cardiomyocytes was
evaluated by CCK-8 assay. The H9C2 and HL-1 cardiomyocytes were
treated with serious dilutions of nano 1 (1, 2, 4, 8, 10, 20, 40, 80
using Co(II) complex as the parallel control in this experiment for
4 h. As results showed in Fig. 5, nano 1 didn't affect the cell
mM),
2
viability of both H9C2 and HL-1 cardiomyocytes, the cell viability
rate were still over 80% after 24 h treatment. These results indicated
that the nano 1 showed no toxicities on H9C2 and HL-1 car-
diomyocytes, it's protective effect on CVB3 virus infected mice was
due to the reducing of the virus burden and improving of the car-
diac functions.
3.5. Molecular docking
Generally, the drug-like or protective features of the ligand are
the capabilities of interacting with double helix structure from DNA
or residues from protein, because most diseases are caused by the
cleavage of double helix structure or the conformation changing of
protein. Molecular docking approach is a tool that could help us to
reveal how ligand interacts with either DNA or protein at the mo-
lecular level. To understand the experimental phenomenon
observed by the experimental results described above, the protein
4
QJU (PDBID) has been chosen to probe the possible interactions
between Co(II) complex, the advantage of using 4QJU as the re-
ceptor is that the structure contains both double helix structure and
residues that belong to common protein. Furthermore, 4QJU is a
widely used target protein for metallic complexes for cytotoxicity
studies including but not limited to Co(II), Zn(II) and Mn(II) [25,26],
so it is a suitable receptor for the myocarditis study of synthesized
Co(II) complex in the current study. The docking pocket that pro-
vided by 4QJU is formed between DNA and protein structures, the
length of the docking grid is set to 22.5 Å which is large enough to
Fig. 6. The summary view of the molecular docking of Co(II) complex with receptor
protein (4QJU) (a), two most favorable binding modes that were found during the
molecular docking, their association binding energies are ꢁ6.2 (b) and ꢁ6.0 (c) kcal/
mol, the energy unfavorable binding mode (d) with its highest binding energy
of ꢁ3.4 kcal/mol among all other 7 possibilities.

6
D.-S. Bai et al. / Journal of Molecular Structure 1199 (2020) 127038
4
. Conclusion
In summary, a dicyanamide-bridged coordination polymer has
https://doi.org/10.1016/j.molstruc.2019.127038.
been successfully prepared by using the bidentate NO donor Schiff
base ligand (2-methoxy-6-((methylimino)methyl)phenol under
the solvothermal conditions. The structure of the as-prepared
complex 1 have been characterized by single crystal X-ray diffrac-
tion studies, which demonstrates that complex 1 has a rod-like 1D
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