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New Developments in Chemical Carcinogenesis by Polycyclic Hydrocarbons and Related Heterocycles: a Review*

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New Developments in Chemical Carcinogenesis by Polycyclic Hydrocarbons and Related Heterocycles: a Review* CANCER RESEARCH VOLUME24 OCTOBER 1964 NUMBER 9 New Developments in Chemical Carcinogenesis by Polycyclic Hydrocarbons and Related Heterocycles: A Review* N. P. Buu-Hoï (Centre National de la Recherche Scientifique, Paris, France) When the last of the famous series of surveys on chemi five. Almost all the then known active hydrocarbons con cal carcinogenesis by Cook and Kennaway appeared in the tained a phenanthrene system, and this fact promoted, American Journal of Cancer in 1940 (18), it brought to an and justified, the theories according to which the meso- end the first chapter of research in that domain, which phenanthrenic double bond (called "K-zone") would play a had seen the discovery of the first families of chemical prominent role in the biochemical interactions between hy carcinogens and had brought to light the first relationships drocarbon and cell components which constitute the early between chemical structure and oncogenic activity. Since stages in the carcinogenic process. The introduction into then, a considerable acceleration of progress in our knowl the molecule of electron-releasing groups (especially methyl edge of chemical carcinogenesis has occurred, with the groups) enhances the 7r-electron density, and hence the discovery of many prolific new families of carcinogens as chemical reactivity, of the K-zone, and should conse well as a wider knowledge of those already known, the quently increase carcinogenicity. Contrariwise, the pres acquisition of the first clues as to the mode of biochemical ence of electron-accepting groups (aldehyde, ketone, nitrile, interaction between carcinogens and cells, and, finally, the carboxyalkyl, etc.), or the replacement of a nuclear first practical applications of the science of chemical car —CH= group by a nitrogen atom, depresses the reactivity cinogenesis to the field of cancer chemotherapy and chemo- of the K-zone, and thus a decrease in carcinogenicity prophylaxis. should be expected. A similar negative effect would also Because of the scope of the progress made and the pro ensue when the interaction between the K-zones and the gressive specialization of the investigators, a review on cell constituents is impeded by steric hindrance arising chemical carcinogenesis along the lines of Cook and Ken through the presence of substituents in those zones. In naway's comprehensive papers seems less and less feasible addition to their K-zones, the majority of the then known within the confines of a single publication and by any single carcinogenic hydrocarbons bore a wieso-anthracenic region group of authors. And so the present paper will be limited ("L-zone"), and in those hydrocarbons bearing the two to the salient facts, interpretations, and theories concerning zones it was observed that the degree of carcinogenic the carcinogenic polycyclic hydrocarbons and their hetero- activity was in inverse proportion to the chemical re cyclic analogs which have been investigated during the activity of the L-zone (the few naphthacene hydrocar last decade. It will comprise four sections: (a) an ex bons, for instance, which had been tested, being all at that amination of the improvements in methods of assay of time found inactive). carcinogenic hydrocarbons and analogous heterocyclics; The fruitfulness of this over-all picture cannot be better (o) a survey of relationships between chemical structure illustrated than in the many instances in which theo and activity in the principal groups of newly investigated retical calculations for carcinogenic activity were subse compounds; (c) a discussion of the experimental evidence quently confirmed by the results of biological testing. thus acquired, with reference to the more recent theories Such was the case with several angular benzacridines (13) of chemical carcinogenesis; and (d) a discussion of the and, more recently, with 3,4:9,10-dibenzopyrene (17, 63). question of the endogenous biosynthesis of carcinogenic However, the intensification of research on chemical hydrocarbons. carcinogenesis that has marked the last decade, and which was due in part to the recognition of the important role of THE EARLY PICTURE OF A CARCINOGENIC polycyclic hydrocarbons in the etiology of certain human HYDROCARBON cancers, has resulted in a considerable volume of new data, From past experimental research and past interpreta in the light of which the former picture of a typical car tions there emerged a classical picture of a carcinogenic cinogenic hydrocarbon has now to be enlarged and even hydrocarbon possessing the following features: It was a revised in several respects. Advances that have been polycyclic condensed aromatic molecule, built up of at least three annelated benzene rings, the optimum number made are the outcome both of improvement in method for maximum carcinogenic activity ranging from four to ology (refinement of the routine methods of biological assay, development of new technics for investigation of the * In honor of the 80th birthday of Prof. A. Lacassagne, under physico-chemical properties of carcinogens) and of the in whose direction much of the work reviewed here has been accom crease in the number of chemical series investigated—and, plished. Received for publication April 24, 1964. within each series, in the number of substances examined. 