Fused bis-azacalixphyrin that reaches NIR-II absorptions

Lavaud, Lucien; Azarias, Cloé; Canard, Gabriel; Pascal, Simon; Galiana, Joachim; Giorgi, Michel; Chen, Zhongrui; Jacquemin, Denis; Siri, Olivier

doi:10.1039/c9cc09021e

Cited by 11 publications

(12 citation statements)

References 35 publications

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“…It was found that the PA spectra directly correlate with the absorption spectra, and a linear dependency of concentration to signal strength was observed [104]. Similarly, a dimeric fused bis-azacalixphyrin (16), sharing an aromatic unit, was reported recently, which exhibited a strong absorption band in the NIR-II window (λ max = 1029 nm, ε = 17,800 M −1 cm −1 ) [105]. This bis-fused 16 could be further fine-tuned, and PA applications are yet to be reported.…”

Section: Pa Probe Development In Nir-ii Rangementioning

confidence: 54%

Photoacoustic Imaging Probes Based on Tetrapyrroles and Related Compounds

Merkes

Zhu

Bahukhandi

et al. 2020

IJMS

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Photoacoustic imaging (PAI) is a rapidly evolving field in molecular imaging that enables imaging in the depths of ultrasound and with the sensitivity of optical modalities. PAI bases on the photoexcitation of a chromophore, which converts the absorbed light into thermal energy, causing an acoustic pressure wave that can be captured with ultrasound transducers, in generating an image. For in vivo imaging, chromophores strongly absorbing in the near-infrared range (NIR; > 680 nm) are required. As tetrapyrroles have a long history in biomedical applications, novel tetrapyrroles and inspired mimics have been pursued as potentially suitable contrast agents for PAI. The goal of this review is to summarize the current state of the art in PAI applications using tetrapyrroles and related macrocycles inspired by it, highlighting those compounds exhibiting strong NIR-absorption. Furthermore, we discuss the current developments of other absorbers for in vivo photoacoustic (PA) applications.

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Section: Pa Probe Development In Nir-ii Rangementioning

confidence: 54%

Photoacoustic Imaging Probes Based on Tetrapyrroles and Related Compounds

Merkes

Zhu

Bahukhandi

et al. 2020

IJMS

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“… 152 bis-ACP / / 894/1,029 / / / / Lavaud et al. 153 CSM2 F-127 / 878/N.A. / PAI PTT imaging-guided NIR-II PTT of tumor Shao et al.…”

Section: Nir-ii Organic Small Molecular Fluorophoresmentioning

confidence: 99%

“…Recently, several small molecules with NIR-II absorption, such as bis-ACP , CSM2 , and Zn 4 -H 2 [Pc(OC 12 H 17 ) 24 ] , have been reported to accomplish PAI-guided NIR-II PTT ( Table 1 ). 153 , 154 , 155 Among them, phthalocyanine-derived Zn 4 -H 2 [Pc(OC 12 H 17 ) 24 ] showed a high photothermal conversion efficiency of 58.3% under the 1,064-nm laser irradiation. Though these molecules had been successfully applied for NIR-II PTT, the photothermal conversion efficiency still needed to be improved.…”

Section: Nir-ii Organic Small Molecular Fluorophoresmentioning

confidence: 99%

Small Molecular NIR-II Fluorophores for Cancer Phototheranostics

et al. 2021

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Summary Phototheranostics integrates deep-tissue imaging with phototherapy (containing photothermal therapy and photodynamic therapy), holding great promise in early diagnosis and precision treatment of cancers. Recently, second near-infrared (NIR-II) fluorescence imaging exhibits the merits of high accuracy and specificity, as well as real-time detection. Among the NIR-II fluorophores, organic small molecular fluorophores have shown superior properties in the biocompatibility, variable structure, and tunable emission wavelength than the inorganic NIR-II materials. What's more, some small molecular fluorophores also display excellent cytotoxicity when illuminated with the NIR laser. This review summarizes the progress of small molecular NIR-II fluorophores with different central cores for cancer phototheranostics in the past few years, focusing on the molecular structures and phototheranostic performances. Furthermore, challenges and prospects of future development toward clinical translation are discussed.

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“…The NICS(0) was selected rather than NICS(1) so as to ensure easy comparison with our previous works. 18,19,22,23 Finally, the vertical transition energies (20 lowest states) have been determined with the rangeseparated CAM-B3LYP functional 35 and the same 6-311+G(2d,p) basis set. During the TD-DFR calculations, the solvent (DMSO) effects were modelled using the non-equilibrium linear-response formulation of the PCM-TD scheme.…”

Section: Dft and Td-dft Calculationsmentioning

confidence: 99%

“…21 To date, ACPs have been identified as photoacoustic imaging probes upon NIR excitation, and the absorption of this family of dyes has been very recently extended to the second transparency window (NIR-II), i.e., beyond 1000 nm thanks to a fused ACP dimer. 21,22 Alongside these achievements, theoretical investigations allowed to predict NIR absorptions for metallated or C-substituted ACPs, 23,24 although such structures remain to be synthesized.…”

Section: Introductionmentioning

confidence: 99%