Abstract
Quinone moieties are present in many drugs such as anthracyclines, daunorubicin, doxorubicin, mitomycin, mitoxantrones and saintopin, which are used clinically in the therapy of solid cancers. The cytotoxic effects of these quinones are mainly due to the following two factors: (i) inhibition of DNA topoisomerase-II and, (ii) formation of semiquinone radical that can transfer an electron to oxygen to produce super oxide, which is catalyzed by flavoenzymes such as NADPH-cytochrome-P-450 reductase. Both semiquinone and super oxide of quinones can generate the hydroxyl radical, which is the cause of DNA strand breaks. 1,4-naphthoquinone contains two quinone groups that have the ability to accept one or two electrons to form the corresponding radical anion or di-anion species. It is probably dependent on the quinone redox cycling that yields "reactive oxygen species" (ROS) as well as arylation reactions, which is common to quinones for biological relevance. In the present review, an attempt has been made to collect the cytotoxicity data on different series of 1,4-naphthoquinones against four different cancer cell lines that are L1210, A549, SNU-1, and K562, which were acquired by using identical method, and has been discussed in terms of QSAR (quantitative structure-activity relationships) to understand the chemical-biological interactions. QSAR results have shown that the cytotoxic activities of 1,4- naphthoquinones depend largely on their hydrophobicity.
Keywords: Hydrophobicity, Molar refractivity, 1,4-Naphthoquinones, Quantitative structure-activity relationships
Anti-Cancer Agents in Medicinal Chemistry
Title: Anti-Cancer Activities of 1,4-Naphthoquinones: A QSAR Study
Volume: 6 Issue: 5
Author(s): Rajeshwar P. Verma
Affiliation:
Keywords: Hydrophobicity, Molar refractivity, 1,4-Naphthoquinones, Quantitative structure-activity relationships
Abstract: Quinone moieties are present in many drugs such as anthracyclines, daunorubicin, doxorubicin, mitomycin, mitoxantrones and saintopin, which are used clinically in the therapy of solid cancers. The cytotoxic effects of these quinones are mainly due to the following two factors: (i) inhibition of DNA topoisomerase-II and, (ii) formation of semiquinone radical that can transfer an electron to oxygen to produce super oxide, which is catalyzed by flavoenzymes such as NADPH-cytochrome-P-450 reductase. Both semiquinone and super oxide of quinones can generate the hydroxyl radical, which is the cause of DNA strand breaks. 1,4-naphthoquinone contains two quinone groups that have the ability to accept one or two electrons to form the corresponding radical anion or di-anion species. It is probably dependent on the quinone redox cycling that yields "reactive oxygen species" (ROS) as well as arylation reactions, which is common to quinones for biological relevance. In the present review, an attempt has been made to collect the cytotoxicity data on different series of 1,4-naphthoquinones against four different cancer cell lines that are L1210, A549, SNU-1, and K562, which were acquired by using identical method, and has been discussed in terms of QSAR (quantitative structure-activity relationships) to understand the chemical-biological interactions. QSAR results have shown that the cytotoxic activities of 1,4- naphthoquinones depend largely on their hydrophobicity.
Export Options
About this article
Cite this article as:
Verma P. Rajeshwar, Anti-Cancer Activities of 1,4-Naphthoquinones: A QSAR Study, Anti-Cancer Agents in Medicinal Chemistry 2006; 6 (5) . https://dx.doi.org/10.2174/187152006778226512
DOI https://dx.doi.org/10.2174/187152006778226512 |
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
-
Biodegradable Polymeric Nanoparticles as the Delivery Carrier for Drug
Current Drug Delivery A Review of Current Animal Models of Osteoarthritis Pain
Current Pharmaceutical Biotechnology Novel Concepts for Anti-Infective Activity of Cytokines, Chemokines and Diverse Agents
Recent Patents on Anti-Infective Drug Discovery Antitumor Activity of Oxali-Titanocene Y in Xenografted CAKI-1 Tumors in Mice
Letters in Drug Design & Discovery Nuclear Imaging and Early Breast Cancer Detection
Current Radiopharmaceuticals Neopterin as a Marker for Immune System Activation
Current Drug Metabolism Endocytosis, Intracellular Traffic and Fate of Cell Penetrating Peptide Based Conjugates and Nanoparticles
Current Pharmaceutical Design Targeted Therapy for Advanced Renal Cell Cancer: Cytokines and Beyond
Current Pharmaceutical Design Editorial [Hot Topic: Bringing Drugs Into the Injured Brain and Keeping Them There (Executive Guest Editors: Dirk M. Hermann and Pauline Patak)]
Current Pharmaceutical Design Taurine-Diabetes Interaction: From Involvement to Protection
Current Diabetes Reviews Red Blood Cell-Encapsulated L-Asparaginase: Potential Therapy of Patients with Asparagine Synthetase Deficient Acute Myeloid Leukemia
Protein & Peptide Letters Synthesis of 1,3,6-Trioxygenated Prenylated Xanthone Derivatives as Potential Antitumor Agents
Letters in Organic Chemistry Biologically Active Selenophenes and Benzo[b]selenophenes
Current Organic Synthesis Rethinking Target Discovery in Polygenic Diseases
Current Topics in Medicinal Chemistry Natural Product Inhibitors of the Ubiquitin-Proteasome Pathway
Current Drug Targets Erythropoietin Withdrawal Leads to the Destruction of Young Red Cells at the Endothelial-Macrophage Interface
Current Pharmaceutical Design Enhanced Hepatic and Kidney Cytochrome P-450 Activities in Nandrolone Decanoate Treated Albino Mice
Drug Metabolism Letters New Advances in the Field of Calcium Channel Antagonists: Cardiovascular Effects and Structure-Activity Relationships
Current Medicinal Chemistry - Cardiovascular & Hematological Agents Immune Modulation of Asian Folk Herbal Medicines and Related Chemical Components for Cancer Management
Current Medicinal Chemistry Thiazolidinediones and Type 2 Diabetes: From Cellular Targets to Cardiovascular Benefit
Current Drug Targets