Novel synthesis and initial preclinical evaluation of 18 F-[FDG] labeled rhodamine: a potential PET myocardial perfusion imaging agent

Al-Jammaz, Ibrahim; Al‐Otaibi, B.; AlHindas, Hussein; Okarvi, Subhani M.

doi:10.1016/j.nucmedbio.2015.06.009

Cited by 14 publications

(18 citation statements)

References 21 publications

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“…11. [207][208][209][210][211][212] The tracers 284-291 were synthesised from the corresponding amine precursor whereas tracers 292-296 were synthesised from oxy-amine precursors. The [ 18 F]FDG building block was employed either in solution (saline or PBS) or azeotropically dried with MeCN prior to use.…”

Section: Fluorine-18 Labelled Alkyl Aminesmentioning

confidence: 99%

“…However, it is noteworthy that Al Jammaz and co-workers obtained the PET myocardial perfusion imaging agent 293 in a radiochemical yield of 97% by just simply passing the reaction mixture through a membrane filter, resulting in 498% radiochemical purity. 212 The in vitro stability of the glycosyl amine tracers are in general high. 210,211 However, at low pH, increased decomposition of the [ 18 F]FDG amines was observed whereas the [ 18 F]FDG oximes were stable towards hydrolysis under these conditions.…”

Section: Fluorine-18 Labelled Alkyl Aminesmentioning

confidence: 99%

“…PET tracers synthesised from [ 18 F]FDG and (a) amine precursors, (b) oxy-amine precursors [207][208][209][210][211][212]. Scheme 51 Synthesis of 5-[18 F]fluoro-5-deoxyribose 299.…”

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confidence: 99%

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Fluorine-18 labelled building blocks for PET tracer synthesis

et al. 2017

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Positron emission tomography (PET) is an important driver for present day healthcare. Fluorine-18 is the most widely used radioisotope for PET imaging and a thorough overview of the available radiochemistry methodology is a prerequisite for selection of a synthetic approach for new fluorine-18 labelled PET tracers. These PET tracers can be synthesised either by late-stage radiofluorination, introducing fluorine-18 in the last step of the synthesis, or by a building block approach (also called modular build-up approach), introducing fluorine-18 in a fast and efficient manner in a building block, which is reacted further in one or multiple reaction steps to form the PET tracer. This review presents a comprehensive overview of the synthesis and application of fluorine-18 labelled building blocks since 2010.

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Section: Fluorine-18 Labelled Alkyl Aminesmentioning

confidence: 99%

Section: Fluorine-18 Labelled Alkyl Aminesmentioning

confidence: 99%

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Fluorine-18 labelled building blocks for PET tracer synthesis

et al. 2017

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“…Maddahi et al used 18 F-FDG as the radiointermediate, and reported the preclinical evaluation of 18 F-FDG-rhodamine [ 26 ]. 18 F-FDG-rhodamine had a good stability in human plasma in vitro.…”

Section: Lipophilic Cationsmentioning

confidence: 99%

Research Progress on 18F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography

Mou

Zhang

2017

Molecules

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Coronary artery disease (CAD) is the leading cause of death in the world. Myocardial perfusion imaging (MPI) plays a significant role in non-invasive diagnosis and prognosis of CAD. However, neither single-photon emission computed tomography nor positron emission tomography clinical MPI agents can absolutely satisfy the demands of clinical practice. In the past decades, tremendous developments happened in the field of 18F-labeled MPI tracers. This review summarizes the current state of 18F-labeled MPI tracers, basic research data of those tracers, and the future direction of MPI tracer research.

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“…16 With regard to 18 F-labeled rhodamines, we first synthesized rhodamine B derivatives bearing 18 F-alkyl 17 and 18 F-polyoxyethylene 18, 19 esters and evaluated them for chemical and pharmacological parameters important to PET-MPI. Subsequently, AlJammaz et al synthesized and evaluated an [ 18 F]FDG-modified amide analogue of rhodamine 123 20 and Trencsényi et al prepared 2-[ 18 F]fluoroethylrhodamine B for the in vitro measurement P-glycoprotein function. 21 Building on our earlier work with rhodamine B, we later compared the pharmacological properties of a series 2-(2-[ 18 F]fluoroethoxy)ethyl ester derivatives bearing different rhodamine cores.…”

Section: Introductionmentioning

confidence: 99%

New chemical and radiochemical routes to [¹⁸F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

et al. 2017

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New chemical and radiochemical syntheses are described for the preparation of [18F]Rho6G-DEG-F, an 18F-labeled analogue of the fluoresecent dye rhodamine 6G, which has shown promise as myocardidal perfusion imaging agent. Tosylated precursors of [18F]Rho6G-DEG-F amenable to 18F-labeling were obtained either through a two-step synthesis from rhodamine 6G lactone (33% yield), or in one step from rhodamine 575 (64% yield), then purified by preparative C18 chromatography. Manual synthesis of [18F]Rho6G-DEG-F was achieved in a single radiochemical step from either the tosylate salt or the tosylate/formate double salt in DMSO under standard nucleophillic aliphatic 18F-fluorination conditions (K[18F]F/K2CO3/Kryptofix 2.2.2.). Incorporation of the [18F]F− was found to be satisfactory (≥34% by TLC), despite the protic character of the precursor molecules. [18F]Rho6G-DEG-F was manually synthesized in final decay-corrected radiochemical yields of 11–26% (tosylate salt) and 9–21% (tosylate/formate double salt). The protocol was transferred to an automated synthesis unit, where the product was obtained in 3–9% radiochemical yield (n=3) decay corrected to start-of-synthesis, >99% radiochemical purity, and a molar activity of 122–267 GBq/μmol (3.3–7.2 Ci/μmol).

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Novel synthesis and initial preclinical evaluation of 18 F-[FDG] labeled rhodamine: a potential PET myocardial perfusion imaging agent

Cited by 14 publications

References 21 publications

Fluorine-18 labelled building blocks for PET tracer synthesis

Fluorine-18 labelled building blocks for PET tracer synthesis

Research Progress on 18F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography

New chemical and radiochemical routes to [¹⁸F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

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Novel synthesis and initial preclinical evaluation of 18 F-[FDG] labeled rhodamine: a potential PET myocardial perfusion imaging agent

Cited by 14 publications

References 21 publications

Fluorine-18 labelled building blocks for PET tracer synthesis

Fluorine-18 labelled building blocks for PET tracer synthesis

Research Progress on 18F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography

New chemical and radiochemical routes to [18F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

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New chemical and radiochemical routes to [¹⁸F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET