Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement

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Abstract

Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticanceractivity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 andC-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGHof hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. Newderivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomericforms by the Barbier-Grignard procedure and three of them were found to be active toward all of the threetargets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed forthe more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpressNF−κB.
Lingua originaleEnglish
Numero di pagine8
RivistaBioorganic Chemistry
Stato di pubblicazionePublished - 2019

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Oleanolic Acid
Triterpenes
Phytochemicals
Cytotoxicity
Antineoplastic Agents
Tumors
Hepatocellular Carcinoma
Carbon
Derivatives
Oxidation
Neoplasms
Therapeutics
ursolic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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@article{e59cc0f618014bf898115dcc7b19e40b,
title = "Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement",
abstract = "Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticanceractivity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 andC-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGHof hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. Newderivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomericforms by the Barbier-Grignard procedure and three of them were found to be active toward all of the threetargets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed forthe more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpressNF−κB.",
author = "{Notarbartolo Di Villarosa}, Monica and Gianfranco Fontana and Manuela Labbozzetta and Maurizio Bruno and Paola Poma and Sergio Rosselli and Alberto Spinella",
year = "2019",
language = "English",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Academic Press Inc.",

}

TY - JOUR

T1 - Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement

AU - Notarbartolo Di Villarosa, Monica

AU - Fontana, Gianfranco

AU - Labbozzetta, Manuela

AU - Bruno, Maurizio

AU - Poma, Paola

AU - Rosselli, Sergio

AU - Spinella, Alberto

PY - 2019

Y1 - 2019

N2 - Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticanceractivity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 andC-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGHof hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. Newderivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomericforms by the Barbier-Grignard procedure and three of them were found to be active toward all of the threetargets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed forthe more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpressNF−κB.

AB - Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticanceractivity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 andC-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGHof hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. Newderivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomericforms by the Barbier-Grignard procedure and three of them were found to be active toward all of the threetargets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed forthe more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpressNF−κB.

UR - http://hdl.handle.net/10447/361992

M3 - Article

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

ER -