Concise synthesis of catechin probes enabling analysis and imaging of EGCg

Yoshida, Akitoshi; Hirooka, Yasuo; Sugata, Yusuke; Nitta, M.; Manabe, Tamiko; Ido, Shunsuke; Murakami, Kouki; Saha, Repon Kumer; Suzuki, Takashi; Ohshima, Motohiro; Yoshida, Akira; Itoh, Ken; Shimizu, Kosuke; Oku, Naoto; Furuta, Takumi; Asakawa, Tomohiro; Wakimoto, Toshiyuki; Kan, Toshiyuki

doi:10.1039/c0cc03676e

Cited by 28 publications

(20 citation statements)

References 31 publications

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“…36, 37 Coupling of the alcohols ( 9a–d ) with aromatic acids 12–16 enlisting 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) and 4-dimethylaminopyrine (DMAP) gave the corresponding esters, 10a–t . 38 Hydrogenolysis of 10k–t with palladium/carbon and hydrogen gas gave 11a–j in high yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

2013

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Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90, however structure-activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure-activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Anti-proliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of four most potent analogues was further evaluated by western blot analyses and degradation of Hsp90-dependent client proteins. Prenyl substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as novel scaffold that exhibit Hsp90 inhibitory activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

2013

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“…Although some studies have visualized its tissue distribution by fluorescence imaging, cerium chloride staining, immunostaining, and radioactive labeling assays, [74][75][76][77] spatiotemporal information has been lacking because of the absence of an analytical technique that can easily detect the localization of the naïve polyphenol. Conventional molecular imaging generally requires labeling steps that are time-consuming, expensive, and laborintensive.…”

Section: Biotransformation and Distribution Of The Green Tea Polymentioning

confidence: 99%

Small molecule-sensing strategy and techniques for understanding the functionality of green tea

Fujimura

2015

Bioscience, Biotechnology, and Biochemistry

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“…However, there is little information about the biodistribution of catechins after their intake; because the synthesis of artificial EGCG is quite complicated, and the detection of catechins or their metabolites in the body is difficult. On the other hand, we recently succeeded in developing a novel method for the synthesis of EGCG and its derivatives, and investigated the intracellular distribution of this synthetic EGCG in human umbilical vein endothelial cells (HUVEC) by using fluorescence-labeled EGCG [7]. The results indicated that a portion of this EGCG accumulates in the mitochondria of these cells, suggesting that mitochondrial dysfunction might be involved in the anti-angiogenic effect of EGCG [7].…”

Section: Introductionmentioning

confidence: 99%

Use of Positron Emission Tomography for Real-Time Imaging of Biodistribution of Green Tea Catechin

et al. 2014

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The aim of this study was to achieve real-time imaging of the in vivo behavior of a green tea polyphenol, catechin, by positron emission tomography (PET). Positron-labeled 4″ -[11C]methyl-epigallocatechin gallate ([11C]Me-EGCG) was orally administered to rats, and its biodistribution was imaged for 60 min by using a small animal PET system. As the result, images of [11C]Me-EGCG passing through the stomach into the small intestines were observed; and a portion of it was quantitatively detected in the liver. On the other hand, intravenous injection of [11C]Me-EGCG resulted in a temporal accumulation of the labeled catechin in the liver, after which almost all of it was transferred to the small intestines within 60 min. In the present study, we succeeded in obtaining real-time imaging of the absorption and biodistribution of [11C]Me-EGCG with a PET system.

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Concise synthesis of catechin probes enabling analysis and imaging of EGCg

Cited by 28 publications

References 31 publications

Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

Small molecule-sensing strategy and techniques for understanding the functionality of green tea

Use of Positron Emission Tomography for Real-Time Imaging of Biodistribution of Green Tea Catechin

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