Abstract
The importance of lipophilicity for pharmacological and toxicological potency of xenobiotics has been recognized for a century. The reference lipophilicity scale is defined by the logarithm of partition coefficient, log P, determined in the loctanol- water partition system. The tediousness of determinations and limited interlaboratory reproducibility of log P, on one hand, and the observations of linear relationship between log P and chromatographic retention parameters, on the other hand, gave rise to the substitution of the former by the readily available chromatographic data. Since its introduction, the reversed-phase high - performance liquid chromatography (HPLC), which has been viewed in terms of partition of a solute between a polar, aqueous mobile phase and a nonpolar stationary phase appeared especially suitable for lipophilicity (hydrophobicity) determination. The method got wide acceptance and has officially been recommended by the OECD. Fundamental relationships between chromatographic parameters are reviewed from the point of view of convenient and reliable lipophilicity measurements. The advantages and disadvantages of the stationary phase materials, which are presently employed for the determination of lipophilicity as well as those of specific HPLC systems and procedures, are critically reported. The literature on the application of chromatographic and electrochromatographic methods for assessment of lipophilicity of xenobiotics is reviewed. A separate paragraph is devoted to interpretation of retention parameters from HPLC systems comprising biomacromolecules. Role of lipophilicity in drug-biomacromolecule interactions is discussed in terms of quantitative structure-retention relationships (QSRR). Finally, reports are analyzed on systemic information which can be extracted by multivariate methods of data processing, like principal component analysis (PCA), from sets of lipophilicity parameters determined in diverse HPLC systems.
Keywords: Chromatographic Retention, electrochromatographic, lipophilicity
Current Medicinal Chemistry
Title: Chromatographic Retention Parameters in Medicinal Chemistry and Molecular Pharmacology
Volume: 10 Issue: 5
Author(s): Antoni Nasal, Danuta Siluk and Roman Kaliszan
Affiliation:
Keywords: Chromatographic Retention, electrochromatographic, lipophilicity
Abstract: The importance of lipophilicity for pharmacological and toxicological potency of xenobiotics has been recognized for a century. The reference lipophilicity scale is defined by the logarithm of partition coefficient, log P, determined in the loctanol- water partition system. The tediousness of determinations and limited interlaboratory reproducibility of log P, on one hand, and the observations of linear relationship between log P and chromatographic retention parameters, on the other hand, gave rise to the substitution of the former by the readily available chromatographic data. Since its introduction, the reversed-phase high - performance liquid chromatography (HPLC), which has been viewed in terms of partition of a solute between a polar, aqueous mobile phase and a nonpolar stationary phase appeared especially suitable for lipophilicity (hydrophobicity) determination. The method got wide acceptance and has officially been recommended by the OECD. Fundamental relationships between chromatographic parameters are reviewed from the point of view of convenient and reliable lipophilicity measurements. The advantages and disadvantages of the stationary phase materials, which are presently employed for the determination of lipophilicity as well as those of specific HPLC systems and procedures, are critically reported. The literature on the application of chromatographic and electrochromatographic methods for assessment of lipophilicity of xenobiotics is reviewed. A separate paragraph is devoted to interpretation of retention parameters from HPLC systems comprising biomacromolecules. Role of lipophilicity in drug-biomacromolecule interactions is discussed in terms of quantitative structure-retention relationships (QSRR). Finally, reports are analyzed on systemic information which can be extracted by multivariate methods of data processing, like principal component analysis (PCA), from sets of lipophilicity parameters determined in diverse HPLC systems.
Export Options
About this article
Cite this article as:
Nasal Antoni, Siluk Danuta and Kaliszan Roman, Chromatographic Retention Parameters in Medicinal Chemistry and Molecular Pharmacology, Current Medicinal Chemistry 2003; 10 (5) . https://dx.doi.org/10.2174/0929867033368268
DOI https://dx.doi.org/10.2174/0929867033368268 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
Call for Papers in Thematic Issues
Advances in Medicinal Chemistry: From Cancer to Chronic Diseases.
The broad spectrum of the issue will provide a comprehensive overview of emerging trends, novel therapeutic interventions, and translational insights that impact modern medicine. The primary focus will be diseases of global concern, including cancer, chronic pain, metabolic disorders, and autoimmune conditions, providing a broad overview of the advancements in ...read more
Approaches to the treatment of chronic inflammation
Chronic inflammation is a hallmark of numerous diseases, significantly impacting global health. Although chronic inflammation is a hot topic, not much has been written about approaches to its treatment. This thematic issue aims to showcase the latest advancements in chronic inflammation treatment and foster discussion on future directions in this ...read more
Cellular and Molecular Mechanisms of Non-Infectious Inflammatory Diseases: Focus on Clinical Implications
The Special Issue covers the results of the studies on cellular and molecular mechanisms of non-infectious inflammatory diseases, in particular, autoimmune rheumatic diseases, atherosclerotic cardiovascular disease and other age-related disorders such as type II diabetes, cancer, neurodegenerative disorders, etc. Review and research articles as well as methodology papers that summarize ...read more
Chalcogen-modified nucleic acid analogues
Chalcogen-modified nucleosides, nucleotides and oligonucleotides have been of great interest to scientific research for many years. The replacement of oxygen in the nucleobase, sugar or phosphate backbone by chalcogen atoms (sulfur, selenium, tellurium) gives these biomolecules unique properties resulting from their altered physical and chemical properties. The continuing interest in ...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
-
Gender Differences in Graduate Bioentrepreneurship Education - A Case Study: University of San Francisco
Technology Transfer and Entrepreneurship (Discontinued) Homo obesus: A Metabotrophin-Deficient Species. Pharmacology and Nutrition Insight
Current Pharmaceutical Design Telomere End Protection in Stem Cells and Cancer Cells
Current Cancer Therapy Reviews Nanomedicine Against Malaria
Current Medicinal Chemistry β-Hydroxy-β-Methylbutyrate as a Countermeasure for Cancer Cachexia: A Cellular and Molecular Rationale
Anti-Cancer Agents in Medicinal Chemistry <i>Ziziphus spina-christi</i> Leaf Extract Mitigates Mercuric Chloride-induced Cortical Damage in Rats
Combinatorial Chemistry & High Throughput Screening Patent Selections
Recent Patents on Endocrine, Metabolic & Immune Drug Discovery Inflammatory Biomarkers for Mood Disorders - A Brief Narrative Review
Current Pharmaceutical Design Effects of Subhypothermia on Ca2+, Mg2+, Excitatory Amino Acids and Plasma Endothelin in Brain Tissues of Mice with Acute Cerebral Infarction
Vascular Disease Prevention (Discontinued) Atherosclerotic Process in Seroreverter Children and Adolescents Exposed to Fetal Antiretroviral Therapy
Current HIV Research Some clinical applications of the electrochemical biosensors
Mini-Reviews in Medicinal Chemistry Clinical Applications of Myostatin Inhibitors for Neuromuscular Diseases
Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry (Discontinued) Cytokine Profile in Patients Infected with Anisakis simplex in Endemic Areas: Dietary Intervention with Polyphenols: A Working Hypothesis
Endocrine, Metabolic & Immune Disorders - Drug Targets Creating Chemical Diversity to Target Protein Kinases
Combinatorial Chemistry & High Throughput Screening <i>Ovine</i> COX-1 Isoenzyme Bio-production
Current Enzyme Inhibition Monoclonal Antibodies: A Review
Current Clinical Pharmacology ADAM8 in Allergy
Inflammation & Allergy - Drug Targets (Discontinued) Advances in Anticancer Antibody-Drug Conjugates and Immunotoxins
Recent Patents on Anti-Cancer Drug Discovery Current Targets for Primary Sclerosing Cholangitis
Current Drug Targets State of the Art on Carbonic Anhydrase Modulators for Biomedical Purposes
Current Medicinal Chemistry