A novel mesoionic carbene based highly fluorescent Pd(ii) complex as an endoplasmic reticulum tracker in live cells

Article abstract of DOI:10.1039/C8DT02778A

A recent study advocates that endoplasmic reticulum (ER) dysfunction may be linked to critical neurotrauma and advanced tauopathy. In this regard, targeting the ER warrants urgent attention towards the therapeutic treatment of neurotrauma-related neurodeg

Full text of DOI:10.1039/C8DT02778A

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ISSN 1477-9226
PAPER
Joseph T. Hupp, Omar K. Farha et al.
Efficient extraction of sulfate from water using
framework
a Zr-metal–organic
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A novel mesoionic carbene based highly fluorescent Pd(II)
complex as an endoplasmic reticulum tracker in live cells
Sanjay K. Verma,a Pratibha Kumari,b Shagufi Naz Ansari,a Mohd Ovais Ansari,a Dondinath Deoria
and Shaikh M. Mobin*a,b,c
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A
recent study advocates that endoplasmic reticulum (ER) understand desired selectivity towards selective organelles,
dysfunction may link to critical neurotrauma and advanced the recognition site of a fluorescent probe is designed in such a
tauopathy. In this regard, targeting ER warrants urgent attention way, that maximizes the binding interactions.13-18
for the therapeutic of neurotrauma-related neurodegeneration. Furthermore, fluorescence recovery after photobleaching
Herein, we report the synthesis of a new N-heterocyclic mesoionic (FRAP) is widely used as a powerful tool for monitoring
carbene based highly fluorescent square-planar Pd(II) complex 1, molecular dynamics of fluorescent-tagged molecules within
with high quantum yield (0.737). Probe 1 shows as a non-toxic living cells by employing confocal microscopes (CSLMs).19
probe for selectively labeling the endoplasmic reticulum in live
cells.
There exist few reports on ER tracking by employing some
metal-complexes,20 oxovanadium(IV) vitamin-B6 Schiff base
complex,21 tunicamycin-treated and organoplatinum(II)
complexes containing bis(N-heterocyclic carbene)22 but all of
these lack FRAP.
Owing to advancement in bio-imaging techniques, the in
vivo subcellular organelles targets and biochemical processes
has gained much attention towards basic biomedical research
and the development of novel clinical diagnostics.1-3 In this
regard, some organic ligand and metal complexes based
probes have been explored.4-6 Among sub-cellular organelles,
Endoplasmic reticulum (ER) plays an important role in
eukaryotic cells7 for the synthesis and processing of proteins,
and calcium storage.8-9 The improper protein folding may
interfere with ER functions. A recent development suggests
that ER dysfunction is directly linked to many metabolic
diseases, such as diabetes, obesity, insulin resistance, critical
neurotrauma and advanced tauopathy.10-12
So far report on Pd complexes being engaged in anti-
bacterial, anti-fungal and anti-viral and more recently the anti-
cancer activities with focus on tumor cell lines like breast and
prostate cancer by using different ligands such as triazole,
dithiocarbamate,23 triphenylphosphines,24 or hydrazine25 and
even curcumin, which is a well-known plant-based compound
with apoptosis-inducing activity on cancer cells has been well
documented. Further, better lipophilicity or solubility results in
enhanced cytostatic activity of Pd(II) complexes. Only one
report is available on Pt(II) complex based ER tracking, but to
the best of our knowledge this is the first report on MIC based
Pd(II) complex as an efficient ER tracker.23-29
Design and synthesis of an appropriate chemical probe as
the tool for the diagnosis and monitoring of disease as well as
biomarkers are the current area of focus. Understanding the
complex molecular interactions in the human physiological
system had posed a challenging task to both chemists as well
as biologist. Therefore, the fluorescent probes have become
popular because of their low cost, sensitive nature and easy-
to-operate and monitor various bioactive molecules in living
systems for both in vitro as well as in vivo studies. To
Herein, we report the synthesis of a phenylene based MIC
ligand forming Pd(II) complex and their biological evaluation
which by large has been ignored till date.
