Polymerization-Enhanced Photosensitization

Wu, Wenbo; Mao, Duo; Xu, Shidang; Kenry, Kenry; Hu, Fang; Li, Xueqi; Kong, Deling; Liu, Bin

doi:10.1016/j.chempr.2018.06.003

Cited by 271 publications

(205 citation statements)

References 59 publications

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“…The synthesis of TBTC8 (Scheme C) was started from substituted benzophenone S9 14a and 4‐bromobenzophenone ( S10 ). McMurry olefination between S9 and 4‐bromobenzophenone ( S10 ) yielded bromide‐functionalized TPE S11 in 46.4% yield, which was used subsequently to synthesize borate S12 in 60.5% yield by using bis(pinacolato)diborane ( S5 ) as the boronation reagent.…”

Section: Resultsmentioning

confidence: 99%

“…Encapsulating AIE PSs into nanoparticles (NPs) using amphipathic polymers as the matrix endows them with good water dispersibility and biocompatibility, which allows them to be applied in both imaging and photosensitization functions 10a,13. In addition, it has been demonstrated that well‐designed AIE PS NPs exhibit good photostability and low dark toxicity, which can be spontaneously excreted after PDT by the stool with little side effects based on pharmacokinetics results …”

Section: Introductionmentioning

confidence: 99%

“…Effective separation of HOMO and LUMO means less conjugation between donor and acceptor, which often leads to short‐wavelength absorption and emission 12a,15. To date, only one AIE PS demonstrated an emission maximum longer than 800 nm with good 1 O 2 generation efficiency, which was achieved by linking a very strong acceptor of tetracyanoanthra‐ p ‐quinodimethanes (TCAQ) to TPE 14b. However, it has an absorption maximum at 520 nm with an extremely low molar absorption coefficient of 4.80 × 10 3 L mol −1 cm −1 .…”

Section: Introductionmentioning

confidence: 99%

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Precise Molecular Engineering of Photosensitizers with Aggregation‐Induced Emission over 800 nm for Photodynamic Therapy

Mao

et al. 2019

Adv Funct Materials

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104

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Owing to efficient singlet oxygen ( 1 O 2 ) generation in aggregate state, photosensitizers (PSs) with aggregation-induced emission (AIE) have attracted much research interests in photodynamic therapy (PDT). In addition to high 1 O 2 generation efficiency, strong molar absorption in longwavelength range and near-infrared (NIR) emission are also highly desirable, but difficult to achieve for AIE PSs since the twisted structures in AIE moieties usually lead to absorption and emission in short-wavelength range. In this contribution, through acceptor engineering, a new AIE PS of TBT is designed to show aggregation-induced NIR emission centered at 810 nm, broad absorption in the range between 300 and 700 nm with a large molar absorption coefficient and a high 1 O 2 generation efficiency under white light irradiation. Further, donor engineering by attaching two branched flexible chains to TBT yielded TBTC8, which circumvented the strong intermolecular interactions of TBT in nanoparticles (NPs), yielding TBTC8 NPs with optimized overall performance in 1 O 2 generation, absorption, and emission. Subsequent PDT results in both in vitro and in vivo studies indicate that TBTC8 NPs are promising candidates in practical application.The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/adfm.201901791.(ROS) to kill cancer cells under light irradiation, has drawn widespread research interests owing to its good spatiotemporal precision, precise controllability, and noninvasiveness, etc. [1] Among which, the process that using emissive PSs as the key agents to find out the tumor site first and then realize PDT has been recognized as cost-effective and time-saving due to the integration of both diagnosis and treatment in one molecule. [2] To achieve effective PDT, smart design of PSs is of essential significance. Ideal properties of PSs include efficient 1 O 2 generation ability for cancer cell ablation, near-infrared (NIR) emission for imaging, strong absorption in long wavelength for easy excitation and good penetration depth, negligible dark toxicity for minimal side effects, and good photostability for continuous light irradiation. [3] Boron-dipyrromethene (BODIPY) derivatives, [4] metal complexes, [5] cyanine derivatives, [6] and porphyrin or chlorin derivatives, [7] are some typical traditional PSs. Heavy atoms are usually used to improve the 1 O 2 generation efficiency of BODIPY derivatives and metal complexes, which usually exhibit nontrivial dark toxicity with weak fluorescence. [4,5] Cyanine-type PSs are famous for their large absorbance in long-wavelength range with bright NIR emission over 800 nm. However, their poor 1 O 2 production capability and low photostability limited their practical application. [6] Porphyrin and chlorin derivatives usually show good 1 O 2 generation, but their light-absorbing capacity in long-wavelength range is generally rather poor, and their emission peaks are relatively blue as compared to those of cyanine-type PSs. [7] Several ...

