Stable aluminium fluoride chelates with triazacyclononane derivatives proved by X-ray crystallography and 18F-labeling study

Shetty, Dinesh; Choi, Soo Young; Jeong, Jae Min; Lee, Ji Youn; Hoigebazar, Lathika; Lee, Yun Sang; Lee, Dong Hoon; Chung, June‐Key; Lee, Myung Chul; Chung, Young Keun

doi:10.1039/c1cc13151f

Cited by 71 publications

(85 citation statements)

References 18 publications

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“…We reported a facile method for 18 F-radiolabeling of peptides previously that involves the binding of a highly stable [ 18 F](AlF) 2+ complex to a metal-binding ligand bound to a peptide (McBride et al, 2009; McBride et al, 2010; Laverman et al, 2010; D’Souza et al, 2011a, 2011b; McBride et al, 2011), and two other groups have recently reported their results using this labeling approach (Liu et al 2011; Shetty et al 2011). This radiolabeling approach has the advantage of rapid binding to the ligand, does not require a dry-down step, and high specific activities can be obtained after a simple SPE purification step to remove unbound 18 F. The procedure does not require expensive automated equipment, but could be easily adapted for use with such equipment.…”

Section: Discussionmentioning

confidence: 99%

“…Although this procedure allows peptides to be fluorinated in one simple step within 30 min, it requires agents to be heated to ~100 °C, which is unsuitable for most proteins and some peptides. We and others have found that an aromatic group attached to one of the nitrogen atoms of the cylcononane ring of the NODA can enhance the yield for the ([ 18 F]AlF) 2+ complexation compared to some alkyl and carboxyl substituents (D’Souza et al, 2011b; McBride et al, 2010: Shetty et al 2011). In this report, we explore the potential for labeling heat-labile compounds with ([ 18 F]AlF) 2+ , using a new ([ 18 F]AlF) 2+ -binding ligand that contains 1,4,7-triazacyclononane-1,4-diacetate (NODA) attached to a methyl phenylacetic acid group (MPA).…”

Section: Introductionmentioning

confidence: 98%

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The radiolabeling of proteins by the [18F]AlF method

McBride¹,

D'Souza²,

Sharkey³

et al. 2012

Applied Radiation and Isotopes

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A new ([18F]AlF)2+-binding ligand that contains 1,4,7-triazacyclononane-1,4-diacetate (NODA) attached to a methyl phenylacetic acid group (MPA) was conjugated to N-(2-aminoethyl)maleimide (EM) to form NODA-MPAEM. The NODA-MPAEM was labeled with ([18F]AlF)2+ at 105 °C in 49–82% yield and conjugated at room temperature to an antibody Fab’ fragment in 69–80% yield (total time ~ 50 min) and with retention of immunoreactivity. These data indicate that the rapid and simple [18F]AlF-labeling method can be easily adapted for preparing heat-sensitive compounds with 18F quickly and in high yields.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

The radiolabeling of proteins by the [18F]AlF method

McBride¹,

D'Souza²,

Sharkey³

et al. 2012

Applied Radiation and Isotopes

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“…39 These characteristics have prompted an increased interest in IEDDA reactions for bioconjugation as well as pretargeting purposes. [39][40][41] To perform this synthetic methodology, the novel [ 18 F]AlF-3, containing the NODA chelator instead of NOTA, was prepared and subsequently reacted with the TCO-functionalized-affibody molecule at room temperature via an IEDDA reaction. This methodology enables the radiofluorination of heatsensitive compounds.…”

Section: Introductionmentioning

confidence: 99%

Efficient [¹⁸F]AlF Radiolabeling of Z_HER3:8698 Affibody Molecule for Imaging of HER3 Positive Tumors

et al. 2016

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The human epidermal growth factor receptor 3 (HER3) is overexpressed in several cancers, being linked to a more resistant phenotype and hence leading to poor patient prognosis. Imaging HER3 is challenging owing to the modest receptor number (<50000 receptors/cell) in overexpressing cancer cells. Therefore, to image HER3 in vivo, high target affinity PET probes need to be developed. This work describes two different [(18)F]AlF radiolabeling strategies of the ZHER3:8698 affibody molecule specifically targeting HER3. The one-pot radiolabeling of ZHER3:8698 performed at 100 °C and using 1,4,7-triazanonane-1,4,7-triacetate (NOTA) as chelator resulted in radiolabeled products with variable purity attributed to radioconjugate thermolysis. An alternative approach based on the inverse electron demand Diels-Alder (IEDDA) reaction between a novel tetrazine functionalized 1,4,7-triazacyclononane-1,4-diacetate (NODA) chelator and the trans-cyclooctene (TCO) functionalized affibody molecule was also investigated. This method enabled the radiolabeling of the protein at room temperature. The [(18)F]AlF-NOTA-ZHER3:8698 and [(18)F]AlF-NODA-ZHER3:8698 conjugates showed a specific uptake at 1 h after injection in high HER3-expressing MCF-7 tumors of 4.36 ± 0.92% ID/g and 4.96 ± 0.65% ID/g, respectively. The current results are encouraging for further investigation of [(18)F]AlF-NOTA-ZHER3:8698 as a HER3 imaging agent.

