NIR-emitting benzene-fused oligo-BODIPYs for bioimaging

Selvaggio, Gabriele; Nißler, Robert; Nietmann, Peter; Patalag, Lukas J.; Patra, Aditya Kumar; Janshoff, Andreas; Werz, Daniel B.; Kruss, Sebastian

doi:10.1039/d1an01850g

Cited by 12 publications

(12 citation statements)

References 53 publications

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“…[21][22][23][24] NIR-emitting organic dyes such as cyanines 25,26 (e.g. indocyanine green, ICG 27 ) and modified boron dipyrromethenes (BODIPYs [28][29][30][31] ) have been successfully employed as fluorophores of versatile chemistry for numerous studies. Additionally, NIR-fluorescent nanomaterials characterized by higher photostability have been also reported.…”

Section: Sebastian Krussmentioning

confidence: 99%

Preparation, properties and applications of near-infrared fluorescent silicate nanosheets

Selvaggio

Kruss

2022

Nanoscale

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Section: Sebastian Krussmentioning

confidence: 99%

Preparation, properties and applications of near-infrared fluorescent silicate nanosheets

Selvaggio

Kruss

2022

Nanoscale

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“…Therefore, signals in the NIR have higher tissue penetration, resulting in better signal-to-noise ratios and substantially lower phototoxicity [1] . Organic NIR fluorescent dyes such as cyanines [3,4] and modified boron dipyrromethenes (BODIPYs) [5,6] have been successfully applied for a number of biological studies, but they may have disadvantages such as fast bleaching, low quantum yield or biocompatibility. Another option is NIR fluorescent nanomaterials, such as semiconducting single-walled carbon nanotubes (SWCNTs) [7][8][9][10][11] , quantum dots [12] , or doped nanoparticles [13] .…”

Section: Introductionmentioning

confidence: 99%

Surfactant Assisted Exfoliation of Near Infrared Fluorescent Silicate Nanosheets

Hill

Abraham

Akhtar

et al. 2023

Preprint

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Fluorophores that emit light in the near infrared (NIR) are advantageous in photonics and imaging due to minimal light scattering, absorption, phototoxicity and autofluorescence in this spectral region. The layered silicate Egyptian Blue (CaCuSi4O10) emits as bulk material bright and stable fluorescence in the NIR and is a promising NIR fluorescent material for (bio)photonics. Here, we demonstrate a surfactant-based (mild) exfoliation procedure to produce nanosheets (EB-NS) of high monodispersity, heights down to 1 nm and diameters <20 nm in large quantities. The approach combines planetary ball milling, surfactant assisted bath sonication and centrifugation steps. It avoids the impurities that are typical for the harsh conditions of tip-sonication. Several solvents and surfactants were tested and we find the highest yield for sodium dodecyl benzyl sulfate (SDBS) and water. The NIR fluorescence emission (λem≈930-940 nm) is not affected by this procedure, is extremely stable and is not affected by quenchers. This enables the use of EB-NS for macroscopic patterning/barcoding of materials in the NIR. In summary, we present a simple and mild route to NIR fluorescent nanosheets that promise high potential as NIR fluorophores for optical applications.

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“…Fluorophores that emit in the NIR window (NIR-I: λ ≈ 750–1000 nm; NIR-II: λ ≈ 1000–1700 nm) present optimal characteristics for bioimaging due to reduced phototoxicity, scattering, absorption and autofluorescence of biological samples at these wavelengths. − Although organic dyes ( e.g. , indocyanine green, modified boron dipyrromethenes, − etc .) and nanomaterials ( e.g.…”

Section: Introductionmentioning

confidence: 99%

Covalently Functionalized Egyptian Blue Nanosheets for Near-Infrared Bioimaging

Selvaggio

Herrmann

Hill

et al. 2022

ACS Appl. Bio Mater.

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Fluorophores emitting in the near-infrared (NIR) wavelength region present optimal characteristics for photonics and especially bioimaging. Unfortunately, only few NIR fluorescent materials are known, and even fewer are biocompatible. For this reason, the scientific interest in designing NIR fluorophores is very high. Egyptian Blue (CaCuSi4O10, EB) is an NIR fluorescent layered silicate that can be exfoliated into fluorescent nanosheets (EB-NS). So far, its surface chemistry has not been tailored, but this is crucial for colloidal stability and biological targeting. Here, we demonstrate covalent surface functionalization of EB nanosheets (EBfunc) via Si–H activation using hydrosilanes with variable functionalities. In the first part of this work, EB-NS are grafted with the visible fluorescent pyrene (Pyr) moieties to demonstrate conjugation by colocalization of the Vis/NIR fluorescence on the (single) EB-NS level. Next, the same grafting procedure was repeated and validated with carboxyl group (COOH)-containing hydrosilanes. These groups serve as a generic handle for further (bio)functionalization of the EB-NS surface. In this way, folic acid (FA) could be conjugated to EB-NS, allowing the targeting of folic acid receptor-expressing cancer cells. These results highlight the potential of this surface chemistry approach to modify EB-NS, enabling targeted NIR imaging for biomedical applications.

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NIR-emitting benzene-fused oligo-BODIPYs for bioimaging

Abstract: Near-infrared (NIR) fluorophores are emerging tools for biophotonics because of their reduced scattering, increased tissue penetration and low phototoxicity. However, the library of NIR fluorophores is still limited. Here, we...

Cited by 12 publications

References 53 publications

Preparation, properties and applications of near-infrared fluorescent silicate nanosheets

Preparation, properties and applications of near-infrared fluorescent silicate nanosheets

Surfactant Assisted Exfoliation of Near Infrared Fluorescent Silicate Nanosheets

Covalently Functionalized Egyptian Blue Nanosheets for Near-Infrared Bioimaging

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