(4-[18F]Fluoro-3-iodobenzyl)guanidine, a Potential MIBG Analog for Positron Emission Tomography

Vaidyanathan, Ganesan; Affleck, Donna J.; Zalutsky, Michael R.

doi:10.1021/jm00047a022

Cited by 57 publications

(38 citation statements)

References 13 publications

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“…However, the short half-life of 11 C requires on-site cyclotron synthesis and limits the practical use of these radiopharmaceuticals. Compounds labeled with 18 F, such as fluoronorepinephrine, fluorometaraminol, fluorodopamine, and 4-18 F-fluoro-3-iodobenzylguanidine, have the potential for imaging neuroendocrine tumors (19)(20)(21)(22)(23)(24)(25). PET using 124 I-MIBG has also been described (26).…”

Section: Discussionmentioning

confidence: 99%

¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma

Sharp¹,

Shulkin²,

Gelfand³

et al. 2009

J Nucl Med

179

129

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Section: Discussionmentioning

confidence: 99%

¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma

Sharp¹,

Shulkin²,

Gelfand³

et al. 2009

J Nucl Med

179

129

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“…Recently, we have reported that substitution of a fluorine atom ortho to the iodine in MIBG resulted in an MIBG analogue, ['311]FIBG, with modestly increased binding, but significantly enhanced retention of radioiodine in SK-N-SH cells in vitro (Vaidyanathan et al, 1997 If [21 'At]AFBG is to be pursued as an endoradiotherapeutic agent, it is critical to understand the mechanisms responsible for its uptake not only in human tumour cells, but also in normal tissues such as heart and adrenals, where uptake-1-mediated localization could be problematical. In SK-N-SH cells, MIBG is taken up by a neuron-specific active uptake-I mechanism (Buck et al, 1985;Smets et al, 1989), a process that has been demonstrated to occur with the analogues [21 'At]MABG (Vaidyanathan and Zalutsky, 1994a), ['8F]FIBG (Vaidyanathan et al, 1994b(Vaidyanathan et al, , 1995 and ['311]FIBG Vaidyanathan et al, 1997).…”

Section: Discussionmentioning

confidence: 99%

“…Recently, a fluorine-containing analogue of MIBG was developed for positron emission tomography (Vaidyanathan et al, 1994b;. This agent, 4-fluoro-3-iodobenzylguanidine (FIBG; Figure 1), also could be labelled with iodine radionuclides (Vaidyanathan et al, 1996).…”

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confidence: 99%

3-[211At]astato-4-fluorobenzylguanidine: a potential therapeutic agent with prolonged retention by neuroblastoma cells

Vaidyanathan

Zhao²,

Larsen³

et al. 1997

Br J Cancer

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Summary An analogue of meta-iodobenzylguanidine (MIBG) in which an aromatic hydrogen was replaced with fluorine has been found to possess many properties similar to those of the parent compound. Moreover, 4-fluoro-3-iodobenzylguanidine (FIBG) (Klingebiel et al, 1989;Garaventa et al, 1991). Although treatment of neuroblastoma with ['311I]MIBG has been shown to be efficacious, improvements in this therapeutic modality are needed and a number of approaches are under active investigation. For example, combination of [311I]MIBG treatment with high-dose chemotherapy and total body irradiation is being pursued (Gaze et al, 1995). For micrometastases, the long-range 3-particles of 'l3I are suboptimal (Sisson et al, 1990; O'Donoghue et al, 1991) and the development of an MIBG analogue labelled with an a-emitter such as 7.2 h half-life 21'At has been advocated (Shapiro et al, 1987;Mairs et al, 1991 (Vaidyanathan and Zalutsky, 1992;Vaidyanathan et al, 1994a). In clonogenic assays with the SK-N-SH human neuroblastoma cell line, the Do value for[21At]MABG was 0.2 kBq mll compared with 384 kBq ml-for no carrier added (n.c.a.) ['311]MIBG, indicating a more than 1000-fold

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“…Both analogues were inferior to MIBG with respect to uptake in NET-expressing SK-N-SH human neuroblastoma cells in vitro and myocardial uptake in normal mice in vivo; however, interest in [ 18 F]MFBG for imaging has recently been revived [17, 18]. Hypothesizing that the lackluster performance of [ 18 F]MFBG and [ 18 F]PFBG might be due to the lack an iodine substituent on its benzene ring, which may be essential for bioactivity, we synthesized 4-[ 18 F]fluoro-3-iodobenzylguanidine ([ 18 F]FIBG) that is essentially MIBG with an added fluorine [19]. Indeed, FIBG was demonstrated to be a superior MIBG analogue [19, 20]; however, its structure was not amenable for single step 18 F-labeling via the classical S N Ar substitution.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of 4-[18F]fluoropropoxy-3-iodobenzylguanidine ([18F]FPOIBG): A novel 18F-labeled analogue of MIBG

