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This book represents a collaborative endeavor by a group of investigators to bring together in a single volume a critical discussion of the major facets of our knowledge, ranging from chemical to clinical aspects, of steroid conjugation. However, the important field of bile acid and bile alcohol conjugation has been discussed only superficially since it was decided arbitrarily to be outside the projected scope of the book. The reader is referred to the companion volume of this book, namely Physical Properties of Steroid Conjugates (by Bernstein, Dusza, and Joseph, Springer-Verlag New York 1968), for complemental information on individual conjugates. The Editors wish to thank Miss Elise Kramer for typing assistance. Also we wish to express our deep appreciation and gratitude to Mrs. Dorothy Budd, our copy-editor, and Mr. J. Joseph for their editorial assistance in making this book possible. SEYMOUR BERNSTEIN Pearl River, N. Y. January, 1970 SAMUEL SOLOMON V11 CONTENTS Preface . . . . VII Nomenclature a, Discussion of Nomenclature System x b, Trivial and Systematic Names. x List of Contributors . . . . . . . . Xl Chemistry: Synthesis and Characterization S. BERNSTEIN, 1. P. DUSZA, and J. P. JOSEPH Enzymological Aspects of Steroid Conjugation A. B. Roy . . . . . . . . . . 74 The Hydrolysis of Steroid Conjugates H. L. BRADLOW . . . . . 131 Isolation of Steroid Conjugates P. K. SITTERI. . . . . . . 182 The Biochemistry of the 3P-Hydroxy-Ll5-Steroid Sulfates K. D. ROBERTS and S. LIEBERMAN 219 Formation, Metabolism, and Transport of Estrogen Conjugates E. DICZFALUSY and M. LEVITZ. . . . . . . . . . . . .
The steroid scaffold continues to be the structural basis of new drugs for a variety of targets and diseases. Indeed, steroids interact with enzymes and receptors in a strikingly specific manner. Chemistry and Biological Activity of Steroids aims to provide an updated overview of recent advances in the medicinal chemistry of steroids. Novel synthetic methods in the steroids field, including steroid biotransformations, new steroids able to tackle steroid receptors, and steroid enzymes with clinical relevance, are critically reviewed in this book. Furthermore, the diverse physiopathological roles of oxysterols and their therapeutic value are also discussed.
Conjugates of Steroid Hormones focuses on the synthesis, isolation, assay, and metabolism of steroid conjugates. The book first offers information on the isolation of steroid conjugates and sulfates of steroid hormones. Topics include separation of steroid conjugates by adsorption, isolation from natural sources, group separation of sulfates and glucuronides, enzymic synthesis, and separation of steroid conjugates by solvent extraction. The manuscript then tackles glucuronides and glycosides of steroid hormones, as well as chemical synthesis and biosynthesis of diconjugates. The text ponders on phosphates of steroid hormones and metabolism of steroid conjugates. Discussions focus on the occurrence of steroid phosphates in biological fluids; metabolism of dehydroepiandrosterone sulfate to estrogens; formation of dehydroepiandrosterone sulfate; and estrogen conjugates. The publication is highly recommended for organic chemists and biochemists.
Under the capable and qualified editorial leadership of Dr. Gerald Litwack, Vitamins and Hormones continues to publish cutting-edge reviews of interest to endocrinologists, biochemists, nutritionists, pharmacologists, cell biologists, and molecular biologists. First published in 1943, Vitamins and Hormones is the longest-running serial published by Academic Press. In the early days of the Serial, the subjects of vitamins and hormones were quite distinct. Now, new discoveries have proved that several of the vitamins function as hormones and many of the substances inferred by the title of the serial function in signal transduction processes. Accordingly, the Editor-in-Chief has expanded the scope of the serial to reflect this newer understanding of function-structure relationships in cellular communication. The Editorial Board now reflects expertise in the field of hormone action, vitamin action, X-ray crystal structure, physiology, and enzyme mechanisms.
Doping, Performance-Enhancing Drugs, and Hormones in Sport: Mechanisms of Action and Methods of Detection examines the biochemistry and bioanalytical aspects of performance-enhancing drugs (PEDs) and other questionable procedures used by athletes to enhance performance. The book informs the specialist of emerging knowledge and techniques and allows the non-specialist to grasp the underlying science and current practice of the discipline. With clear and compelling language appropriate for a broad spectrum of readers, this book provides background on prevalence, types of agents, their actual or supposed benefits, and their negative effects on health. The technical aspects of detection are discussed, followed by a discussion of why detection is a problematic and still-evolving science. To facilitate comprehension, each chapter is organized in a uniform way with six sections: (1) standard medical uses, (2) why the drugs are used by athletes, (3) biological mechanism of action, (4) what research says about efficacy in improving performance, (5) major health side effects from use and abuse in sport, and 6) concluding key points. - Presents the scientific concepts of how performance enhancers work, how they are used, and how they are detected and masked from detection - Features language that is neither simplistic to scientists nor too sophisticated for a large, diverse global audience - Provides a short "close-up in each chapter to illustrate key topics that engage, entertain, and create a novel synthesis of thought
Metabolic Conjugation and Metabolic Hydrolysis, Volume I is a comprehensive account of the main conjugation mechanisms and hydrolytic reactions. Topics covered range from the metabolic conjugates of steroids and N-hydroxy compounds to the effects of conjugated steroids on enzymes. The glucuronic acid pathway is also discussed, along with sulfoconjugation and sulfohydrolysis. Comprised of eight chapters, this volume first looks at the history of conjugation mechanisms before proceeding to developments in metabolic conjugations. The isolation, recognition, enzymic formation and hydrolysis, and the possible significance of steroid N-acetylglucosaminides and glucosides are considered. The book also examines the mechanisms involved in the enzymic formation of N-hydroxy compounds; the pathways by which N-hydroxy compounds may be further metabolized in vivo; and the chemical properties of conjugates of N-hydroxy compounds, particularly as these properties are related to the generation of reactive cations or free radicals in vivo. The possible role of conjugates of N-hydroxy compounds in the mechanism of carcinogenesis by aromatic amines and their N-acyl derivatives is also analyzed. Finally, glycoprotein and mucopolysaccharide hydrolysis and the role of hydrolases in cellular death are described. This monograph will be a useful resource for biologists, biochemists, physiologists, and pharmacologists.
This book is aimed at the large number of people who need to use chemometrics but do not wish to understand complex mathematics, therefore it offers a comprehensive examination of the field of chemometrics without overwhelming the reader with complex mathematics. * Includes five chapters that cover the basic principles of chemometrics analysis. * Provides two chapters on the use of Excel and MATLAB for chemometrics analysis. * Contains 70 worked problems so that readers can gain a practical understanding of the use of chemometrics.