Capturing aqueous [18F]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [18F]-labeled aryltrifluoroborate

Ting, Richard; Lo, Justin; Adam, Michael J.; Ruth, Thomas J.; Perrin, David M.

doi:10.1016/j.jfluchem.2008.01.011

Cited by 41 publications

(44 citation statements)

References 12 publications

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“…If a PET scanner is not available, standard scintigraphic devices can still be used to register the positron-generated γ-rays (42−44). Consistent with previous studies of 18 F-labeled aryltrifluoroborates, no signal is observed in bone structure (Figures 3A and 4), demonstrating the in vivo stability of the aryl trifluoroborate to solvolysis and release of free 18 F (22,23,45). …”

Section: Discussionsupporting

confidence: 91%

Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

et al. 2010

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We combine a novel boronate trap for F− with a near-infrared fluorophore into a single molecule. Attachment to targeting ligands enables localization by positron emission tomography (PET) and near-infrared fluorescence (NIRF). Our first application of this generic tag is to label Lymphoseek (tilmanocept), an agent designed for receptor-specific sentinel lymph node (SLN) mapping. The new conjugate incorporates 18F− in a single, aqueous step, targets mouse SLN rapidly (1 h) with reduced distal lymph node accumulation, permits PET or scintigraphic imaging of SLN, and enables NIRF-guided excision and histological verification even after 18F decay. This embodiment is superior to current SLN mapping agents such as nontargeted [99mTc]sulfur colloids and Isosulfan Blue, as well as the phase III targeted ligand [99mTc]SPECT Lymphoseek counterpart, species that are visible by SPECT or visible absorbance separately. Facile incorporation of 18F into a NIRF probe should promote many synergistic PET and NIRF combinations.

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Section: Discussionsupporting

confidence: 91%

Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

et al. 2010

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“…Indeed a Hammett analysis demonstrated that the rate constant for solvolytic defluoridation was found to correlate log-linearly with standard s-values (r $ À1). This finding provided a chemical rationale as to why various aryltrifluoroborates are readily solvolyzed in water while others are considerably more stable [6], and guided the screening, identification, and synthesis of two chemically similar aryltrifluoroborates with extraordinary aqueous stability which was attributed to judicious placement of electron withdrawing substituents on the aryl ring [7,8]. One of these compositions was subsequently affixed to biotin and its in vivo stability was imaged by 18 F-PET [7].…”

Section: Introductionmentioning

confidence: 94%

Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH

Asadi

Perrin

2009

Journal of Fluorine Chemistry

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“…Thus it is desirable to minimize the amount of excess precursor to maintain high SA. In macroscale reactions this is difficult, because the [46,47]. It should be noted that the same principles can be applied to other carrier-added situations or to the labeling of proteins or other species where the labeled and unlabeled forms cannot be separated; in all such cases, it is critical to minimize the starting material in order to obtain high SA.…”

Section: High Specific Activitymentioning

confidence: 99%

Advantages of Radiochemistry in Microliter Volumes

Keng

Sergeev

Dam

2016

Perspectives on Nuclear Medicine for Molecular Diagnosis and Integrated Therapy

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Positron emission tomography (PET) provides quantitative 3D visualization of physiological parameters (e.g., metabolic rate, receptor density, gene expression, blood flow) in real time in the living body. By enabling measurement of differences in such characteristics between normal and diseased tissues, PET serves as vital tool for basic research as well as for clinical diagnosis and patient management. Prior to a PET scan, the patient is injected with a short-lived tracer labeled with a positron-emitting isotope. Safe preparation of the tracer is an expensive process, requiring specially trained personnel and high-cost equipment operated within hot cells. The current centralized manufacturing strategy, in which large batches are prepared and divided among many patients, enables the most commonly used tracer (i.e., [ 18 F]FDG) to be obtained at an affordable price. However, as the diversity of tracers increases, other strategies for cost reduction will become necessary. This challenge is being addressed by the development of miniaturized radiochemistry instrumentation based on microfluidics. These compact systems have the potential to significantly reduce equipment cost and shielding while increasing diversity of tracers produced in a given facility. The most common approach uses "flow-through" microreactors, which leverage the ability to precisely control reaction conditions to improve synthesis times and yields. Several groups have also developed "batch" microreactors which offer significant additional advantages such as reduced reagent consumption, simpler purifications, and exceptionally high specific activity, by reducing operating volumes by orders of magnitude. In this chapter, we review these "batch" approaches and the advantages of using small volumes, with special emphasis on digital microfluidics, in which reactions have been performed with volumes as low as~1 μL.

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Capturing aqueous [18F]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [18F]-labeled aryltrifluoroborate

Cited by 41 publications

References 12 publications

Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH

Advantages of Radiochemistry in Microliter Volumes

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Capturing aqueous [18F]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [18F]-labeled aryltrifluoroborate

Cited by 41 publications

References 12 publications

Fast 18F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

Fast 18F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH

Advantages of Radiochemistry in Microliter Volumes

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Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

Fast ¹⁸F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes