Journal of Photochemistry & Photobiology, B: Biology 241 (2023) 112674

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Journal of Photochemistry & Photobiology, B: Biology

journal homepage: www.elsevier.com/locate/jphotobiol

Unadulterated BODIPY nanoparticles as light driven antibacterial agents for

treating bacterial infections and promoting wound healing
Qiaoxia Shi a, Xinyuan Wang a, Hongxin Liu a, Zhigang Xie b, Min Zheng a, *
a
School of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, 2055 Yanan Street, Changchun, Jilin 130012, PR
China
b
State Key Laboratory of Polymer Chemistry and Physics, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin
130022, PR China

A R T I C L E I N F O A B S T R A C T

Keywords: Antimicrobial photodynamic therapy (aPDT) is an effective strategy to eliminate bacteria without inducing
Antimicrobial photodynamic therapy bacterial resistance. As typical aPDT photosensitizers, most of boron-dipyrromethene (BODIPY) are hydrophobic,
Boron-dipyrromethene and nanometerization is imperative to render them dispersible in physiological media. Recently, carrier-free
Carrier-free
nanoparticles (NPs) are formed via the self-assembly of BODIPYs without the help of any surfactants or auxil­
Self-assembly
Nanoparticle
iaries, arousing people’s interest. So as to fabricate carrier-free NPs, BODIPYs usually need to be derived into
Wound healing dimers, trimers, or amphiphiles through complex reactions. Few unadulterated NPs were obtained from BODIPYs
with precise structures. Herein, BNP1-BNP3 were synthesized by the self-assembly of BODIPY, which showed
excellent anti-Staphylococcus aureus ability. Among them, BNP2 could effectively fight bacterial infections and
promote wound healing in vivo.

1. Introduction
Bacterial infections are a serious threat to human health [1–4],
hitherto, although lots of antibiotics have been developed for the
treatment of bacteria-caused diseases. The overuse of antibiotics greatly
increases the bacterial resistance, which brings great difficulties to cure
numerous infectious diseases [5]. To address this issue, it is still a great
challenge to explore antibiotic-free therapeutic mode to inactivate
pathogens [6,7]. Antimicrobial photodynamic therapy (aPDT) is an
effective method that can eradicate bacterial by utilizing photosensi­
tizers (PSs) to generate toxic reactive oxygen species (ROS) under the
illumination of suitable light [8].
Boron-dipyrromethene (BODIPY) and its derivatives are a kind of
robust dyes, which have attracted extensive attention because of their
abundant chemical structures, good photostability, easy modification
and excellent optical properties [9,10]. Many BODIPY dyes have been
successfully applied in sensing [11–13], bioimaging [14–17], and cancer
treatment [18–21]. Especially, some BODIPYs are promising PSs for
photodynamic therapy of tumor [22]. By contrast, just a little work on
photodynamic inactivation of bacteria have been reported [23–25].
Due to the inherent hydrophobicity, most of the BODIPY dyes are
insoluble in physiological medium, they need to be dissolved in organic
solvents and then diluted with aqueous medium. However, the strong
hydrophobicity leads to the precipitation from water solution often oc­
curs, which is the biggest obstacles for their biomedical applications
[26,27]. One feasible way to solve this problem is the nanometerization
of small molecules by the assembly with polymers [28–30]. However,
the shortcomings including inevitable toxicity of carriers, uncontrolled
leakage of dyes and poor experimental reproducibility are hard to
overcome [31–33].
Recently, the carrier-free strategy that constructing organic nano­
particles (NPs) via the self-assembly of small molecules has attracted
increasing attention, which possesses the advantages of almost 100%
loading rate, precise molecular structures, good colloidal stability and
repeatable synthesis [34]. In order to construct carrier-free NPs, BODI­
PYs have to be derived into dimers [35–38], trimers [39], or amphi­
philes [40–42] via complicated synthesis steps. As far as we know, rare
BODIPYs with simple structures can form NPs without any surfactants or
auxiliaries [43,44].
Herein, a BODIPY derivative (Scheme 1) could self-assemble into
NPs (BNP1-BNP3) via a convenient nanoprecipitation method [45–47].
Among them, BNP2 had good water solubility, stability and cyto­
compatibility, which could eradicate Staphylococcus aureus (S. aureus) by
producing the singlet oxygen (1O2) under green LED light. The potent

* Corresponding author.
E-mail address: zhengm@ciac.ac.cn (M. Zheng).

https://doi.org/10.1016/j.jphotobiol.2023.112674
Received 12 September 2022; Received in revised form 1 February 2023; Accepted 21 February 2023
Available online 24 February 2023
1011-1344/© 2023 Elsevier B.V. All rights reserved.
Q. Shi et al.
antibacterial activity enabled BNP2 to cure bacterial infections and
accelerate wound healing.
2. Results and Discussion
2.1. Synthesis and Characterization
BODIPY was synthesized according to previous reports [9,48,49],
and BNP1-BNP3 were prepared by nanoprecipitation method. Take
BNP2 as an example: the tetrahydrofuran (THF) solution of BODIPY was
added dropwise to water, stirred overnight until THF was completely
volatilized, then dialyzed against deionized water. The preparation
procedures of BNP1 and BNP3 were similar to BNP2, except that the
solvent used to dissolve BODIPY was acetone and acetone containing
1.5% (mass ratio) 1,2-propanediol, respectively. The concentration of
BNPs was calculated according to the standard curve of BODIPY
(Fig. S1). The hydrodynamic diameter (HD) of BNP1-BNP3 determined
by dynamic light scattering (DLS) was 248.6, 224, and 188.3 nm,
respectively (Fig. 1A). The size of BNP2 remained almost unchanged
after 120 d of storage (Fig. S2), indicating that BNP2 had good colloidal
stability. Transmission electron microscopy (TEM) image demonstrated
that BNP2 was quasi-spherical nanoparticle with an average size of
~120 nm (Fig. 1B), which was smaller than HD due to the shrinkage of
BNP2 in the solid state. The zeta potentials of BNP1-BNP3 were 0.288,
0.207 and 0.021 mV, respectively. In the UV–vis absorption spectra of
BNP1-BNP3 (Fig. 1C), an absorption maximum was observed at 543 nm,
which was red-shifted by 8 nm relative to BODIPY (535 nm).
2.2. Detection of 1O2
1
O2 generation ability of BNPs aqueous solution was assessed by
using indocyanine green (ICG). As shown in Fig. 1D and Fig. S3, in the
presence of BNPs, the absorbance of ICG gradually decreased with the
prolongation of green LED illumination time. After 160 s, the absor­
bance of ICG decreased by 41, 68 and 44% in BNP1-BNP3 groups,
respectively, implying that BNP2 had the highest 1O2 generation ability.
BNP2 was selected as the typical representative to evaluate the 1O2-
generating capacity in S. aureus cells by using 1O2 detection kit (DCFH-
DA). Bacteria were treated with PBS and BNP2, respectively. Bacteria in
the PBS + L and BNP2 + L groups were exposed to green LED light.
Subsequent staining was performed according to the manufacturer’s
instructions and the results were observed using a confocal laser scan­
ning microscope (CLSM). As depicted in Fig. 2, the BNP2 + L group
showed bright green fluorescence, indicating that BNP2 could produce
Scheme 1. Synthesis and antibacterial application of BNP2 in vivo.
