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
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
-
Nitrogen-Containing Heterocycles as Anticancer Agents: An Overview
Anti-Cancer Agents in Medicinal Chemistry Synthesis, Biological Evaluation and Molecular Dynamics Simulation Studies of Novel Diphenyl Ethers
Medicinal Chemistry Integrins as A New Target for Cancer Treatment
Anti-Cancer Agents in Medicinal Chemistry Transport Mechanism-Based Drug Molecular Design: Novel Camptothecin Analogues to Circumvent ABCG2-associated Drug Resistance of Human Tumor Cells
Current Pharmaceutical Design Histone and Non-Histone Targets of Dietary Deacetylase Inhibitors
Current Topics in Medicinal Chemistry Cytotoxic T Cell Reponses Against Immunoglobulin in Malignant and Normal B Cells: Implications for Tumor Immunity and Autoimmunity
Current Pharmaceutical Design Current Advances in Therapy for Metastatic Melanoma
Current Cancer Therapy Reviews Biological Basis of Novel Therapies for Myelodysplastic Syndrome
Current Cancer Therapy Reviews Editorial from Editor-in-Chief
Current Respiratory Medicine Reviews Anticancer Screening and Structure Activity Relationship Study of Some Semicarbazides and 1,2,4-Triazolin-5-ones
Letters in Drug Design & Discovery PARP Inhibitor Development for Systemic Cancer Targeting
Anti-Cancer Agents in Medicinal Chemistry Identification and Targeting of Tumor Escape Mechanisms: A New Hope for Cancer Therapy?
Current Pharmaceutical Design Natural Antibodies: Protecting Role of IgM in Glioblastoma and Brain Tumours
Current Pharmaceutical Design G-Protein Coupled Receptor 124 (GPR124) in Endothelial Cells Regulates Vascular Endothelial Growth Factor (VEGF)-Induced Tumor Angiogenesis
Current Molecular Medicine Nanomedicine to Deal With Cancer Cell Biology in Multi-Drug Resistance
Mini-Reviews in Medicinal Chemistry Strategic siRNA Screening Approaches to Target Cancer at the Cancer Research UK Beatson Institute
Combinatorial Chemistry & High Throughput Screening Comparative Proteomics and Bioinformatics Analysis of Tissue from Non-Small Cell Lung Cancer Patients
Current Proteomics Effects of Bioactive Compounds from Carrots (Daucus carota L.), Polyacetylenes, Beta-Carotene and Lutein on Human Lymphoid Leukaemia Cells
Anti-Cancer Agents in Medicinal Chemistry microRNAs and Esophageal Cancer - Implications for Pathogenesis and Therapy
Current Pharmaceutical Design Cachexia and Oxidative Stress in Cancer: An Innovative Therapeutic Management
Current Pharmaceutical Design