1511 Downloaded from cancerres.aacrjournals.org on September 25, 2021. © 1964 American Association for Cancer Research. 1512 Cancer Research Vol. 24, October 1964 IMPROVEMENTS IN METHODOLOGY OF ASSAYS hydrocarbons which are barely active on the skin or sub Although the use of various animal species including cutaneously readily induce hepatomas when given by other rodents (rats and hamsters) is still extremely valu mouth, but also this route can often make possible the pro duction of both benign and malignant tumors of the upper able for specific experiments in carcinogenesis (induction of digestive tract; for instance, both 5,6-benzopyrido(2',3': hormone-dependent tumors, cancers of the liver, etc.), all l,2)carbazole and 5,6-benzopyrido(3',2':l,2)carbazole, the evidence points overwhelmingly to the necessity of using the mouse for the detection and evaluation of local given orally, elicit a high percentage of multiple papillomas carcinogenicity in polycyclic molecules, because in mice and epidermoid epitheliomas of the foresto mach (43). Appreciation of différencesin susceptibility of male and there exist strains (such as the Paris Radium Institute female mice.—Originally, the evaluations of carcinogenic strain XVII nc/Z) which almost never spontaneously de velop tumors of the type to be expected from the experi activity of hydrocarbons and analogs were made irrespec ments; and once these experimental tumors have been tive of the sex of the mice, and in the few cases where this induced, their growth is less likely to be influenced by factor was taken into account no differences or only extraneous factors (diet, environment, hormonal factors, negligible ones were noted (2, 7, 26). Leiter and Shear (52), however, using 3,4-benzopyrene (III) in marginal etc.)- Diversification of the tests.—Foran accurate evaluation doses (0.1-0.05 mg.) and a large number of animals, found of the carcinogenic activity of polycyclic hydrocarbons in that, with the strain of mice they used, there was a greater mice, it has become imperative to make use of all three of susceptibility in the males, 52 per cent of which developed the following tests: skin-painting, subcutaneous injection, tumors compared with only 36 per cent of the females. and oral administration. It has long been known that More recent research done with strain XVII nc/Z of the many hydrocarbons which readily elicit skin tumors were Radium Institute has confirmed this inequality of action inactive when administered by subcutaneous injection— of 3,4-benzpyrene (sarcoma index determined in 154 male this is in particular the case of 3,4-benzophenanthrene (I) mice, 91, and in 162 females, 47) and shown that even and its derivatives. The reverse—i.e., substances active greater sex differences in susceptibility exist with many hydrocarbons tested by subcutaneous injection. Further more, in several instances it was the female mice in which cancer was more easily induced than males. Thus, 3,4:8, 9-dibenzopyrene (IV) is considerably more sarcomagenic in when given subcutaneously and inactive on skin-painting— is at least as frequent: for instance, naphtho(2',3':3,4)- pyrene, which has been found inactive on the skin, later proved quite sarcomagenic (12). An added value of the CHO subcutaneous injection procedure springs from the fact that many carcinogens can be tested on the skin only with great difficulty or even not at all, either because they are readily oxidized in the air, especially in the presence of light (e.g., the naphthacene and higher linear hydro the male than in the female mouse ; in one experiment with carbons), or because they are too poorly soluble in the this substance 34 out of 35 male animals developed a usual solvents (e.g., condensed hydrocarbons with more sarcoma in situ, whereas out of ten females, cancer was than six benzene rings, such as the tribenzopyrenes). A induced only in one (51). Similarly, with 2,3-phenylene- last important advantage is the possibility of injecting very pyrene (V), the sarcoma index1 was 27 for the males and small amounts of substance (sometimes, as with 1,2:4,5- only 5 for the females. Pronounced sex differences are dibenzopyrene (46), a single dose of 0.6 mg. is sufficient), also observed with nitrogen heterocyclic compounds: for thus permitting tests to be performed with compounds instance, with 5,6-benzopyrido(2',3':l,2)carbazole the so difficult to prepare that they are available only sarcoma index was 64 in the males as against only 7 in the in limited quantities. Indeed, it is often expedient females (47). Conversely, with 6-formyl-12-methylan- to employ minimal amounts of the substance for thanthrene (VI), the sarcomagenic effect was considerably injection, when, for instance, the compounds possess greater in the females than in the males.
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