Photochemistry and Photobiology of Nucleic Acids. Chemistry

599 Pages·1976·60.08 MB·English

by  Shih-Yi Wang (Eds.)

Contributors
Michel Charlier
Malcolm Daniels
Dov Elad
Catherine Fenselau
G. J. Fisher
William W. Hauswirth
Claude Hélène
D. P. Hollis
H. E. Johns
Isabella L. Karle
Thérèse Montenay-Garestier
G. Scholes
Shih Yi Wang
Photochemistry and
Photobiology of
Nucleic Acids
Volume I
Chemistry
EDITED BY
Shih Yi Wang
Department of Biochemistry
School of Hygiene and Public Health
The Johns Hopkins University
Baltimore, Maryland
ACADEMIC PRESS New York San Francisco London 1976
A Subsidiary of Harcourt Brace Jovanovich, Publishers
COPYRIGHT © 1976, BY ACADEMIC PRESS, INC.
ALL RIGHTS RESERVED.
NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR
TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC
OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY
INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT
PERMISSION IN WRITING FROM THE PUBLISHER.
ACADEMIC PRESS, INC.
Ill Fifth Avenue, New York, New York 10003
United Kingdom Edition published by
ACADEMIC PRESS, INC. (LONDON) LTD.
24/28 Oval Road, London NW1
Library of Congress Cataloging in Publication Data
Main entry under title:
Photochemistry and photobiology of nucleic acids.
Includes bibliographies and index.
CONTENTS: v. 1. Chemistry.-v. 2. Photobiology.
1. Nucleic acids. 2. Photochemistry. 3. Photo-
biology. I. Wang, Shih Yi, (date)
QD433.P48 547'.596 75-26528
ISBN 0-12-734601-5 (v. 1)
PRINTED IN THE UNITED STATES OF AMERICA
List of Contributors
Numbers in parentheses indicate the pages on which the authors' contributions begin.
Michel Charlier (381), Centre de Biophysique Moléculaire, Orleans,
Cedex, France
Malcolm Daniels (23, 109), Chemistry Department, Oregon State Uni-
versity, Corvallis, Oregon
Dov Elad (357), Department of Chemistry, The Weizmann Institute of
Science, Rehovot, Israel
Catherine Fenselau (419), Department of Pharmacology and Experi-
mental Therapeutics, The Johns Hopkins University, School of
Medicine, Baltimore, Maryland
G. J. Fisher (169, 225),* Department of Medical Biophysics, University
of Toronto, and The Ontario Cancer Institute, Toronto, Ontario,
Canada
William W. Hauswirth (109), Department of Biochemical and Bio-
physical Sciences, The Johns Hopkins University, School of Hygiene
and Public Health, Baltimore, Maryland
Claude Helene (381), Centre de Biophysique Moléculaire, Orleans,
Cedex, France
D. P. Hollis (447), Department of Physiological Chemistry, The Johns
Hopkins School of Medicine, Baltimore, Maryland
H. E. Johns (169, 225), Department of Medical Biophysics, University
of Toronto, and The Ontario Cancer Institute, Toronto, Ontario,
Canada
Isabella L. Karle (483), Laboratory for the Structure of Matter, Naval
Research Laboratory, Washington, D. C.
* Present address: Department of Nuclear Medicine and Radiobiology, Centre Hopi-
talier Universitaire, Universite de Sherbrooke, Sherbrooke, Quebec, Canada.
