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学者姓名：柯美荣
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Abstract ：
Phthalocyanines (Pcs) are considered promising in cancer phototherapy. However, their maximum absorption wavelengths are only around 700 nm, which cannot allow deep tissue penetration and leads to poor therapeutic efficacy. To expand their clinical application, significantly shifting their absorption to longer wavelengths is urgently required. Dye J-aggregates exhibit a redshifted absorption relative to its monomer. However, Pc J-aggregates with enormous-redshifted and intense absorption is rarely reported, and little is known about the relationships between Pc structure and J-aggregation. Herein, such Pc J-aggregates are ingeniously conceived. With a yeast β-D-glucan-ursodeoxycholic acid conjugate as a potential tumor-associated macrophages (TAMs)-targeting carrier and 1-(4-carboxyethylphenoxy) zinc (II) phthalocyanine (Pc1) as a model, Pc1 J-aggregate nanoparticle (NanoPc1) is obtained via ultrasonication-aided emulsification-solvent evaporation technique. NanoPc1 displays strong absorption at 830 nm, with a 156 nm redshift. Further investigation on another twenty-four Pcs demonstrates that unsubstituted zinc (II) or magnesium (II) Pc and hydrophobic mono-substituted zinc (II) or magnesium (II) Pcs with mono-substituted phenoxy or phenylthio or naphthoxy as a substituent can readily form desired Pc J-aggregates with significant redshifts (140–165 nm). The other Pcs fail to form expected J-aggregates probably due to absence of central metals, steric hindrance on central metals (atoms), forming axial coordination on central metals, disorder tendency during self-assembly or hydrophilicity. The theoretical calculation indicates that Pc1 in its J-aggregates exhibits a spiral-like arrangement, and the reduction in the energy gap between HOMO and LUMO and variation of intermolecular π-π interaction caused by J-aggregate formation are responsible for the huge redshift. Additionally, using NanoPc1 as an exemplar, such Pc J-aggregate nanoparticles are substantiated to afford TAMs-targeted and efficient tri-modal imaging and photothermal therapy in a H22 mouse model. © 2024 Elsevier B.V.
Keyword ：
J-aggregate J-aggregate Large redshift Large redshift Multimodal phototheranostics Multimodal phototheranostics Phthalocyanine Phthalocyanine Yeast glucan Yeast glucan
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| GB/T 7714 | Tang, F. , Yu, H. , Huang, Y. et al. Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics [J]. | Chemical Engineering Journal , 2024 , 496 . |
| MLA | Tang, F. et al. "Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics" . | Chemical Engineering Journal 496 (2024) . |
| APA | Tang, F. , Yu, H. , Huang, Y. , Zhao, X. , Chen, Z. , Ma, H. et al. Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics . | Chemical Engineering Journal , 2024 , 496 . |
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Abstract ：
With a view to developing highly efficient photosensitizers for photodynamic therapy, herein, we prepared a series of tetra-substituted zinc(II) phthalocyanine analogues (ZPOP, ZPSP, ZPNP, and ZPNPM) modified with O-, S-, and N-bridging substituents, respectively. Compared to O- and S-bridging analogues, the N-bridging phthalocyanines showed eminent red-shifted Q band absorption (750-780 nm) and excellent reactive oxygen species (ROS) generation ability (Phi Delta = 0.90-0.97), due to the HOMO destabilization, as well as the smaller Delta EST. To improve the hydrophility and biocompatibility, we further prepared two N-bridging zinc(II) phthalocyanines (ZPN1 and ZPN2) modified with morpholine and N,N-dimethylamine moieties, respectively, along with their quaternized counterparts (QZPN1 and QZPN2). These compounds exhibited NIR-absorbing Q bands at 774-777 nm and efficient ROS generation ability in aqueous solutions, especially formulated with 1 % Cremophor EL (Cel). In vitro studies indicated that ZPN2 exhibited the highest photodynamic activity against HepG2 cells (IC50 = 0.44 +/- 0.02 mu M), because of superior cellular uptake and moderate ROS generation ability. Moreover, ZPN2 could selectively accumulate and retain in tumor tissue of H22 tumor-bearing mice. The work presents a new strategy for the development of NIR-absorbing photosensitizers.
Keyword ：
N -bridging phthalocyanine N -bridging phthalocyanine Near-infrared Near-infrared Photodynamic therapy Photodynamic therapy Reactive oxygen species Reactive oxygen species
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| GB/T 7714 | Ke, Mei-Rong , Wang, Chao , He, Qinxue et al. N-bridging tetra-substituted zinc(II) phthalocyanines with Q-band absorption up to 780 nm and eminent photosensitizing activities for photodynamic therapy [J]. | DYES AND PIGMENTS , 2024 , 227 . |
| MLA | Ke, Mei-Rong et al. "N-bridging tetra-substituted zinc(II) phthalocyanines with Q-band absorption up to 780 nm and eminent photosensitizing activities for photodynamic therapy" . | DYES AND PIGMENTS 227 (2024) . |
| APA | Ke, Mei-Rong , Wang, Chao , He, Qinxue , Que, Rongbin , Wei, Ying , Zheng, Bi-Yuan et al. N-bridging tetra-substituted zinc(II) phthalocyanines with Q-band absorption up to 780 nm and eminent photosensitizing activities for photodynamic therapy . | DYES AND PIGMENTS , 2024 , 227 . |
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The development of a simple drug formulation capable of achieving both activatable type I photoreaction and tumor-responsive release of immunomodulator is crucial for advancing photodynamic immunotherapy (PDIT). Herein, we present a nanostructured photosensitizer (NP5) that is activated by the acidic tumor microenvironment to produce type I reactive oxygen species (ROS) under light irradiation and release the immunomodulator demethylcantharidin (DMC) for PDIT. The NP5 is formed by self-assembly of a versatile phthalocyanine molecule which is composed of DMC and phthalocyanine linked via a pH-responsive amide bond. NP5 produces minimal ROS under light irradiation at the condition of pH 7.4. However, NP5 can release DMC at the condition of pH 6.5 and concurrently trigger type I photoreactions. The results of in vivo experiments indicate that NP5-mediated PDIT induce the increase of cytotoxic T lymphocytes and decrease of regulatory T lymphocytes, which can effectively inhibit the bilateral tumor growth. This work is anticipated to serve as a reference for the development of innovative agents for precise PDIT of hypoxic tumors.
Keyword ：
Activatable photosensitizer Activatable photosensitizer Demethylcantharidin Demethylcantharidin Photodynamic immunotherapy Photodynamic immunotherapy Phthalocyanine Phthalocyanine Type I Type I
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| GB/T 7714 | Zhang, Ling , Que, Rong-Bin , Ke, Ting-Ting et al. A tumor-pH-responsive phthalocyanine as activatable type I photosensitizer for improved photodynamic immunotherapy [J]. | JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY , 2024 , 261 . |
| MLA | Zhang, Ling et al. "A tumor-pH-responsive phthalocyanine as activatable type I photosensitizer for improved photodynamic immunotherapy" . | JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY 261 (2024) . |
| APA | Zhang, Ling , Que, Rong-Bin , Ke, Ting-Ting , Wang, Chao , Xie, Wei , Sun, Hong-Jie et al. A tumor-pH-responsive phthalocyanine as activatable type I photosensitizer for improved photodynamic immunotherapy . | JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY , 2024 , 261 . |
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Abstract ：
