Water-Soluble Aza-BODIPYs: Biocompatible Organic Dyes for High Contrast <i>In Vivo</i> NIR-II Imaging

Godard, Amélie; Kalot, Ghadir; Pliquett, Jacques; Busser, Benoît; Guével, Xavier Le; Wegner, K. David; Resch‐Genger, Ute; Rousselin, Yoann; Coll, Jean‐Luc; Denat, Franck; Bodio, Ewen; Goze, Christine; Sancey, Lucie

doi:10.1021/acs.bioconjchem.0c00175

Cited by 69 publications

(68 citation statements)

References 34 publications

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“…To investigate the tumor cell accumulation capacity of aza-SWIR-BSH-01 compounds, the first set of experiments was conducted on brain tumor cells U-251 MG and U-87 MG using SWIR-WAZABY-01, a SWIR emitting aza-BODIPY structurally close to aza-SWIR-BSH-01 but without BSH (see Godard et al [29]). While the fluorescent signal of SWIR-WAZABY-01 was more compatible with in vivo experiments, due to its emission in the SWIR optical region, it was still detectable by conventional fluorescence microscopy for in vitro investigations.…”

Section: In Vitro Distribution and Bnct Efficacymentioning

confidence: 99%

“…The main challenge of this compound was its fluorescence emission properties that can mostly be measured after 800 nm. A dedicated confocal We recently reported the use of a B-functionalized aza-BODIPY emitting in the SWIR region and accumulating in tumors via EPR effect (Enhanced permeability and retention effect) with high and prolonged Tumor/Healthy Muscle ratio (between 5 and 30, from 24 to 168 h post-injection) without the need of tethering vector [29]. SWIR fluorophores enable to reach a penetration depth of 1 to 10 mm with increased resolution of the images as compared to those obtained with NIR-I probes [42,43].…”

Section: In Vitro Distribution and Bnct Efficacymentioning

confidence: 99%

“…For preclinical studies, optical imaging (OI) can be also used [25,26]. Among the different optical probes, boron-dipyrromethene dyes (BODIPYs, Figure 1a) are very versatile organic fluorophores with tunable optical properties from the visible to the NIR-I (Near Infrared) and SWIR (Short Wave Infrared) optical windows [27][28][29], which display excellent photophysical properties controlled by substitution pattern conferring a strong interest for these compounds as theranostic tools [30,31]. Moreover, the fluorine atoms on the boron could be substituted by acetylides bearing ammonium groups for engrafting functional groups to increase the water-solubility and to conjugate them with chelates for OI/PET, OI/SPECT bimodal imaging [32][33][34][35], and therapeutic moieties [31,36,37].…”

Section: Introductionmentioning

confidence: 99%

“…Very recently, we used this strategy on a particular Donor-Acceptor-Donor' aza-BODIPY structure, which emits in the SWIR region, yielding a water-soluble derivative SWIR-WAZABY-01 (See the ESI and Reference [29]; WAZABY for Water-Soluble aza-BODIPY). SWIR-WAZABY-01 could accumulate in vivo very efficiently at the tumor site, without any vectorization, showing high SWIR contrast for up to one week [29]. aza-SWIR-BSH-01, (d) absorption and emission spectra of aza-SWIR-BSH-01 in DMSO [29].…”

Section: Introductionmentioning

confidence: 99%

“…SWIR-WAZABY-01 could accumulate in vivo very efficiently at the tumor site, without any vectorization, showing high SWIR contrast for up to one week [29]. aza-SWIR-BSH-01, (d) absorption and emission spectra of aza-SWIR-BSH-01 in DMSO [29].…”

Section: Introductionmentioning

confidence: 99%

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Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Kalot

