Aminoglycoside Antibiotics by Irving R. HooperAminoglycoside Antibiotics by Irving R. Hooper

Aminoglycoside Antibiotics

byIrving R. Hooper, Y. Ito, T. Koeda

Paperback | November 18, 2011

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Title:Aminoglycoside AntibioticsFormat:PaperbackDimensions:372 pagesPublished:November 18, 2011Publisher:Springer-Verlag/Sci-Tech/TradeLanguage:English

The following ISBNs are associated with this title:

ISBN - 10:3642685811

ISBN - 13:9783642685811

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Table of Contents

1 The Naturally Occurring Aminoglycoside Antibiotics.- A. Introduction.- B. Aminoglycoses and Noncyclitol Aminoglycosides.- I. Aminoglycose Derivatives.- II. Disaccharides and Pseudodisaccharides.- III. Trisaccharides.- C. Aminocyclitol Aminoglycosides Containing Streptamine, 2-Deoxystreptamine, or Their Derivatives.- I. Monosubstituted Streptamine and 2-Deoxystreptamine Aminoglycosides.- 1. 4- or 6-Substituted Cyclitol.- 2. 5-Substituted Cyclitol.- II. Disubstituted 2-Deoxystreptamine Aminoglycosides.- 1. 4,5-Disubstituted Cyclitol.- 2. 4,6-Disubstituted Cyclitol.- III. 1-N-Acyl Substituted Cyclitol.- D. Aminoglycosides with Cyclitol Aglycones Other than Streptamine or 2-Deoxystreptamine.- I. Nonbasic Cyclitol.- II. Monoaminocyclitol.- III. Diaminocyclitol.- References.- 2 Total Synthesis and Chemical Modification of the Aminoglycoside Antibiotics.- A. Introduction.- B. Several Reactions and Methods Generally Useful for the Synthesis of Aminoglycoside Antibiotics.- I. Simultaneous Protection of Vicinal Trans-Equatorial Amino and Hydroxyl Groups.- II. Selective Cyclic Acetalation.- III. 1,2-cis-Glycosylation of Aminosugars.- IV. Selective Deoxygenation Reactions.- 1. 3-Deoxygenation.- 2. 3,4-Dideoxygenation.- V. Selective N-Protection via Temporary Metal Chelation of Vicinal and Nonvicinal Amino-Hydroxy or Amino-Amino Groups.- VI. Determination of the Configurations of Aminopyranosides and Aminocyclitols by the Shift in Optical Rotation Due to Copper(II) Chelate Formation.- C. Total Synthesis and Modification of Aminoglycoside Antibiotics.- I. Streptomycin Group.- 1. Total Synthesis of Streptomycin and Dihydrostreptomycin.- 2. Chemical Modification of Streptomycin and Dihydrostreptomycin.- II. Pseudodisaccharides Containing 4-Substituted 2-Deoxystreptamine - Paromamine, Neamine, and Related Compounds.- 1. Synthesis of Paromamine and Neamine.- 2. Deoxygenated Derivatives.- 3. Epimerized Derivatives.- 4. Amino-Deoxy Derivatives.- 5. Derivatives Having a Side Chain or Longer Chain.- 6. 1-N-Acyl Derivatives.- 7. Other Derivatives.- III. Pseudotrisaccharides Containing 4,5-Disubstituted 2-Deoxystreptamine - Ribostamycin, Butirosins, and Related Compounds.- 1. Synthesis of Ribostamycin and Related Pseudotrisaccharides.- 2. Deoxy Derivatives.- 3. 1-N-Acyl and 1-N-Alkyl Derivatives of 4,5-Disubstituted Pseudotrisaccharides.- IV. Pseudotetra- and Pseudopentasaccharides Containing 4,5-Disubstituted 2-Deoxystreptamine - Neomycins, Paromomycins, Lividomycins, and Related Compounds.- 1. Total Synthesis of Neomycin C.- 2. Synthesis of Analogs of Neomycin, Paromomycin, and Lividomicin B.- 3. Amino-Deoxy Derivatives.- 4. N-Alkyl Derivatives.- 5. 1-N-Acyl Derivatives.- V. Pseudotrisaccharides Containing 4,6-Disubstituted 2-Deoxystreptamine - Kanamycin, Tobramycin, Gentamicin, and Related Compounds.- 1. Kanamycins and Their Derivatives.- 2. Gentamicins and Related Compounds.- 3. Sisomicin, Its Derivatives, and Related Unsaturated Compounds.- 4. 1-N-Acylgentamicins and 1-N-Acylsisomicins.- 5. Seldomycin Modifications.- 6. Other 4,6-Disubstituted Derivatives.- VI. Other Groups.- 1. Kasugamycin and Its Modifications.- 2. Spectinomycin Group.- 3. Fortimicins, Istamycins, and Related Compounds.- 4. Sorbistins and Analogs.