Abstract
A 30-membered piperidine ring-fused aromatic sulfonamide library was synthetized, including N-arylsulfonyl 1,2,3,4-tetrahydroquinolines, 1,2,3,4-tetrahydroisoquinolines and 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles. The compounds induced oxidative stress and glutathione depletion in HT168 melanoma and K562 leukemia cells and in micromolar concentrations exerted cytotoxic effects. Among the tested sulfonamides, compounds 21, 22, 23, 35 and 41 exhibited 100% cytotoxic effects with low (< 10 µM) EC50 values on K562 cells. The cytotoxicity of lead compound 22 was investigated in 24 different cancer cell lines, and it was found to be active against leukemia, melanoma, glioblastoma, and liver, breast and lung cancer cells, as confirmed by classical biochemical and holographic microscopic analyses.
Keywords: Sulfonamide, tetrahydroquinoline, tetrahydroisoquinoline, tetrahydropyridoindle, anticancer agent, oxidative stress.
Medicinal Chemistry
Title:Aromatic Sulfonamides Containing a Condensed Piperidine Moiety as Potential Oxidative Stress-Inducing Anticancer Agents
Volume: 9 Issue: 7
Author(s): Ramóna Madácsi, Iván Kanizsai, Liliána Z. Fehér, Márió Gyuris, Béla Ózsvári, András Erdélyi, János Wölfling and László G. Puskás
Affiliation:
Keywords: Sulfonamide, tetrahydroquinoline, tetrahydroisoquinoline, tetrahydropyridoindle, anticancer agent, oxidative stress.
Abstract: A 30-membered piperidine ring-fused aromatic sulfonamide library was synthetized, including N-arylsulfonyl 1,2,3,4-tetrahydroquinolines, 1,2,3,4-tetrahydroisoquinolines and 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles. The compounds induced oxidative stress and glutathione depletion in HT168 melanoma and K562 leukemia cells and in micromolar concentrations exerted cytotoxic effects. Among the tested sulfonamides, compounds 21, 22, 23, 35 and 41 exhibited 100% cytotoxic effects with low (< 10 µM) EC50 values on K562 cells. The cytotoxicity of lead compound 22 was investigated in 24 different cancer cell lines, and it was found to be active against leukemia, melanoma, glioblastoma, and liver, breast and lung cancer cells, as confirmed by classical biochemical and holographic microscopic analyses.
Export Options
About this article
Cite this article as:
Madácsi Ramóna, Kanizsai Iván, Fehér Z. Liliána, Gyuris Márió, Ózsvári Béla, Erdélyi András, Wölfling János and Puskás G. László, Aromatic Sulfonamides Containing a Condensed Piperidine Moiety as Potential Oxidative Stress-Inducing Anticancer Agents, Medicinal Chemistry 2013; 9 (7) . https://dx.doi.org/10.2174/1573406411309070004
DOI https://dx.doi.org/10.2174/1573406411309070004 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
Call for Papers in Thematic Issues
Carbohydrates in Computational and Medicinal Chemistry
Carbohydrates are the most essential organic molecules and are involved in the maintenance of various physiological and metabolic processes in living organisms. Carbohydrate-based compounds have come to the attention of researchers because of their significant contributions to biological functions, such as cell development and cell proliferation, connections between several cells, ...read more
Recent Advances in the Medicinal Chemistry of Cancer
Scope of the Thematic Issue: Correlation between structure and function is one of the important aspects of the success of anti-cancer compounds associated with their structure-activity interactions, physiology, biochemical, molecular, and genetic processes. Overcoming these obstacles is key to obtaining further insights into developments in rational drug design, bioorganic chemistry, ...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
-
Thromboembolic Events in Patients Treated with Anti-Angiogenic Drugs
Current Vascular Pharmacology Molecular and Cellular Activities of Vitamin E Analogues
Mini-Reviews in Medicinal Chemistry Lung Cancer Chemotherapy, New Treatment and Related Patents
Recent Patents on Anti-Cancer Drug Discovery α7 nAChR in Airway Respiratory Epithelial Cells
Current Drug Targets <i>In Silico</i> Study of the Active Compounds of <i>Lindera aggregata</i> (Sims) Kosterm as Anti-coronavirus
Current Nutrition & Food Science Mesenchymal Stem Cells: Key Actors in Tumor Niche
Current Stem Cell Research & Therapy Mechanism of Cancer Drug Resistance and the Involvement of Noncoding RNAs
Current Medicinal Chemistry Preparation of Quercetin Loaded Microparticles and their Antitumor Activity against Human Lung Cancer Cells (A549) in vitro
Current Pharmaceutical Biotechnology Structural Models of Protein-DNA Complexes Based on Interface Prediction and Docking
Current Protein & Peptide Science Antigene and Antiproliferative Effects of Triplex-Forming Oligonucleotide (TFO) Targeted on hmgb1 Gene in Human Hepatoma Cells
Anti-Cancer Agents in Medicinal Chemistry Chalcones in Cancer: Understanding their Role in Terms of QSAR
Current Medicinal Chemistry Omega-3 Polyunsaturated Fatty Acids and Depression: A Review of the Evidence
Current Pharmaceutical Design Clinical Next Generation Sequencing for Precision Medicine in Cancer
Current Genomics ABC Transporters and the Blood-Brain Barrier
Current Pharmaceutical Design Cancer Vaccines: Emphasis on Pediatric Cancers
Current Pharmaceutical Design Mitochondrial Tolerance to Drugs and Toxic Agents in Ageing and Disease
Current Drug Targets A Patent Review on the Use of L-Asparaginase in the Treatment of Acute Lymphocytic Leukemia
Recent Advances in Drug Delivery and Formulation Targeted Drug Delivery for Breast Cancer Treatment
Recent Patents on Anti-Cancer Drug Discovery Phase I Clinical Trial of Exherin (ADH-1) in Patients with Advanced Solid Tumors
Current Clinical Pharmacology MicroRNA-21: From Cancer to Cardiovascular Disease
Current Drug Targets