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Precise Molecular Engineering of Photosensitizers with Aggregation‐Induced Emission over 800 nm for Photodynamic Therapy

Mao

et al. 2019

Adv Funct Materials

Self Cite

104

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“…[9d, 13] Thereby,aconvenient yet efficient chemical design strategy to enhance ISC is fascinating and practical. Herein, we established two strategies to effectively enhance the efficiencyo fP Ss,n amely polymerization-facilitated photosensitization [14] and D-A even-odd effect. As shown in Figure 1, several AIEgens based on electrondonating triphenylamine (T)a nd electron-accepting benzothiadiazole (B)units were synthesized and well characterized (Supporting Information, Schemes S1-S7).…”

mentioning

confidence: 99%

Strategies to Enhance the Photosensitization: Polymerization and the Donor–Acceptor Even–Odd Effect

et al. 2018

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Ap articular challenge in the design of organic photosensitizers (PSs) with donor-acceptor (D-A) structures is that it is based on trial and error rather than specific rules.Now these challenges are addressed by proposing two efficient strategies to enhance the photosensitization efficiency:p olymerization-facilitated photosensitization and the D-A evenodd effect. Conjugated polymers have been found to exhibit ah igher 1 O 2 generation efficiency than their small molecular counterparts.F urthermore,P Ss with A-D-A structures show enhanced photosensitization efficiency over those with D-A-D structures.T heoretical calculations suggest an enhanced intersystem crossing (ISC) efficiency by these strategies.B oth in vitro and in vivo experiments demonstrate that the resulting materials can be used as photosensitizers in image-guided photodynamic anticancer therapy. These guidelines are applicable to other polymers and small molecules to lead to the development of new PSs.

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“…Figure S10, Supporting Information, shows the calculation principles, and Table 1 shows the calculation results. [40][41][42] After chlorophyll-rich CBQDs bind with copper ions to form CBQD-Cu, the fluorescence of CBQDs is quenched. Comparison of these two values showed that the E ST of chlorophyll-copper complex is far lower than that of chlorophyll.…”

mentioning

confidence: 99%

A Distinctive Spinach‐Based Carbon Nanomaterial with Chlorophyll‐Rich and Near‐Infrared Emission for Simultaneous In Vivo Biothiol Imaging and Dual‐Enhanced Photodynamic Therapy of Tumor

Liu

Zhang

Zhao

et al. 2019

Advanced Therapeutics

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Photodynamic therapy (PDT) is a new treatment modality against local lesions, particularly in malignant tumors. However, higher biothiol concentrations in tumor cells will decrease the efficacy of PDT. To tackle the above challenges, a distinctive spinach-based carbon nanomaterial called "chlorophyll-rich biomass quantum dots" (CBQDs) with near-infrared emission is prepared, and the CBQDs are further bound with copper ions forming CBQD-Cu nanocomposites, which are used as a new fluorescence nanoprobe and highly efficient photosensitizer for simultaneous in vivo near-infrared fluorescence imaging of biothiol and dual-enhanced PDT of tumors. The mechanism of action is studied and it is shown that the binding of chlorophyll and copper ions on the surface of CBQDs reduces the energy level difference of the chlorophyll molecules, which results in an increase of reactive oxygen species (ROS) achieving enhanced PDT. On the other hand, the copper ions on the CBQD-Cu surface can also bind with biothiol which decreases the concentration of free biothiol in tumor cells, and further enhances PDT. At the same time, the combination of copper ions and biothiol opens the fluorescence of CBQDs, which realizes near-infrared fluorescence imaging of biothiol. Hence, the CBQD-Cu is used as a highly effective nanomedicine for the recognition and treatment of tumors.Photodynamic therapy (PDT) is a new treatment modality against local lesions, particularly in malignant tumors. PDT uses photosensitizers that selectively aggregate inside the human body. When these are irradiated with light of a specific wavelength, the photosensitizers undergo a series of photochemical reactions to generate reactive oxygen species (ROS), which can kill tumors

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Polymerization-Enhanced Photosensitization

Cited by 271 publications

References 59 publications

Precise Molecular Engineering of Photosensitizers with Aggregation‐Induced Emission over 800 nm for Photodynamic Therapy

Precise Molecular Engineering of Photosensitizers with Aggregation‐Induced Emission over 800 nm for Photodynamic Therapy

Strategies to Enhance the Photosensitization: Polymerization and the Donor–Acceptor Even–Odd Effect

A Distinctive Spinach‐Based Carbon Nanomaterial with Chlorophyll‐Rich and Near‐Infrared Emission for Simultaneous In Vivo Biothiol Imaging and Dual‐Enhanced Photodynamic Therapy of Tumor

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