Vaidyanathan

McDougald

Koumarianou

et al. 2015

Nuclear Medicine and Biology

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Introduction Radioiodinated meta-iodobenzylguanidine (MIBG), a norepinephrine transporter (NET) substrate, has been extensively used as an imaging agent to study the pathophysiology of the heart and for the diagnosis and treatment of neuroendocrine tumors. The goal of this study was to develop an 18F-labeled analogue of MIBG that like MIBG itself could be synthesized in a single radiochemical step. Towards this end, we designed 4-fluoropropoxy-3-iodobenzylguanidine (FPOIBG). Methods Standards of FPOIBG and 4-fluoropropoxy-3-bromobenzylguanidine (FPOBBG) as well as their tosylate precursors for labeling with 18F, and a tin precursor for the preparation of radioiodinated FPOIBG were synthesized. Radiolabeled derivatives were synthesized by nucleophilic substitution and electrophilic iododestannylation from the corresponding precursors. Labeled compounds were evaluated for NET transporter recognition in in vitro assays using three NET-expressing cell lines and in biodistribution experiments in normal mice, with all studies performed in a paired-label format. Competitive inhibition of [125I]MIBG uptake by unlabeled benzylguanidine compounds was performed in UVW-NAT cell line to determine IC50 values. Results [18F]FPOIBG was synthesized from the corresponding tosylate precursor in 5.2 ± 0.5% (n = 6) overall radiochemical yields starting with aqueous fluoride in about 105 min. In a paired-label in vitro assay, the uptake of [18F]FPOIBG at 2 h was 10.2 ± 1.5%, 39.6 ± 13.4%, and 13.3 ± 2.5%, in NET-expressing SK-N-SH, UVW-NAT, and SK-N-BE(2c) cells, respectively, while these values for [125I]MIBG were 57.3 ± 8.1%, 82.7 ± 8.9%, and 66.3 ± 3.6%. The specificity of uptake of both tracers was demonstrated by blocking with desipramine. The 125I-labeled congener of FPOIBG gave similar results. On the other hand, [18F]FPOBBG, a compound recently reported in the literature, demonstrated much higher uptake, albeit less than that of co-incubated [125I]MIBG. IC50 values for FPOIBG were higher than that obtained for MIBG and FPOBBG. Unlike the case with [18F]FPOBBG, the heart uptake [18F]FPOIBG in normal mice was significantly lower than that of MIBG. Conclusion Although [18F]FPOIBG does not appear to warrant further consideration as an 18F-labeled MIBG analogue, analogues wherein the iodine in it is replaced with a chlorine, fluorine or hydrogen might be worth pursuing. Advances in knowledge and implications for patient care An 18F-labeled analogue of the well-known radiopharmaceutical MIBG could have significant impact, potentially improving imaging of NET related disease in cardiology and in the imaging of neuroendocrine tumors. Although 18F-labeled analogues of MIBG have been reported including LMI1195, we undertook this work hypothesizing that based on its greater structural similarity to MIBG, FPOIBG might be a better analogue than LMI1195.

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(4-[18F]Fluoro-3-iodobenzyl)guanidine, a Potential MIBG Analog for Positron Emission Tomography

Cited by 57 publications

References 13 publications

¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma

¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma

3-[211At]astato-4-fluorobenzylguanidine: a potential therapeutic agent with prolonged retention by neuroblastoma cells

Synthesis and evaluation of 4-[18F]fluoropropoxy-3-iodobenzylguanidine ([18F]FPOIBG): A novel 18F-labeled analogue of MIBG

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(4-[18F]Fluoro-3-iodobenzyl)guanidine, a Potential MIBG Analog for Positron Emission Tomography

Cited by 57 publications

References 13 publications

123I-MIBG Scintigraphy and 18F-FDG PET in Neuroblastoma

123I-MIBG Scintigraphy and 18F-FDG PET in Neuroblastoma

3-[211At]astato-4-fluorobenzylguanidine: a potential therapeutic agent with prolonged retention by neuroblastoma cells

Synthesis and evaluation of 4-[18F]fluoropropoxy-3-iodobenzylguanidine ([18F]FPOIBG): A novel 18F-labeled analogue of MIBG

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¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma

¹²³I-MIBG Scintigraphy and ¹⁸F-FDG PET in Neuroblastoma