18F-FESB: synthesis and automated radiofluorination of a novel18F-labeled pet tracer forβ-amyloid plaques

Kumar, Piyush; Zheng, Weizhong; McQuarrie, S.A.; Jhamandas, Jack H.; Wiebe, Leonard I.

doi:10.1002/jlcr.1011

Cited by 7 publications

(6 citation statements)

References 21 publications

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“…[263] The radiosynthesis of the potential Alzheimers disease imaging compound [ 18 F]FESB was found to be significantly enhanced when the ionic liquid 1-butyl-3methylimidazolium tetrafluoroborate ([bmim][BF 4 ]) was used during the 18 F-fluorination step. [264] 4. Radiolabeling with Oxygen-15 and Nitrogen-13…”

Section: Miscellaneous 18 F-labeling Reactionsmentioning

confidence: 99%

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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Positron emission tomography (PET) is a powerful and rapidly developing area of molecular imaging that is used to study and visualize human physiology by the detection of positron-emitting radiopharmaceuticals. Information about metabolism, receptor/enzyme function, and biochemical mechanisms in living tissue can be obtained directly from PET experiments. Unlike magnetic resonance imaging (MRI) or computerized tomography (CT), which mainly provide detailed anatomical images, PET can measure chemical changes that occur before macroscopic anatomical signs of a disease are observed. PET is emerging as a revolutionary method for measuring body function and tailoring disease treatment in living subjects. The development of synthetic strategies for the synthesis of new positron-emitting molecules is, however, not trivial. This Review highlights key aspects of the synthesis of PET radiotracers with the short-lived positron-emitting radionuclides (11)C, (18)F, (15)O, and (13)N, with emphasis on the most recent strategies.

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Section: Miscellaneous 18 F-labeling Reactionsmentioning

confidence: 99%

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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“…Such competitive elimination is known to occur in the presence of the strongly basic fluoride ion if the rate of fluorination is slow. 33,34 Because these efforts to synthesize 11 from the nosylates 4 and 5 were not successful, the DAST-assisted fluorination of 3a was pursued (Scheme 2). This afforded the desired fluorinated product, methyl-…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Design, Synthesis, and Preliminary Biological Evaluation of 6-O-Glucose–Azomycin Adducts for Diagnosis and Therapy of Hypoxic Tumors

et al. 2012

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Several 2-nitroimidazole-based molecules (NIs) are used as clinical hypoxic tumor radiodiagnostics, but they are not effective as radiosensitizers/radiochemotherapeutics. These NIs permeate tumor cells nonselectively via diffusion, and in therapy, where high doses are required, their dose limiting toxicities preclude success. The synthesis and preliminary in vitro evaluations of three glucoazomycins, members of a novel class of C6-O-glucose-linked-azomycin conjugates that are putative substrates of glucose transport proteins (GLUTs) and possess hypoxia-selective radiosensitization features, are now reported. The hypoxia-dependent upregulation of several GLUTs provides a rational basis to develop these glucoazomycins because more selective uptake in hypoxic cells would decrease systemic toxicities at effective doses. Calculated partition coefficients (ClogP, -1.70 to -2.99) predict rapid in vivo clearance for low systemic toxicity. In vitro experimental data show that glucoazomycins are radiosensitizers and that they competitively inhibit glucose uptake.

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“…Kung and co-workers also independently developed 2-arylbenzothiazole derivatives as neutral ThT derivatives ( [107], benzofuran (47)(48)(49)(50)(51)(52)(53)(54) [108,109] or imidazopyridine (100)(101)(102)(103)(104), in the place of benzothiazolium. Among them, a benzofuran derivative [ 11 C]50 showed potential for in vivo amyloid imaging: high binding affinity (Ki: 0.7 nM) for A and good brain clearance (2 min-to-30 min ratio = 13.6).…”

Section: Thioflavin-t Analoguesmentioning

confidence: 97%

“…The styrylbenzene framework was also used by other researchers for the development of amyloid imaging agents such as ISB, IMSB, and so on [99][100][101]. Although [ 125 I]ISB (10) and [ 125 I]IMSB (11) showed high binding affinity to A aggregates, their BBB permeabilities were very low, probably due to their carboxylic acid groups.…”

Section: Congo Red Analoguesmentioning

confidence: 97%

Recent Advances in the Development of Amyloid Imaging Agents

Furumoto

Okamura²,

Iwata³

et al. 2007

CTMC

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Excessive amyloid-beta (Abeta) deposition in the brain is one of the most crucial events in the early pathological stage of Alzheimer's disease (AD). Therefore, Abeta deposits have enough potential to become a useful biomarker for not only an early diagnosis of AD, but also for the assessment of the clinical efficacy of anti-Abeta therapies, if they can be measured non-invasively and reliably in living patients. As a potent candidate technique to measure this biomarker, PET amyloid imaging using a radioligand for Abeta deposits has received much attention. A large number of Abeta ligands have been synthesized and evaluated as candidates for amyloid imaging agents. These can be classified into six categories of derivatives: Congo-red, Thioflavine T, stilbene, vinylbenzoxazole, DDNP, and miscellaneous. Many of these derivatives exhibit high binding affinities to Abeta fibrils (below 20 nM) and some of them also show excellent brain pharmacokinetic profiles. The concept of amyloid imaging is currently being tested in human PET studies using optimized amyloid imaging agents. Despite the small number of subjects, these studies have demonstrated sufficiently promising results. This review article provides an overview of recent advances in the development of amyloid imaging agents, and includes: a summary of the fundamental basis and clinical significance of amyloid imaging; lists of binding affinity data for 135 compounds classified into 12 molecular frameworks; a comprehensive discussion of the in vitro and in vivo features of representative Abeta ligands; and a discussion of the current state of clinical evaluation of these amyloid imaging agents (PIB, SB-13, BF-227, and FDDNP).

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18F-FESB: synthesis and automated radiofluorination of a novel18F-labeled pet tracer forβ-amyloid plaques

Cited by 7 publications

References 21 publications

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Design, Synthesis, and Preliminary Biological Evaluation of 6-O-Glucose–Azomycin Adducts for Diagnosis and Therapy of Hypoxic Tumors

Recent Advances in the Development of Amyloid Imaging Agents

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18F-FESB: synthesis and automated radiofluorination of a novel18F-labeled pet tracer forβ-amyloid plaques

Cited by 7 publications

References 21 publications

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

Design, Synthesis, and Preliminary Biological Evaluation of 6-O-Glucose–Azomycin Adducts for Diagnosis and Therapy of Hypoxic Tumors

Recent Advances in the Development of Amyloid Imaging Agents

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Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography