Abstract
The 9-(bromoalkyl)-1,4-dimethyl-9H-carbazole (2a-d) derivatives, characterized by the presence of five or seven methylenic spacer groups bonded to the carbazole nitrogen, have been synthesized from the corresponding 1,4- dimethyl-9H-carbazole and appropriate dibromoalkane following a general synthetic method. All the prepared species have been fully characterized by means of IR, and 1H and 13C NMR spectroscopy, GC-MS and Elemental analysis. Good crystals of the 2c have been obtained and the crystal structure has been solved by means of X-ray diffractometry. In order to study the cytotoxic effect of 2a, 2b, 2c, 2d carbazole derivatives on A2780 ovarian cancer cells, we performed MTT assay after exposure of this cell population to those compounds in a concentration range from 1 to 10μM. Finally, we want to verify whether the cytotoxic effect of the 2c carbazole is mediated by apoptotic mechanisms, by performing chromatin condensation assay on the A2780 cell cultures upon the carbazole treatment at concentration of 10 μM for 72h. All together our data demonstrate that carbazole derivatives exert inhibitory effects on ovarian cancer cell growth, highlighting a stronger and a dose-dependent anti proliferative activity displayed by 2c carbazole, designating this compound, as a better candidate in the treatment of human ovarian cancer.
Keywords: A2780 ovarian cancer cells, Apoptosis, Carbazole derivatives, X-Ray structure, Heterocycles, MTT.
Current Topics in Medicinal Chemistry
Title:Crystallographic Study and Biological Evaluation of 1,4-dimethyl-N-alkylcarbazoles†
Volume: 15 Issue: 11
Author(s): Carmela Saturnino, Anna Caruso, Pasquale Longo, Anna Capasso, Attilio Pingitore, Maria Cristina Caroleo, Erika Cione, Mariarita Perri, Francesco Nicolo, Viviana Mollica Nardo, Luigi Monsu Scolaro, Maria Stefania Sinicropi, Maria Rosaria Plutino and Hussein El-Kashef
Affiliation:
Keywords: A2780 ovarian cancer cells, Apoptosis, Carbazole derivatives, X-Ray structure, Heterocycles, MTT.
Abstract: The 9-(bromoalkyl)-1,4-dimethyl-9H-carbazole (2a-d) derivatives, characterized by the presence of five or seven methylenic spacer groups bonded to the carbazole nitrogen, have been synthesized from the corresponding 1,4- dimethyl-9H-carbazole and appropriate dibromoalkane following a general synthetic method. All the prepared species have been fully characterized by means of IR, and 1H and 13C NMR spectroscopy, GC-MS and Elemental analysis. Good crystals of the 2c have been obtained and the crystal structure has been solved by means of X-ray diffractometry. In order to study the cytotoxic effect of 2a, 2b, 2c, 2d carbazole derivatives on A2780 ovarian cancer cells, we performed MTT assay after exposure of this cell population to those compounds in a concentration range from 1 to 10μM. Finally, we want to verify whether the cytotoxic effect of the 2c carbazole is mediated by apoptotic mechanisms, by performing chromatin condensation assay on the A2780 cell cultures upon the carbazole treatment at concentration of 10 μM for 72h. All together our data demonstrate that carbazole derivatives exert inhibitory effects on ovarian cancer cell growth, highlighting a stronger and a dose-dependent anti proliferative activity displayed by 2c carbazole, designating this compound, as a better candidate in the treatment of human ovarian cancer.
Export Options
About this article
Cite this article as:
Saturnino Carmela, Caruso Anna, Longo Pasquale, Capasso Anna, Pingitore Attilio, Cristina Caroleo Maria, Cione Erika, Perri Mariarita, Nicolo Francesco, Mollica Nardo Viviana, Monsu Scolaro Luigi, Stefania Sinicropi Maria, Rosaria Plutino Maria and El-Kashef Hussein, Crystallographic Study and Biological Evaluation of 1,4-dimethyl-N-alkylcarbazoles†, Current Topics in Medicinal Chemistry 2015; 15 (11) . https://dx.doi.org/10.2174/1568026615666150317222444
DOI https://dx.doi.org/10.2174/1568026615666150317222444 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
Call for Papers in Thematic Issues
Chemistry Based on Natural Products for Therapeutic Purposes
The development of new pharmaceuticals for a wide range of medical conditions has long relied on the identification of promising natural products (NPs). There are over sixty percent of cancer, infectious illness, and CNS disease medications that include an NP pharmacophore, according to the Food and Drug Administration. Since NP ...read more
Current Trends in Drug Discovery Based on Artificial Intelligence and Computer-Aided Drug Design
Drug development discovery has faced several challenges over the years. In fact, the evolution of classical approaches to modern methods using computational methods, or Computer-Aided Drug Design (CADD), has shown promising and essential results in any drug discovery campaign. Among these methods, molecular docking is one of the most notable ...read more
Drug Discovery in the Age of Artificial Intelligence
In the age of artificial intelligence (AI), we have witnessed a significant boom in AI techniques for drug discovery. AI techniques are increasingly integrated and accelerating the drug discovery process. These developments have not only attracted the attention of academia and industry but also raised important questions regarding the selection ...read more
From Biodiversity to Chemical Diversity: Focus of Flavonoids
Flavonoids are the largest group of polyphenols, plant secondary metabolites arising from the essential aromatic amino acid phenylalanine (or more rarely from tyrosine) via the phenylpropanoid pathway. The flavan nucleus is the basic 15-carbon skeleton of flavonoids (C6-C3-C6), which consists of two phenyl rings (A and B) and a heterocyclic ...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
- Announcements
Related Articles
-
DNA Methylation, An Epigenetic Mode of Gene Expression Regulation in Reproductive Science
Current Pharmaceutical Design Incidentally Detected Increased FDG Uptake in Bowel and its Correlation with Hystopathological Data: Our Experience in a Case Series Study
Current Radiopharmaceuticals NF-κB Signaling Pathway Inhibitors as Anticancer Drug Candidates
Anti-Cancer Agents in Medicinal Chemistry Patent Selections:
Recent Patents on Biotechnology Synthesis and Biological Evaluation of 3-Substituted-4-(4-methylthio phenyl)-1HPyrrole Derivatives as Potential Anticancer Agents
Anti-Cancer Agents in Medicinal Chemistry Clinical Applications of Positron Emission Tomography (PET) Imaging in Medicine: Oncology, Brain Diseases and Cardiology
Current Radiopharmaceuticals The Urokinase Receptor Interactome
Current Pharmaceutical Design Cytotoxic and Antitumor Potentialities of Aporphinoid Alkaloids
Current Medicinal Chemistry - Anti-Cancer Agents Nutlins and Ionizing Radiation in Cancer Therapy
Current Pharmaceutical Design HSP90 Inhibitors: Multi-Targeted Antitumor Effects and Novel Combinatorial Therapeutic Approaches in Cancer Therapy
Current Medicinal Chemistry Structural and Mechanistic Bases of the Anticancer Activity of Natural Aporphinoid Alkaloids
Current Topics in Medicinal Chemistry The Role of Snail in EMT and Tumorigenesis
Current Cancer Drug Targets Perspectives in Nanomedicine-Based Research Towards Cancer Therapies
Current Nanoscience Insights in microRNAs Biology
Current Topics in Medicinal Chemistry An Emerging Strategy for Cancer Treatment Targeting Aberrant Glycogen Synthase Kinase 3β
Anti-Cancer Agents in Medicinal Chemistry Immunohistochemical Expression of Melatonin Receptor MT1 and Glucose Transporter GLUT1 in Human Breast Cancer
Anti-Cancer Agents in Medicinal Chemistry New Poly(3-hydroxybutyrate) Microparticles with Paclitaxel Sustained Release for Intraperitoneal Administration
Anti-Cancer Agents in Medicinal Chemistry Targeting Different Pathways Using Novel Combination Therapy in Triple Negative Breast Cancer
Current Cancer Drug Targets Construction of Macromolecular Assemblages in Eukaryotic Processes and their Role in Human Disease: Linking RINGs Together
Current Protein & Peptide Science From French Paradox to Cancer Treatment: Anti-cancer Activities and Mechanisms of Resveratrol
Anti-Cancer Agents in Medicinal Chemistry