Pd(II) complex
1 was synthesized by the Cu(I) catalyzed click
reaction of 4-ethynyl toluene and sodium azide in the
presence of sodium ascorbate and copper sulfate in tert-
butanol and water mixture, then the resulted product was
converted to its triazolium iodide salt. This triazolium salt on
reaction with PdCl2 in the presence of base resulted in the
formation of the complex
1
(Scheme 1). The Pd(II) complex
1
is
a.Discipline of Chemistry.
highly soluble in dichloromethane and ethyl acetate.
characterized by 1H, 13C NMR, FTIR, mass spectroscopy and
1
was
b.Discipline of Biosciences and Biomedical Engineering
c. Discipline of Metallurgy Engineering and Materials Science, Indian Institute of
Technology Indore, Simrol, Khandwa Road, Indore 453552, India.
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
further authenticated by single crystal X-ray studies. The FTIR
spectroscopy of
1 reveals the band at ~
3100-3000 cm-1 which
correspond to the presence of aromatic (C-H) stretching
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vibrations.30 The 1H NMR spectrum showed the absence of
triazolium signal substituted with palladium. The 1H NMR
spectra of the
1 shows the absence of azolium C–H proton
which was observed at δ = 8.43 ppm for its parent 1-methyl-4-
(p-tolyl)-1H-1,2,3-triazole compound. The resonance for the
aryl C–H protons (δ = 7.37 ppm) is significantly downfield
shifted compared to their corresponding resonance (δ = 7.21
ppm) in complex
protons of pyridine ring were detected as multiplet at δ = 8.93,
7.78–7.80 and 7.66 ppm. Upon complex formation ( ) the
1 (Figs. S1 and S3). The resonance for the C–H
1
resonance for α-hydrogen atom of the pyridine ring (δ = 8.93)
was more downfield shifted compared to their corresponding
resonance in free pyridine (δ = 8.62).31 The resonance for the
characteristic carbene carbon atom was observed at δ = 137.1
ppm in the 13C NMR spectra of complex
1 which is quite similar
Fig. 1 (a) Perspective view of 1 (b) Helical view of
intermolecular I2...H4−C4 interacꢀons
1 via
to corresponding compound (δ = 137.6 ppm).32 The resonance
for the α-carbon atom of the pyridine ring appeared downfield
shifted: δ = 154.5 ppm (Figs. S2 and S4), compared to their
corresponding resonances in free pyridine. The LC-MS
.
The packing diagram of 1 reveals the presence of C–H⋯I
interaction. The intermolecular C(4)–H(4) I(2) interactions,
⋯
3.092 Å, involve the donor carbon atom of the phenyl group
and the acceptor I(2) atom of the other molecule leading to
the formation of 1D-polymeric chains (Fig. S7) resembling
spectrum of Pd(II) complex
[M+ 2Cl]+ (Fig. S5) which supports the formation of the Pd(II)
complex
1 having peak 697.7 corresponds to
1
.
single-stranded helical structure of
1 via I2...H4−C4 interaction
I
along b-axis (Figs. 1b and S8).
N
N
N
N
NaN3, CH3I, RT
Sodium ascorbate
CuSO4.5H2O
N
N
DMF, CH3I
8 h, 80°C
t-BuOH/H2O
1-methyl-4-(p-tolyl)-1H-1,2,3-triazole
4-Ethynyltoluene
Intermediate
N
N
I
N
PdCl2, Pyridine
Pd
KI, K2CO3
24 h, 80 °C
N
I
(1)
Fig. 2 UV-visible (black) and fluorescence spectrum (blue) of
1
at room temperature in 10-4 M tetrahydrofuran
the complex
solution.
Scheme 1 Schematic representation of synthesis of Pd(II) complex 1.