2
Journal of Photochemistry & Photobiology, B: Biology 241 (2023) 112674
1
O2 within the bacteria under green light irradiation.
2.3. Antibacterial Photodynamic Activity in Vitro
On the basis of the above results, we investigated the antibacterial
photodynamic effects of BNP1-BNP3 (10 ng/mL) against S. aureus in
vitro. Without light irradiation, a large number of colonies grew on the
plates of the BNP1-BNP3 treatment groups (Fig. 3A), the bacterial sur­
vival rates were about 98% (Fig. 3B), and the growth curves were similar
to the control group (Fig. 3C), proving that BNP1-BNP3 had no dark
toxicity to bacteria. As exposure to green LED light (18 mW cm− 2, 5
min), the bacteriostatic effect of BNP1-BNP3 was very significant, no
colonies grew on the plates, and there was still no amplification after 33
h (Fig. 3D), indicating they had excellent antibacterial activity.
Next, we assessed the photodynamic effects of BNP1-BNP3 on
S. aureus biofilms by using crystal violet (CV) staining. As shown in
Fig. 4A, under the condition of no light, the BNP1-BNP3 treated groups
formed biofilms, so the biofilms on the wells of the 96-well plates were
stained purple by CV. In the presence of light (18 mW cm− 2, 5 min), the
bacteria treated with 10 ng/mL of BNP1-BNP3 could not form biofilms,
and after the addition of CV, the wells of the 96-well plate remained
colorless due to absence of biofilms. The biomass was as low as 1%
(Fig. 4B), indicating that BNP1-BNP3 could effectively inhibit the for­
mation of S. aureus biofilm.
Then we selected BNP2 as the representative for Live/Dead staining
to study antibacterial mechanism. S. aureus were treated with PBS and
BNP2, and stained with SYTO 9 (green fluorescence, live bacteria) and
propidium iodide (PI, red fluorescence, dead bacteria) after irradiating
with green light, then were observed by CLSM. As shown in Fig. 4C, no
obvious red fluorescence was observed in PBS group, indicating that cell
membrane was intact. While, S. aureus in BNP2 groups emitted intense
red fluorescence, proving that cell membrane was damaged and the
bacteria died. The above results further confirmed that BNP2 could
rapidly inactivate S. aureus by destroying cell membrane.
2.4. Antibacterial Activity of BNP2 In Vivo
The mouse wound infection model was established to evaluate the
antibacterial activity of BNP2 in vivo. First, 12 female Kunming mice
were randomly divided into 4 groups. After the mouse was anesthetized,
circular wound with diameter about 0.8 cm was formed on the back
skin. Subsequently, wound infections of each mouse were induced with
S. aureus (1 × 107 CFU/mL), then were treated with PBS and BNP2 (350
ng/mL). The light groups (PBS + L and BNP2 + L) were irradiated with
Q. Shi et al. Journal of Photochemistry & Photobiology, B: Biology 241 (2023) 112674

Fig. 1. (A) HD of BNP1-BNP3. (B) TEM image of BNP2. (C) UV–vis absorption spectra of BNP1-BNP3 and BODIPY. (D) Time-dependent photobleaching of ICG
induced by 1O2 generated from BNP1-BNP3 (200 ng/mL) under green LED light (18 mW cm− 2). (For interpretation of the references to colour in this figure legend,
the reader is referred to the web version of this article.)

Fig. 2. CLSM images of intracellular 1O2 generation in S. aureus cells treated with PBS and BNP2 (10 ng/mL) in the absence or presence of green light (18 mW cm− 2,
5 min). (For interpretation of the references to colour in this figure legend, the reader is referred to the web version of this article.)

green LED light (18 mW cm− 2) for 5 min. Wound photos were taken
(Fig. 5A), the wound areas were measured to calculate the wound
healing rates (Fig. 5B), and mock images of wounds were drawn
(Fig. 5C). After 14 d of treatment, the wounds of mice in the BNP2 + L
group were almost completely healed. Their healing rates were as high
as 90.7%, and the bacteria on the wounds surface were negligible, which
were sharp contrast with the other three treatment groups where there
were still large-sized wounds and a mass of bacteria on the wounds
surface (Fig. 5D and E). During the whole treatment period, the weight
of mice in each group increased steadily (Fig. 6A), indicating that BNP2
did not cause any adverse effect on mice and had good biological safety.
On the 14th day, the wound skin tissues of mice were stained with he­
matoxylin and eosin (H&E). As depicted in Fig. 6B, the wounds of mice
in the PBS, PBS + L and BNP2 groups had severe inflammation, while no
obvious inflammation was observed in the BNP2 + L group.
The wound tissues of BNP2 + L group regenerated blood vessels, and
new hair follicles formed, indicating that the inflammation was signifi­
cantly relieved. The results mentioned above demonstrated that the
photodynamic antibacterial activity of BNP2 could effectively combat
bacterial infections of wounds in vivo and promote wound healing.
2.5. Biosafety Assessment of BNP2
The biosafety of BNP2 was assessed by 4,5-dimethylthiazol-2-yl)-2,5-
diphenyltetrazolium bromide (MTT) and hemolysis assay. First, mouse
fibroblasts (L929) were used to evaluate the cytocompatibility of BNP2
by MTT assay. As shown in Fig. 6C, when the concentration reached to
1000 ng/mL, the survival rate of L929 was still greater than 90%,
verifying BNP2 had good cytocompatibility. Next, hemolysis experiment
was performed using mouse blood. Compared with the positive control
(Triton X-100), the hemolytic capacity of BNP2 was negligible (Fig. 6D),
confirming BNP2 had good hemocompatibility.
3. Conclusions
In summary, carrier-free BNPs were synthesized via the self-
assembly of BODIPY, which had high ROS generation capacity. BNP1-
BNP3 exhibited excellent anti-S. aureus activity, which could kill bac­
teria and inhibit the formation of biofilm. In addition, in vivo experi­
ments proved that BNP2 could cure bacterial infections of wounds and
accelerate wound healing. This work provides a new strategy of

3
Q. Shi et al. Journal of Photochemistry & Photobiology, B: Biology 241 (2023) 112674

Fig. 3. (A) Photographs and (B) survival rates of colony forming units (CFU) on solid plates after 10 ng/mL of BNP1-BNP3 treatment of S. aureus. Growth curves of
S. aureus treated with BNP1-BNP3 (10 ng/mL) without (C) or with (D) green light irradiation (18 mW cm− 2, 5 min). (For interpretation of the references to colour in
this figure legend, the reader is referred to the web version of this article.)

Fig. 4. (A) Photographs and (B) quantification of residual biofilms stained with CV. (C) CLSM images of Live/Dead staining of S. aureus after treating with PBS and
BNP2 under green light irradiation (18 mW cm− 2, 5 min). (For interpretation of the references to colour in this figure legend, the reader is referred to the web version
of this article.)

constructing unadulterated NPs as effective PDT agents for biomedical Zhigang Xie: Resources, Supervision. Min Zheng: Conceptualization,
applications. Resources, Supervision, Writing – review & editing, Data curation.

CRediT authorship contribution statement Declaration of Competing Interest

Qiaoxia Shi: Methodology, Investigation, Software, Writing – orig­ The authors declare no conflicts of interest.
inal draft. Xinyuan Wang: Investigation. Hongxin Liu: Investigation.

4
Q. Shi et al. Journal of Photochemistry & Photobiology, B: Biology 241 (2023) 112674

Fig. 5. (A) Time-dependent images and (B) wound healing rates of wounds in different treatment groups, which were infected by S. aureus. (C) Mock images of
wounds within 14 d of treatment (1 d: red; 3 d: yellow; 5 d: green; 7 d: blue; 14 d: pink). (D) Photographs and (E) bacterial survival of colonies on solid plates from
wounds. (For interpretation of the references to colour in this figure legend, the reader is referred to the web version of this article.)

Fig. 6. (A) Mice body weight changes during the treatment. (B) H&E staining images of wound skin tissues in different treatment groups (red arrows: blood vessels;
green arrows: hair follicles). (C) Cell viability of L929 treated with different concentrations of BNP2. (D) Hemolysis rate of BNP2 at 350 ng/mL. (For interpretation of
the references to colour in this figure legend, the reader is referred to the web version of this article.)

5
Q. Shi et al.
Data availability
The authors do not have permission to share data.
Acknowledgements
The financial support from the National Natural Science Foundation
of China (No. 51873023), and the Science and Technology Development
Plan of Changchun City (No. 21ZY38).
Appendix A. Supplementary Data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.jphotobiol.2023.112674.
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