Doxorubicin - 1st Edition - ISBN: 9780120592807, 9780323139731

Doxorubicin

1st Edition

Anticancer Antibiotics

Authors: Federico Arcamone
eBook ISBN: 9780323139731
Imprint: Academic Press
Published Date: 28th January 1981
Page Count: 369
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Description

Doxorubicin: Anticancer Antibiotics details the development of doxorubicin as a wide-spectrum antitumor antibiotic. The book begins by tracing the discovery and development of doxorubicin, highlighting factors such as (a) the involvement of organic chemistry at an early stage, which allowed the rapid identification of doxorubicin and ensured its prompt availability for the clinical trials; (b) the well-established, pioneering expertise in experimental chemotherapy of Professor Aurelio di Marco and his group at Istituto Nazionale Tumori, Milan; and (c) the highly motivated interest of experienced clinicians. The remaining chapters provide an overview of basic studies in the area of medicinal chemistry and related fields that have resulted from doxorubicin development. Such studies have been concerned with both biochemical and biophysical investigations at the molecular level and at different levels of biological organization. A large body of work aimed at developing synthetic procedures for the drug and for new related analogs of potential clinical usefulness has also been carried out.

Table of Contents


Preface

Acknowledgments

1 Discovery and Development of Doxorubicin

Antitumor Activity of an Anthracycline Pigment

Anthracyclines and Anthracyclinones: The First Decade

Daunorubicin

The Isolation of Doxorubicin

The Structure and Stereochemistry of Doxorubicin

Antitumor Activity on Experimental Tumors

Clinical Activity of Doxorubicin

Analytical Development and Synthesis of Radiolabeled Doxorubicin

Conjugates and Complexes of Doxorubicin as Antitumor Agents

References

2 Total Synthesis of Doxorubicin and Related Compounds

Wong's Synthesis of Daunomycinone

Other Syntheses Starting from 3-Methoxyphthalate and a Tetralin or Their Equivalents

Closure of Ring A in Substituted Anthraquinones and Their Derivatives

Applications of the Diels - Alder Reaction for the Construction of Ring A

Other Syntheses Based on Diels-Alder Condensation

Syntheses Based on Different Principles

The Carbohydrate Moiety

Other Studies Related to Ring A Functionalization

References

3 Molecular Interactions

X-Ray Diffraction Studies

Association and Dissociation Equilibria in Solution

Oxidoreduction Behavior

Complexes with Metal Ions

The DNA Intercalation Complex

Protein Binding

Phospholipids

Mucopolysaccharides

Effect of Respiratory Processes in Subcellular Preparations

Interference with Redox Reactions and Formation of Radicals

Inhibition of (Na+ + K+) ATPase and of Ion Transport in Subcellular Preparations

References

4 Studies with Living Systems

Uptake and Distribution in Cultured Sensitive Cells

Effects of DNA-Related Cell Functions in Vitro

Other Studies in Cultured Cells

Studies with Resistant Cells

Studies with Cultured Heart Cells

Metabolism

Pharmacokinetics

Pharmacological Properties in Whole Mammalian Systems

References

5 Analogues Modified in Ring A Substitution

Derivatization at C-13 and C-14

Side-Chain Oxidative Degradation

Modifications at C-9 and C-10

Substitution at C-8

4-Demethoxy-7,10-Ethanodaunomycinone

References

6 Analogues Modified in the Aminosugar Residue

The L-Arabino Analogues and the Development of 4'-Epidoxorubicin

Other Analogues Modified at C-4'

Other Configurational Analogues

Other Functional Analogues

Disaccharides

Amides

N,N-Dimethyldaunorubicin

Nonsugar Derivatives

References

7 Analogues Modified in the Anthraquinone Chromophore

Synthesis of 4-Demethoxydaunorubicins

Properties of 4-Demethoxydaunorubicins

Other Synthetic Approaches to 4-Demethoxy Analogues

New Ring D-Substituted 4-Demethoxydaunorubicins and 4-Demethoxydoxorubicins

Replacement of 4-O-Methyl and Other Alkyl Groups

The 6-O-Methyl and 11-O-Methyl Derivatives

5-Iminodaunorubicin

Recent Developments

References

8 New Developments in Biosynthetic Anthracyclines

The Rhodomycins and Related Compounds

Pyrromycinone and Aklavinone Glycosides

Biosynthetic Glycosides Related to Daunorubicin

Other Anthracycline Antibiotics

The Biosynthesis of the Anthracyclines

Microbial Transformations

References

Index




Details

No. of pages:
369
Language:
English
Copyright:
© Academic Press 1981
Published:
Imprint:
Academic Press
eBook ISBN:
9780323139731

About the Author

Federico Arcamone