Single crystal suitable for X-ray diffraction study was
obtained by slow evaporation of the dichloromethane-hexane
The electronic absorption and emission spectra of the
were recorded in tetrahydrofuran solution. The absorption
bands of at 233, 282 and 371 nm is attributed to the π→π*
1
solution of
in monoclinic P21/n space group reveals the formation of the
mononuclear (Table S1). The Pd(II) atom in is coordinated
1 at room temperature. Complex 1 that crystallizes
1
(aromatic moiety) and n→π* (triazole and pyridine) transitions
respectively, for ligand moiety, occurring due to the hetero-
1
1
by a C-donor from MIC ligand and N-donor from pyridine, in a
trans-fashion and remaining coordination sites are occupied by
two iodide donors (Fig. 1a) forming square planar geometry
around the Pd atom. The C9–Pd1–N4 bond angle is almost
linear with 177.77(5)°and the Pd1–C9 (1.967(8) Å) and Pd1–N4
(2.100(6) Å) bond lengths are in the range previously described
for Pd(II) MIC complexes.33-34 The dihedral angle between the
NHC plane {N1 N2 N3 C8 C9} and the phenyl ring plane {C2 C3
C4 C5 C6 C7} is found to be 43.09° (Fig. S6). The Pd–Py and
triazole carbon-Pd moieties are twisted in the opposite
aromatic moiety (Fig. 2). The fluorescence emission data of
was recorded in tetrahydrofuran solution upon excitation at
λex = 371 nm. The emission spectrum of exhibited the highest
intensity band at 405 and 430 nm via vibronic splitting (Figure
2). Moreover, the Stokes shifts of Pd (II) complex found to be
was found to be very
1
1
1
34 and 59 nm. The quantum yield of
high, 0.737 (Fig. 2).
1
We have recorded the emission spectra of Pd(II) complex
1
in 1% DMSO with various solvents (Acetonitrile/THF/Methanol
/Water) and found that the emission band splits into two
partially resolved bands except in water (Fig. S9). This may be
direction, thus featuring anti-geometry of the complex
1a).
1 (Fig.
due to the strong hydrogen bonding between complex
1 and
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H2O which lock the molecule for the vibronic coupling. label enormous population of cells; which was detected in live
Fluorescence intensity of was found to be trivial quenching suspension cells by flow cytometer. Rapid population-based
1
at high pH (phosphate buffer saline containing 1% DMSO at fluorescence statistic data of flow cytometry is further
various pH) this may be due to the formation of electron donor supported by the pictorial images of confocal laser scanning
1,2,3-triazole/iodine, through photo induced electron transfer microscope.
(PET) under basic conditions.
decrease in pH upto 3.1 and quite stable up to pH 7.4 (Fig. 3A).
Fluorescence emission of was also investigated in micelles of
1 showed slightly red shifted with
1
positively charged cetyl-trimethyl-ammonium bromide (CTAB)
and negatively charged sodium dodecyl sulfate (SDS) at 5.0
mM and 2.0 mM concentration respectively for mimicking the
probe in the cell membranes (Fig. 3B and Fig. 3C). In addition,
the fluorescence behaviors of the
1 was unaffected at studied
pH range, indicating that the binding of the probe to the
micelles efficiently shields the probe from the aqueous
environment. These results imply that the
1 can be localized in
the membrane phases rather than in the aqueous phase in the
cells.
The Pd(II) complexes are known for their extraordinary
photoluminescence due to the σ-donating property of the
anionic carbons, which effectively raises the energy of the d-d
states, diminishing their deactivating effect.33-34 Further, the
Fig. 4 HeLa cells co-labeled with 1 (100 μM) and organelle
markers. (a) ER-Tracker Red for Endoplasmic Reticulum (1 μM);
(b) MitoTracker Red CMXRos (80 nM) for mitochondria; (c)
LysoTracker Red DND-99 (100 nM) for lysosomes. The images
from left to right shows L-lyso (column 1), organelle trackers
(column 2) phase contrast (column 3), and Overlay 1: overlay
of the 1st and 2nd columns. Overlay 2: overlay of the 1st, 2nd and
3rd columns. Scale bar: 40 μm.
photoluminescence spectra of 1 shows two separate electronic
transitions at 370 and 392 nm attributed to π*→π and π*→n
transitions for ligand moiety (Fig. S10) upon excitation at 25 °C
(λex = 282 nm) as expected in such Pd(II)/Pt(II) complexes.35-37
Fig. 3 (A) Fluorescence emission spectra of Pd(II) complex
1 (10
μM) at different pH {1% DMSO in PBS (Phosphate-buffered
saline)} solution upon excitation at 371 nm (B) In the presence
of 5.0 mM, CTAB (positively charged micelles) (C) In the
presence of 2.0 mM, SDS (negatively charged micelles).
The highly fluorescent nature of
the role of in live cells as a potential candidate for cellular
organelles marker. To initiate biological activities, the probe
1 prompted us to explore
1
1
Fig. 5 ER selective imaging of living HeLa cells treated with 1.
Live HeLa cells treated with 1 (100 μM) and ER-tracker Red (1
μM). The fluorescence emission of 1 (blue), ER-tracker Red
(red) Colocalization of these two fluorophores is overlay 1 and
was checked for it cytotoxicity on both cancerous as well as
normal cells i.e. HeLa (cervical cancer cells) and HEK 293
(human embryonic kidney cells 293) cell and was found to be
non-toxic at the concentration upto 180 μM for 24 h as proved
by cell viability assay using MTT (Fig. S11). Further, Flow
cytometry acquire superior quality fluorescence signals with an
elevated spatial resolution from significant population of cells
2 (pink). Pearson colocalization graph (yellow). Probe 1: λex
405 nm; λem = 415˗470 nm; ER-Tracker Red λex = 559 nm; λem
580˗700 nm.
=
=
in flow.38-40 Probe
1 labeled HeLa cells were estimated by flow
To confirm the initial cellular location of probe
treated with probe and images were captured in both blue
and red channel, probe is fluorescent in blue channel and non-
fluorescent in red channel, hence probe was excited by
1, HeLa cells
cytometry (Fig. S12). Mean fluorescence intensity of huge
number of cells shifted from quadrant Q3-2 (control) to Q4-3
(treated) (Fig. S12a) and subsequent shift in histogram towards
higher intensity was also observed (Fig. S12b). Moreover,
mean fluorescence intensity of untreated cells was as low as
62 as compared to treated cells having higher mean
1
1
405nm not by 599nm (Fig. S13). So that we performed co-
localization experiments with three commercially available red
fluorescent organelle trackers (ER-Tracker Red for endoplasmic
fluorescence intensity 2759. This indicates
1 can uniformly
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reticulum, MitoTracker Red CMXRos for mitochondria and reasons (i) diffusion of soluble fluorescent probe
LysoTracker Red DND99 for lysosome). The fluorescent co- membrane and (ii) due to the movement of
localization images (pink) of with those organelle trackers organelles. On the contrary, the ER-Tracker Red shows very
(Fig. 4) indicated that overlapped well with ER-tracker Red poor photostability with the intensity being reduced to 20% of
1
in ER
1
between
1
1
with high Pearson’s co-localization coefficient Rr = 0.75 (Fig. 4a the initial intensity after 1800 scans, and could not recover
and Fig. 5). However, poor co-registration effect having Rr back during laser scanning.
value = 0.44, 0.49 for mitochondria and lysosome, respectively
3D tumor spheroids possess numerous features that mimic
(Figure 4b and 4c). Moreover, Manders’ coefficients were in vivo tumors such as cell-cell interaction, hypoxia cells at
calculated having Manders' M1 = 0.901 and Manders' M2 = center and a well-oxygenated outer layer of the cells. In order
0.679 signifying good colocalization of probe
tracker red (red) on a per-pixel level. This demonstrates that images were captured every 2μm along the Z-axis.
