Abstract
Background: Natural products and their derivatives are widely used to treat cancer and other diseases associated with ROS- and RNS-induced damages. Methods: A series of paramagnetic modified curcumin analogs and 3,5-diarylidene-piperidones (DAP) have been designed, synthesized, and characterized on their anti-proliferative and antioxidant activity.
Results: Biological characterization of the new compounds supported the earlier results that incorporation of a nitroxide moiety or its precursor into curcumin or diarylidenylpiperidone (DAP) scaffolds resulted in anti-proliferative effect toward cancerous cell-lines in case of aryl hydroxy and/or methoxy substituent containing derivatives, suggesting their potential for targeted therapeutic applications.
In case of basic side chain derivatives, nitroxide incorporation gave unambiguous results, however in tendency the more accessible DAP derivatives had stronger anti-proliferative effect. In most cases, the nitroxide incorporation increased the TEAC value (proton and electron donation capability) of DAP derivatives.
Conclusions: Among the compounds synthesized and investigated the spin-labeled curcumin and 3,5-bis(4-hydroxy-3-methoxybenzylidene)piperidin-4-one derivatives were the most effective antiproliferative and antioxidant derivatives.
Keywords: Antioxidants, anti-proliferative compounds, curcuminoids, nitroxides, Pabon reaction, structure-activity relationship.
Medicinal Chemistry
Title:Synthesis and Biological Evaluation of Curcumin-Nitroxide-Based Molecular Hybrids as Antioxidant and Anti-Proliferative Agents
Volume: 13 Issue: 8
Author(s): Balazs Bognar, M. Lakshmi Kuppusamy, Esha Madan, Tamas Kalai, Maria Balog, Jozsef Jeko, Periannan Kuppusamy and Kalman Hideg*
Affiliation:
- Department of Organic and Medicinal Chemistry, Medical Faculty of University of Pecs, Szigeti st. 12. Pecs,Hungary
Keywords: Antioxidants, anti-proliferative compounds, curcuminoids, nitroxides, Pabon reaction, structure-activity relationship.
Abstract: Background: Natural products and their derivatives are widely used to treat cancer and other diseases associated with ROS- and RNS-induced damages. Methods: A series of paramagnetic modified curcumin analogs and 3,5-diarylidene-piperidones (DAP) have been designed, synthesized, and characterized on their anti-proliferative and antioxidant activity.
Results: Biological characterization of the new compounds supported the earlier results that incorporation of a nitroxide moiety or its precursor into curcumin or diarylidenylpiperidone (DAP) scaffolds resulted in anti-proliferative effect toward cancerous cell-lines in case of aryl hydroxy and/or methoxy substituent containing derivatives, suggesting their potential for targeted therapeutic applications.
In case of basic side chain derivatives, nitroxide incorporation gave unambiguous results, however in tendency the more accessible DAP derivatives had stronger anti-proliferative effect. In most cases, the nitroxide incorporation increased the TEAC value (proton and electron donation capability) of DAP derivatives.
Conclusions: Among the compounds synthesized and investigated the spin-labeled curcumin and 3,5-bis(4-hydroxy-3-methoxybenzylidene)piperidin-4-one derivatives were the most effective antiproliferative and antioxidant derivatives.
Export Options
About this article
Cite this article as:
Bognar Balazs , Kuppusamy M. Lakshmi, Madan Esha, Kalai Tamas , Balog Maria, Jeko Jozsef , Kuppusamy Periannan and Hideg Kalman *, Synthesis and Biological Evaluation of Curcumin-Nitroxide-Based Molecular Hybrids as Antioxidant and Anti-Proliferative Agents, Medicinal Chemistry 2017; 13 (8) . https://dx.doi.org/10.2174/1871520617666170522124712
DOI https://dx.doi.org/10.2174/1871520617666170522124712 |
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
-
Renal Complications of Fabry Disease
Current Pharmaceutical Design Comparison of Fentanyl, Remifentanil, Sufentanil and Alfentanil in Combination with Propofol for General Anesthesia: A Systematic Review and Meta-analysis of Randomized Controlled Trials
Current Clinical Pharmacology Conceptual Model of Medication Adherence in Older Adults with High Blood Pressure-An Integrative Review of the Literature
Current Hypertension Reviews How to Measure Exercise Performance
Current Respiratory Medicine Reviews Nitrones: A Potential New Alternative as Therapeutic Agents
Current Organic Chemistry Intra - and Intercellular Calcium Handling in Pulmonary Arterial Hypertension
Medicinal Chemistry Platelets and Vascular Risk: An Option for Treatment
Current Pharmaceutical Design Multifactorial Regulation of GPER Expression in Cancer Cells and Cardiomyocytes
Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry (Discontinued) Aging Liver: Can Exercise be a Better Way to Delay the Process than Nutritional and Pharmacological Intervention? Focus on Lipid Metabolism
Current Pharmaceutical Design Mechanisms of Esophageal Protection, Gastroprotection and Ulcer Healing by Melatonin. Implications for the Therapeutic use of Melatonin in Gastroesophageal Reflux Disease (GERD) and Peptic Ulcer Disease
Current Pharmaceutical Design Pregnancy and Postpartum Influences on Rheumatoid Arthritis Activity:Natures Model to Investigate Systemic Biological Mechanisms in the Disease
Current Rheumatology Reviews Oxidative Stress and Post-Stroke Depression: Possible Therapeutic Role of Polyphenols?
Current Medicinal Chemistry Role of Central and Peripheral Chemoreceptors in Vasopressin Secretion Control
Endocrine, Metabolic & Immune Disorders - Drug Targets Editorial: (Persistent Elevation of Blood Pressure in Children and Adolescents is Associated with Arterial Hypertension and Premature Atherosclerosis in Adults. Is it Possible to Reverse this?)
Current Vascular Pharmacology Computed Tomography Imaging of the Coronary Arteries: State of the Art Applications and Recent Patents
Recent Patents on Medical Imaging Natriuretic Peptides in Heart Failure and Post-Myocardial Infarction
Current Hypertension Reviews Editorial: Liraglutide and Cardiometabolic Effects: More than Just Another Antiobesity Drug?
Current Vascular Pharmacology A Viewpoint on Angiotensin-Converting Enzyme 2, Anti-Hypertensives and Coronavirus Disease 2019 (COVID-19)
Infectious Disorders - Drug Targets Drug Repositioning for Treatment of Movement Disorders: From Serendipity to Rational Discovery Strategies
Current Topics in Medicinal Chemistry Neuropeptides as Therapeutic Targets to Combat Stress-Associated Behavioral and Neuroendocrinological Effects
CNS & Neurological Disorders - Drug Targets