Synthesis of <sup>125</sup>I-Labeled Oligonucleotides from Tributylstannylbenzamide Conjugates

Mw, Reed; Ig, Panyutin; Hamlin, Donald K.; Dd, Lucas; Ds, Wilbur

doi:10.1021/bc970016n

Cited by 14 publications

(5 citation statements)

References 15 publications

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“…As a means to explore the targeting ability and pharmacokinetics of oligonucleotides directly in vivo, noninvasive imaging is a method of choice and several groups have reported labeling methods with γ emitters (Dewanjee et al, 1994;Hnatowich et al, 1995;Cammilleri et al, 1996;Charlton et al, 1997;Reed et al, 1997;Hjelstuen et al, 1998;Fujibayashi et al, 1999) and with positron emitters for positron emission tomography (PET) (Dolle ´et al, 1997;Hedberg et al, 1997;Tavitian et al, 1998;Hedberg et al, 1998;Yngve et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

et al. 2000

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Evaluation of oligonucleotides for biomedical applications requires different in vivo and in vitro approaches (pharmacokinetics, biodistribution, macro- and microimaging, metabolism,.), that are performed with different radioisotopes according to the temporal and spatial resolution needed. A method to introduce radioactive isotopes of halogens (fluorine, bromine, and iodine) in a small and stable molecule has been developed. Radiosynthons can then be conjugated with any given oligonucleotide in one step to create the appropriate radiotracer. This general radiolabeling procedure for oligonucleotides is efficient to synthesize (18)F-, (76)Br-, and (125)I-oligonucleotides for biological needs. Applications of the method to biodistribution, metabolism, in vivo and ex vivo imaging of (125)I- and (18)F-labeled oligonucleotides are reported.

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Section: Introductionmentioning

confidence: 99%

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

et al. 2000

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“…This transforming growth factor a targeted ASO probe provided information on the biodistribution of intratumoral administrated ASO ( Cammilleri et al, 1996 ). In 1997, Reed et al chemically modified oligonucleotide 5′-end with tributylstannylbenzamide and realized rapid and efficient radioiodination ( Reed et al, 1997 ). This work developed a general and carrier-free strategy for oligonucleotides radioiodination.…”

Section: Radiohalogensmentioning

confidence: 99%

Radiolabeling of functional oligonucleotides for molecular imaging

Liu

Xia

Ding

et al. 2022

Front. Bioeng. Biotechnol.

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Molecular imaging has greatly advanced basic biology and translational medicine through visualization and quantification of molecular events in a cellular context and living organisms. Nuclear medicine, including positron emission tomography (PET) and single-photon emission tomography (SPECT), is one of the most representative molecular imaging modalities which is widely used in clinical theranostics. Recently, numerous molecular imaging agents have been developed to improve the quality and expand the applicable diseases of molecular imaging. Based on the choice of specific imaging agents, molecular imaging is capable of studying tumor biological activities, detecting tumor metastasis, and imaging Alzheimer’s disease-related amyloid proteins. Among these imaging agents, functional oligonucleotides-based imaging probes are becoming increasingly important due to their unique features. Antisense oligonucleotides, small interfering RNA, and aptamers are privileged molecular tools in precision medicine for cancer diagnosis and treatment. These chemically synthesized oligonucleotides without batch-to-batch variations are flexible to incorporate with other molecules without affecting their functionalities. Therefore, through the combination of oligonucleotides with radioisotopes, a series of molecular imaging agents were developed in the past decades to achieve highly sensitive and accurate biomedical imaging modalities for clinical theranostic. Due to the nature of oligonucleotides, the strategies of oligonucleotide radiolabeling are different from conventional small molecular tracers, and the radiolabeling strategy with rational design is highly correlated to the imaging quality. In this review, we summarize recent advancements in functional oligonucleotide radiolabeling strategies and respective molecular imaging applications. Meanwhile, challenges and future development insights of functional oligonucleotide-based radiopharmaceuticals are discussed in the end.

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“…Activation at the 3-position of the sugar with a phosphoramidate group allowed the intermediate to be incorporated into an oligonucleotide that was ultimately radioiodinated using [I-125]-iodide and various oxidants. Reed, et al, [42] also prepared a radioiodinated oligonuleotide via iododestannylation . In their synthesis, however, they utilized a sequence that contained a terminal hexamethyleneamine to which a 4-tributylstannylbenzoyl moiety could be conjugated.…”

Section: A Radiolabeled Nucleoside Analogsmentioning

confidence: 99%

Synthesis of Auger Electron-Emitting Radiopharmaceuticals

Hanson

2000

CPD

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Targeted radiotherapy using Auger electron-emitting pharmaceuticals offers both advantages and challenges compared to alternative alpha - or beta -emitting agents. The low energy Auger electrons deposit their energy within the target cell thereby minimizing collateral damage. To achieve this effect, however, the radiopharmaceutical must incorporate the appropriate radionuclide, be efficiently synthesized, and once administered, be distributed selectively to its biological target. This review covers the synthesis of agents which have prepared over the past decade either as Auger electron-emitting radiopharmaceuticals or which have the potential as such. While not an exhaustive review, the major classes of agents, such as hormone receptor ligands, nucleoside analogs and intercalating agents are described.

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Synthesis of ¹²⁵I-Labeled Oligonucleotides from Tributylstannylbenzamide Conjugates

Cited by 14 publications

References 15 publications

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

Radiolabeling of functional oligonucleotides for molecular imaging

Synthesis of Auger Electron-Emitting Radiopharmaceuticals

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Synthesis of 125I-Labeled Oligonucleotides from Tributylstannylbenzamide Conjugates

Cited by 14 publications

References 15 publications

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

General Method to Label Antisense Oligonucleotides with Radioactive Halogens for Pharmacological and Imaging Studies

Radiolabeling of functional oligonucleotides for molecular imaging

Synthesis of Auger Electron-Emitting Radiopharmaceuticals

Contact Info

Product

Resources

About

Synthesis of ¹²⁵I-Labeled Oligonucleotides from Tributylstannylbenzamide Conjugates