the probe is highly selective towards localization in penetrates to depth of 48μm whereas ER tracker
Endoplasmic reticulum and also compatible for counter penetrates upto 24μm depth (Fig. S14, S15 and Movie S3,
staining with LysoTracker Red and Mito Tracker Red. Movie 4). This suggests that the compound 1 exhibited more
1 (blue) and ER to explore 1 towards 3D tumor spheroids, the fluorescence
1
1
a
~
~
The photostability plays an important role for any marker in fluorescence in deep layer cells of spheroids as compared to
the cell to observe long-term imaging during physiological and standard dye.
morphological alterations in a stipulated time. In this regard,
the photostability of
1 was studied in live HeLa cells and was
Conclusions
compared with commercially available ER-Tracker Red.
Fluorescence intensity initially decreases and after 200 scans it
reaches 70% due to photobleaching but gradually recover
again upto 98% after 1800 scans (Fig. 6, Movies S1 and S2).
In conclusion, we report a rare example of the synthesis of
new organometallic MIC based mononuclear Pd(II) complex
The higher quantum yield and non-toxic nature of make it a
potential candidate for inter-cellular uptake. The fluorescence
behavior of was unaffected at broad pH range, indicating
that the binding of the probe to the micelles efficiently shields
the probe from the aqueous environment. Thus specifically
1.
1
1
1
targets ER of live cells and plays an important role in the
movement of particles between organelles due to
fluorescence recovery after photobleaching (FRAP) property.
1
shows rare FRAP property as compared to so far reported Pd /
Pt complexes as well as commercially available ER-Tracker Red.
All these properties make
commercial use.
1 as a potential candidate for its
Conflicts of interest
“There are no conflicts to declare”.
Acknowledgments
Authors are grateful to the Sophisticated Instrumentation
Centre (SIC), IIT Indore for providing characterization facilities.
SKV is grateful to SERB for providing National Post-doctoral
Fellowship, PK, SNA are thankful to MHRD, New Delhi for
fellowship, MOA is thankful to IIT Indore for his internship.
SMM is thankful to SERB-DST (Project No, EMR/2016/001113),
New Delhi, Govt. of India and IIT Indore for financial support.
This work is dedicated to Professor Dr. Dietmar Stalke on his
60th birthday.
Fig. 6 Comparisons of the photostability of probe 1 and ER-
Tracker Red in HeLa cell lines. (a) Confocal images of 1 (100
μM, λex = 405nm, λem = 415–470 nm) and ER-Tracker Red (1
μM, λex = 559 nm, λem = 580–700 nm) for photobleaching in
HeLa cells. (b) Comparative Photostability Graph of ER-Tracker
Red and 1.
Notes and references
Crystal data of 1: C16H18I2N4Pd, M = 626.54, monoclinic P21/n, Z =
4, T = 293(2) K, F(000) = 1176.0, a = 10.7786(5) Å, b = 8.1520(3)
Å, c = 23.4486(10) Å, α = 90°, β = 99.338(4)°, γ = 90°, V =
2033.06(15) Å3, size = 0.25 × 0.23 × 0.2, Index ranges = -14 ≤ h ≤
This results the fluorescence recovery after photobleaching
(FRAP) in case of 1. This may be due to any of the following
4 | J. Name., 2012, 00, 1-3
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DOI: 10.1039/C8DT02778A
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A novel mesoionic carbene based highly fluorescent Pd(II)
complex as a endoplasmic reticulum tracker in live cells
Sanjay K. Verma,a Pratibha Kumari,b Shagufi Naz Ansari,a Mohd Ovais Ansari,a Dondinath
Deoria and Shaikh M. Mobin*a,b,c
Synthesis of new organometallic MIC based mononuclear Pd(II) complex 1, specifically target
ER of live cells and plays an important role in the movement of particles between organelles due
to fluorescence recovery after photobleaching (FRAP) property.