Novel NIR-II organic fluorophores for bioimaging beyond 1550 nm

Li, Yang; Liu, Yufang; Li, Qianqian; Tian, Tian; Zhou, Wenyi; Cui, Yan; Wang, Xikun; Cheng, Xiaoding; Ding, Qihang; Wang, Xiaofei; Wu, Junzhu; Deng, Hai; Li, Yanqin; Meng, Xianli; Deng, Zixin; Hong, Xuechuan; Xiao, Yuling

doi:10.1039/c9sc06567a

Cited by 149 publications

(112 citation statements)

References 69 publications

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“…As shown in Figure A, when the phenyl‐thienyl conjugated bridges (e.g., PT, PPT, PTT) were installed on the two sides of the BBTD core, their absorption was in the region of 640–860 nm, while their emission was around 1070 nm. [ 14 ] Compared to the phenyl‐thienyl conjugated bridges, the conjugation of the triarylamine (TPA) unit was weak, but the absorption and emission were maintained almost at the same level because of the electron‐donating characters of TPA. [ 15 ] When a thiophene bridge (TPAT) was added, the absorption and emission can be up to 920 and 1150 nm, respectively.…”

Section: Resultsmentioning

confidence: 99%

Near‐Infrared Fluorescence/Photoacoustic Agent with an Intensifying Optical Performance for Imaging‐Guided Effective Photothermal Therapy

Huang

et al. 2020

Advanced Therapeutics

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Near-infrared fluorescent agents generally exhibit typical push-pull electron characteristics, and their optical behaviors are closely related to their molecular structures. Benzobisthiadiazole moiety as a classic electron acceptor has been typically used to design the Donor-Acceptor-Donor (D-AD) type of fluorescent/photoacoustic agents with emission in the second near-infrared window. In this work, two strategies are examined to intensify their absorption/fluorescence and fluorescence/photoacoustic imaging performance: 1) the conjugated bridges are amplified by installing two electron-rich thiophenes and one styrene on two sides of the benzobisthiadiazole core and 2) the N,N-dimethylamino group is employed to replace the traditional diphenylamine to strengthen the electron donor. This agent shows the maximum absorption and fluorescence emission at 942 and 1302 nm, respectively. Its superior in vitro and vivo data confirms that the nanoparticles of this compound complexed with 1,2-distearoyl-sn-glycero-3phosphoethanolamine-N-[methoxy(polyethyleneglycol)] (DSPE-PEG) can not only perform real-time and high-contrast noninvasive near-infrared fluorescence/photoacoustic imaging of tumors (980 nm laser irradiation) but also effectively ablate the tumor cells by photothermal therapy implementing the dual-modality imaging method. In particular, its longer wavelength absorption and emission successfully improves the fluorescence/ photoacoustic imaging performance. These observations highlight its potential to be used as a promising therapeutic platform for cancer.

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Section: Resultsmentioning

confidence: 99%

Near‐Infrared Fluorescence/Photoacoustic Agent with an Intensifying Optical Performance for Imaging‐Guided Effective Photothermal Therapy

Huang

et al. 2020

Advanced Therapeutics

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“…luorescence imaging in the second near-infrared window (NIR-II, 1000-1700 nm) has been widely used in biological and biomedical research, because the light in this wavelength region is capable of deep penetration, and cellular autofluorescence is minimal [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] . Our initial progress toward the first small-molecule organic NIR-II dye entailed the formation of the fluorophore CH1055 from benzo-bis(1,2,5-thiadiazole) (BBTD), which absorbed light at~750 nm and fluoresced at 1055 nm [18][19][20] .…”

mentioning

confidence: 99%

Upconversion NIR-II fluorophores for mitochondria-targeted cancer imaging and photothermal therapy

et al. 2020

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NIR-II fluorophores have shown great promise for biomedical applications with superior in vivo optical properties. To date, few small-molecule NIR-II fluorophores have been discovered with donor-acceptor-donor (D-A-D) or symmetrical structures, and upconversion-mitochondria-targeted NIR-II dyes have not been reported. Herein, we report development of D-A type thiopyrylium-based NIR-II fluorophores with frequency upconversion luminescence (FUCL) at ~580 nm upon excitation at ~850 nm. H4-PEG-PT can not only quickly and effectively image mitochondria in live or fixed osteosarcoma cells with subcellular resolution at 1 nM, but also efficiently convert optical energy into heat, achieving mitochondria-targeted photothermal cancer therapy without ROS effects. H4-PEG-PT has been further evaluated in vivo and exhibited strong tumor uptake, specific NIR-II signals with high spatial and temporal resolution, and remarkable NIR-II image-guided photothermal therapy. This report presents the first D-A type thiopyrylium NIR-II theranostics for synchronous upconversion-mitochondria-targeted cell imaging, in vivo NIR-II osteosarcoma imaging and excellent photothermal efficiency.

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“…FLI is a widely used imaging modality in the NIR‐II region that benefited from the fast development of the NIR‐II fluorescent nanomaterials and dyes 15 . Up to now, there were several types of materials that have been demonstrated for NIR‐II FLI, such as semiconducting single‐walled carbon nanotubes, 16,17 quantum dots (QDs), 18‐22 lanthanide‐doped nanoparticles, 23‐26 and organic dyes 27‐32 . Due to the minimized tissue scattering and absorption, these NIR‐II FLI contrast agents provide significantly enhanced signal‐to‐noise ratio and has achieved high‐quality imaging for a fine structure of vascular and tumor imaging in deep tissues 28,29,33 …”

Section: Imaging Modalities In the Nir‐ii Regionmentioning

confidence: 99%

Cancer nanotheranostics in the second near‐infrared window

Jiang

Huang

et al. 2020

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Nanotheranostics is an attractive and fast developing nanomedicine technology that integrates both diagnostics and therapeutics in a single nanoplatform. It ensures consistent spatiotemporal distribution and uniform targeting of the imaging and therapeutic agents, thus desirable for real‐time monitoring of in situ therapeutic effects and long‐term tailorable therapeutics in accordance to disease prognosis for personalized medicine. Optical stimuli of nanotheranostics offer easy and precise controllability to combat cancer. Compared with the conventional use of visible and the first near‐infrared region light, using the second near‐infrared (NIR‐II) region light as the incident excitation enables cancer nanotheranostics to go deeper and with enhanced theranostic efficiency. Realizing the extraordinary advantages of accomplishing cancer nanotheranostics in the NIR‐II region, burgeoning research efforts were devoted to this field. This review aims to analyze the available imaging and therapeutic approaches to realize nanotheranostics in the NIR‐II region, and to summarize the current applications of cancer nanotheranostics in the NIR‐II region. In the end, we will discuss the challenges and outlook on the possible perspectives in the field.

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Novel NIR-II organic fluorophores for bioimaging beyond 1550 nm

Abstract: Novel NIR-II organic fluorophores were designed and synthesized using an AIE and highly twisted donor–acceptor distortion strategy for bio-imaging beyond 1550 nm.

Cited by 149 publications

References 69 publications

Near‐Infrared Fluorescence/Photoacoustic Agent with an Intensifying Optical Performance for Imaging‐Guided Effective Photothermal Therapy

Near‐Infrared Fluorescence/Photoacoustic Agent with an Intensifying Optical Performance for Imaging‐Guided Effective Photothermal Therapy

Upconversion NIR-II fluorophores for mitochondria-targeted cancer imaging and photothermal therapy

Cancer nanotheranostics in the second near‐infrared window

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