A gold-complex initiated functionalization of biologically active polyphenols applied to a <sup>18</sup>F-labeled chemical probe

Liu, Z.; Fukagawa, Yasuo; Yamano, Masaharu; Tago, Tetsuro; Iwai, Kumiko; Hirano, Keiichi; Kumazoe, Motofumi; Toyohara, Jun; Tachibana, Hiroki; Tanaka, Hiroshi

doi:10.1039/d3ob00856h

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00856h

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A gold-complex initiated functionalization of biologically active polyphenols applied to a ¹⁸F-labeled chemical probe

Z. Liu

Yasuo Fukagawa

Masaharu Yamano

et al.

Abstract: (-)-Epigallocatechin gallate (EGCG), a key component of green tea, as therapeutic effects with anticancer and antiallergic properties., exerted through its binding to the 67-kDa laminin receptor. The functionalization of EGCG...

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Cited by 3 publications

References 29 publications

(27 reference statements)

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¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

Iida,

Tago,

Tada

et al. 2023

Asian J Org Chem

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In the development of an efficient 18F‐labeling method for the synthesis of PET tracers, it is essential not only to improve the efficiency of [18F]fluorine incorporation into a carrier but also to minimize non‐radioactive side products from the precursor. Highly reactive sulfonate esters are promising precursors for 18F‐nucleophilic fluorination under mild conditions. However, the expected labeling efficiency from the precursor is often hampered by its competitive degradation due to coexisting bases during 18F‐fluorination. In this report, we designed a 2‐methyl‐6‐nitrobenzenesulfonate (2‐MeNs) ester as a precursor for 18F‐fluorination, in which the methyl group suppresses hydrolysis of the sulfonate ester via steric hindrance. An increase in labeling efficiency in the 18F‐labeling of a neopentyl labeling group was observed for the neopentyl 2‐MeNs ester compared with that of the 2‐nitrobenzenesulfonate ester. Ultimately, we achieved the automated synthesis of an 18F‐labeled amino acid using a neopentyl labeling group by using a 2‐MeNs ester as a precursor.

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¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

Iida,

Tago,

Tada

et al. 2023

Asian J Org Chem

Self Cite

View full text Add to dashboard Cite

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Development of a Neopentyl ²¹¹At‐Labeled Activated Ester Providing In Vivo Stable ²¹¹At‐Labeled Antibodies for Targeted Alpha Therapy

Tada,

Kaizuka,

Kannaka

et al. 2024

ChemMedChem

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In this study we developed a neopentyl 211At‐labeled activated ester that incorporates a triazole spacer and applied it to the synthesis of an 211At‐labeled cetuximab. The activated ester was synthesized via the nucleophilic 211At‐astatination of a neopentyl sulfonate carrying two long alkyl chains that serve as a lipid tag, which was followed by the hydrolysis of an acetal. Additionally, we developed a novel Resin‐Assisted Purification and Deprotection (RAPD) protocol involving a solid‐phase extraction of the protected 211At‐labeled compound from the mixture of the labeling reaction, hydrolysis of the acetal on the resin, and finally an elution of the 211At‐labeled activator from the resin. This method allows the synthesis of an 211At‐labeled activated ester with high purity through a simplified procedure that circumvents the need for HPLC purification. Using this 211At‐labeled activated ester, we efficiently synthesized 211At‐labeled cetuximab in 27±1% radiochemical yield with 95% radiochemical purity. This 211At‐activated ester demonstrated high reactivity, and enabled the completion of the reaction with the antibody within 10 min. In comparative biodistribution studies between 211At‐labeled cetuximab and the corresponding 125I‐labeled cetuximab in normal mice, both the thyroid and stomach showed radioactivity levels that were less than 1.0% of the injected dose.

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Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps

Yu,

Ren,

Coghi

et al. 2024

Molbank

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Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we designed and synthesized a novel EGCG-valine derivative 4 by replacing the gallic acid with a valine moiety in four steps. The structural elucidation of derivative 4 was performed using NMR, IR, mass, and UV spectroscopies. Additionally, the physicochemical properties of 4 were predicted by SwissADME, showing improved drug-like parameters and intestinal absorption compared to the parent compound EGCG.

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A gold-complex initiated functionalization of biologically active polyphenols applied to a ¹⁸F-labeled chemical probe

Abstract: (-)-Epigallocatechin gallate (EGCG), a key component of green tea, as therapeutic effects with anticancer and antiallergic properties., exerted through its binding to the 67-kDa laminin receptor. The functionalization of EGCG...

Cited by 3 publications

References 29 publications

¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

Development of a Neopentyl ²¹¹At‐Labeled Activated Ester Providing In Vivo Stable ²¹¹At‐Labeled Antibodies for Targeted Alpha Therapy

Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps

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A gold-complex initiated functionalization of biologically active polyphenols applied to a 18F-labeled chemical probe

Abstract: (-)-Epigallocatechin gallate (EGCG), a key component of green tea, as therapeutic effects with anticancer and antiallergic properties., exerted through its binding to the 67-kDa laminin receptor. The functionalization of EGCG...

Cited by 3 publications

References 29 publications

18F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an 18F‐Labeled Amino Acid**

18F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an 18F‐Labeled Amino Acid**

Development of a Neopentyl 211At‐Labeled Activated Ester Providing In Vivo Stable 211At‐Labeled Antibodies for Targeted Alpha Therapy

Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps

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Product

Resources

About

A gold-complex initiated functionalization of biologically active polyphenols applied to a ¹⁸F-labeled chemical probe

¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

¹⁸F‐Fluorination of 2‐Methyl‐6‐nitrobenzenesulfonate Ester and its Application for the Synthesis of an ¹⁸F‐Labeled Amino Acid**

Development of a Neopentyl ²¹¹At‐Labeled Activated Ester Providing In Vivo Stable ²¹¹At‐Labeled Antibodies for Targeted Alpha Therapy