From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates

Liu, Zhibo; Chao, D. S.; Li, Ying; Ting, Richard; Oh, Jaewhan; Perrin, David M.

doi:10.1002/chem.201405829

Cited by 55 publications

(48 citation statements)

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“…18 Between the publication of these two studies, an exhaustive and highly detailed examination of organotrifluoroborate hydrolysis was carried out by Lennox and Lloyd-Jones, largely under conditions reminiscent of those used in Suzuki coupling reactions (THF/H 2 O, Cs 2 CO 3 , 55°C). 19 This study revealed that although some organotrifluoroborate reagents (e.g., isopropyl, β-styryl, anisyl) hydrolyzed directly and rapidly to generate the corresponding boronic acid derivatives, others (e.g., alkynyl, p-nitrophenyl) hydrolyze extremely slowly, in line with the observations of Perrin.…”

Section: Perspectivementioning

confidence: 99%

Organotrifluoroborates: Another Branch of the Mighty Oak

2015

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Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules. Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure. Currently >600 structurally diverse reagents of this class are commercially available, and >850 such compounds have been reported from the author's laboratory. The organotrifluoroborates can be utilized as shelf-stable precursors to a variety of end products through simple functional group transformations and have also been employed as partners in cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or individual formats. Within the realm of cross-coupling reactions, organotrifluoroborates provide a practical entry to substructural entities not readily accessed using other organometallic reagents, and most recently, the development of a novel mechanistic paradigm for cross-coupling promises to expand the range of accessible cross-coupling partners even further to include both single- and two-electron processes.

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Section: Perspectivementioning

confidence: 99%

Organotrifluoroborates: Another Branch of the Mighty Oak

2015

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“…The first problem was solved by designing and synthesizing a new generation of organotrifluoroborates that are stable in vivo 22,23 . The second problem was largely solved by exploring 18 F radiolabeling at high levels of activity to increase the specific activity of 18 F radiotracers up to ~555 GBq/µmol (refs.…”

Section: Introductionmentioning

confidence: 99%

“…7,24), which is orders of magnitude higher than in our previous reports 25–27 . Nevertheless, to advance this approach to a general and clinician-friendly method, we developed a novel B- 18 F radiosynthon by screening a series of organotrifluoroborates 22 . This compound combines high in vivo stability, synthetic and bioconjugation simplicity, and convenient 18 F-labeling technology, which is based on 18 F- 19 F isotope exchange (IEX) of the 19 F-containing modified biomolecule 28 , and it represents the core of this protocol and has smoothly solved the third problem 22 .…”

Section: Introductionmentioning

confidence: 99%

One-step 18F labeling of biomolecules using organotrifluoroborates

et al. 2015

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Herein we present a general protocol for the functionalization of biomolecules with an organotrifluoroborate moiety so that they can be radiolabeled with aqueous 18F fluoride (18F−) and used for positron emission tomography (PET) imaging. Among the β+-emitting radionuclides, fluorine-18 (18F) is the isotope of choice for PET, and it is produced, on-demand, in many hospitals worldwide. Organotrifluoroborates can be 18F-labeled in one step in aqueous conditions via 18F–19F isotope exchange. This protocol features a recently designed ammoniomethyltrifluoroborate, and it describes the following: (i) a synthetic strategy that affords modular synthesis of radiolabeling precursors via a copper-catalyzed ‘click’ reaction; and (ii) a one-step 18F-labeling method that obviates the need for HPLC purification. Within 30 min, 18F-labeled PET imaging probes, such as peptides, can be synthesized in good chemical and radiochemical purity (>98%), satisfactory radiochemical yield of 20–35% (n > 20, non-decay corrected) and high specific activity of 40–111 GBq/µmol (1.1–3.0 Ci/µmol). The entire procedure, including the precursor preparation and 18F radiolabeling, takes 7–10 d.

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“…Less than 1% [ 19 F]- 4 defluoridation is observed following 7 days of room temperature incubation with fetal bovine serum in 19 F NMR fluoride studies (Supporting Information Figure S1). 35 …”

Section: Methodsmentioning

confidence: 99%

¹⁸F-Positron Emitting/Trimethine Cyanine-Fluorescent Contrast for Image-Guided Prostate Cancer Management

et al. 2018

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[18/19F]-4, an anionic GCPII/PSMA inhibitor for image-guided intervention in prostate cancer, is described. [19F]-4 is radiolabeled with a radiochemical yield that is ≥27% and a molar activity of 190 ± 50 mCi/μmol in a <1 h, one-step, aqueous isotopic exchange reaction. [19F]-4 allows PSMA expression to be imaged by fluorescence (FL) and [18F]-PET. PC3-PIP (PSMA-positive, EC50 = 6.74 ± 1.33 nM) cancers are specifically delineated in mice that bear 3 million (18 mg) PC3-PIP and PC3 (control, PSMA-negative) cells. Colocalization of [18/19F]-4 PET, fluorescence, scintillated biodistribution, and PSMA expression are observed.

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From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates

Cited by 55 publications

References 50 publications

Organotrifluoroborates: Another Branch of the Mighty Oak

Organotrifluoroborates: Another Branch of the Mighty Oak

One-step 18F labeling of biomolecules using organotrifluoroborates

¹⁸F-Positron Emitting/Trimethine Cyanine-Fluorescent Contrast for Image-Guided Prostate Cancer Management

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From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates

Cited by 55 publications

References 50 publications

Organotrifluoroborates: Another Branch of the Mighty Oak

Organotrifluoroborates: Another Branch of the Mighty Oak

One-step 18F labeling of biomolecules using organotrifluoroborates

18F-Positron Emitting/Trimethine Cyanine-Fluorescent Contrast for Image-Guided Prostate Cancer Management

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Product

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¹⁸F-Positron Emitting/Trimethine Cyanine-Fluorescent Contrast for Image-Guided Prostate Cancer Management