Quinone-Based Compounds in Drug Discovery

Trends and Applications

1st Edition - October 25, 2024
Imprint: Academic Press
Editors: Umar Ali Dar, Mohd. Shahnawaz, Khalid Rehman Hakeem
Language: English
Paperback ISBN:
9 7 8 - 0 - 4 4 3 - 2 4 1 2 6 - 0
eBook ISBN:
9 7 8 - 0 - 4 4 3 - 2 4 1 2 5 - 3

Quinone-Based Compounds in Drug Discovery: Trends and Applications provides a comprehensive and up-to-date overview of the latest advances in the field of drug discovery using qui… Read more

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Quinone-Based Compounds in Drug Discovery: Trends and Applications provides a comprehensive and up-to-date overview of the latest advances in the field of drug discovery using quinone-based materials. The book covers various aspects of quinone-based materials such as their synthesis, characterization, and applications in drug discovery, consolidating current research. It introduces quinones in the pharmacology context and then describes current developments in drugs for key diseases and conditions. Final chapters deal with the regulatory and commercial framework to take quinone-based drugs to the market.

This book will benefit a wide range of readers, including researchers, scientists, and graduate students in the field of drug discovery. Chemists and biochemists will also benefit from the contents of this book.

Title of Book
Cover image
Title page
Table of Contents
Copyright
Dedication
Contributors
About the editors
Preface
Acknowledgments
Chapter 1. Introduction to quinone-based materials in drug discovery
1.1 Introduction
1.2 Chemical properties of quinones
1.3 Natural sources and occurrence of quinones in living organisms
1.4 Role of quinones in biological processes and signaling pathways
1.5 Quinone-based materials in drug discovery
1.5.1 Design considerations for developing quinone-based drugs
1.5.1.1 Structure-activity relationship (SAR)
1.5.2 Electron-withdrawing or donating groups
1.5.3 Linker design
1.5.4 Prodrug strategies
1.6 Strategies for synthesizing and modifying quinone-based compounds
1.7 Pharmacokinetic and toxicological aspects of quinone-based drugs
1.8 Quinone-based anticancer agents
1.9 Quinones as antimicrobial agents
1.9.1 Major mechanisms of action and targets of quinone-based antimicrobial agents
1.9.2 Limitations of using quinones as antimicrobial agents
1.10 Quinone-based materials in neurodegenerative diseases
1.10.1 Challenges and future perspectives in utilizing quinones for neuroprotection
1.11 Conclusion and future directions
Chapter 2. Marine-derived quinones: a potential source for drug discovery
2.1 Introduction
2.2 Definition of marine-derived quinones
2.3 Importance of marine-derived quinones in drug discovery
2.3.1 Structural diversity
2.3.2 Biologically active compounds
2.3.3 Drug targets and mechanisms of action
2.3.4 Overcoming drug resistance
2.3.5 Biodiversity and untapped potential
2.4 Biological sources of marine-derived quinones
2.5 Marine invertebrates
2.5.1 Sponges (phylum Porifera)
2.5.1.1 Avarol
2.5.1.2 Spongiaquinone-1
2.5.1.3 Halenaquinone
2.5.1.4 Nakijiquinones
2.5.2 Tunicates (phylum Cordata)
2.6 Marine microorganisms
2.6.1 Fungi
2.6.2 Algae
2.6.3 Bacteria
2.7 Pharmacological potential of marine-derived quinones
2.8 Anticancer activity
2.9 Antimicrobial activity
2.9.1 Antibacterial activity
2.9.2 Antifungal activity
2.10 Antiinflammatory activity
2.11 Antioxidant activity
2.12 Other pharmacological activities
2.13 Antiviral
2.14 Antiparasitic activity
2.15 Neuroprotective activity
2.16 Cardiovascular effects
2.17 Enzyme inhibition
2.18 Challenges and future directions in marine-derived quinone research
2.18.1 Challenges in marine-derived quinone research
2.18.2 Sample collection and access
2.18.3 Compound identification
2.18.4 Bioactivity screening
2.18.5 Synthesis and supply
2.19 Future directions in marine-derived quinone research
2.19.1 Ecological significance
2.19.2 Drug development
2.19.3 Mode of action studies
2.19.4 Synergy and combination studies
2.19.5 Structure-activity relationship (SAR) studies
2.20 Conclusion
Chapter 3. Naturally occurring and structural analogues of quinones offering new research directions for the discovery of anticancer drugs
3.1 Introduction
3.2 Benzoquinone (1)
3.2.1 Thymoquinone (5)
3.2.2 Anticancer activity of TQ
3.2.3 Mechanisms of anti-cancer activity
3.3 Embelin (8)
3.3.1 Activity of embelin against different cancers
3.3.2 Mechanisms of anti-cancer activity
3.4 Streptonigrin (15)
3.5 Mitomycin C (16)
3.6 Naphthoquinone (3)
3.6.1 Plant-derived naphthoquinones
3.6.2 Juglone (17)
3.6.3 Lawsone (18)
3.6.4 Plumbagin (19)
3.6.5 Lapachol (20)
3.6.6 Shikonin (21)
3.6.7 Menadione (44)
3.7 Anthraquinone (4)
3.7.1 Emodin (54)
3.7.2 Aloe-emodin (55)
3.7.3 Rhein (56)
3.7.4 Mechanisms of anti-cancer activity
3.7.5 Damnacanthal (57)
3.7.6 Chrysophanol (58)
3.7.7 Daunorubicin (59)
3.7.8 Doxorubicin (64)
3.8 Future perspective
3.8.1 Targeted therapies and personalized medicine
3.8.2 Combination therapies
3.8.3 Drug delivery systems
3.8.4 Resistance mechanisms
3.8.5 Clinical trials and regulatory approval
3.9 Conclusions
Chapter 4. Understanding quinone derivatives antibacterial and antimicrobial activities relies on the structural activity relationship
4.1 Introduction
4.1.1 Benzoquinone (1)
4.1.2 Embelin (2)
4.1.3 Mechanisms of action
4.2 Thymoquinone (3)
4.2.1 Mechanisms of action
4.3 Dithymoquinone (4)
4.3.1 Mechanisms of action
4.4 Ubiquinone (5)
4.5 Naphthoquinone (6)
4.5.1 Structure activity relationships of naphthoquinone and its derivatives
4.5.2 Lawsone (7)
4.5.3 Juglone (8)
4.5.4 Menadione (9)
4.5.5 Plumbagin (10)
4.5.6 Naphthazarin (11)
4.5.7 Shikonin (12)
4.6 Anthraquinone (49)
4.6.1 Alizarin (50)
4.6.2 Chrysophanol (51)
4.6.3 Purpurin (52)
4.6.4 Emodin (53)
4.6.5 Aloe emodin (54)
4.6.6 Rhein (55)
4.7 Future perspective
4.8 Conclusions
Chapter 5. Quinones as antioxidants
5.1 Introduction
5.1.1 Basic chemistry of quinones
5.1.2 Benzoquinones
5.1.3 Naphthoquinones
5.1.4 Anthraquinones
5.1.5 Polycyclic quinones
5.1.6 Hydroquinones
5.1.7 Quinones with side chains
5.2 Electron transfer properties of quinones
5.3 Redox reactions involving quinones
5.4 Antioxidant mechanisms of quinones
5.4.1 Direct antioxidant activity of quinones
5.4.1.1 Quenching of reactive oxygen species (ROS)
5.4.2 Scavenging of free radicals
5.5 Indirect antioxidant activity of quinones
5.5.1 Regeneration of other antioxidants (e.g., vitamin E, ascorbic acid)
5.6 Modulation of antioxidant enzyme activity (e.g., catalase, superoxide dismutase)
5.7 Sources of quinones with antioxidant properties
5.7.1 Natural sources of quinones
5.7.1.1 Quinones in plants and their biological functions
5.7.2 Quinones in foods and their potential health benefits
5.8 Synthetic quinones with antioxidant properties
5.8.1 Design and synthesis of quinone-based antioxidants
5.9 Structure-activity relationships of synthetic quinones
5.10 Biological activities of quinones as antioxidants
5.10.1 Protection against oxidative damage
5.10.1.1 Quinones as lipid peroxidation inhibitors
5.11 Quinones as protein oxidation inhibitors
5.12 Potential therapeutic applications of quinones
5.12.1 Quinones as anticancer agents
5.13 Quinones as neuroprotective agents
5.14 Quinones as anti-inflammatory agents
5.15 Safety and limitations of quinones as antioxidants
5.15.1 Potential toxicity and side effects of quinones
5.16 Factors affecting the efficacy of quinones as antioxidants
5.17 Dosage considerations and interactions with other drugs
5.17.1 Dosage considerations
5.17.2 Drug-drug interactions
5.18 Conclusion
5.19 Prospects plant pathogen and research
Chapter 6. Quinones in the treatment of cardiovascular diseases
6.1 Introduction
6.2 Manifestations and indications of cardiovascular disease
6.2.1 Chest pain or discomfort (angina)
6.2.2 Shortness of breath
6.2.3 Fatigue
6.2.4 Palpitations
6.2.5 Dizziness or lightheadedness
6.2.6 Swelling (edema)
6.3 Risk factors of cardiovascular disease
6.3.1 Modifiable risk factors
6.3.1.1 Hypertension
6.3.1.2 High cholesterol
6.3.1.3 Smoking
6.3.1.4 Diabetes
6.3.1.5 Obesity
6.3.1.6 Physical inactivity
6.3.1.7 Unhealthy diet
6.3.1.8 Stress
6.3.1.9 Alcohol consumption
6.3.2 Non-modifiable risk factors
6.3.2.1 Gender
6.3.2.2 Age
6.3.2.3 Family history
6.3.3 Other risk factors
6.3.3.1 Sleep apnea
6.3.3.2 Chronic kidney disease
6.3.3.3 Certain medical conditions
6.3.3.4 The development of preeclampsia
6.3.3.5 Race and ethnicity
6.3.3.6 Others
6.4 Quinones in the treatment of cardiovascular diseases
6.4.1 Aloe-emodin
6.4.2 Aloin
6.4.3 Chrysophanol
6.4.4 Cryptotanshinone
6.4.5 Emodin
6.4.6 Plumbagin
6.4.7 Rhein
6.4.8 Shikonin
6.4.9 TanshinoneIIA
6.4.10 Danthron
6.4.11 Embelin
6.4.12 Purpurin
6.5 Molecular docking
6.6 Challenges and limitations in using quinones for CVD
6.7 Future directions and potential developments
6.8 Conclusion
Abbreviation
Chapter 7. Quinones: A promising remedy for respiratory health
7.1 Introduction
7.2 Quinones for the management of respiratory diseases and enhancement of respiratory health
7.2.1 Quinones in the management of COPD; (chronic obstructive pulmonary diseases)
7.3 Quinones in the management of asthma
7.3.1 Quinones in the management of pneumoconiosis
7.3.2 Quinones in the management of interstitial lung diseases
7.3.3 Quinones in the management of lung cancer
7.3.4 Quinones in the management of bacteria and virus-induced respiratory disorders
7.3.5 Quinones in the management of fungal-induced respiratory disorders
7.4 Conclusion
Chapter 8. Quinone-based materials in immunotherapy
8.1 Introduction
8.2 Synthesis and structural aspects of quinone-based materials
8.2.1 Design and development of quinone-derived immunotherapeutic agents
8.2.2 Rational design strategies
8.2.2.1 Functional group modification
8.2.3 Synthetic routes and methodologies in quinone-based material synthesis for immunotherapy
8.2.3.1 Oxidative coupling
8.2.3.2 Electrochemical synthesis
8.2.3.3 Catalytic methodologies
8.2.3.4 Biomimetic approaches
8.2.4 Interaction of quinone materials with immune cells in immunotherapy
8.2.4.1 Mechanisms of interaction
8.2.4.2 Immunomodulatory effects of quinone-derived compounds
8.2.5 Cellular interactions and immunomodulation
8.2.5.1 Macrophage polarization
8.2.5.2 T cell activation and differentiation
8.2.6 Formulation and delivery strategies for quinone-based immunotherapeutic agents
8.2.6.1 Nanotechnology in immunotherapy
8.2.6.2 Liposomal delivery systems in immunotherapy
8.2.6.3 Polymeric nanoparticles in immunotherapy
8.2.7 Formulation optimization for improved bioavailability and stability
8.2.7.1 Enhanced solubility and stability in quinone compounds
8.2.7.2 Cyclodextrin complexation
8.2.7.3 Co-delivery systems in immunotherapy
8.2.7.4 Co-encapsulation in nanoparticles
8.2.7.5 Enhanced therapeutic outcomes
8.3 Antibacterial and antifungal effects of quinone-based materials
8.3.1 Role of quinones in chemotherapy and antimicrobial agents
8.3.2 Use of quinone-containing chemicals in disease prevention and treatment
8.3.2.1 Free radical processes (FRP) and their implications
8.3.3 Research on quinones and azoles in radiation metabolite generation
8.3.4 Role of quinoid structures in radiation chemistry and therapeutic applications
8.3.5 Quinone-based antibiotics in battling bacterial infections
8.3.6 Addressing bacterial proliferation and biofilm infections
8.3.7 Quinone-driven antibiotics: Unveiling potent biocidal attributes
8.3.8 Quinone-based antibiotics: Unveiling antibiofilm potency
8.4 Antitumoral and anticancer effects of quinone-based materials
8.5 Quinone-based materials as radiosensitizers
8.6 Regulating the tumor microenvironment with quinone-based materials
8.6.1 Quinone-based materials in cancer treatment
8.6.1.1 Mechanisms of action
8.6.2 Clinical applications
8.6.2.1 Enhancing chemotherapy efficacy
8.6.2.2 Overcoming drug resistance
8.6.2.3 Immune response
8.7 Challenges and opportunities in the development of quinone-based materials for immunotherapy
8.7.1 Challenges
8.7.1.1 Toxicity
8.7.1.2 Stability
8.7.1.3 Off-target effects
8.7.2 Opportunities
8.7.2.1 Redox cycling
8.7.2.2 Immune response
8.7.2.3 Responsive tumor treatments
8.7.2.4 Diverse biological activities
8.8 Conclusion
Chapter 9. Quinones as antiinflammatory agents
9.1 Introduction
9.2 Benzoquinones
9.2.1 Embelin
9.2.2 Thymoquinone
9.2.3 Z-ligustilide
9.2.4 Flexibilisquinone
9.2.5 Belamcandaquinone A
9.2.6 2-octaprenyl-1,4-benzoquinone
9.3 Naphthoquinones
9.3.1 Lawsone
9.3.2 Juglone
9.3.3 Shikonin
9.3.4 Acetylshikonin
9.3.5 Plumbagin
9.3.6 Menadione
9.3.7 Diosquinone
9.3.8 β-lapachone
9.4 Anthraquinones
9.4.1 Emodin
9.4.2 Chrysophanol
9.4.3 Physcion
9.4.4 Rhein
9.4.5 Damnacanthal
9.4.6 Rubiadin
9.4.7 Purpurin
9.5 Other antiinflammatory compounds with quinone motif
9.5.1 Pyrroloquinoline quinone
9.5.2 Sesquiterpene quinones/quinols
9.6 Conclusion
Chapter 10. Quinones as potential therapeutic agents for metabolic disorders
10.1 Introduction
10.2 Quinones: A diverse class of compounds
10.3 Biological functions and significance
10.4 Industrial applications
10.4.1 Dye and pigment industry
10.4.2 Medicine and pharmaceuticals
10.4.3 Energy storage
10.5 Chemical synthesis
10.6 Metabolic disorders: An overview
10.6.1 Metabolic disorders and their impact on health
10.6.1.1 Impact on health
10.7 Diagnosis and management
10.8 The need for effective therapeutic approaches to treat metabolic disorders: Contrasting the potential of quinones
10.8.1 The potential of quinones as therapeutics
10.9 Challenges and considerations
10.10 Quinones: Properties and classification
10.10.1 The chemical structure of quinones: A comprehensive exploration
10.10.2 Variations in Quinone structure
10.10.3 The role of quinones in various biological processes
10.11 Applications of quinones
10.11.1 Exploring the diversity of quinones: A comprehensive analysis of different types
10.11.2 Vitamin K and Naphthoquinone derivatives
10.12 The multifaceted role of quinones in biological processes
10.12.1 Electron transfer and energy production: Illuminating the powerhouses of cells
10.12.2 Redox regulation and antioxidant defense: Preserving cellular equilibrium
10.12.3 Enzymatic reactions and metabolism: The molecular architects of biochemical pathways
10.12.4 Cellular signaling and communication: Orchestrating Harmonious dialogues
10.12.5 Pigmentation and coloration: Painting nature's canvas
10.12.6 Defense mechanisms: Chemical guardians of organisms
10.12.7 Biomedical applications: Paving the path to health and wellness
10.12.7.1 Harnessing quinones to combat oxidative stress in metabolic disorders
10.12.7.2 Unraveling the role of quinones in lipid metabolism and regulation: A comprehensive analysis
10.12.7.3 Antiinflammatory
10.13 Future directions and therapeutic potential
10.13.1 Clinical trails
10.13.2 Challenge address
10.14 Conclusion
Chapter 11. Quinones as photosensitizers for photodynamic therapy
11.1 Introduction
11.2 Reactive oxygen species
11.2.1 Singlet oxygen
11.2.1.1 Biological significance of singlet oxygen
11.2.2 Superoxide anion radical
11.2.3 Hydroxyl radical
11.3 Photosensitizer (PS)
11.4 Photodynamic therapy
11.5 PDT of quinone
11.5.1 Influence of different substituents on the generation of ROS
11.5.2 Perylquinone sensitizers: Hypocrellins and hypericin
11.6 Redox cycling of quinone
11.6.1 Enzymatic reduction of quinones and its cytotoxicity
11.7 Effect of electron donor on ROS generation
11.8 Biochemistry of ROS
11.9 Photocleavage of DNA
11.10 Detection of ROS
11.10.1 Optical methods
11.10.1.1 Detection of superoxide anion (O2•−)
11.10.1.2 Detection of hydroxyl radical
11.10.1.3 Detection of 1O2
11.10.2 EPR method
11.10.2.1 Detecting superoxide anion through the spin trapping method
11.10.2.2 1O2 detection by EPR-TEMPL method
11.11 Conclusion
Chapter 12. Quinones as redox-active materials for energy applications
12.1 Introduction
12.2 Related works
12.3 Characterization of quinones
12.3.1 Electrical and optical properties
12.3.2 Properties of quinones
12.3.3 Exposure route and pathways
12.3.4 Battery energy consumption
12.3.5 Energy storage mechanism in quinones
12.4 Research findings
12.5 Discussion
12.6 Conclusion
Chapter 13. Synthetic strategies for the preparation of quinone-based materials
13.1 Introduction
13.1.1 Background of interest
13.2 Major synthetic strategies of quinone materials
13.2.1 Diels–Alder cycloaddition reaction
13.2.2 Coupling of the aldehydes with lithiated hydroquinone ethers
13.2.3 Radical decarboxylation and quinone addition reaction
13.2.4 Grignard reagent conjugated addition to α,β-unsaturated carbonyl group
13.2.5 Reductive alkylation of enones
13.2.6 Cross-coupling reaction
13.2.7 Furylation of quinones
13.2.8 Furan polyene cationic cyclization
13.3 Other strategies for the synthesis of quinone materials
13.3.1 Biosynthetic technologies
13.3.2 Primmorph culture
13.4 Conclusion
Chapter 14. Analytical techniques for the characterization of quinone-based materials
14.1 Introduction
14.2 Applications of characterization and analysis techniques for quinone-based materials
14.3 Characterizations and analysis of quinone-based materials
14.3.1 UV–Vis characterization of quinone
14.3.2 FTIR characterization of quinone
14.3.3 HPLC characterization of quinone
14.3.4 Electrochemical analysis of quinone-based materials
14.4 Conclusion
Chapter 15. Synthesis, application and regulatory consideration for the development of quinone-based drugs
15.1 Introduction
15.2 Diverse applications
15.3 Natural and synthetic sources
15.4 Regulatory considerations
15.5 The international regulation
15.6 Patent and intellectual property protection of quinone based drugs
15.7 Conclusion
Chapter 16. Intellectual property considerations for quinone-based materials
16.1 Introduction
16.2 Importance and applications of quinone-based materials
16.2.1 Biomedicine
16.2.2 Sensors
16.2.3 Catalysis
16.2.4 Energy storage
16.2.5 Electronics
16.3 Understanding intellectual property (IP)
16.3.1 Definition and types of IP
16.3.1.1 Patents
16.3.1.2 Trademarks
16.3.1.3 Copyrights
16.3.1.4 Trade secrets
16.3.1.5 Plant varieties
16.3.1.6 Industrial designs
16.4 Importance of IP in scientific research and material development
16.4.1 Encouraging investment
16.4.2 Enabling commercialization
16.4.3 Promoting knowledge sharing
16.4.4 Incentivizing innovation
16.4.5 Protecting investments
16.4.6 Facilitating collaboration
16.4.7 Driving economic growth
16.5 Overview of patents in material science
16.6 Importance of patents in material science
16.6.1 Process of obtaining a patent
16.7 Review of existing patents on quinone-based materials
16.8 Analysis of successful patent applications
16.9 Conclusions
Chapter 17. Commercialization of quinone-based drugs
17.1 Introduction
17.2 Antibacterial effects of quinones
17.3 Drug effects of quinones and commercialization
17.3.1 Anthracyclines
17.3.2 Mitomycin C
17.3.3 Mitoxantrone
17.3.4 Aziridinyl benzoquinones
17.3.5 Streptonigrin
17.3.6 Lapachols
17.3.7 Actinomycin D
17.4 Conclusion
Chapter 18. Clinical development of quinone-based drugs
18.1 Introduction
18.2 Quinones
18.3 Quinone-based molecular electrochemistry and their contributions to medicinal chemistry
18.4 Quinones and their importance in drugs
18.5 The effects of quinones and clinical studies
18.6 Conclusion
Index

Umar Ali Dar

Umar Ali Dar currently works as an assistant professor on contract basis at the Department of Chemistry, University of Ladakh, Kargil Campus, Ladakh UT, India. During his doctoral thesis, he worked on “Chemistry of Porphyrin and Quinone based Compounds and their Metal Complexes: Synthesis and Structural Studies” under the supervision of Prof. S. A. Shah at the Department of Chemistry, National Institute of Technology (NIT), Jammu and Kashmir UT, India, and was awarded his Ph.D. in February 2022. During his M. Phil degree, he worked on “Synthesis, characterization of first row transition metal complexes of 2-bromo- 3-hydroxy-1,4-naphthoquinone under the supervision of Prof. Sunita A. Salunke. Dr. Dar specializes in organic and inorganic synthesis of porphyrin and quinone compounds for a disparate range of applications. He is also interested in secondary metabolites, pharmaceuticals, and drug discovery.

Affiliations and expertise

Assistant Professor, Department of Chemistry, University of Ladakh, Kargil Campus, India

Mohd. Shahnawaz

Dr. Shahnawaz have more than 6 years of teaching and research experience after obtaining his doctoral degree. Recently, Dr. Mohd. Shahnawaz got selected as an Associate Professor at Biofuel Institute, School of the Environment and Safety Engineering, Jiangsu University, Zhenjiang, China. In 2020, he got selected as a postdoc fellow at Yeungnam University, South Korea; however, due to the COVID-19 scenario, he was not able to join. He has several years of teaching and postdoctoral research experience. Dr. Shahnawaz worked on bioremediation of polythene at the Botany Department, SP Pune University, during his doctoral research with Prof. A. B. Ade. He is recipient of various fellowships awarded by the SPPU, UGC-BSR, UGC-MANF, and DST-SERB. His research interest is in Biofuels, Microbiology, Bioremediation, and Plant Biotechnology. Besides working on the bioconversion of lignocellulosic biomass into biofuels, he is also focused on the mitigation of microplastic using bioremediation technology.

Affiliations and expertise

Assistant Professor, Department of Botany, University of Ladakh, Kargil Campus, India

Khalid Rehman Hakeem

Dr. Khalid Rehman Hakeem (PhD) is Professor at King Abdulaziz University, Jeddah, Saudi Arabia. He has more both teaching and research experience in plant eco-physiology, biotechnology and molecular biology, medicinal plant research, plant-microbe-soil interactions as well as in environmental studies. He has served as the visiting scientist at Jinan University, Guangzhou, China. He has more than 110 research publications in peer-reviewed international journals has extensive book publishing experience as well. He is included in the advisory board of Cambridge Scholars Publishing, UK. He is a fellow of Plantae group of the American Society of Plant Biologists, member of the World Academy of Sciences, member of the International Society for Development and Sustainability, Japan, and member of Asian Federation of Biotechnology, Korea.

Affiliations and expertise

Professor, Department of Biological Sciences, Faculty of Science, King Abdulaziz University, Jeddah, Makkah Province Kingdom of Saudi Arabia

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Quinone-Based Compounds in Drug Discovery

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