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“…27–29 Others have confirmed the AlF fluorination potential using RGD peptides and some simple derivatives of NODA. 30–32 …”

Section: Introductionmentioning

confidence: 99%

New Lyophilized Kit for Rapid Radiofluorination of Peptides

et al. 2012

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Radiolabeling compounds with positron-emitting radionuclides often involves a time-consuming, customized process. Herein, we report a simple lyophilized kit formulation for labeling peptides with 18F, based on the aluminum-fluoride procedure. The prototype kit contains IMP485, a NODA (1,4,7-triazacyclononane-1,4-diacetate)-MPAA (methyl phenylacetic acid)-di-HSG (histamine-succinyl-glycine) hapten-peptide, [NODA-MPAA-D-Lys(HSG)-D-Tyr-D-Lys(HSG)-NH2], used for pretargeting, but we also examined a similar kit formulation for a somatostatin-binding peptide [IMP466, NOTA-D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Throl] bearing a NOTA ligand to determine if the benefits of using a kit can be extended to other AlF-binding peptides. The NODA-MPAA ligand forms a single stable complex with (AlF)2+ in high yields. In order to establish suitable conditions for a facile kit, the formulation was optimized for pH, peptide to Al3+ ratio, bulking agent, radioprotectant, and the buffer. For optimal labeling, the kit was reconstituted with an aqueous solution of 18F− and ethanol (1:1), heated at 100–110 °C for 15 min, and then simply and rapidly purified using one of two equally effective solid-phase extraction (SPE) methods. Al18F-IMP485 was isolated as a single isomer complex, in high yield (45–97%) and high specific activity (up to 223 GBq/μmol), within 20 min. The labeled product was stable in human serum at 37 °C for 4 h and in vivo, urine samples showed the intact product was eliminated. Tumor targeting of the Al18F-IMP485 in nude mice bearing human colon cancer xenografts pretargeted with an anti-CEACAM5 bispecific antibody showed very low uptake (0.06% ± 0.02 ID/g) in bone, further illustrating its stability. At 1 h, pretargeted animals had high Al18F-IMP485 tumor uptake (28.1% ± 4.5 ID/g), with ratios of 9 ± 4, 123 ± 38, 110 ± 43 and 120 ± 108 for kidney, liver, blood and bone, respectively. Tumor uptake remained high at 3 h post-injection, with increased tumor/nontumor ratios. The NOTA-somatostatin-binding peptide also was fluorinated with good yield and high specific activity in the same kit formulation. However, yields were somewhat lower than those achieved with IMP485 containing the NODA-MPAA ligand, likely reflecting this ligand's superior binding properties over the simple NOTA. These studies indicate that 18F-labeled peptides can be reproducibly prepared as stable Al-F complexes with good radiochemical yield and high specific activity using a simple, one-step, lyophilized kit followed by a rapid purification by SPE that provides the 18F-peptide, ready for patient injection within 30 min.

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Stable aluminium fluoride chelates with triazacyclononane derivatives proved by X-ray crystallography and 18F-labeling study

Abstract: A single crystal structure of an aluminium-fluoride complex of a model compound (NODA-benzyl) was studied to understand the co-ordination chemistry. Series of ligands with an extra carboxylic acid linker for biomolecule conjugation were studied for improved (18)F-labeling applications.

Cited by 71 publications

References 18 publications

The radiolabeling of proteins by the [18F]AlF method

The radiolabeling of proteins by the [18F]AlF method

Efficient [¹⁸F]AlF Radiolabeling of Z_HER3:8698 Affibody Molecule for Imaging of HER3 Positive Tumors

New Lyophilized Kit for Rapid Radiofluorination of Peptides

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Stable aluminium fluoride chelates with triazacyclononane derivatives proved by X-ray crystallography and 18F-labeling study

Abstract: A single crystal structure of an aluminium-fluoride complex of a model compound (NODA-benzyl) was studied to understand the co-ordination chemistry. Series of ligands with an extra carboxylic acid linker for biomolecule conjugation were studied for improved (18)F-labeling applications.

Cited by 71 publications

References 18 publications

The radiolabeling of proteins by the [18F]AlF method

The radiolabeling of proteins by the [18F]AlF method

Efficient [18F]AlF Radiolabeling of ZHER3:8698 Affibody Molecule for Imaging of HER3 Positive Tumors

New Lyophilized Kit for Rapid Radiofluorination of Peptides

Contact Info

Product

Resources

About

Efficient [¹⁸F]AlF Radiolabeling of Z_HER3:8698 Affibody Molecule for Imaging of HER3 Positive Tumors