ix
X LIST OF CONTRIBUTORS
Thérèse Montenay-Garestier (381), Laboratoire de Biophysique, Mu-
seum National d'Histoire Naturelle, Paris, France
G. Scholes (521), Laboratory of Radiation Chemistry, University of
Newcastle upon Tyne, England
Shih Yi Wang (1, 295), Department of Biochemistry, School of Hygiene
and Public Health, The Johns Hopkins University, Baltimore,
Maryland
Preface
The prospect of understanding living processes through physical
and chemical principles has attracted many physical scientists to the
study of molecular biology. Since the mid 1930's, their enthusiasm
plus that of biologists has brought about unparalleled advances in
many areas of biology. One of the areas which requires the actual inter-
action of physicists, chemists, and biologists is photobiology. It is this
interaction which is particularly fascinating and has drawn many to
the study of photobiology. Such a trend proved to be fruitful in the
study of photochemistry of nucleic acid components, and early work
led to the isolation and characterization of ultraviolet photoproducts
of pyrimidines. This discovery, in turn, touched off a high level of
activity in the study of photobiology of nucleic acids at the molecular
level. Current activity in this area is unprecedented in the history of
photobiological studies. This intensive and concerted effort has re-
sulted in the recognition not only of processes of repair of and of pro-
tection against irradiation damage in biological systems but also of the
possible relevancy of pyrimidine photoproducts to mutagenesis and
carcinogenesis.
This two-volume treatise provides a judicious review of these excit-
ing developments with up-to-date information as well as the necessary
background knowledge. The chapters, each a self-contained entity, are
concise and authoritive reviews by a group of researchers who are
active in their respective areas. Since this is a vigorous field of study,
the range of statements necessarily extends from those with a high
probability of continuing certainty to those that are speculative but
potentially of heuristic value. This should convey to our readers the
explorative attitude of the investigators and the excitement inherent in
xi
xii PREFACE
this research. While the orientation of each chapter naturally reflects
the interests and viewpoint of the author, there has been a genuine
effort to present a critical treatment of the existing data.
Volume I is concerned with the UV-induced physical and chemical
alterations in nucleic acid components including pyrimidines, purines,
their nucleosides and nucleotides, and related compounds. In addi-
tion, chapters on mass and nuclear magnetic resonance spectrometry
and crystal and molecular structural determinations by x-ray diffrac-
tion are included. Together with the pertinent examples, a brief discus-
sion of the theory and techniques is also presented in each chapter.
This should be of considerable help to those who, although not per-
sonally involved in the interpretation of data, may wish to understand
and possibly evaluate reported findings. Also, the close relationship
between the chemical effects of UV light and x- or γ-radiation prompted
the inclusion of a chapter on radiation chemistry for the purpose of
comparison.
Volume II is concerned with the biological effects due to stable UV-
induced alterations in critical cellular macromolecules including cell
death, growth delay, mutagenesis, and carcinogenesis. The fact that
the problem has been most successfully pursued by assuming DNA to
be the macromolecule most relevant to cell pathology is reflected in
most of the chapters. It is also necessary to consider the photochemical
and photobiological properties of RNA's which are also essential in
cellular functions. Although knowledge about protein and amino acid
photochemistry is less advanced than that of nucleic acids, a chapter
dealing with the UV-induced cross-linkings of proteins with nucleic
acids is appropriate. This knowledge may be required for a full under-
standing of the mode of action of UV on cells, since it is improbable
that biological effects can be explained solely in terms of damage to
nucleic acids. Later chapters delve into the mechanisms that provide
some protection against and are capable of repairing damage caused by
UV photons and by ionizing radiation (also chemical mutagens) in
organisms ranging from viruses to mammalian cells. These repair
processes which were initially of concern only to photobiologists have
gained the interest of investigators in other areas of molecular biology.
Apparently, repair processes play a role in monitoring and preserving
the structural integrity of DNA during physiological processes such as
replication and transcription. Because of this widespread interest,
research of these repair processes has mushroomed in recent years.
Although the study of photoreactivation may have been effectively
covered in a single chapter, such a treatment of the vast existing
PREFACE xiii
literature on "dark repair'' would have been insufficient. Additionally,
knowledge concerning these complex processes is in a state of flux.
For these reasons such a review has not been included in these vol-
umes.
This treatise should serve as an authoritative and important refer-
ence work for researchers active in the study of photochemistry and
photobiology in nucleic acids as well as for advanced undergraduate
and graduate students interested in this field. Since this is an inter-
disciplinary area, an attempt has been made to direct our writings to
an audience which includes physicists, chemists, biologists, and
physicians.
