Water-Soluble NIR-Absorbing Rylene Chromophores for Selective Staining of Cellular Organelles

Kaloyanova, Stefka; Zagranyarski, Yulian; Ritz, Sandra; Mária, Hanulová; Koynov, Kaloian; Vonderheit, Andreas; Müllen, Kläus; Peneva, Kalina

doi:10.1021/jacs.5b10425

Cited by 70 publications

(46 citation statements)

References 37 publications

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“…The 650 nm wavelength can be used in monitoring the conjugate during purification with C18 Reversed Phase LC Column. The emission peak at ~680 nm is located in the near-infrared (NIR) transparent biological window (650–900 nm), and optical range is preferred for clinical translation because of its deeper penetration through overlying biological tissue [29,30,31,32,33]. The absorption and emission spectra of Cy5-B and Cy5-BF 3 ( 18 F) are nearly identical.…”

Section: Resultsmentioning

confidence: 99%

A Conjugate of Pentamethine Cyanine and 18F as a Positron Emission Tomography/Near-Infrared Fluorescence Probe for Multimodality Tumor Imaging

Kommidi

Chen

et al. 2017

IJMS

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The novel synthesis of a dual-modality, pentamethine cyanine (Cy5) fluorescent, 18F positron emission tomography (PET) imaging probe is reported. The probe shows a large extinction coefficient and large quantum yield in the biologically transparent, near-infrared window (650–900 nm) for in vivo fluorescent imaging. This fluorophore bears the isotope, 18F, giving a 18F-PET/near-infrared fluorescent (NIRF), bi-modal imaging probe, that combines the long-term stability of NIRF and the unlimited penetration depth of PET imaging. The bi-modal probe is labeled with 18F in a quick, one-step reaction, which is important in working with the rapid decay of 18F. The bi-modal probe bears a free carboxyl group, highlighting a PET/NIRF synthon that can be conjugated onto many advanced biomolecules for biomarker-specific in vivo dual-modal PET/NIR tumor imaging, confocal histology, and utility in multi-fluorophore, fluorescence-guided surgery. Its potential in vivo biocompatibility is explored in a quick proof-of-principal in vivo study. The dye is delivered to A549 xenograft flank-tumors to generate PET and NIRF signals at the tumor site. The tumor distribution is confirmed in ex vivo gamma counting and imaging. Pentamethine cyanine (Cy5) has the ability to preferentially accumulate in tumor xenografts. We substitute the PET/NIRF probe for Cy5, and explore this phenomenon.

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Section: Resultsmentioning

confidence: 99%

A Conjugate of Pentamethine Cyanine and 18F as a Positron Emission Tomography/Near-Infrared Fluorescence Probe for Multimodality Tumor Imaging

Kommidi

Chen

et al. 2017

IJMS

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“…Because cereulide is not soluble in water,arequisite of the fluorogenic probe is that it have good performance in organic or mixed organic-aqueous solvents. Therefore, we selected ap erylenemonoimidea st he fluorescentr eporter [12] and aK + -selective phenylaza[18]crown-6-lariat-ether [13] or at riazacryptand [14] as the recognition units and bonded both moieties in every case by Suzuki coupling (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Potassium‐Ion‐Selective Fluorescent Sensors To Detect Cereulide, the Emetic Toxin of B. cereus, in Food Samples and HeLa Cells

et al. 2017

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We report the development of new chemical probes for cereulide, a toxic metabolite produced by specific strains of Bacillus cereus, through displacement of potassium cations from a preformed specific complex and a subsequent change in the fluorescence emission. For this purpose, we designed fluorescent probes for potassium cations that were suitable for displacement assays with cereulide from organic extracts. The fluorescence detection of natural cereulide in rice samples was achieved by using synthetic cereulide as a reference and a potassium fluorescent reporter, and this was found to be useful as a portable and fast method for the in situ detection of cereulide in food extracts. To study the fate of cereulide in live cells, we designed a procedure that was suitable for live‐cell microscopy imaging of HeLa cells by comparing the cellular location of the potassium fluorogenic probe, which stained intracellular endolysosomes, in the absence and presence of cereulide; we concluded that in the presence of cereulide, the fluorescence of the probe was decreased because of complexation of the potassium ions by cereulide.

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“…After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (dichloromethane/hexane = 1/10, v/v) to give a sticky oil (3.6 g, 67.1%). 1 13 2-(5-Tributyltinthiophen-2-yl)-9,9-bis(6′-bromohexyl)fluorene (6). Compound 6 was prepared similarly as described for compound 4.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Water-Soluble Conjugated Oligoelectrolytes for Near-Infrared Fluorescence Biological Imaging

Woo

Park

Jeong

et al. 2016

ACS Appl. Mater. Interfaces

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Near-infrared (NIR) fluorophores attract increasing attention as a molecular marker (or probe) for in vivo and in vitro biological fluorescence imaging. Three types of new NIR fluorescent conjugated oligoelectrolytes (COEs: Q-FlTBTTFl, Q-FlBBTFl, and Q-FlTBBTTFl) are synthesized with quaternized ammonium ionic groups in their side-chains for water solubility. The emission wavelength is modulated in the range 600-1300 nm, by adjusting the intramolecular charge transfer in the molecular backbone based on the electron-rich fluorene (and/or thiophene) and electron-deficient benzo[2,1,3]thiadiazole (or benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole) moieties. The COEs show a remarkably larger Stokes shift (147-276 nm) compared to commercial rhodamine and cyanine dyes in water, avoiding self-quenching and interference from the excitation backscattered light. The photoluminescence (PL) quantum efficiency is improved substantially by up to 27.8% in water by fabricating a vesicular complex, COE/v, with a block ionomer, poly[(ethylene oxide)-block-(sodium 2-acrylamido-2-methyl-1-propanesulfonate)]. In vitro cellular uptake images with the COEs are obtained with good biocompatibility by confocal single-photon and two-photon microscopy. The ex vivo and in vivo images of a mouse xenograft model treated with the Q-FlBBTFl/v exhibit a substantially stronger fluorescence signal at the tumor site than at the other organs, highlighting the potential of the COE/v as an NIR fluorescent imaging agent for the diagnosis of cancer.

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Water-Soluble NIR-Absorbing Rylene Chromophores for Selective Staining of Cellular Organelles

Cited by 70 publications

References 37 publications

A Conjugate of Pentamethine Cyanine and 18F as a Positron Emission Tomography/Near-Infrared Fluorescence Probe for Multimodality Tumor Imaging

A Conjugate of Pentamethine Cyanine and 18F as a Positron Emission Tomography/Near-Infrared Fluorescence Probe for Multimodality Tumor Imaging

Potassium‐Ion‐Selective Fluorescent Sensors To Detect Cereulide, the Emetic Toxin of B. cereus, in Food Samples and HeLa Cells

Synthesis and Characterization of Water-Soluble Conjugated Oligoelectrolytes for Near-Infrared Fluorescence Biological Imaging

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