Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents

Doona Song; Jee Sun Yang; Seo Joong Kim; Bo Kyung Kim; Song Kyu Park; Misun Won; Hwan Mook Kim; Kang Yell Choi; Kyeong Lee; Kiho Lee; Gyoonhee Han

doi:10.1016/j.bmc.2012.11.027

Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents

Doona Song, Jee Sun Yang, Seo Joong Kim, Bo Kyung Kim, Song Kyu Park, Misun Won, Hwan Mook Kim, Kang Yell Choi, Kyeong Lee, Kiho Lee, Gyoonhee Han

Department of Pharmacy

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

7 Scopus citations

Abstract

RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.

Original language	English
Pages (from-to)	788-794
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2012.11.027
State	Published - 1 Feb 2013

Keywords

Aliphatic amido/sulfonamido-quaternary ammonium salts
GTPase rat sarcoma (Ras)
NSC126188
Perifosine
RhoB

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2012.11.027

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title = "Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents",

abstract = "RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.",

keywords = "Aliphatic amido/sulfonamido-quaternary ammonium salts, GTPase rat sarcoma (Ras), NSC126188, Perifosine, RhoB",

author = "Doona Song and Yang, {Jee Sun} and Kim, {Seo Joong} and Kim, {Bo Kyung} and Park, {Song Kyu} and Misun Won and Kim, {Hwan Mook} and Choi, {Kang Yell} and Kyeong Lee and Kiho Lee and Gyoonhee Han",

year = "2013",

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doi = "10.1016/j.bmc.2012.11.027",

language = "English",

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T1 - Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents

AU - Song, Doona

AU - Yang, Jee Sun

AU - Kim, Seo Joong

AU - Kim, Bo Kyung

AU - Park, Song Kyu

AU - Won, Misun

AU - Kim, Hwan Mook

AU - Choi, Kang Yell

AU - Lee, Kyeong

AU - Lee, Kiho

AU - Han, Gyoonhee

PY - 2013/2/1

Y1 - 2013/2/1

N2 - RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.

AB - RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.

KW - Aliphatic amido/sulfonamido-quaternary ammonium salts

KW - GTPase rat sarcoma (Ras)

KW - NSC126188

KW - Perifosine

KW - RhoB

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U2 - 10.1016/j.bmc.2012.11.027

DO - 10.1016/j.bmc.2012.11.027

M3 - Article

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AN - SCOPUS:84872294735

SN - 0968-0896

VL - 21

SP - 788

EP - 794

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 3

ER -

Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents

Abstract

Keywords

UN SDGs

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