Phthalocyanines (Pcs) are considered promising in cancer phototherapy. However, their maximum absorption wavelengths are only around 700 nm, which cannot allow deep tissue penetration and leads to poor therapeutic efficacy. To expand their clinical application, significantly shifting their absorption to longer wavelengths is urgently required. Dye J-aggregates exhibit a redshifted absorption relative to its monomer. However, Pc Jaggregates with enormous-redshifted and intense absorption is rarely reported, and little is known about the relationships between Pc structure and J-aggregation. Herein, such Pc J-aggregates are ingeniously conceived. With a yeast beta-D-glucan-ursodeoxycholic acid conjugate as a potential tumor-associated macrophages (TAMs)targeting carrier and 1-(4-carboxyethylphenoxy) zinc (II) phthalocyanine (Pc1) as a model, Pc1 J-aggregate nanoparticle (NanoPc1) is obtained via ultrasonication-aided emulsification-solvent evaporation technique. NanoPc1 displays strong absorption at 830 nm, with a 156 nm redshift. Further investigation on another twentyfour Pcs demonstrates that unsubstituted zinc (II) or magnesium (II) Pc and hydrophobic mono-substituted zinc (II) or magnesium (II) Pcs with mono-substituted phenoxy or phenylthio or naphthoxy as a substituent can readily form desired Pc J-aggregates with significant redshifts (140-165 nm). The other Pcs fail to form expected J-aggregates probably due to absence of central metals, steric hindrance on central metals (atoms), forming axial coordination on central metals, disorder tendency during self-assembly or hydrophilicity. The theoretical calculation indicates that Pc1 in its J-aggregates exhibits a spiral-like arrangement, and the reduction in the energy gap between HOMO and LUMO and variation of intermolecular it-it interaction caused by J-aggregate formation are responsible for the huge redshift. Additionally, using NanoPc1 as an exemplar, such Pc J-aggregate nanoparticles are substantiated to afford TAMs-targeted and efficient tri-modal imaging and photothermal therapy in a H22 mouse model.
Keyword ：
J -aggregate J -aggregate Large redshift Large redshift Multimodal phototheranostics Multimodal phototheranostics Phthalocyanine Phthalocyanine Yeast glucan Yeast glucan
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| GB/T 7714 | Tang, Fengxiang , Yu, Haodong , Huang, Yanzong et al. Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics [J]. | CHEMICAL ENGINEERING JOURNAL , 2024 , 496 . |
| MLA | Tang, Fengxiang et al. "Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics" . | CHEMICAL ENGINEERING JOURNAL 496 (2024) . |
| APA | Tang, Fengxiang , Yu, Haodong , Huang, Yanzong , Zhao, Xue , Chen, Zixuan , Ma, Honglin et al. Phthalocyanine J-aggregate nanoparticles with enormous-redshifted and intense absorption: Potential structure-J-aggregation relationships and application in tumor-associated macrophages-targeted phototheranostics . | CHEMICAL ENGINEERING JOURNAL , 2024 , 496 . |
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Although specific responsive theranostics biomaterials were essencial for precision medicine, the univariate responsive strategy was restricted by high false-positive rates. Herein, we designed a novel phthalocyanine-iron-based complex FeS2@PcD, as a theranostics nanoreactor, which was program-regulated by bivariate factors of H+ and H2O2 in tumor microenvironment (TME). We found that FeS2@PcD had the excellent capability of tumor fluorescence imaging (FLI), with a 52.21-fold increase in fluorescence signal by the programmable response, while the signal of the univariate factor was almost unchanged. We also revealed that FeS2@PcD reacted with H+ to release PcD and produced Fe2+, then Fe2+ was further oxidized by H2O2 to produce Fe3+, finally recovering the fluorescence of PcD whose fluorescence activity was significantly suppressed due to the photoinduced electron transfer (PET) effect. Notably, except for fluorescence signal, magnetic resonance (MR) signal and sonosensitive activity of FeS2@PcD also changed from "OFF" state to "ON" state under the programmable regulation of H+ and H2O2. The program-regulated strategy based on FeS2@PcD realized specific fluorescence and MR dual-modality imaging-guided sono/chemodynamic therapies, representing a promising precision medicine approach.
Keyword ：
Dual -modality imaging Dual -modality imaging Programmable -regulation Programmable -regulation Sonosensitization Sonosensitization Specific Fe 3+-response Specific Fe 3+-response Tumor microenvironment Tumor microenvironment
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| GB/T 7714 | Li, Dong , Pan, Jie , Xu, Shuyu et al. Programmable phthalocyanine-iron-based nanoreactor for fluorescence/ magnetic resonance dual-modality imaging-guided sono/ chemodynamic therapies [J]. | CHEMICAL ENGINEERING JOURNAL , 2023 , 452 . |
| MLA | Li, Dong et al. "Programmable phthalocyanine-iron-based nanoreactor for fluorescence/ magnetic resonance dual-modality imaging-guided sono/ chemodynamic therapies" . | CHEMICAL ENGINEERING JOURNAL 452 (2023) . |
| APA | Li, Dong , Pan, Jie , Xu, Shuyu , Cheng, Bingwei , Wu, Shuaiying , Dai, Qixuan et al. Programmable phthalocyanine-iron-based nanoreactor for fluorescence/ magnetic resonance dual-modality imaging-guided sono/ chemodynamic therapies . | CHEMICAL ENGINEERING JOURNAL , 2023 , 452 . |
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Phthalocyanines are potentially promising photosensitizers (PSs) for photodynamic therapy (PDT), but the inherent defects such as aggregation-caused quenching effects and non-specific toxicity severely hinder their further application in PDT. Herein, we synthesized two zinc(II) phthalocyanines (PcSA and PcOA) monosubstituted with a sulphonate group in the alpha position with "O bridge" and "S bridge" as bonds and prepared a liposomal nanophotosensitizer (PcSA@Lip) by thin-film hydration method to regulate the aggregation of PcSA in the aqueous solution and enhance its tumor targeting ability. PcSA@Lip exhibited highly efficient production of superoxide radical (O-2(center dot-)) and singlet oxygen (O-1(2)) in water under light irradiation, which were 2.6-fold and 15.4-fold higher than those of free PcSA, respectively. Furthermore, PcSA@Lip was able to accumulate selectively in tumors after intravenous injection with the fluorescence intensity ratio of tumors to livers was 4.1:1. The significant tumor inhibition effects resulted in a 98% tumor inhibition rate after PcSA@Lip was injected intravenously at an ultra-low PcSA@Lip dose (0.8 nmol g(-1) PcSA) and light dose (30 J cm(-2)). Therefore, the liposomal PcSA@Lip is a prospective nanophotosensitizer possessing hybrid type I and type II photoreactions with efficient photodynamic anticancer effects.
Keyword ：
anticancer anticancer fluorescence imaging fluorescence imaging liposome liposome photodynamic therapy photodynamic therapy phthalocyanine phthalocyanine
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| GB/T 7714 | Chen, Zixuan , Zhao, Yuan-Yuan , Li, Li et al. A Sulfur-Bridging Sulfonate-Modified Zinc(II) Phthalocyanine Nanoliposome Possessing Hybrid Type I and Type II Photoreactions with Efficient Photodynamic Anticancer Effects [J]. | MOLECULES , 2023 , 28 (5) . |
| MLA | Chen, Zixuan et al. "A Sulfur-Bridging Sulfonate-Modified Zinc(II) Phthalocyanine Nanoliposome Possessing Hybrid Type I and Type II Photoreactions with Efficient Photodynamic Anticancer Effects" . | MOLECULES 28 . 5 (2023) . |
| APA | Chen, Zixuan , Zhao, Yuan-Yuan , Li, Li , Li, Ziqing , Fu, Shuwen , Xu, Yihui et al. A Sulfur-Bridging Sulfonate-Modified Zinc(II) Phthalocyanine Nanoliposome Possessing Hybrid Type I and Type II Photoreactions with Efficient Photodynamic Anticancer Effects . | MOLECULES , 2023 , 28 (5) . |
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Abstract ：
A series of alpha-tetra-substituted phthalocyanines (M = 2H, Cu, Co, Ni) with morpholinyl moieties and their corresponding quaternized derivatives have been synthesized. The spectroscopic and photosensitizing properties, photothermal effects, aggregation trend, and partition coefficients of these phthalocyanines are evaluated. Besides, we appraised their photothermal and photodynamic activities against C. albicans and E. coli under nearinfrared (NIR) light irradiation (680 nm). The results show that cationic phthalocyanines are more efficacies in killing bacteria and fungi than their neutral analogues. For copper (II) phthalocyanine 4b and metal-free phthalocyanine 7b, their photodynamic activities play a key role in antimicrobial treatment, while for other phthalocyanines, their photothermal effects play a major role. Moreover, metal-free phthalocyanine 7b exhibits an ideal synergistic photothermal/photodynamic antimicrobial activity and shows the highest photocytotoxicity among all the compounds. The IC90 values of 7b towards C. albicans and E. coli are as low as 1.12 mu M and 0.47 mu M, respectively, while others have IC90 values ranging from 3.31 mu M to 50 mu M, implying that 7b would be a good candidate for future antimicrobial applications.
Keyword ：
albicans albicans C C coli coli E E Morpholinyl Morpholinyl photodynamic antimicrobial photodynamic antimicrobial Photothermal Photothermal Phthalocyanine Phthalocyanine therapy therapy
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| GB/T 7714 | Fan, Ping-Ping , Li, Shun-Li , Zheng, Bi-Yuan et al. Synthesis and photothermal/photodynamic antimicrobial activities of phthalocyanines tetra-substituted by morpholinyl moieties [J]. | DYES AND PIGMENTS , 2023 , 212 . |
| MLA | Fan, Ping-Ping et al. "Synthesis and photothermal/photodynamic antimicrobial activities of phthalocyanines tetra-substituted by morpholinyl moieties" . | DYES AND PIGMENTS 212 (2023) . |
| APA | Fan, Ping-Ping , Li, Shun-Li , Zheng, Bi-Yuan , Zheng, Bing-De , Lv, Li-Li , Ke, Mei-Rong et al. Synthesis and photothermal/photodynamic antimicrobial activities of phthalocyanines tetra-substituted by morpholinyl moieties . | DYES AND PIGMENTS , 2023 , 212 . |
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Unlike traditional methods of modifying phthalocyanines (Pcs), we herein report a smart and visible way to switch the aromaticity of silicon(iv) phthalocyanines via a reversible nucleophilic addition reaction of the Pc skeleton induced by alkalis and acids, leading to an interesting allochroism phenomenon and the switching of photosensitive activities.
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| GB/T 7714 | Ke, Mei-Rong , Chen, Zixuan , Shi, Jie et al. A smart and visible way to switch the aromaticity of silicon(iv) phthalocyanines [J]. | CHEMICAL COMMUNICATIONS , 2023 , 59 (65) : 9832-9835 . |
| MLA | Ke, Mei-Rong et al. "A smart and visible way to switch the aromaticity of silicon(iv) phthalocyanines" . | CHEMICAL COMMUNICATIONS 59 . 65 (2023) : 9832-9835 . |
| APA | Ke, Mei-Rong , Chen, Zixuan , Shi, Jie , Wei, Ying , Liu, Hao , Huang, Shuping et al. A smart and visible way to switch the aromaticity of silicon(iv) phthalocyanines . | CHEMICAL COMMUNICATIONS , 2023 , 59 (65) , 9832-9835 . |
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In order to reduce the intramolecular charge-transfer (ICT) effect of amine groups on the photophysical properties of zinc (II) phthalocyanine (ZnPc), tertiary amines were covalently connected with ZnPc ring via ethyl phydroxybenzoate or diethyl 5-hydroxyisophthalate. Six new tertiary amine-modified ZnPcs were therefore synthesized and characterized. Meanwhile, the corresponding quaternary ammonium ZnPcs were also synthesized. The effects of different substitution ways (mono-substitutions, symmetrical tetra-substitutions, or asymmetric tetra-substitutions) and the numbers of different substitutions on the photophysical and physicochemical properties of these ZnPcs were studied. All twelve ZnPcs had relatively high singlet oxygen quantum yields (& phi;& UDelta; = 0.32-0.68) and fluorescence quantum yields (& phi;F = 0.23-0.40), where the amine-containing substituents did not show obvious ICT effect. All ZnPcs showed effective phototoxicity towards breast cancer cells (IC50 = 63-366 nmol/L). Among them, three tetra-substituted ZnPcs containing quaternary ammonium groups (4aN, 4bN and 4cN) showed the best in vitro anticancer photodynamic activities with IC50 = 64-76 nmol/L, which owned to their relatively high cellular uptake. The tumor inhibition rate of 4aN on H22 tumor-bearing mice reached 87% (4aN dose: 3 nmol/g; light dose: 685 nm, 135 J/cm2).
Keyword ：
Cancer Cancer Photodynamic therapy Photodynamic therapy Photosensitizer Photosensitizer Phthalocyanine Phthalocyanine Structure-activity relationship Structure-activity relationship
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| GB/T 7714 | Zhang, Ling , Zhao, Yuan-Yuan , Chen, Zi-Xuan et al. Synthesis, characterization and photodynamic antitumor activity of amine-modified zinc (II) phthalocyanines [J]. | DYES AND PIGMENTS , 2023 , 218 . |
| MLA | Zhang, Ling et al. "Synthesis, characterization and photodynamic antitumor activity of amine-modified zinc (II) phthalocyanines" . | DYES AND PIGMENTS 218 (2023) . |
| APA | Zhang, Ling , Zhao, Yuan-Yuan , Chen, Zi-Xuan , Cheng, Yun-Tong , Zheng, Bi-Yuan , Ke, Mei-Rong et al. Synthesis, characterization and photodynamic antitumor activity of amine-modified zinc (II) phthalocyanines . | DYES AND PIGMENTS , 2023 , 218 . |
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Photothermal therapy (PTT) possesses a great promise for tumor therapy due to its effective tumor inhibition and minimal invasiveness. Nevertheless, most of organic photothermal agents (PTAs) suffer from poor photothermal conversion efficiency, and the residues of PTAs may cause the problem of side effects. Herein, we utilize a molecular surgery approach to develop a self-degradable nanostructured PTA (NanoPcDA2). NanoPcDA2 exhibited a remarkable photothermal conversion efficiency. In addition, NanoPcDA2 showed an outstanding tumor accumulation after intravenous injection, and 92% tumor growth was suppressed in the mice tumor model at a low light dose of 300 J cm(-2) and a NanoPcDA2 dose of 0.8 nmol g(-1). Moreover, NanoPcDA2 can be degraded by singlet oxygen (O-1(2)) produced by itself and lose its photoactivity after PTT. Notably, the photodegradation products of NanoPcDA2 have negligible cytotoxicity. In this way, it not only contributes to resolve the potential phototoxicity problems of residual PTAs, but also can expedite the metabolism of PTAs to avert the potential biotoxicity of drug accumulation.
Keyword ：
Biosecurity Biosecurity Nanostructure Nanostructure Photothermal therapy Photothermal therapy Phthalocyanine Phthalocyanine Self-degradation Self-degradation
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| GB/T 7714 | Zhao, Yuan -Yuan , Chen, Zixuan , Zhang, Ling et al. A self-degradable nanostructured phthalocyanine assembly with high photothermal efficacy to enhanced biosecurity in photothermal therapy [J]. | CHEMICAL ENGINEERING JOURNAL , 2023 , 474 . |
| MLA | Zhao, Yuan -Yuan et al. "A self-degradable nanostructured phthalocyanine assembly with high photothermal efficacy to enhanced biosecurity in photothermal therapy" . | CHEMICAL ENGINEERING JOURNAL 474 (2023) . |
| APA | Zhao, Yuan -Yuan , Chen, Zixuan , Zhang, Ling , Qin, Xue-Wei , Liu, Hao , Zheng, Bi-Yuan et al. A self-degradable nanostructured phthalocyanine assembly with high photothermal efficacy to enhanced biosecurity in photothermal therapy . | CHEMICAL ENGINEERING JOURNAL , 2023 , 474 . |
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