Radiolabelling of isopeptide Nε-(γ-glutamyl)-l-lysine by conjugation with N-succinimidyl-4-[18F]fluorobenzoate

Wüst, F.; Hultsch, Christina; Bergmann, Ralf; Johannsen, B.; Henle, Thomas

doi:10.1016/s0969-8043(03)00161-1

Cited by 72 publications

(43 citation statements)

References 17 publications

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“…The advantages of peptides as targeting agents include their rapid clearance from tissues allowing for the maximal target/ background ratio to be achieved in the shortest time frame, their minimal immunogenicity, and that they can be synthesized relatively easily to high purity. Furthermore, reliable, standard synthetic procedures allow the rapid incorporation of several radioisotopecontaining 'prosthetic' groups into peptides (21)(22)(23)(24)(25)(26)(27) (29)(30)(31). The key region of the loop, which is conserved in many FMDV serotypes (28,(32)(33)(34)(35), is the RGDLXXL motif, where X indicates the location of a nonspecific amino acid.…”

Section: Introductionmentioning

confidence: 99%

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

et al. 2007

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Expression of the epithelial-specific integrin A v B 6 is low or undetectable in most adult tissues but may be increased during wound healing and inflammation and is up-regulated dramatically by many different carcinomas, making A v B 6 a promising target for the in vivo detection of cancer using noninvasive imaging. In addition, A v B 6 is recognized as promoting invasion and correlates with aggressive behavior of human cancers and thus agents that recognize A v B 6 specifically in vivo will be an essential tool for the future management of A v B 6 -positive cancers. Recently, we identified the peptide NAVPNLRGDLQV-LAQKVART (A20FMDV2), derived from foot-and-mouth disease virus, as a potent inhibitor of A v B 6 . Using flow cytometry and ELISA, we show that this peptide is highly selective, inhibiting A v B 6 -ligand binding with a IC 50 of 3 nmol/L, an activity 1,000-fold more selective for A v B 6 than for other RGDdirected integrins (A v B 3 , A v B 5 , and A 5 B 1 ). A20FMDV2 was radiolabeled on solid-phase using 4-[18 F]fluorobenzoic acid, injected into mice bearing both A v B 6 -negative and A v B 6 -positive (DX3puro/DX3puroB6 cell lines) xenografts and imaged using a small animal positron emission tomography (PET) scanner. Rapid uptake (<30 min) and selective retention (>5 h) of radioactivity in the A v B 6 -positive versus the A v B 6 -negative tumor, together with fast renal elimination of nonspecifically bound activity, resulted in specific imaging of the A v B 6 -positive neoplasm. These data suggest that PET imaging of A v B 6 -positive tumors is feasible and will provide an important new tool for early detection and improved management of many types of cancers. [Cancer Res 2007;67(16):7833-40]

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Section: Introductionmentioning

confidence: 99%

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

et al. 2007

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“…A large number of 18 F-labeled prosthetic groups have been developed that can be attached to biomolecules via acylation, amidation, imidation, alkylation reactions, photochemical conjugation, and solidphase syntheses. 1,3 The acylation approach using N-succinimidyl-4-[…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of N‐succinimidyl 4‐[¹⁸F]fluorobenzoate ([¹⁸F]SFB) for protein labeling

Tang

Zeng

et al. 2008

Labelled Comp Radiopharmac

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An efficient preparation of N‐succinimidyl 4‐[18F]fluorobenzoate ([18F]SFB) based on a convenient three‐step, one‐pot procedure is described. [18F]Fluorination of the precursor ethyl 4‐(trimethylammonium triflate)benzoate gave ethyl 4‐[18F]fluorobenzoate. Saponification of the ethyl 4‐[18F]fluorobenzoate with aqueous tetrapropylammonium hydroxide yielded the corresponding 4‐[18F]fluorobenzoate salt ([18F]FBA), which was then treated with N,N,N,N′‐tetramethyl‐O‐(N‐succinimidyl)uronium hexafluorophosphate. The purified [18F]SFB was used for the labeling of Avastin™ (Bevacizumab) through [18F]fluorobenzoylation of the Avastin's α‐amino groups. The decay‐corrected radiochemical yields of [18F]SFB were as high as 44% (based on [18F]fluoride (n=10) with a synthesis time of less than 60 min. [18F]Avastin was produced in decay‐corrected radiochemical yields of up to 42% (n=5) within 30 min (based on [18F]SFB). The radiochemical purities of [18F]SFB and [18F]Avastin were greater than 95%. Copyright © 2008 John Wiley & Sons, Ltd.

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“…18 F]fluorobenzoate ([ 18 F]SFB) is widely used for conjugation with primary amines at physiological conditions [3]- [6]. However, the synthesis of […”

Section: F-labeled Bifunctional Agents N-succinimidyl-4-[mentioning

confidence: 99%

Fluorine-18 Radiochemistry: A Novel Thiol-Reactive Prosthetic Group, [18F]FBAMPy

Moore¹,

Akula²,

Kabalka³

2016

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Radiolabelling of isopeptide Nε-(γ-glutamyl)-l-lysine by conjugation with N-succinimidyl-4-[18F]fluorobenzoate

Cited by 72 publications

References 17 publications

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

Facile synthesis of N‐succinimidyl 4‐[¹⁸F]fluorobenzoate ([¹⁸F]SFB) for protein labeling

Fluorine-18 Radiochemistry: A Novel Thiol-Reactive Prosthetic Group, [18F]FBAMPy

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Radiolabelling of isopeptide Nε-(γ-glutamyl)-l-lysine by conjugation with N-succinimidyl-4-[18F]fluorobenzoate

Cited by 72 publications

References 17 publications

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

Use of a Peptide Derived from Foot-and-Mouth Disease Virus for the Noninvasive Imaging of Human Cancer: Generation and Evaluation of 4-[18F]Fluorobenzoyl A20FMDV2 for In vivo Imaging of Integrin αvβ6 Expression with Positron Emission Tomography

Facile synthesis of N‐succinimidyl 4‐[18F]fluorobenzoate ([18F]SFB) for protein labeling

Fluorine-18 Radiochemistry: A Novel Thiol-Reactive Prosthetic Group, [18F]FBAMPy

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Facile synthesis of N‐succinimidyl 4‐[¹⁸F]fluorobenzoate ([¹⁸F]SFB) for protein labeling