Preparation of radioidinated insulin and thyroid stimulating hormone using 1,3,4,6-tetrachloro-3α, 6α-diphenylglycouril (Iodogen) for radioimmunoassay

Pillai, M.R.A.; Gupte, J. H.; Jyotsna, T.; Mani, R. S.

doi:10.1007/bf02037222

Cited by 7 publications

(4 citation statements)

References 11 publications

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“…The use of CAT as an oxidant for iodination of biomolecules has been widely reported. ,, However, there is concern about direct exposure of proteins to the oxidant that is soluble in aqueous reaction media. , Consequently, the water-insoluble oxidant iodogen is often used because it can be employed as a thin film coated onto the wall of the reaction vial, which minimizes direct interaction with the biomolecule being labeled. Given the insoluble nature of fluorous compounds in media typically employed for biomolecule iodination reactions, the ability of 4 to effectively label proteins was investigated.…”

Section: Resultsmentioning

confidence: 99%

“…The use of CAT as an oxidant for iodination of biomolecules has been widely reported. 10,42,43 However, there is concern about direct exposure of proteins to the oxidant that is soluble in aqueous reaction media. 43,44 Consequently, the water-insoluble oxidant iodogen is often used 45 because it can be employed as a thin film coated onto the wall of the reaction vial, which minimizes direct interaction with the biomolecule being labeled.…”

Section: ■ Introductionmentioning

confidence: 99%

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Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Dzandzi¹,

Beckford-Vera²,

Genady

et al. 2015

J. Org. Chem.

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A fluorous oxidant that can be used to introduce radioiodine into small molecules and proteins and generate iodinated tetrazines for bioorthogonal chemistry has been developed. The oxidant was prepared in 87% overall yield by combining a fluorous amine with tosyl chloride, followed by chlorination using aqueous sodium hypochlorite. A crystal structure of the oxidant, which is a fluorous analogue of chloramine-T, was obtained. The compound was shown to be stable for 7 days in EtOH and for longer than three months as a solid. The oxidant was effective at promoting the labeling of arylstannanes using [(125)I]NaI, where products were isolated in high specific activity in yields ranging from 46% to 86%. Similarly, iodinated biologically active proteins (e.g., thrombin) were successfully produced, as well as a radioiodinated tetrazine, through a concomitant oxidation-halodemetalation reaction. Because of its fluorous nature, unreacted oxidant and associated reaction byproducts can be removed quantitatively from reaction mixtures by passing solutions through fluorous solid phase extraction cartridges. This feature enables rapid and facile purification, which is critical when working with radionuclides and is similarly beneficial for general synthetic applications.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Dzandzi¹,

Beckford-Vera²,

Genady

et al. 2015

J. Org. Chem.

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“…The significant advantage is the small amount of oxidizing agent used when contrasted to the chloramine-T method. Therefore, damages caused by exposure to the overabundance oxidizing agent are minimized . Then, iodogen was insoluble in water and remained coated on the reaction vial, and therefore, the oxidant could be easily removed from the reaction solution without the need for any additional reductants .…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, damages caused by exposure to the overabundance oxidizing agent are minimized. 25 Then, iodogen was insoluble in water and remained coated on the reaction vial, and therefore, the oxidant could be easily removed from the reaction solution without the need for any additional reductants. 26 Furthermore, the iodogen oxidation was achieved at pH 7.4 and avoided a neutralization step before purification.…”

Section: ■ Introductionmentioning

confidence: 99%

Micro-SPECT Imaging of Acute Ischemic Stroke with Radioiodinated Riboflavin in Rat MCAO Models via Riboflavin Transporter Targeting

Chen

Peng

et al. 2022

ACS Chem. Neurosci.

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Riboflavin transporter-3 (RFVT3) is a recently discovered and novel biomarker for the theranostics of nervous system diseases. RFVT3 is significantly overexpressed in cerebral injury after ischemic stroke. Herein, we first reported an RFVT3targeted tracer 131 I-riboflavin ( 131 I-RFLA) for SPECT imaging of ischemic stroke in vivo. 131 I-RFLA was radiosynthesized by the iodogen-coating method. 131 I-RFLA possessed a radiochemical yield of 69.2 ± 3.7% and greater than 95% radiochemical purity. The representative SPECT/CT images using 131 I-RFLA demonstrated the conspicuously increased tracer uptake in the cerebral injury by comparison with the contralateral normal brain at 1 h and 3 and 7 d after stroke. Ex vivo autoradiography demonstrated that the ratio of infarcted to normal brain uptake was 3.63 and it was decreased to 1.98 after blocking, which reconfirmed the results of SPECT images. Importantly, a significant correlation was identified between RFVT3 expression and brain injury by H&E and immunohistochemistry staining. Therefore, RFVT3 is a new and potential biomarker for the early diagnosis of ischemic stroke. In addition, 131 I-RFLA is a promising SPECT tracer for imaging RFVT3-related ischemic cerebral injury in vivo.

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Preparation of no‐carrier‐added [¹²⁴I]A₁₄‐iodoinsulin as a radiotracer for positron emission tomography

Glaser

Brown

Law

et al. 2001

Labelled Comp Radiopharmac

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A14‐Iodoinsulin is a close biochemical and pharmacological mimic of insulin. Human insulin was labelled in its A chain tyrosine‐14 residue by direct iodination with the positron‐emitter iodine‐124 (β+=25.6%; t1/2=4.15 days) to provide a radiotracer for imaging with positron emission tomography (PET). Several reagents were compared for conversion of cyclotron‐produced [124I]iodide into a reactive species for the labelling reaction. Radiochemical yields from the use of Iodo‐Gen®, Chloramine‐T, N‐bromosuccinimide or lactoperoxidase–hydrogen peroxide were similar [35% (n=1), 33±9% (n=10), 32±11% (n=25) or 33% (n=2), respectively]. [124I]A14‐Iodoinsulin was separated from unreacted insulin and radioactive by‐products by tandem reverse phase HPLC and rapidly formulated for intravenous injection by adsorption on a Sep‐Pak tC18‐Plus® cartridge, followed by elution with 10 mM hydrochloric acid–ethanol (1:1 v/v, 1 ml). This radiotracer can now be obtained in useful radioactivities at high effective specific radioactivity and is now being applied to PET studies of its biodistribution in living subjects. Copyright © 2001 John Wiley & Sons, Ltd.

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Preparation of radioidinated insulin and thyroid stimulating hormone using 1,3,4,6-tetrachloro-3α, 6α-diphenylglycouril (Iodogen) for radioimmunoassay

Cited by 7 publications

References 11 publications

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Micro-SPECT Imaging of Acute Ischemic Stroke with Radioiodinated Riboflavin in Rat MCAO Models via Riboflavin Transporter Targeting

Preparation of no‐carrier‐added [¹²⁴I]A₁₄‐iodoinsulin as a radiotracer for positron emission tomography

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Preparation of radioidinated insulin and thyroid stimulating hormone using 1,3,4,6-tetrachloro-3α, 6α-diphenylglycouril (Iodogen) for radioimmunoassay

Cited by 7 publications

References 11 publications

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Micro-SPECT Imaging of Acute Ischemic Stroke with Radioiodinated Riboflavin in Rat MCAO Models via Riboflavin Transporter Targeting

Preparation of no‐carrier‐added [124I]A14‐iodoinsulin as a radiotracer for positron emission tomography

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Preparation of no‐carrier‐added [¹²⁴I]A₁₄‐iodoinsulin as a radiotracer for positron emission tomography