Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Zang, Qiguang; Yu, Junzhi; Yu, Wei; Qian, Jun; Hu, Rongrong; Tang, Ben Zhong

doi:10.1039/c8sc00633d

Cited by 59 publications

(35 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Meanwhile, studies have shown that in the aggregate states, AIE PSs are able to offer effective 1 O 2 production . 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%

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

Mao

et al. 2019

Adv Funct Materials

104

View full text Add to dashboard Cite

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 ...

show abstract

Section: Introductionmentioning

confidence: 99%

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

Mao

et al. 2019

Adv Funct Materials

104

View full text Add to dashboard Cite

show abstract

“…S25 †), which is usually observed in D-A type compounds. 46,47 The intensied PL intensity is due to the formation of aggregates, representing a typical AIE signature. The AIE amplitude increases from MTPE-TP1 to MTPE-TP3, especially there is a notable enhancement for MTPE-TP3, which is likely due to the more twisted molecular geometry and inhibition of intermolecular interactions in the aggregate state.…”

Section: Resultsmentioning

confidence: 99%

Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens

Duan

Cai

et al. 2020

Chem. Sci.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Worthy of note, homoleptic zinc(II) dipyrromethene complexes and large organic aromatic systems, which were encapsulated with the same polymer matrix but with different terminal group were also found mostly in the lysosomes. [108][109][110] Following this, the cellular uptake mechanism of NP in A549 cells was investigated. As there is a higher demand for biotin in rapidly growing cells than in healthy cells, biotin and its conjugates are rapdily internalized by the sodium multivitamin transporter (SMVT), which is overexpressed in a variety of cancers.…”

Section: Resultsmentioning

confidence: 99%

Polymeric Encapsulation of a Ruthenium Polypyridine Complex for Tumor Targeted 1- and 2-Photon Photodynamic Therapy

Karges¹,

Li²,

Zeng³

et al. 2020

Preprint

View full text Add to dashboard Cite

Photodynamic therapy is a medical technique, which is gaining increasing attention to treat various types of cancer. Among the investigated classes of photosensitizers, the use of Ru(II) polypyridine complexes is gaining momentum. However, the currently investigated compounds generally show poor cancer cell selectivity. As a consequence, high drug doses are needed, which can cause side effects. To overcome this limitation, there is a need for the development of a suitable drug delivery system to increase the amount of PS delivered to the tumor. Herein, we report on the encapsulation of a promising Ru(II) polypyridyl complex into polymeric nanoparticles with terminal biotin groups. Thanks to this design, the particles showed much higher selectivity for cancer cells in comparison to non-cancerous cells in a 2D monolayer and 3D multicellular tumor spheroid model. As a highlight, upon intravenous injection of an identical amount of the Ru(II) polypyridine complex, an improved accumulation inside an adenocarcinomic human alveolar basal epithelial tumor of a mouse by a factor of 8.7 compared to the Ru complex itself was determined. The nanoparticles were found to have a high phototoxic effect upon 1-photon (500 nm) or 2-photon (800 nm) excitation with an eradication of an adenocarcinomic human alveolar basal epithelial tumor inside a mouse. Overall, this work describes, to the best of our knowledge, the first <i>in vivo</i> study demonstrating the cancer cell selectivity of a very promising Ru(II)-based PDT photosensitizer encapsulated into polymeric nanoparticles with terminal biotin groups.

show abstract

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging

Abstract: Azabenzanthrone derivatives with high phototoxicity and efficient emission are designed for photodynamic therapy and deep-tissue imaging.

Cited by 59 publications

References 36 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

Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens

Polymeric Encapsulation of a Ruthenium Polypyridine Complex for Tumor Targeted 1- and 2-Photon Photodynamic Therapy

Contact Info

Product

Resources

About