Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities

Feng Pai Chou; Wen Chen Hsu; Sheng Cih Huang; Chin Yuan Chang; Ya Sheng Chiou; Chia Tse Tsai; Jason Wenjay Lyu; Wei Ting Chen; Tung Kung Wu

doi:10.1039/c9cc09415f

Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities

Feng Pai Chou, Wen Chen Hsu, Sheng Cih Huang, Chin Yuan Chang, Ya Sheng Chiou, Chia Tse Tsai, Jason Wenjay Lyu, Wei Ting Chen, Tung Kung Wu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

We report here that pregnenolonyl-α-glucoside (2), a steryl glycoside synthesized directly from pregnenolone and glucose via a consecutive multienzyme-catalyzed process, exhibits marked dose-dependent cytotoxic activity against HT29, AGS, and ES-2 cells with IC₅₀ values of 23.5 to 50.9 μM. An in vitro CYP17A1 binding pattern assay and protein-ligand docking model support that 2, like abiraterone, binds in the active site heme iron pocket of CYP17A1.

Original language	English
Pages (from-to)	1733-1736
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	11
DOIs	https://doi.org/10.1039/c9cc09415f
State	Published - 7 Feb 2020

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title = "Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities",

abstract = "We report here that pregnenolonyl-α-glucoside (2), a steryl glycoside synthesized directly from pregnenolone and glucose via a consecutive multienzyme-catalyzed process, exhibits marked dose-dependent cytotoxic activity against HT29, AGS, and ES-2 cells with IC50 values of 23.5 to 50.9 μM. An in vitro CYP17A1 binding pattern assay and protein-ligand docking model support that 2, like abiraterone, binds in the active site heme iron pocket of CYP17A1.",

author = "Chou, {Feng Pai} and Hsu, {Wen Chen} and Huang, {Sheng Cih} and Chang, {Chin Yuan} and Chiou, {Ya Sheng} and Tsai, {Chia Tse} and Lyu, {Jason Wenjay} and Chen, {Wei Ting} and Wu, {Tung Kung}",

year = "2020",

month = feb,

day = "7",

doi = "10.1039/c9cc09415f",

language = "English",

volume = "56",

pages = "1733--1736",

journal = "Chemical Communications",

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TY - JOUR

T1 - Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities

AU - Chou, Feng Pai

AU - Hsu, Wen Chen

AU - Huang, Sheng Cih

AU - Chang, Chin Yuan

AU - Chiou, Ya Sheng

AU - Tsai, Chia Tse

AU - Lyu, Jason Wenjay

AU - Chen, Wei Ting

AU - Wu, Tung Kung

PY - 2020/2/7

Y1 - 2020/2/7

N2 - We report here that pregnenolonyl-α-glucoside (2), a steryl glycoside synthesized directly from pregnenolone and glucose via a consecutive multienzyme-catalyzed process, exhibits marked dose-dependent cytotoxic activity against HT29, AGS, and ES-2 cells with IC50 values of 23.5 to 50.9 μM. An in vitro CYP17A1 binding pattern assay and protein-ligand docking model support that 2, like abiraterone, binds in the active site heme iron pocket of CYP17A1.

AB - We report here that pregnenolonyl-α-glucoside (2), a steryl glycoside synthesized directly from pregnenolone and glucose via a consecutive multienzyme-catalyzed process, exhibits marked dose-dependent cytotoxic activity against HT29, AGS, and ES-2 cells with IC50 values of 23.5 to 50.9 μM. An in vitro CYP17A1 binding pattern assay and protein-ligand docking model support that 2, like abiraterone, binds in the active site heme iron pocket of CYP17A1.

UR - http://www.scopus.com/inward/record.url?scp=85079077358&partnerID=8YFLogxK

U2 - 10.1039/c9cc09415f

DO - 10.1039/c9cc09415f

M3 - Article

C2 - 31938799

AN - SCOPUS:85079077358

VL - 56

SP - 1733

EP - 1736

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 11

ER -

Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities

Abstract

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