An attempt was made to further a balanced viewpoint by requesting
two or more scholars, active in the respective areas, to review each
chapter. I wish to thank all of these reviewers, some of whom are
contributors, for their most helpful criticisms, comments, and sugg3s-
tions. These reviewers include the late Ruth F. Hill (York University);
A. A. Lamola (Bell Laboratory); E. Fahr (Universität Würzburg); J. E.
Cleaver (Imperial Cancer Research Fund Laboratory); M. W. Logue
(University of Maryland, Baltimore County); J. R. Williams (Temple
University); B. A. Bridges (Medical Research Council); J. F. Ward (Uni-
versity of California, Los Angeles); W. A. Summers (University of
Oklahoma); H. Werbin, W. Harm, C. S. Rupert (The University of
Texas at Dallas); L. Brand, T. Merz, J. L. Alderfer, R. M. Herriott, P. C.
Huang, J. Scocca (The Johns Hopkins University); and, in particular,
William Hauswirth who read and commented on major portions of
the text.
Finally, I wish to thank my colleagues in this endeavor. Particular
gratitude goes to Drs. John Jagger and Michael H. Patrick for discus-
sions on the organization of Volume II for which Dr. Patrick has
served as coordinator; to Elizabeth Hopkins Roth, Patricia Whiting
Linton, and Jane Entwisle Shipley for their editorial assistance; to
Sally Vasek who dealt effectively with the typing and illustrations of
all of the edited manuscripts; and to the staff of Academic Press for
their cooperation and efficient processing of this publication.
Shih Yi Wang
Contents of Volume II
Physical and Chemical Properties of DNA
M. H. Patrick
Photochemistry of DNA and Polynucleotides: Photoproducts
M. H. Patrick and R. O. Rahn
Photochemistry of DNA: Secondary Structure, Photosensitization, Base Sub-
stitution, and Exogenous Molecules
Ronald O. Rahn and Michael H. Patrick
Ultraviolet Inactivation of Biological Systems
John /agger
The Radiation-Induced Addition of Proteins and Other Molecules to Nucleic
Acids
Kendric C. Smith
Repair of UV-Irradiated Biological Systems: Photoreactivation
Helga Harm
Photochemistry and Photobiology of Ribonucleic Acids, Ribonucleoproteins,
and RNA Viruses
Milton P. Gordon, Chaog Wei Huang, and Jakob Hurter
Mutation in Ultraviolet Light —Damaged Microorganisms
C. O. Doudney
DNA Base Damage Induced by Ionizing Radiation
Peter A. Cerutti
Appendix: Abbreviations for Pyrimidine Photoproducts
xv
Introductory Concepts
for Photochemistry of
Nucleic Acids
Shih Yi Wang
A. Introduction 1
B. Basic Aspects of Photochemistry 2
1. Nature of Light 2
2. Interaction of Light with Chemical Systems 5
3. Absorption and Kinetics 9
4. Nature of Electronic Excitation 13
5. Photodissociation and Franck-Condon Principle 16
6. Photophysical Deactivation Processes 19
7. Remarks 20
References 20
A. Introduction
This chapter serves as an introduction to these volumes. It is a brief
discussion of the basic aspects of photochemistry and, hopefully, will
help to introduce basic concepts to readers who are new to the field.
However, since this book is aimed at a diversified audience, many
readers may find this review superfluous. For a more detailed in-
troduction to photochemistry, the reader may take advantage of some
of the excellent monographs published recently, many of which have
been beneficial to this author. Some of these are listed as general ref-
erences at the end of the chapter. This list is a partial one since no at-
tempt was made to compile an exhaustive bibliography.
Since our primary concern is nucleic acids and their ultraviolet
(UV) radiation behavior, an introduction to the fundamentals of these
two aspects should be included. This is treated in Chapter 1, Volume
II and Chapter 4, Volume II, respectively, where it is germane, rather
than at the outset. However, two points must be kept in mind from the
beginning. First, the properties of individual bases or nucleotides may
l