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
-
Systemic Drug Delivery Systems for Bone Tissue Regeneration– A Mini Review
Current Pharmaceutical Design Synthesis, Antibacterial Activity, Interaction with Nucleobase and Molecular Docking Studies of 4-Formylbenzoic Acid Based Thiazoles
Medicinal Chemistry Recent Patents in Glycan-Based Cancer Biomarkers and Discovery Technologies
Recent Patents on Biomarkers The Antitumor Activity of a Novel Fluorobenzamidine against Dimethylhydrazine- Induced Colorectal Cancer in Rats
Anti-Cancer Agents in Medicinal Chemistry Internal and External Triggering Mechanism of “Smart” Nanoparticle-Based DDSs in Targeted Tumor Therapy
Current Pharmaceutical Design Determination of Dysregulated miRNA Expression Levels by qRT-PCR after the Application of Usnic Acid to Breast Cancer
Anti-Cancer Agents in Medicinal Chemistry The Use of Cyclodextrins Nanoparticles for Oral Delivery
Current Medicinal Chemistry Cytokines as Anti-Angiogenic Agents in Haematological Malignancies
Current Cancer Drug Targets Meet Our Editorial Board Member
Mini-Reviews in Medicinal Chemistry The Production of Solid Dosage Forms from Non-Degradable Polymers
Current Pharmaceutical Design Recent Advances in the Development of Immunoadhesins for Immune Therapy and as Anti-Infective Agents
Recent Patents on Anti-Infective Drug Discovery Significance of Prion and Prion-Like Proteins in Cancer Development, Progression and Multi-Drug Resistance
Current Cancer Drug Targets Health Consequences of Catabolic Synthesis of Hippuric Acid in Humans
Current Clinical Pharmacology HPV Vaccination in Adolescents: From Clinical Data to Implementation and Practice
Current Cancer Therapy Reviews Therapeutic Potential of Melatonin in the Regulation of MiR-148a-3p and Angiogenic Factors in Breast Cancer
MicroRNA Drug Targets in Infections with Ebola and Marburg Viruses
Infectious Disorders - Drug Targets Bioactive Peptides Sensitize Cells to Anticancer Effects of Oxaliplatin in Human Colorectal Cancer Xenografts in Nude Mice
Protein & Peptide Letters Evaluation of Tissue and Serum Expression Levels of Lactate Dehydrogenase Isoenzymes in Patients with Head and Neck Squamous Cell Carcinoma
Anti-Cancer Agents in Medicinal Chemistry The Role of Dietary Approach in Irritable Bowel Syndrome
Current Medicinal Chemistry miR-203 Suppresses the Proliferation and Metastasis of Hepatocellular Carcinoma by Targeting Oncogene ADAM9 and Oncogenic Long Non-coding RNA HULC
Anti-Cancer Agents in Medicinal Chemistry