- 5. Minosaminomycin.- 6. Alpha,Alpha-Trehalosamine.- References.- 3 Biosynthesis and Mutasynthesis of Aminoglycoside Antibiotics.- A. Introduction.- I. Historical Background.- II. Methodology.- 1. Application of Labeled Compounds.- 2. Application of Cell-Free Extracts of Mycelia or Enzymes.- 3. Application of Mutants.- III. Plasmid Involvement.- 1. General Aspects.- 2. Plasmid Involvement in Aminoglycoside Synthesis.- 3. Experimental Methods.- B. Biosynthesis of Major Aminoglycosides.- I. Streptomycin and Bluensomycin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- 3. Correlation with Cell Wall Biosynthesis.- 4. Plasmid Involvement.- II. Neomycin and Paromomycin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- 3. Plasmid Involvement.- III. Ribostamycin, Xylostasin, and Butirosin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- 3. Glucosamine Auxotroph and Butirosin Biosynthesis.- 4. Plasmid Involvement.- IV. Kanamycin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- 3. Plasmid Involvement.- V. Gentamicin and Sisomicin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- VI. Spectinomycin (Actinospectacin).- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- VII. Kasugamycin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- 3. Plasmid Involvement.- VIII. Validamycin.- 1. Biosynthesis of Subunits.- 2. Subunit Assembly.- IX. Miscellaneous Aminoglycosides.- 1. 1,4-Diaminocyclitol Aminoglycosides.- 2. Monoaminocyclitol Aminoglycosides.- 3. Apramycin.- X. Comprehensive Discussion on the Biosynthesis of Aminoglycosides.- C. Mutational Biosynthesis (Mutasynthesis).- D. Conclusion.- References.- 4 Antibacterial Activity of Aminoglycoside Antibiotics.- A. Introduction.- B. Drug Resistance Plasmids.- I. The Discovery of R Factors.- II. The Discovery of Nonconjugative Resistance (r) Plasmids.- C. Resistance Patterns of Bacteria.- D. Bacterial Strains Resistant to Aminoglycoside Antibiotics.- I. Drug Resistance Mediated by R Plasmids.- II. Antibacterial Activity of Aminoglycoside Antibiotics.- E. Conclusion.- References.- 5 Mechanism of Action of Aminoglycoside Antibiotics.- A. The Effects on Bacterial Cells and Their Components.- I. In vivo Effects on Bacteria in Relation to Mode of Action.- II. Interference with Protein Synthesis in vitro.- III. Localization of Drug Sensitivity, Resistance, and Dependence on the Ribosome.- IV. Interaction with Ribosomes and Ribosomal Components.- 1. Binding of Streptomycin to the Ribosome and Ribosomal Subunits.- 2. Binding Site of Streptomycin on the Ribosome.- 3. Binding of Kanamycin to the Ribosome and Ribosomal Subunits.- 4. Binding of Other Aminoglycosides to the Ribosome and Ribosomal Subunits.- V. Interference with Ribosomal Functions.- 1. Inhibition of Initiation of Protein Synthesis.- 2. Chain Elongation Processes Affected.- 3. Interference with Termination.- VI. Interaction with Bacterial Cell Envelope.- 1. Membrane Damage.- 2. Uptake of Streptomycin by Bacterial Cells.- 3. Drug Resistance Due to Transport Barriers.- VII. Structure-Activity Relationships.- 1. Structure Required for Codon Misreading Activity.- 2. Structure Needed for the Inhibition of Translocation.- B. Effects on Mammalian or Eukaryotic Cells and Their Components.- I. Interaction with Ribosomes and Interference with Ribosomal Functions.- II. Interaction with Tubulin and Microtubules.- III. Interaction with Actin.- IV. Interaction with Membrane or Phospholipid.- C. Peptide Antibiotics Showing Similar Mechanisms of Inhibition of Ribosomal Functions.- I. Viomycin.- 1. Inhibition of Protein Synthesis.- 2. Binding to Ribosomes and Ribosomal Subunits.- 3. Localization of Drug Resistance in the Ribosome.- 4. Mechanism of Translocation Inhibition.- II. Negamycin.- D. Discussion.- E. Summary.- I. Localization of Drug Sensitivity, Resistance, and Dependence on the Ribosome.