Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

Herryawan Ryadi Eziwar Dyari, Tristan Rawling, Kirsi Bourget, Michael Murray

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

Original languageEnglish
Pages (from-to)7459-7464
Number of pages6
JournalJournal of Medicinal Chemistry
Volume57
Issue number17
DOIs
Publication statusPublished - 11 Sep 2014

Fingerprint

Epoxy Compounds
Fatty Acids
Breast Neoplasms
Acids
Carbamates
JNK Mitogen-Activated Protein Kinases
Cyclin D1
G1 Phase
Cell Cycle Checkpoints
Amides
Caspase 3
Antineoplastic Agents
Urea
Down-Regulation
Adenosine Triphosphate
Cell Proliferation
Apoptosis
Growth

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery
  • Medicine(all)

Cite this

Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells. / Eziwar Dyari, Herryawan Ryadi; Rawling, Tristan; Bourget, Kirsi; Murray, Michael.

In: Journal of Medicinal Chemistry, Vol. 57, No. 17, 11.09.2014, p. 7459-7464.

Research output: Contribution to journalArticle

@article{7f87d69b989944a7b84ee01ae696d69d,
title = "Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells",
abstract = "ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.",
author = "{Eziwar Dyari}, {Herryawan Ryadi} and Tristan Rawling and Kirsi Bourget and Michael Murray",
year = "2014",
month = "9",
day = "11",
doi = "10.1021/jm501083y",
language = "English",
volume = "57",
pages = "7459--7464",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

AU - Eziwar Dyari, Herryawan Ryadi

AU - Rawling, Tristan

AU - Bourget, Kirsi

AU - Murray, Michael

PY - 2014/9/11

Y1 - 2014/9/11

N2 - ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

AB - ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

UR - http://www.scopus.com/inward/record.url?scp=84907191994&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907191994&partnerID=8YFLogxK

U2 - 10.1021/jm501083y

DO - 10.1021/jm501083y

M3 - Article

C2 - 25144895

AN - SCOPUS:84907191994

VL - 57

SP - 7459

EP - 7464

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 17

ER -