A Dual Anticancer Efficacy Molecule: A Selective Dark Cytotoxicity Photosensitizer

Chen, Jyun-Wei; Chang, Cheng-Chung

doi:10.1021/acsami.6b07715

Cited by 16 publications

(10 citation statements)

References 50 publications

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“…Unexpectedly, a higher quantum yield of CSP was observed in polar (protic) solvents, except for water. In previous studies, we investigated the AIEE properties to discuss the fluorescence behavior of solid-state and aqueous fluorogens, and we observed the formation of fluorescent organic nanoparticles (FONs) [33][34][35]. Briefly, the AIE phenomenon was easily detected in the emission spectra in THF/H 2 O mixed solvents, as shown in Figure 3, which was also supported by the fluorescence microscopy and SEM images (Figure 3d,e).…”

Section: Pet and Aieementioning

confidence: 52%

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

Chang

2020

Molecules

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The major challenge in the fabrication of fluorescent silica nanoparticles (FSNs) based on dye-doped silica nanoparticles (DDSNs) is aggregation-caused fluorescence quenching. Here, we constructed an FSN based on a double emission enhancement (DEE) platform. A thio-reactive fluorescence turn-on molecule, N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide (CS), was bound to a silane coupling agent, (3-mercaptopropyl)-trimethoxysilane (MPTMS), and the product N-butyl-4-(3-(trimethoxysilyl-propylthio)styryl)-1,8-naphthalimide (CSP) was further used to fabricate a core–shell nanoparticle through the Stöber method. We concluded that the turn-on emission by CSP originated from the photoinduced electron transfer (PET) between the maleimide moiety and the CSP core scaffold, and the second emission enhancement was attributed to the aggregation-induced emission enhancement (AIEE) in CSP when encapsulated inside a core–shell nanoparticle. Thus, FSNs could be obtained through DEE based on a combination of PET and AIEE effects. Systematic investigations verified that the resulting FSNs showed the traditional solvent-independent and photostable optical properties. The results implied that the novel FSNs are suitable as biomarkers in living cells and function as fluorescent visualizing agents for intracellular imaging and drug carriers.

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Section: Pet and Aieementioning

confidence: 52%

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

Chang

2020

Molecules

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“…Although MeAcd12C and MedAcd12P were observed to enter cells and showed fluorescent speckles in the cytoplasm, the results did not coincide well with the optical properties, which presented very low quantum yield in H 2 O. Considering that the two compounds were designed as surfactant-like chromophores along with the presence of fluorescent speckles, we further investigated whether the fluorescent speckles were due to the aggregation-induced emission (AIE) effects [34,35]. The AIE effects on MeAcd12C and MedAcd12P were examined under varying H 2 O/THF mixed solvent system ratios ( Figure S5).…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Application in Cell Imaging of Acridone Derivatives

Chan

Lai

et al. 2020

Applied Sciences

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Tricyclic acridone derivatives have been extensively developed as antimicrobial, antimalarial, and antitumor drugs due to their broad spectrum of drug design and biological activity. In this study, we developed a surfactant-like acridone scaffold that contained two vinylpyridines and a dodecyl pyridine chain. The acridone scaffold decorated the dodecyl pyridine chain by N-bromosuccinimide reagent. The surfactant-like core scaffold incorporated with 4-vinylpyridines at the 2- and 7-positions via a Heck coupling reaction. Subsequently, the acridone derivatives were methylated onto these pyridine groups. Here we developed two similar acridone derivatives, MedAcd12C and MedAcd12P. The MedAcd12C incorporated two pyridine groups, and MedAcd12P incorporated three pyridine groups. MedAcd12C and MedAcd12P have two identical vinylpyridines and the different anchor tails at the N10 position. Their physicochemical properties, cell compatibility, and photoluminescence were demonstrated. Although both compounds have no fluorescence emission in water solution, MedAcd12P and MedAcd12C significantly appeared with orange light emission in the cellular imaging. We suggested that the surfactant-like scaffold promoted the drugs’ self-assembly and caused the aggregation-induced emission (AIE) after cellular uptake. This innovative design endowed acridone derivatives with an AIE and traceability for cell imaging.

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“…SA (BCRC 10,451) and E. coli (BCRC 11,634) were used in the antibacterial assay; four types of small molecular compounds (cpd.1, cpd.2, cpd.3, and cpd.4), which were reported in our previous works [ 12 – 14 ] and briefly described in the supplementary materials, were used as the photodynamic agents; nutrient agar (Merck kGaA, 1.05450.0500) and nutrient broth (Merck kGaA, 1.05443.0500) were prepared for bacterial culture.…”

Section: Methodsmentioning

confidence: 99%

Dual-acting antibacterial porous chitosan film embedded with a photosensitizer

Liu

Lin

Lee

et al. 2020

Science and Technology of Advanced Materials

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This study proposes to develop a dual-acting antibacterial film of porous chitosan (Cs) embedded with small molecular compound, which possesses photosensitive characteristics with bactericidal efficacy, to promote the accelerated recovery of infectious wounds. The Cs/small molecular compound (Cs-cpd.2) dressing was prepared using the freeze-drying method. Characterization of the synthesized Cs-cpd.2 indicated that it has high porosity and moisture absorption effect, hence enhancing the absorption of wound exudate. Experimental results showed that Cs-cpd.2 dressing has good bactericidal and bacteriostatic effects on Staphylococcus aureus under visiblelight irradiation and has antibacterial effect in the dark. It was also found that the small molecular compound does not have cytotoxicity at a dose of 0-5 μM. Furthermore, Cs-cpd.2 that contained small molecular compound with a concentration of 0.3-1 μM has positive effect on both the cell viability rate and cell proliferation rate of human fibroblast CG1639. Cs-cpd.2 can significantly promote cell proliferation when the small molecular compound and the basic fibroblast growth factor bFGF were added together. Therefore, the proposed Cs-cpd.2 dressing is feasible for photodynamic therapy (PDT) and clinical wound dressing applications.

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A Dual Anticancer Efficacy Molecule: A Selective Dark Cytotoxicity Photosensitizer

Cited by 16 publications

References 50 publications

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

Synthesis and Application in Cell Imaging of Acridone Derivatives

Dual-acting antibacterial porous chitosan film embedded with a photosensitizer

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