- II. Binding of Aminoglycosides to the Ribosome.- III. Inhibition of Initiation of Protein Synthesis.- IV. Stimulation of Codon Misreading.- V. Interference with Aminoacyl-tRNA Binding.- VI. Inhibition of Translocation of Peptidyl-tRNA.- VII. Interference with Termination of Protein Synthesis.- VIII. The Effects on Cell Membrane.- IX. Uptake of Aminoglycosides by Bacterial Cells.- X. Effects on Mammalian or Eukaryotic Cell Components.- References.- 6 Mechanisms of Resistance to Aminoglycoside Antibiotics.- A. Introduction.- B. Biochemical Mechanisms of Resistance.- I. Discovery of Enzymes Involved in Resistance.- II. Resistance to 2-Deoxystreptamine-Containing Antibiotics.- 1. 3?-Phosphotransferase [APH (3?)].- 2. 5?-Phosphotransferase [APH (5?)].- 3. 2?-Phosphotransferase [APH (2?)].- 4. 2?-Adenylyltransferase [AAD (2?)].- 5. 4?-Adenylyltransferase [AAD (4?)].- 6. 6?-Acetyltransferase [AAC (6?)].- 7. 3-Acetyltransferase [AAC (3)].- 8. 2?-Acetyltransferase [AAC (2?)].- III. Resistance to Streptomycins.- 1. 3?-Adenylyltransferase [AAD (3?)].- 2. 3?-Phosphotransferase [APH (3?)].- 3. 6-Adenylyltransferase [AAD (6)] and 6-Phosphotransferase [APH (6)].- IV. Resistance to Fortimicins.- V. Immobilization of Enzymes.- VI. Structural Elucidation of Modified Antibiotics by Spectrometry.- VII. Similarity to Enzymes Involved in Biosynthesis.- C. Derivatives Active Against Resistant Strains.- D. Conclusion.- References.- 7 Toxicology and Pharmacology of Aminoglycoside Antibiotics.- A. Introduction.- B. Nephrotoxicity of Aminoglycosides.- I. Nephrotoxicity of Individual Aminoglycosides.- II. Intensification of Nephrotoxicity of Aminoglycosides by Concomitant Use with Other Drugs.- III. Reduction of Nephrotoxicity of Aminoglycosides by Concomitant Use of Other Drugs.- IV. Experimental Methods for Investigating Nephrotoxicity.- 1. Determination of Lysozyme.- 2. Determination of Alanine Aminopeptidase (AAP) Activity.- 3. Determination of N-Acetyl-?-D-Glucosaminidase (NAG)Activity.- 4. Determination of ?2-Microglobulin.- C. Ototoxicity of Aminoglycosides.- I. Effects of Cochlear Hair Cells.- II. Effects on Vestibular Organs.- III. Ototoxicity by Concomitant Use of Aminoglycosides with Other Drugs.- IV. Correlation Between Renal Toxicity and Ototoxicity of Aminoglycosides.- V. Transfer Routes of Aminoglycosides into the Inner Ear Fluids.- VI. Fetal Ototoxicity of Aminoglycosides.- D. Acute Lethal Toxicity of Aminoglycosides.- E. Correlation Between Chemical Structure and LD50 Values of Aminoglycosides.- I. Kanamycin Group.- II. Gentamicin Group.- III. Neomycin Group.- IV. Ribostamycin Group.- F. General Pharmacology of Aminoglycosides.- I. Effect on Neuromuscular Junctions.- II. General Pharmacologic Actions, Especially on Smooth Muscle and Cardiovascular System.- G. Pharmacokinetics.- I. Recent Progress in Assay Methods for Aminoglycosides in Serum and Other Body Fluids.- 1. Microbiologic Assay.- 2. Radioimmunoassay.- 3. High-Performance Liquid Chromatography (HPLC).- 4. Enzymatic Assay.- II. Pharmacokinetics of Aminoglycosides.- 1. Compartment Models for Pharmacokinetic Analysis and Calculation of Parameters.- 2. Pharmacokinetic Parameters in Normal Animals.- 3. Pharmacokinetic Parameters in Human with Normal Renal Function.- 4. Relationship Between Serum Level, Acute Toxicity, and Mode of Administration in Experimental Animals.- III. Metabolism and Excretion.- 1. Metabolism.- 2. Excretion.- IV. Tissue Distribution.- 1. Tissue Distribution in Animals.- 2. Tissue Distribution in Humans.- V. Accumulation in Kidneys.- 1. Renal Accumulation in Animals.- 2. Renal Accumulation in Humans.- VI. Binding to Biopolymers.- 1. Binding to Heparin.- 2. Binding to Serum Proteins.- VII. Relationship Between Renal Function and Pharmacokinetics: Clinical Applications.- References.