Godard

Busser

et al. 2020

Cells

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Boron neutron capture therapy (BNCT) is a radiotherapeutic modality based on the nuclear capture of slow neutrons by stable 10B atoms followed by charged particle emission that inducing extensive damage on a very localized level (<10 μm). To be efficient, a sufficient amount of 10B should accumulate in the tumor area while being almost cleared from the normal surroundings. A water-soluble aza-boron-dipyrromethene dyes (BODIPY) fluorophore was reported to strongly accumulate in the tumor area with high and BNCT compatible Tumor/Healthy Tissue ratios. The clinically used 10B-BSH (sodium borocaptate) was coupled to the water-soluble aza-BODIPY platform for enhanced 10B-BSH tumor vectorization. We demonstrated a strong uptake of the compound in tumor cells and determined its biodistribution in mice-bearing tumors. A model of chorioallantoic membrane-bearing glioblastoma xenograft was developed to evidence the BNCT potential of such compound, by subjecting it to slow neutrons. We demonstrated the tumor accumulation of the compound in real-time using optical imaging and ex vivo using elemental imaging based on laser-induced breakdown spectroscopy. The tumor growth was significantly reduced as compared to BNCT with 10B-BSH. Altogether, the fluorescent aza-BODIPY/10B-BSH compound is able to vectorize and image the 10B-BSH in the tumor area, increasing its theranostic potential for efficient approach of BNCT.

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Section: In Vitro Distribution and Bnct Efficacymentioning

confidence: 99%

Section: In Vitro Distribution and Bnct Efficacymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Kalot

Godard

Busser

et al. 2020

Cells

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Light‐Responsive Nanoassemblies: Advancing Biomedical Innovation

Sia,

Tey,

Low

2024

Adv Funct Materials

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The integrative use of light and nanoassemblies has made a profound impact in the biomedical field for diagnosis, drug delivery, and phototherapy. Recent advances in the development of light‐responsive nanoassemblies showcase their capabilities in facilitating targeted diagnosis and therapy with minimal invasiveness, shaping the future of personalized medicine. In this work, the fundamental differences between types of light in biomedical applications, and the application of light‐responsive nanoassemblies in diagnosis and therapy are described, their biosafety profile is overviewed and discussed, and the translational challenges and potential clinical outlook of this emerging field are outlined.

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Rigidity Bridging Flexibility to Harmonize Three Excited‐State Deactivation Pathways for NIR‐II‐Fluorescent‐Imaging‐Guided Phototherapy

Huang

Yang

et al. 2021

Adv Healthcare Materials

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Small organic phototherapeutic molecules of the second near-infrared (NIR-II) window (1000-1700 nm) serve as promising candidates for theranostics. However, developing such versatile agents for fluorescence-guided photodynamic/photothermal therapy remains a demanding task stirred by competitive energy dissipation pathways, including radiative decay, internal conversion, and intersystem crossing. To the best of current knowledge, the current paradigm for addressing the issue has deliberately approached the optimum balance among three deactivation processes through offsetting from each other, possibly leading to a comprehensively compromised theranostic efficacy. Few reports aim to modulate the three deactivation pathways excluding sacrificing any one of them. Herein, a molecular design strategy to construct a phototherapeutic organic fluorophore CCNU-1060, armed with NIR-II luorescence-guided phototherapeutic properties, is rationally developed. With a flexible motor, tetraphenylethene, bridged to the rigidified coplanar core boron-azadipyrromethene, the desired CCNU-1060 is subsequently encapsulated into an amphiphilic matrix to form CCNU-1060 nanoparticles (NPs), which match or transcend its precursor NJ-1060 NPs in the three energy dissipation processes. CCNU-1060 NPs are utilized to realize high-spatial vessel imaging and effective NIR-II fluorescence-guided phototherapeutic tumor ablation. This study unlocks a viewpoint of molecular engineering that simultaneously regulates multiple energy dissipation pathways for the construction of versatile phototherapy agents.

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Water-Soluble Aza-BODIPYs: Biocompatible Organic Dyes for High Contrast In Vivo NIR-II Imaging

Cited by 69 publications

References 34 publications

Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Aza-BODIPY: A New Vector for Enhanced Theranostic Boron Neutron Capture Therapy Applications

Light‐Responsive Nanoassemblies: Advancing Biomedical Innovation

Rigidity Bridging Flexibility to Harmonize Three Excited‐State Deactivation Pathways for NIR‐II‐Fluorescent‐Imaging‐Guided Phototherapy

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