Radiosynthesis of no-carrier-added meta-[124I]iodobenzylguanidine for PET imaging of metastatic neuroblastoma

Green, Michael; Lowe, Jonathan; Kadirvel, Manikandan; McMahon, Adam; Westwood, Nigel; Chua, Sue Siew Chen; Brown, Gavin

doi:10.1007/s10967-016-5073-1

Cited by 15 publications

(10 citation statements)

References 17 publications

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“…Available PET tracers for the assessment of pheochromocytomas or paragangliomas are F-18-fludeoxyglucose (FDG), somatostatin receptor targeting tracers such as Ga-68-DOTATATE and rarely-used PET-tracers like C-11-hydroxyephedrine (mHED), F-18-fluoro-dopa, F-18-fluorodopamine or I-124 MIBG. However, these radiotracers suffer from disadvantages such as long halflife and high cost (I-124), the need for an onsite-cyclotron (C-11), a complex radiosynthesis (F-18 fluoro-dopa, F-18 fluorodopamine) or a low specificity for pheochromocytoma and paraganglioma (somatostatin receptor targeting tracers) (12)(13)(14). N- [3-bromo-4-(3-(18)F-fluoro-propoxy)-benzyl]-guanidine (F-18flubrobenguane, formerly known as LMI1195) is a novel, F-18 labeled radiotracer which has a high homology to MIBG and can visualize norepinephrine-transporters with a high affinity and specificity (15).…”

Section: Discussionmentioning

confidence: 99%

First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

Kessler

Schlitter²,

Krönke

et al. 2020

J Nucl Med

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Rationale: Pheochromocytomas and paragangliomas are a rare tumor entity originating from adreno-medullary chromaffin cells in the adrenal medulla or in sympathetic, paravertebral ganglia outside the medulla. Especially small lesions are difficult to detect by conventional CT or MR imaging and even by SPECT imaging with currently available radiotracers (e.g. MIBG). The novel PETradiotracer F-18-flubrobenguane could change the diagnostic paradigm in suspected pheochromocytomas and paragangliomas due to its homology to MIBG and the general advantages of PET-imaging. Aim of this retrospective analysis was to evaluate F-18-flubrobenguane in pheochromocytomas and paragangliomas and to investigate the biodistribution in patients. Methods: 24 Patients with suspected pheochromocytoma and paraganglioma underwent PET/CT or PET/MRI at 63±24 min p.i. after injection of 256±33 MBq F-18-flubrobenguane. SUVmean and SUVmax values of organs were measured with spherical volume-of-interests. Threshold segmented volume-of-interests were used to measure SUVmean/max of the tumor lesions. One reader evaluated all crosssectional imaging datasets (CT or MRI) separately as well as the PET hybrid datasets and reported lesion number and size. A three point-scale indicating the diagnostic certainty for a positive lesion was assigned.

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Section: Discussionmentioning

confidence: 99%

First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

Kessler

Schlitter²,

Krönke

et al. 2020

J Nucl Med

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“…PET with [ 18 F]FDG that is used for detection of many malignances, among them neuroblastoma, is based on the characteristic glucose metabolism (Warburg effect) of many cancer cells . More specific tracers for neuroblastoma imaging are also considered, among them PET with [ 124 I] m IBG, which can be taken up by the NAT present in most neuroblastoma cells. Other compounds with relation to the catecholamine metabolism of neuroblastoma cells are 6‐[ 18 F]FDA and its precursor 6‐[ 18 F]FDOPA .…”

Section: Discussionmentioning

confidence: 99%

“…It is also taken up by organic cation transporter (OCT)–expressing cells present in kidney, liver, and many other organs . Instead of scintigraphy with [ 123 I] m IBG, PET could be an interesting alternative for neuroblastoma imaging, eg, with 124 I‐labeled m IBG ([ 124 I] m IBG) . 6‐[ 18 F]Fluorodopamine (6‐[ 18 F]FDA) that is taken up by the DAT and NAT as well as its precursor, 6‐[ 18 F]FDOPA, are also considered for PET in neuroblastoma .…”

Section: Introductionmentioning

confidence: 99%

Fast enzymatic synthesis of n.c.a. 6‐[¹⁸F]fluorodopamine (FDA) from n.c.a. 6‐[¹⁸F]FDOPA and the fate of 6‐FDOPA and 6‐FDA in neuroblastoma and Caki‐1 cells after their uptake

