Enhanced photodynamic therapy through supramolecular photosensitizers with an adamantyl-functionalized porphyrin and a cyclodextrin dimer

Article abstract of DOI:10.1039/d0cc03574b

A supramolecular photosensitizer was constructed using a tetra-adamantane-functionalized porphyrin and a dimer of permethyl-β-cyclodextrin through host-guest interaction and self-assembly. The porphyrin/cyclodextrin alternating structure of supramolecular

Full text of DOI:10.1039/d0cc03574b

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S. J. Connon, M. O. Senge et al.
Conformational control of nonplanar free base porphyrins:
towards bifunctional catalysts of tunable basicity
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DOI: 10.1039/D0CC03574B
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Enhanced Photodynamic Therapy through Supramolecular
Photosensitizers with Adamantyl-functionalized Porphyrin and
Cyclodextrin-dimer
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Lei Xia, Jian Wu, Baoxuan Huang, Yun Gao, Jia Tian* and Weian Zhang*
A
supramolecular photosensitizer was constructed by
Supramolecular chemistry, as “chemistry beyond the
tetra-adamantane-functionalized porphyrin and
a
dimer of molecule” based on the intermolecular non-covalent
9
permethyl-β-cyclodextrin through host-guest interaction and interactions, has aroused great interest due to its dynamic
1
0
self-assembly. The porphyrin/cyclodextrin alternating structure of and reversible nature. In the past decades, considerable
supramolecular photosensitizers not only enhances the water efforts have been made to develop supramolecular systems
solubility of photosensitizers, but also effectively inhibit the and explore their applications in catalysis, electronic devices,
1
1
aggregation-induced quenching of porphyrin photosensitizers.
sensors, and nanomedicine. Among various non-covalent
interactions, host-guest interaction has been extensively
pursued in supramolecular systems by the introduction of
In recent years, photodynamic therapy (PDT) has attracted a
broad range of attentions due to its spatiotemporal selectivity
12
macrocyclic hosts.
Cyclodextrins (CDs), as an crucial
1
and non-invasiveness in cancer treatments. Essentially, a PDT
macrocyclic host, have been widely used because of the
specific recognition with guests, good water solubility and
process involves the employment of oxygen, light and
photosensitizers (PSs) which can be activated by the specific
13
biocompatibility. Permethyl-β-cyclodextrin has larger cavity
2
light with a suitable wavelength, and generate cytotoxic
and high binding ability to guests in aqueous solution, which is
regarded as the key point to construct supramolecular
architectures. It can not only improve the water-solubility of
1
reactive oxygen species (ROS), such as singlet oxygen ( O
2
) that
3
would cause tumor ablation. Therefore, an appropriate
14
4
photosensitizer is the essential factor in PDT. Porphyrins and
PSs, but also integrate PSs into well-organized supramolecular
materials to attenuate their aggregation. Thus, the
construction of cyclodextrin/PS supramolecular system by
host-guest strategy is undoubtedly recognized as a promising
solution for enhanced PDT.
their derivatives are the common and typical photosensitizers;
however, the large ring conjugated structure of porphyrins
leads to their poor biostability and aggregation-induced
fluorescence quenching, which leads to the low PDT efficiency
5
and hampers the clinical practice in PDT. Various strategies
Herein, we develop a supramolecular photosensitizer by
have been reported to overcome these problems including
physical encapsulation by nanocarriers and chemical
functionalization of hydrophilic motifs. However, because of
tetra-adamantane porphyrin (TPP-Ad
dextrin-dimer (β-CD ) via host-guest interaction. β-CD
TPP-Ad were synthesized through the combination of click
4
) and permethyl-
β
-cyclo-
2
2
and
6
4
the weak interaction between cargoes and nanocarriers, the
premature leakage of PSs ineluctably occurs in transportation
7
processes and induces side effects. In addition, chemical
functionalization of PSs mainly includes sophisticated synthesis
procedure and purification. Thus, the facile construction of
“
isolated” photosensitizers with high biosafety and stability is
8
still a big challenge in PDT practice.
Shanghai Key Laboratory of Functional Materials Chemistry, East China University
of Science and Technology, 130 Meilong Road, Shanghai 200237, China
*
E-mail: tianjia@ecust.edu.cn; wazhang@ecust.edu.cn
Scheme 1 Illustration of the supramolecular photosensitizer with
TPP-Ad /CD alternating structure, cell endocytosis and
phototherapy process of TPP-Ad /CD assemblies.
4
2
†Electronic Supplementary Information (ESI)
available.
See
DOI: 10.1039/x0xx00000x
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2
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chemistry and coupling reactions. Due to the host-guest group (PEG-Ad) was co-assembled with TPP-Ad
Journal Name
and β-CD to
4
View Article Online
2
interaction between adamantane and cyclodextrin, the obtained supramolecular photosensiDtiOzeI:r1s0.10(3a9s/Dsi0gCnCe0d3574aBs
supramolecular photosensitizer obtained from TPP-Ad and TPP-Ad /CD /PEG). To confirm the PDT efficacy of
β-CD (assigned as TPP-Ad /CD ), would self-assemble into supramolecular PSs, free porphyrins (TPP-Ad ) and the
nanoparticles with an alternating structure, which could complex of TPP-Ad and permethyl- -cyclodextrin (assigned as
weaken the aggregation of porphyrins and achieve improved TPP-Ad /CD) were applied as control groups.
water solubility, particularly, higher singlet oxygen production UV-vis spectra showed that the absorbance of TPP-Ad
and PDT efficiency (Scheme 1). The improvement of and TPP-Ad /CD /PEG was much stronger than those of
photophysical properties of porphyrins was demonstrated by TPP-Ad and TPP-Ad /CD complexes (Fig. S17) owing to the
4
4
2
2
4
2
4
4
β
4
/CD
4 2
4
2
4
4
fluorescence and UV-visible spectroscopy. Moreover, in vitro increased solubility and formation of nanosized assemblies
and in vivo studies were used to testify the superior anticancer with supramolecular alternating structures. Moreover,
efficiency of supramolecular PSs.
The synthetic steps of TPP-Ad
TPP-Ad
4
/CD
2
and TPP-Ad
4
/CD
2
/ PEG assemblies had higher
and TPP-Ad /CD
4
and β-CD
2
are presented in fluorescence intensities than that of TPP-Ad
4
4
Supporting Information (Scheme S1-S5 and Fig. S1-S10). A assemblies (Fig. 2a). Since the assemblies contained the same
1
nuclear magnetic resonance spectroscopy ( H NMR) titration content of porphyrins and cyclodextrins, it can be believed
experiment was performed by fixing the concentration of that the formation of supramolecular PSs inhibits the
TPP-Ad
4
at 5 mM and changing the concentration of β-CD
2
aggregation of porphyrins and leads to stronger fluorescence.
In addition, the hydrodynamic sizes of assemblies in
with different molar ratios (1:1, 1:2, 1:4, 1:8) to study the
host-guest interaction (Fig. 1). The proton peaks of the CD ring aqueous solution examined by dynamic laser scattering (DLS)
, H ) and adamantane group (H , H ) were gradually technology, were shown in Fig. 2b, which displayed that all of
broaden as the concentration of β-CD increased, and peaks the CD-containing samples possessed uniform sizes with a
corresponding to H , H slightly shifted to downfield. narrow size distribution. The TEM image of TPP-Ad /CD
UV-vis absorption spectra of the mixture of TPP-Ad and assemblies exhibited spherical structures with the size about
β-CD presented that the maximum absorption of TPP-Ad at 120 nm (Fig. 2c), which was in agreement with the DLS results.
25 nm gradually increased upon the addition of β-CD (Fig.
and β-CD
(H
1
2
3
4
1
5
2
3
4
4
2
4
2
4
4
2
1,3-Diphenylisobenzofuran (DPBF) was used as a singlet oxy-
1
S12), indicating that the inclusion of TPP-Ad
4
2
gen detection reagent to assess O
2
generation capability. As
enhanced the water solubility of TPP-Ad
4
. The stoichiometry of shown in Fig. S18, the absorbance of DPBF at 425 nm in each
complexes between β-CD and TPP-Ad was confirmed by Job’s sample showed a downward trend with the irradiation time
2
4
plot method (Fig. S13). Fluorescence titration data showed a increased. The absorption variations of different samples
similar trend of fluorescence enhancement with increasing the
feed ratio of β-CD
the complexation of β-CD
water solubility and fluorescence yield of porphyrins. The
complexation ratio of β-CD and TPP-Ad was further studied
2
and TPP-Ad
4
(Fig. S14), which indicated that
2
and TPP-Ad
4
promoted both the
2
4
and presented a 2:1 stoichiometry (Fig. S15).
Furthermore, the complexation constant (K
a
4
) of host and
-1
guest was calculated to be (2.61 ± 0.19) × 10 M by non-
linear curve-fitting (Fig. S16). The strong host-guest binding
force provided an important basis for the formation of supra-
molecular alternating structure, and the 2:1 stoichiometry also
illustrated the existence of supramolecular structure.
Hydrophilic polyethylene glycol with an adamantane terminal
Fig. 2 (a) Fluorescence spectra of TPP-Ad4, TPP-Ad
TPP-Ad /CD and TPP-Ad /CD
solution at room temperature. (b) DLS results of TPP-Ad
TPP-Ad /CD and TPP-Ad /CD
solution. (c) A TEM image of TPP-Ad /CD supramolecular
4
/CD,
4
2
4
2
/PEG assemblies in aqueous
4
/CD,
4
2
4
2
/PEG assemblies in aqueous
1
Fig. 1 Partial H NMR spectra in d-DMSO/D
solution (400 MHz) of TPP-Ad
at a fixed concentration of 5 mM nanoparticles. (d) Degradation rate of DPBF (detection of singlet
with different concentrations of β-CD
: (A) 5 mM, (B) 10 mM, (C) oxygen production) in different solution upon light irradiation. (e)
2
O (1/100, v/v) mixed
4
2
4
2
2
0 mM, (D) 40 mM. The figure in the black box on the right is a Intracellular ROS production treated with different samples and
partially enlarged view.
laser irradiation, using DCFH-DA as a probe. Scale bar 50 μm.
2
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against irradiation time were plotted in Fig. 2d. TPP-Ad
4
/CD
2
cytotoxicity of all samples. After the irradiation VwieiwthArt6ic6le0Onnlimne
light on formula-cultured cancer cells,DOthI: of
cancer cells showed a significant downward trend with the
increase of TPP concentration (Fig. 3c). When the
concentration of porphyrin was up to 40 μg/mL, the cell
1
e
10.
s
1
u
0
r
3
v
9
i
/
v
D
a
0
l
CCra
0
t
3
e
574
B
and TPP-Ad
4 2
/CD /PEG showed excellent
2
O production
capacity, and the DPBF in two sample solutions was degraded
by 28% and 34% within 210 s, respectively. In addition,
intracellular ROS production of 4T1 cells was investigated using
the fluorescent probe 2’,7’-dichlorodi-hydrofluorescein
diacetate (DCFH-DA). As depicted in Fig. 2e, with the presence
of 660 nm laser irradiation, cells incubated with TPP-Ad
exhibited negligible fluorescence. Moreover, the fluorescence
4 2
intensity in cells treated with TPP-Ad /CD
viability of cancer cells treated with TPP-Ad
TPP-Ad /CD /PEG reduced to 14% and 12%, respectively,
showing excellent photodynamic efficiency. In contrast,
TPP-Ad and TPP-Ad /CD groups exhibited relatively low
4 2
/CD and
4
2
4
4
4
phototoxicity. It was attributed to the fact that the alternating
or host-guest structure formed by porphyrin/cyclodextrin motifs
TPP-Ad
TPP-Ad
4
/CD
/CD, demonstrating that photosensitizer nanoparticles effectively inhibited the aggregation of porphyrins and
2
4 2 4 2
/PEG was much stronger than that of in the TPP-Ad /CD and TPP-Ad /CD /PEG supramolecular PSs
4
improved their water-solubility, resulted in enhanced
photophysical properties and photodynamic efficiency.
In vivo fluorescence imaging was performed to study the
with supramolecular alternating structures possessed higher
intracellular ROS production. Therefore, the well-designed
supramolecular photosensitizers with alternating structures
1
4 2
accumulation and retention of TPP-Ad /CD /PEG in the tumor
had strong
2
O production capacity, expecting to exhibit
site (Fig. 4a). Fluorescence intensity of tumor area gradually
increased and reached a maximum at 24 h, indicating that
supramolecular PSs successfully enriched in the tumor site by
enhanced permeability and retention effect (EPR).
superior antitumor efficiency in vitro and in vivo studies.
Confocal laser scanning microscope (CLSM) was used to
study the cellular uptake behavior of all samples against 4T1
tumor cells (Fig. 3a). The red fluorescence intensity of
porphyrins in all samples after the cells incubated for 24 h was
much brighter than that for 4 h, demonstrating that cellular
uptake behavior was time-dependent. The average
fluorescence intensity of porphyrins in all samples (24 h) was
plotted (Fig. S19). Obviously, the cell suspensions containing
TPP-Ad
4
/CD
2
4 2
and TPP-Ad /CD /PEG assemblies showed
stronger fluorescence than the others, which may contribute
to weaker porphyrin aggregation and effective cellular uptake
for supramolecular PSs with alternating structures.
To further investigate the cytotoxicity of TPP-Ad
4
,
TPP-Ad /CD, TPP-Ad /CD and TPP-Ad /CD /PEG, 3-(4,5-
4
4
2
4
2
dimethyl-thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT)
assay was then performed (Fig. 3b). In the dark, cell viabilities
of TPP-Ad /CD, TPP-Ad /CD and TPP-Ad /CD /PEG groups
4 4 2 4 2
were higher than 90%, undoubtedly indicating the low dark
Fig. 4 (a) In vivo real-time fluorescence imaging of 4T1
tumor-bearing mice after injecting TPP-Ad /CD /PEG assembly
4 2
solution. (b) Tumor volume growth curves of different groups in 12
days. (c) Body weight of mice after different treatments in 12 days.
(d) Photographs of tumors retrieved from different groups of
mice. (e) Tumor weight of different groups of mice. Values are
mean ± standard deviation (SD) (n = 4), Student’s t-test, *p < 0.05;
/PEG) for 4 h or 24 h. Scale bar: 50 μm. (b) In vitro **p < 0.01. (f) H&E stained tumor tissue slices in different
Fig. 3 (a) CLSM images of 4T1 cells incubated with different
samples (I: TPP-Ad
4 4 4 2
, II: TPP-Ad /CD, III: TPP-Ad /CD , IV:
TPP-Ad /CD
4
2
dark cytotoxicity of four groups towards 4T1 cells. (c) Phototoxicity treatment groups. Scale bar: 300 μm. Different treatments: PBS
of different groups towards 4T1 cells. Values are mean ± standard
alone, TPP-Ad
TPP-Ad
4 4
/CD2, TPP-Ad4+L (light), TPP-Ad /CD+L,
/CD2+L and TPP-Ad /CD /PEG+L.
4 2
deviation (SD) (n = 3), Student’s t-test, *p < 0.05; **p < 0.01.
4
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Moreover, tumor-bearing mice were randomly divided into
six groups with different formula (saline alone, TPP-Ad /CD
/CD +L,
/PEG+L) to further evaluate in vivo photodynamic
effect. The tumor volume growth rate was recorded every
other day after treatments and shown in Fig. 4b. The saline
alone and TPP-Ad /CD without light groups had similar tumor
4 2
growth trends. In comparison, the groups with light irradiation
showed relatively strong tumor growth-inhibiting. Among
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inhibited the growth of tumors. As control groups, the tumor
volumes of TPP-Ad +L and TPP-Ad /CD+L groups increased to
0 times and 7 times within 12 days compared to the origin
4 2 4 2
/CD and TPP-Ad /CD /PEG groups effectively
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th
4
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dissected and tumor tissues were obtained. Tumor images
(
(
Fig. 4d) and the average tumor weight of different groups
Fig. 4e) also demonstrated that TPP-Ad /CD /PEG exhibited
4
2
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of tissue sections. As can be seen in Fig. S20, the major organ
slices exhibited no noticeable signs of organ damage; however,
the trend of tissue ablation in tumor slices can be clearly
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2
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4
alternating structures can effectively improve the solubility
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The authors thank the financial supports by the National
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Conflicts of interest
There are no conflicts to declare.
7
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Zhang, ACS Appl. Mater. Interfaces, 2020. DOI:
0.1021/acsami.0c07333.
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