Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

Yan, Dingyuan; Wu, Qian; Wang, Dong; Tang, Ben Zhong

doi:10.1002/anie.202006191

Cited by 87 publications

(47 citation statements)

References 166 publications

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“…On the one hand, the observed increase in fluorescence is fully consistent with the ESPT fluorescence mechanism because water can also interact with the solute through the formation of hydrogen bonds [37]. On the other hand, aggregation-induced emission (AIE) should not be ruled out [42][43][44]. In this case, water is considered as an aggregating solvent, while DMSO, i-PrOH or THF are known to be non-aggregating solvents, and the aggregates formed are able to fluoresce as a result of a reduced possibility of nonradiative relaxation.…”

Section: Photophysical Properties Of Cinnoline-based Azide-amine Pairsupporting

confidence: 61%

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

et al. 2021

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A new type of fluorogenic and fluorochromic probe based on the reduction of weakly fluorescent 4-azido-6-(4-cyanophenyl)cinnoline to the corresponding fluorescent cinnoline-4-amine was developed. We found that the fluorescence of 6-(4-cyanophenyl)cinnoline-4-amine is strongly affected by the nature of the solvent. The fluorogenic effect for the amine was detected in polar solvents with the strongest fluorescence increase in water. The environment-sensitive fluorogenic properties of cinnoline-4-amine in water were explained as a combination of two types of fluorescence mechanisms: aggregation-induced emission (AIE) and excited state intermolecular proton transfer (ESPT). The suitability of an azide–amine pair as a fluorogenic probe was tested using a HepG2 hepatic cancer cell line with detection by fluorescent microscopy, flow cytometry, and HPLC analysis of cells lysates. The results obtained confirm the possibility of the transformation of the azide to amine in cells and the potential applicability of the discovered fluorogenic and fluorochromic probe for different analytical and biological applications in aqueous medium.

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Section: Photophysical Properties Of Cinnoline-based Azide-amine Pairsupporting

confidence: 61%

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

et al. 2021

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“…The resulting photodynamic nanospheres with negative charges killed more than 99% of spherical bacteria but less than 1% of rod-shaped bacteria [3]. Rather than quenching ROS generation for traditional PSs [46], aggregation boosts ROS generation for AIE-PSs [47]. Therefore, AIE-PSs are promising candidates to form photodynamic nanospheres by simple aggregation without further decoration.…”

Section: Introductionmentioning

confidence: 99%

A new class of nitrobenzoic acid-based AIE photosensitizers for highly efficient photodynamic antibacterial therapy

et al. 2021

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Photodynamic therapy (PDT) has been drawing more and more attention in the antibacterial field. Traditional photosensitizers (PSs) tend to aggregate in aqueous media, which reduces the generation of reactive oxygen species (ROS) and seriously affects the photodynamic efficacy. Many efforts have been made to prevent aggregation of traditional PSs. By contrast, aggregation-induced emission PSs (AIE-PSs) take advantage of aggregation to boost ROS generation and fluorescence intensity. However, the efficacies of the reported antibacterial AIE-PSs are poor. Herein, we report a new class of highly effective antibacterial AIE-PSs based on nitrobenzoic acid structure. TTVBA, a negatively charged AIE-PS, can not only selectively kill spherical bacteria (Staphylococcus aureus (S. aureus)) rather than rod-shaped bacteria (Escherichia coli (E. coli)), but also be easily extended to several AIE-PSs (TTVBP1-3) with positive charges and broad-spectrum antibacterial activity. We demonstrate that TTVBP2 can kill 3.0 log 10 of S. aureus at very low concentration (125 nmol L −1 ), TTVBP3 can kill 4.7 log 10 of Staphylococcus epidermidis (S. epidermidis) at a concentration of 1 µmol L −1 and 3.8 log 10 of E. coli at 5 µmol L −1 , thus enabling them among the most effective antibacterial AIE-PSs reported so far. Meanwhile, these AIE-PSs exhibit excellent wash-free imaging ability for bacteria by simple mixing with bacteria. We thus envision that TTVBA, a nitrobenzoic acid-based extendable AIE-PS, provides a new route for the design of AIE-PSs in antibacterial treatment.

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“…DOX is a well‐known aggregation‐caused quench dye, which has a fluorescence quenching effect when loaded in the DNA‐tetra skeleton. In order to enhance DOX fluorescence, DSAI, a fluorescent probe with typical aggregation‐induced emission (AIE) features, [ 22 ] is also loaded in the DNA‐tetra structure mainly via intercalation, presenting green fluorescence. FRET process proceeds from DSAI to DOX, which efficiently enhances the emission intensity of DOX, resulting in bright red fluorescence of the fabricated DNA nanomaterial.…”

Section: Introductionmentioning

confidence: 99%

Graphene Oxide Based Fluorescent DNA Aptasensor for Liver Cancer Diagnosis and Therapy

Liu

Wang

et al. 2021

Adv Funct Materials

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Graphene-oxide based fluorescent DNA aptasensors for the in vivo application remain a challenging task. We demonstrate for the first time such a nanomaterial for in vivo diagnosis and therapy of liver tumor with good biocompatibility and high selectivity. This DNA nanomaterial comprising of DNA tetrahedron and aptamers, aggregation-induced emission luminogen (AIEgens) and antitumor drug doxorubicin, is fabricated and attached on GO surface. Additionally, this GO-based fluorescent DNA nanodevice is also constructed by using microfluidic chip for liver tumor cell screening. File list (2) download file view on ChemRxiv Manuscript 20210308-Ke净版.docx (2.26 MiB) download file view on ChemRxiv Manuscript 20210308-Ke净版.pdf (1.27 MiB)

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Innovative Synthetic Procedures for Luminogens Showing Aggregation‐Induced Emission

Cited by 87 publications

References 166 publications

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

A new class of nitrobenzoic acid-based AIE photosensitizers for highly efficient photodynamic antibacterial therapy

Graphene Oxide Based Fluorescent DNA Aptasensor for Liver Cancer Diagnosis and Therapy

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