Kuçi

Ehrlichmann

Sauer

et al. 2019

Labelled Comp Radiopharmac

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The catecholamine analogue [123I]mIBG has been used for scintigraphic imaging of neuroblastoma since 1984. It is taken up by the noradrenaline transporter (NAT), which is present in most neuroblastoma cells. An alternative imaging method could be PET with 6‐[18F]fluorodopamine, which is also taken up by NAT, but—in contrast to mIBG—also by dopamine transporter (DAT), present in neuroblastoma cells (NAT > DAT). An enzymatic method was established allowing a rapid, quantitative transformation of FDOPA to FDA by DOPA decarboxylase within 25 minutes. This strategy was applied to [18F]FDOPA, which was produced via nucleophilic synthesis (RCY 15%, 10 GBq, 50 GBq/μmol) and subsequently converted to [18F]FDA (RCY 35%‐50%, n = 5). Uptake and metabolism of FDOPA and FDA were analyzed in human Kelly and SK‐N‐SH neuroblastoma cell lines and in human Caki‐1 kidney cells that can take up catecholamines and mIBG via an organic cation transporter (OCT). FDOPA and FDA were taken up by all three cells, but FDOPA could only be converted to FDA in neuroblastoma cells. As today, [18F]FDOPA is well available in high yields, efficient enzymatic conversion to [18F]FDA to be used for NAT/DAT PET imaging in neuroendocrine tumors is an attractive, alternative synthesis route.

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“…A common method used to prepare radioactive-iodine labeled MIBG involves the isotope replacement reaction of cold-MIBG ( 127 I-MIBG) with radioactive iodide [1] [15]. The precursor is mixed and reacted with a solution of the sodium salt of 123/124/131 I containing ammonium sulfate, sodium acetate, glacial acetic acid, and sodium phosphate buffer, at 175˚C for 1 h. The product 123/124/131 I-MIBG is then chromatographically separated from the solution on a C-18 preparative column.…”

Section: Introductionmentioning

confidence: 99%

Determination of Impurities and Degradation Products/Causes for <i>m</i>-Iodobenzylguanidine Using HPLC-Tandem Mass Spectrometry

Chen¹,

Chang²,

Lee³

et al. 2019

AJAC

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m-Iodobenzylguanidinium hemisulfate (MIBGHS) is a precursor in the preparation of radioiodine-labeled m-iodobenzylguanidine (MIBG), which is used as a radio-imaging and therapy agent for neuroendocrine tumors and myocardial sympathetic nerve function. To ensure the quality and efficacy of the medicine and prevent side effects, the precursor purity, source of impurity, and derivatives have to be determined. In this study, the purity of synthesized MIBGHS and the amount of contaminants therein were determined by high-performance liquid chromatography and ultraviolet detection, gradient eluted by ammonium formate aqueous solution and acetonitrile mobile phase on both C8 and phenyl type column. The impurities were identified on the basis of molecular and fragmented ion mass spectra using of electrospray ionization triple quadrupole tandem mass spectrometry. The results revealed the presence of process-related impurities including m-bromobenzylguanidine (MBrBG) and overreacted byproducts. Stress test results indicated that MIBGHS is stable under acidic and dry thermal conditions for at least 72 h but MIBG aqueous solution was deteriorated slowly when exposed to UV light, thermal, oxidative and alkaline environments. Thus, m-iodobenzylamine, the starting material intended for the synthesis of MIBGHS should be analyzed to ensure that it is free from m-bromobenzylamine impurity. Stored under normal condition (−18˚C), MIBGHS is stable for at least 12 months. The chemically labile guanidine and amine groups in MIBGHS are the major causes of its instability, while iodide loss from the phenyl group is a minor cause.

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Radiosynthesis of no-carrier-added meta-[124I]iodobenzylguanidine for PET imaging of metastatic neuroblastoma

Cited by 15 publications

References 17 publications

First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

Fast enzymatic synthesis of n.c.a. 6‐[¹⁸F]fluorodopamine (FDA) from n.c.a. 6‐[¹⁸F]FDOPA and the fate of 6‐FDOPA and 6‐FDA in neuroblastoma and Caki‐1 cells after their uptake

Determination of Impurities and Degradation Products/Causes for <i>m</i>-Iodobenzylguanidine Using HPLC-Tandem Mass Spectrometry

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Radiosynthesis of no-carrier-added meta-[124I]iodobenzylguanidine for PET imaging of metastatic neuroblastoma

Cited by 15 publications

References 17 publications

First Experience Using 18F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

First Experience Using 18F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

Fast enzymatic synthesis of n.c.a. 6‐[18F]fluorodopamine (FDA) from n.c.a. 6‐[18F]FDOPA and the fate of 6‐FDOPA and 6‐FDA in neuroblastoma and Caki‐1 cells after their uptake

Determination of Impurities and Degradation Products/Causes for &lt;i&gt;m&lt;/i&gt;-Iodobenzylguanidine Using HPLC-Tandem Mass Spectrometry

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First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

First Experience Using ¹⁸F-Flubrobenguane PET Imaging in Patients with Suspected Pheochromocytoma or Paraganglioma

Fast enzymatic synthesis of n.c.a. 6‐[¹⁸F]fluorodopamine (FDA) from n.c.a. 6‐[¹⁸F]FDOPA and the fate of 6‐FDOPA and 6‐FDA in neuroblastoma and Caki‐1 cells after their uptake

Determination of Impurities and Degradation Products/Causes for <i>m</i>-Iodobenzylguanidine Using HPLC-Tandem Mass Spectrometry