Abstract
Oleanolic acid ketones, oximes, lactams and nitriles were obtained. Complete spectral characterizations (IR, 1H NMR, 13C NMR, DEPT and MS) of the synthesized compounds are presented. The derivatives had oxo, hydroxyimino, lactam or nitrile functions at the C-3 position, an esterified or unmodified carboxyl group at the C- 17 location and, in some cases, an additional oxo function at the C-11 position. The new compounds were tested for cytotoxic activity on the HeLa, KB, MCF-7 and Hep-G2 cancer cell lines with the application of MTT [3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] test. Among the tested compounds, some oximes and all lactams proved to be the most active cytotoxic agents. These triterpenes significantly inhibited the growth of the HeLa, KB, MCF-7 and Hep-G2 cancer cell lines at micromolar concentrations.
Keywords: Beckmann rearrangement, cytotoxic activity, lactams of oleanolic acid, oleanolic acid derivatives, triterpenes.
Anti-Cancer Agents in Medicinal Chemistry
Title:Oleanolic Acid A-lactams Inhibit the Growth of HeLa, KB, MCF-7 and Hep-G2 Cancer Cell Lines at Micromolar Concentrations
Volume: 16 Issue: 5
Author(s): Barbara Bednarczyk-Cwynar, Piotr Ruszkowski, Teresa Bobkiewicz-Kozlowska and Lucjusz Zaprutko
Affiliation:
Keywords: Beckmann rearrangement, cytotoxic activity, lactams of oleanolic acid, oleanolic acid derivatives, triterpenes.
Abstract: Oleanolic acid ketones, oximes, lactams and nitriles were obtained. Complete spectral characterizations (IR, 1H NMR, 13C NMR, DEPT and MS) of the synthesized compounds are presented. The derivatives had oxo, hydroxyimino, lactam or nitrile functions at the C-3 position, an esterified or unmodified carboxyl group at the C- 17 location and, in some cases, an additional oxo function at the C-11 position. The new compounds were tested for cytotoxic activity on the HeLa, KB, MCF-7 and Hep-G2 cancer cell lines with the application of MTT [3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] test. Among the tested compounds, some oximes and all lactams proved to be the most active cytotoxic agents. These triterpenes significantly inhibited the growth of the HeLa, KB, MCF-7 and Hep-G2 cancer cell lines at micromolar concentrations.
Export Options
About this article
Cite this article as:
Bednarczyk-Cwynar Barbara, Ruszkowski Piotr, Bobkiewicz-Kozlowska Teresa and Zaprutko Lucjusz, Oleanolic Acid A-lactams Inhibit the Growth of HeLa, KB, MCF-7 and Hep-G2 Cancer Cell Lines at Micromolar Concentrations, Anti-Cancer Agents in Medicinal Chemistry 2016; 16 (5) . https://dx.doi.org/10.2174/1871520615666150907095756
DOI https://dx.doi.org/10.2174/1871520615666150907095756 |
Print ISSN 1871-5206 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5992 |
Call for Papers in Thematic Issues
Induction of cell death in cancer cells by modulating telomerase activity using small molecule drugs
Telomeres are distinctive but short stretches present at the corners of chromosomes and aid in stabilizing chromosomal makeup. Resynthesis of telomeres supported by the activity of reverse transcriptase ribonucleoprotein complex telomerase. There is no any telomerase activity in human somatic cells, but the stem cells and germ cells undergone telomerase ...read more
Role of natural compounds as anti anti-cancer agents
Cancer is considered the leading cause of worldwide mortality, accounting for nearly 10 million deaths in 2022. Cancer outcome can be improved through an appropriate screening and early detection and through an efficient clinical treatment. Chemotherapy remains an important approach in treatment o f several types of cancers, even though ...read more
Signaling and enzymatic modulators in cancer treatment
Cancer accounts for nearly 10 million deaths in 2022 and is considered the leading cause of worldwide mortality. Cancer outcome can be improved through an appropriate screening and early detection and through an efficient clinical treatment. Chemotherapy, radiotherapy and surgery are the most important approach for the treatment of several ...read more
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Identification of Multiple Subcellular Locations for Proteins in Budding Yeast
Current Bioinformatics Molecular Docking of 4-ethoxychalcones on Oxidoreductase/Pirin Inhibitors and Cytotoxic Evaluation on Breast/Skin Cancer Cell Lines
Letters in Drug Design & Discovery Advanced Cardiac Imaging of Radiation-induced Injury - a Review
Current Medical Imaging Serpins for Diagnosis and Therapy in Cancer
Cardiovascular & Hematological Disorders-Drug Targets A Review: Hair Health, Concerns of Shampoo Ingredients and Scalp Nourishing Treatments
Current Pharmaceutical Biotechnology Anti-Diarrheal Drug Repositioning in Tumour Cell Cytotoxicity
Anti-Cancer Agents in Medicinal Chemistry Intestinal Absorption Enhancement Via the Paracellular Route by Fatty Acids, Chitosans and Others: A Target for Drug Delivery
Current Drug Delivery Folic Acid Conjugated Chitosan Nanoparticles for Tumor Targeting of Therapeutic and Imaging Agents
Pharmaceutical Nanotechnology Copper and Iron-assisted Palladium-catalyzed Direct Arylation of Azoles with Arylboronic Acids under Ligand and Base-free Conditions
Letters in Organic Chemistry The Drug Targeting and Delivery Approach Applied to Pt-Antitumour Complexes. A Coordination Point of View
Current Medicinal Chemistry A Comprehensive Overview of the Synthesis of Tetrahydrocarbazoles and its Biological Properties
Mini-Reviews in Organic Chemistry Vitamin D Analogs as Modulators of Vitamin D Receptor Action
Current Topics in Medicinal Chemistry Mitochondrial Permeability Transition as Target of Anticancer Drugs
Current Pharmaceutical Design Impact of Magnetic Nanoparticles in Biomedical Applications
Recent Patents on Drug Delivery & Formulation Co-formulation of P-glycoprotein Substrate and Inhibitor in Nanocarriers: An Emerging Strategy for Cancer Chemotherapy
Current Cancer Drug Targets Vitamins for Cancer Prevention and Treatment: An Insight
Current Molecular Medicine New Pharmacological Approaches to the Cholinergic System: An Overview on Muscarinic Receptor Ligands and Cholinesterase Inhibitors
Recent Patents on CNS Drug Discovery (Discontinued) Topoisomerase II Inhibitors and Poisons, and the Influence of Cell Cycle Checkpoints
Current Medicinal Chemistry In Silico Identification of MicroRNAs Predicted to Regulate the Drug Metabolizing Cytochrome P450 Genes
Drug Metabolism Letters Recent Advances in Optical Cancer Imaging of EGF Receptors
Current Medicinal Chemistry