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      Fast 18F Labeling of a Near-Infrared Fluorophore Enables Positron Emission Tomography and Optical Imaging of Sentinel Lymph Nodes

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          Abstract

          We combine a novel boronate trap for F − with a near-infrared fluorophore into a single molecule. Attachment to targeting ligands enables localization by positron emission tomography (PET) and near-infrared fluorescence (NIRF). Our first application of this generic tag is to label Lymphoseek (tilmanocept), an agent designed for receptor-specific sentinel lymph node (SLN) mapping. The new conjugate incorporates 18F − in a single, aqueous step, targets mouse SLN rapidly (1 h) with reduced distal lymph node accumulation, permits PET or scintigraphic imaging of SLN, and enables NIRF-guided excision and histological verification even after 18F decay. This embodiment is superior to current SLN mapping agents such as nontargeted [ 99mTc]sulfur colloids and Isosulfan Blue, as well as the phase III targeted ligand [ 99mTc]SPECT Lymphoseek counterpart, species that are visible by SPECT or visible absorbance separately. Facile incorporation of 18F into a NIRF probe should promote many synergistic PET and NIRF combinations.

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          Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.

          Tobias L. Ross, Johannes Ermert, Carsten Hocke … (2007)
          Diaryliodonium salts containing the 2-thienyl group as an example of an electron-rich heteroaromatic moiety proved to be very potent precursors for the nucleophilic, regioselective no-carrier-added (nca) radiofluorination of various arenes. It even allowed the nucleophilic introduction of nca [18F]fluoride into electron-rich arene compounds in one step. The influences of the substitution pattern, of counteranions, and of different reaction conditions were studied. Effects of counterions could be explained by the influence of solvent on ion pair separation of precursor salts. Different aryl(2-thienyl)iodonium salts were used as precursors, where the homoaromatic group systematically varied from bearing electron-deficient to electron-rich substituents. Relative rates of exchange kinetics correlated linearly with Hammett constants of the appropriate substituents confirming a nucleophilic aromatic substitution reaction of high reactivity and low selectivity.
          Article 0 comments Cited 54 times – based on 0 reviews     Review now
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            Radioguided sentinel lymph node biopsy in breast cancer surgery.

            Bradley H Strauss, Serena Bagnasco, G Paganelli … (2001)
            The concept of sentinel lymph node biopsy in breast cancer surgery relates to the fact that the tumor drains in a logical way through the lymphatic system, from the first to upper levels. Therefore, the first lymph node met (the sentinel node) will most likely be the first to be affected by metastasis, and a negative sentinel node makes it highly unlikely that other nodes are affected. Because axillary node dissection does not improve prognosis of patients with breast cancer (being important only to stage the axilla), sentinel lymph node biopsy might replace complete axillary dissection to stage the axilla in clinically N0 patients. Sentinel lymph node biopsy would represent a significant advantage as a minimally invasive procedure, considering that, after surgery, about 70% of patients are found to be free from metastatic disease, yet axillary node dissection can lead to significant morbidity. Furthermore, histologic sampling errors can be reduced if a single (sentinel) node is assessed extensively rather than few histologic sections in a high number of lymph nodes per patient. Although the pattern of lymph drainage from breast cancer can be variable, the mammary gland and the overlying skin can be considered as a biologic unit in which lymphatics tend to follow the vasculature. Therefore, considering that tumor lymphatics are disorganized and relatively ineffective, subdermal and peritumoral injection of small aliquots of radiotracer is preferred to intratumoral administration. (99m)Tc-labeled colloids with most of the particles in the 100- to 200-nm size range would be ideal for radioguided sentinel node biopsy in breast cancer. Lymphoscintigraphy is an essential part of radioguided sentinel lymph node biopsy because images are used to direct the surgeon to the site of the node. The sentinel lymph node should have a significantly higher count than that of background (at least 10:1 intraoperatively). After removal of the sentinel node, the axilla must be reexamined to ensure that all radioactive sites are identified and removed for analysis. The sentinel lymph node should be processed for intraoperative frozen section examination in its entirety, based on conventional histopathology and, when needed, immune staining with anticytokeratin antibody. The success rate of radioguidance in localizing the sentinel lymph node in breast cancer surgery is about 94%--97% in institutions where a high number of procedures are performed and approaches 99% when combined with the vital blue dye technique. At present, there is no definite evidence that negative sentinel lymph node biopsy is invariably correlated with negative axillary status, except perhaps for T1a-b breast cancers, with a size of < or =1 cm. Randomized clinical trials should elucidate the impact of avoiding axillary node dissection on patients with a negative sentinel lymph node on the long-term clinical outcome of patients.
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              Arylfluoroborates and alkylfluorosilicates as potential PET imaging agents: high-yielding aqueous biomolecular 18F-labeling.

              Richard Ting, Michael J. Adam, Thomas Ruth … (2005)
              Organometalloid compositions of silicon and boron permit rapid, high-yielding, one-step radiolabeling of a covalently linked protein ligand (biotin) under aqueous conditions to give the corresponding alkyltetrafluorosilicates and aryltrifluoroborate salts. Biotin was chosen as a test ligand for protein targeting because of its quantitative interaction with avidin, which in turn allowed us to calculate fluoridation yields that approach 80-100%. The silicate was found to be moderately stable to hydrolysis, whereas the borate appears to be so stable that its hydrolytic decomposition was not readily measured. With the stability of both compounds ascertained, this work describes a novel and robust radiolabeling method that may find use in the development of positron emission tomography radiopharmaceuticals.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Bioconjug Chem
                Journal ID (publisher-id): bc
                Journal ID (coden): bcches
                Title: Bioconjugate Chemistry
                Publisher: American Chemical Society
                ISSN (Print): 1043-1802
                ISSN (Electronic): 1520-4812
                Publication date (Electronic): 27 September 2010
                Publication date (Print): 20 October 2010
                Volume: 21
                Issue: 10
                Pages: 1811-1819
                Affiliations
                Department of Pharmacology 0647, Department of Radiology, and Howard Hughes Medical Institute, University of California, San Diego, La Jolla, California 92093
                Author notes
                [* ] To whom correspondence should be addressed.
                [†]

                Department of Pharmacology 0647.

                [‡]

                Department of Radiology.

                [§]

                Howard Hughes Medical Institute.

                Article
                DOI: 10.1021/bc1001328
                PMC ID: 2957852
                PubMed ID: 20873712
                SO-VID: 8b46ff6e-7090-4e55-907f-ea48afa14213
                Copyright © Copyright © 2010 American Chemical Society
                License:

                This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.

                History
                Date received : 11 March 2010
                Date revision received : 24 June 2010
                Date: 27 September 2010
                Date: 20 October 2010
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 bc1001328
                document-id-new-14 bc-2010-001328
                ccc-price

                ScienceOpen disciplines: Biochemistry
                Data availability:
                ScienceOpen disciplines: Biochemistry

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