J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

Liu, Zhipeng; Li, Kang; Duan, Xingchen; Jiang, Zhiyong; Zhang, Guoqiang; Chen, Yuncong

doi:10.21203/rs.3.rs-122847/v1

Cited by 6 publications

(10 citation statements)

References 40 publications

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“…In spite of the 3D geometry of the IRFP898 has not been reported, a ring shape of IRFP898 with the 16 α , 16 β helix subunits and 32 bacteriochlorophyll a could still be demonstrated by cryo-EM with 8.5 Å resolution. 40 As revealed by the cryo-EM, the bacteriochlorophylls of IRFP1032 are arranged in the head to tail structure to form the so-called J aggregation, 38,41–43 Figure 1b, 1d. The strong electronic coupling between the J aggregated chlorophylls renders the individual chlorophylls to act coherently as a single molecule.…”

Section: Resultsmentioning

confidence: 99%

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Near Infrared-II Fluorescent protein for In-vivo Imaging

Sun

2022

Preprint

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In vivo fluorescent imaging in the second near-infrared window (NIR-II) provides an excellent approach for understanding the biological processes in substantially scattered tissue environments with reasonable temporal-spatial resolution. In spite of an enormous amount of organic and inorganic NIR-II fluorophores developed, there is no NIR-II fluorescent protein reported. Here, we present the first NIR-II fluorescent protein, IRFP1032 which exhibits strong exciton absorption and emission in the NIR-II region, with exciton extinction coefficient about 4.1 ×106 M-1cm-1 at the excitation maximum 1008 nm, emission maximum of 1032 nm, and emission quantum yield about 0.84%. The IRFP1032 is found to be the brightest NIR-II fluorophore ever reported (brightness of 3.4 × 104 M-1cm-1 in PBS) which is thousands-fold brighter than IR26 in DCM. Taking the advantage of the excellent photo-properties of the NIR-II fluorescent proteins, a collection of high-quality in vivo imaging research was realized, for instance, real time observation of blood flow dynamics, dual-channel imaging of the lymphatic/blood vessel network and the trajectories of single bacterial cell travelling in blood vessels. Moreover, a mammalian expression vector was constructed for the IRFP1032, and the corresponding NIR-II fluorescence was able to be recorded unambiguously. The promising NIR-II in vivo imaging properties of IRPF1032 demonstrated here would open a new scene in fluorescent protein-based imaging.

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Section: Resultsmentioning

confidence: 99%

“…As revealed by the cryo-EM, the bacteriochlorophylls of IRFP1032 are arranged in the head to tail structure to form the so-called J aggregation, 38,[41][42][43] Figure 1b, 1d. The strong electronic coupling between the J aggregated chlorophylls renders the individual chlorophylls to act coherently as a single molecule.…”

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confidence: 99%

Near Infrared-II Fluorescent protein for In-vivo Imaging

Sun

2022

Preprint

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“…The well-known J/H aggregation would introduce strong electronic coupling leading to a red/blue shifted absorption in comparison to the individual molecule, as illustrated in Figure 2e. 30,31 In most of the cases, the aggregated molecules orient to each other neither in the ideal H nor J geometry. Nevertheless, the electronic coupling between each other remains significant.…”

Section: Aggregation Of Moleculesmentioning

confidence: 99%

Molecular Aggregation Induced Photoacoustics for NIR-II in vivo Imaging

Chang

Liu

et al. 2022

Preprint

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Molecular aggregation induced photo-properties alteration has been found to play a crucial role in the light induced processes, such as aggregation induced emission (AIE) and J aggregation induced dramatic absorption red shift. The light induced acoustic process (photoacoustic) is also considered to be one of the most essential characters of the light absorbing molecules. However, to the best of our knowledge, the molecular aggregation induced photoacoustic effect (MAIPA) has never been reported. Herein, we report the first MAIPA effect for which the PA intensity is dominated by the molecular aggregation, rather than by absorbance as usual concerned. Molecular aggregation induces a strong electronic coupling effect, resulting in significant absorption suppression from the individual state to highly aggregated state (around 5 molecules aggregated). However, the corresponding PA efficiency was found to be about 2-orders of magnitude greater for the latter. A well-behaved linear correlation between the molecular aggregation level and MAIPA effect was observed. The surprisingly significant MAIPA effect was realized via novel NIR-II squaraine-benzothiopyrylium dyes. Excellent photophysical properties of the novel NIR-II dyes were achieved, such as large absorption extinction coefficient and high photostability. Thanks to the relatively narrow FWHM and the high PA efficiency of SQN2@PMAOPEG and ZC825@BSA, in vivo multiplex PA imaging was demonstrated for tumor tissue and macrophage cells, blood and lymphoid vessels.

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“…As one of the most famous classical dyes, BODIPY (4,4-difluoro-4-bora-3a,4a-diazas-indacene) dyes (29) are recently recognized as promising J-aggregation scaffolds in parallel with cyanine, squaraine, perylenediimide, and chlorophyll dyes (30)(31)(32)(33)(34). Numbers of NIR-Iabsorbing BODIPY J-aggregates were developed and demonstrated the application potential in biophotonics (35)(36)(37)(38)(39)(40)(41)(42).…”

Section: Introductionmentioning

confidence: 99%

Discovery of BODIPY J-aggregates with absorption maxima beyond 1200 nm for biophotonics

et al. 2022

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Organic dyes with absorption maxima in the second near-infrared window (NIR-II; 1000 to 1700 nm) are of great interest in biophotonics. However, because of the lack of appropriate molecular scaffolds, current research in this field is limited to cyanine dyes, and developing NIR-II–absorbing organic dyes for biophotonics remains an immense challenge. Here, we rationally designed an ethenylene-bridged BODIPY scaffold featuring excellent J-aggregation capabilities and revealed that the bridging ethylene unit is crucial for intermolecular J-coupling regulation. By integrating the electron-donating groups into the scaffold, we obtained a BODIPY dye, BisBDP2, with a J-aggregate absorption maximum of around 1300 nm. BisBDP2 J-aggregates show excellent photothermal performance, including intense photoacoustic response, and a high photothermal conversion efficiency value of 63%. In vivo results demonstrate the potential of J-aggregates for photoacoustic imaging and photothermal ablation of deep-seated tumors. This study will speed up the exploration of NIR-II–absorbing J-aggregates for future biophotonic applications.

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J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

Cited by 6 publications

References 40 publications

Near Infrared-II Fluorescent protein for In-vivo Imaging

Near Infrared-II Fluorescent protein for In-vivo Imaging

Molecular Aggregation Induced Photoacoustics for NIR-II in vivo Imaging

Discovery of BODIPY J-aggregates with absorption maxima beyond 1200 nm for biophotonics

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