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Tumorigenicityof Bay-Regionepoxidesand Other Derivativesof Chrysene and Phenanthrenein Newbornmice

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Tumorigenicityof Bay-Regionepoxidesand Other Derivativesof Chrysene and Phenanthrenein Newbornmice [CANCERRESEARCH39,5063-5068,December1979] 0008-5472/79/0039-0000502.00 Tumorigenicityof Bay-RegionEpoxideSand Other Derivativesof Chrysene and Phenanthrenein NewbornMice Mildred K. Buening, Wayne Levin,1 Jean M. Karle, Haruhiko Yagi, Donald M. Jerina, and Allan H. Conney Department of Biochemistry and Drug Metabolism, Hoffmann-La Roche Inc., Nutley, New Jersey 071 10 (M. K. B., W. L., A. H. C.], and Laboratory of Bioorganic Chemistry, National Institute of Arthritis, Metabolism, and Digestive Diseases, NIH, Bethesda, Maryland 20205 [J. M. K., H. Y., D. M. J.j ABSTRACT nogenic activity (4). Chrysene, which has one more benzene ring than does phenanthrene, is a symmetrical molecule with The tumorigenic activities of several derivatives of chrysene 2 identical bay regions (Chart 1). Chrysene has weak activity and phenanthrene were tested in newborn Swiss-Webster in carcinogenicity tests (4, 11). Quantum mechanical aspects mice. The compounds were administered i.p. in doses of 0.2, of the bay region theory predict (6) that bay-region 1,2-diol 0.4, and 0.8 @tmolonthe first, eighth, and 15th days of life. 3,4-epoxides of chrysene and phenanthrene should have sim Experiments were terminated when the animals were 38 to 42 ilar chemical reactivities. Kinetic studies of their solvolysis in weeks old. The only tumors found in control mice were lung water from pH 2 to 10 have established that this is indeed the adenomas; 15% of the control animals developed these pul case (19). Since the calculations also predict that these 1,2- monary tumors with an average of 0.1 7 tumor/mouse. (±)- diol-3,4-epoxides should be the most reactive of the possible 1fi, 2a-Dihydroxy-3a ,4a-epoxy- 1,2,3,4-tetrahydrochmysene isomemicbenzo-ningdiol-epoxides of the 2 hydrocarbons, these (diol epoxide-2) with the benzylic 1-hydroxyl group trans to the diol-epoxides and their dihydrodiol precursors are prime can bay-region epoxide oxygen was the most potent chrysene didates as ultimate and proximate carcinogens, respectively derivative tested. It induced pulmonary tumors in 98% of the (5, 6). mice, with an average of 15.9 tumors/mouse. (±)-lfl,2a-Di In a bacterial mutagenicity test, chrysene 1,2-dihydmodiol3 hydroxy-3/3,4fl-epoxy-1 ,2,3,4-tetrahydmochmysene(diol epox was metabolically activated by hepatic enzymes to products ide-i ), in which the bay-region epoxide oxygen is cis to the that were 20 times more mutagenic to strain TA 100 of Sal benzylic 1-hydroxyl group, had little if any tumorigenic activity monella typhimurium than were the metabolites formed from at the dose tested. trans-i ,2-Dihydroxy-i ,2-dihydmochrysene chmysene,chrysene 3,4-dihydrodiol, or chrysene 5,6-dihydro and 1,2-dihydrochrysene, the immediate metabolic precursors diol (24). When the double bond in the 3,4-position of chrysene of a bay-region diol-epoxide and a bay-region tetmahydmoepox 1,2-dihydrodiolwassaturated,theresultingtetrahydrodiol ide, respectively, were the next most active chmysenederiva could not be metabolically activated to mutagenic metabolites. tives tested; they produced pulmonary tumors in 73 to 75% of In a study of the tumor-initiating activities of chrysene and its the mice, with an average of 2. 1 to 2.2 tumors/mouse. 3,4- 3 metabolically possible dihydmodiolson mouse skin, chrysene Epoxy-i ,2,3,4-tetrahydrochrysene (bay-region epoxide) in 3,4- and 5,6-dihydrodiol had no significanttumorigenic activity, duced pulmonary tumors in 71% of the mice, with an average but chrysene 1,2-dihydrodiol had about twice the tumonigenic of 1.26 tumors/mouse. trans-3,4-Dihydroxy-3,4-dihydrochmy activity of the parent hydrocarbon (11). When the double bond sene, 3,4-dihydrochrysene, and trans-5,6-dihydmoxy-5,6-di in the 3,4-positionof chrysene1,2-dihydrodiolwas saturated, hydrochrysene had little or no tumorigenic activity. Chrysene the resulting tetrahydrodiol had less than 25% of the tumomi itself had little or no tumorigenic activity in the lung but pro genic activity of chrysene 1,2-dihydrodiol. These results mdi duced a 25% incidence of hepatic tumors in male mice, with cate that chrysene 1,2-dihydrodiol is a proximate carcinogenic an average of 0.42 tumor/mouse. Chrysene derivatives which metabolite and suggest that the 3,4-position of the molecule is induced a large number of pulmonary tumors also induced a critical site for further metabolism to an ultimate carcinogenic some hepatic tumors and lymphomas. Phenanthrene and its metabolite. derivatives were less tumorigenic than chrysene and its deny atives. Phenanthrene, 1,2-dihydrophenanthrene, and the two diastereomenic bay-region diol-epoxides of phenanthrene had region is the sterically hindered region between the 4- and 5-positions of little or no tumorigenic activity, but the bay-region tetrahydro phenanthrene. The bay regions in chrysene are between carbon atoms 4 and 5 epoxide, 3,4-epoxy-i ,2,3,4-tetrahydrophenanthrene, had and between carbon atoms 10 and 11. Due to the symmetry of chrysene, these 2 bay regions are identical (Chart 1). some activity. This compound induced pulmonary tumors in 3 The abbreviations used are: chrysene 1 ,2-dihydrodiol, trans-i ,2-dihydroxy 45% of the mice, with an average of 0.74 tumor/mouse. It also 1,2-dihydrochrysene; chrysene 3,4- and 5,6-dihydrodiol, other transdihydrodiols of chrysene; 1 2-H2 chrysene, 1,2-dihydrochrysene; 3,4-H2 chrysene, 3,4-dihy induced a few hepatic tumors and lymphomas. drochrysene; chrysene H4-3,4-epoxide, 3,4-epoxy-i ,2,3,4-tetrahydrochrysene; chrysene 1,2-diol-3,4-epoxide-1, (±)-lfI,2a-dihydroxy-3f1,4$-epoxy-1,2,3,4-tet INTRODUCTION rahydrochrysene; chrysene 1,2-diol-3,4-epoxide-2, (±)-i$,2a-dihydroxy-3a,4a- epoxy-i ,2,3,4-tetrahydrochrysene; i 2-H2 phenanthrene, 1,2-dihydrophenan threne; phenanthrene H4-3,4-epoxide, 3,4-epoxy-i ,2,3,4-tetrahydrophenan Phenanthrene, the simplest polycyclic aromatic hydrocarbon threne; phenanthrene 1,2-dlol-3,4-epoxide-i , (±)-i @,2a-dihydroxy-3fl,4fl with a bay region,2 is generally considered to have no carci epoxy-i ,2,3,4-tetrahydrophenanthrene; phenanthrene 1,2-diol-3,4-epoxide-2, (±)-ifl,2a-dihydroxy-3a,4a-epoxy-i ,2,3,4-tetrahydrophenanthrene; benzo(a) pyrene 7,8-dlol-9,1 0-epoxide, one or more of the four isomers of the dia ReceivedJuly6, 1979;acceptedSeptember13, 1979 stereomeric 9.10-epoxides derived from (+)- or (—)-trans-7,8-dihydroxy-7,8- 1 To whom requests for reprints should be addressed. dihydrobenzo(a)pyrene, in which the epoxide is cis (diol-epoxide-1 ) or trans (diol 2 A bay region is present in a polycyclic aromatic hydrocarbon when an epoxide-2) to the benzylic 7-hydroxyl group; DMSO, dimethyl sulfoxide. Where angular benzo ring is present in the molecule. The simplest example of a bay enantiomers are possible, racemic mixtures were used in the present study. DECEMBER1979 5063 Downloaded from cancerres.aacrjournals.org on September 29, 2021. © 1979 American Association for Cancer Research. M. K. Buening et a!. @ OM..,OH BLU:Ha (ICR) strain were obtained from Blue Spruce Farms, @ 0 0 @Iecl@POH Altamont, N. V., 1 to 9 days before partumition.Within 24 hr of OH @H birth, 1 0 pups in each litter were given i.p. injections of the first CHRYSENE CHRYSENE CHRYSENE dose of compound. The mice were given a total dose of 1.4 .2- DIPIYDRODIOL 34. DIHYDRODIOL 5,6-DINYDRODIOI. ... .. Bay @zmolofcompound dIvIded Into 3 InjectIons of 0.2, 0.4, and 0.8 @tmoI,administeredon the first, eighth, and 15th days of life. @ o:9@@ cx9@ ControlmiceweregiveninjectionsofDMSO.Themicewere :@.‘ 0 0 0 0 0 housed in plastic cages with corncob bedding and were fed R.g*on ,2.H@ CNRYStNE 3,4'H2 CHRYSENE CHRYSENE Purina laboratory chow (Ralston Purina Co. St. Louis Mo.) ad H4 @3,4-EPOXlDE CHRYSENE libitum. The mice were weaned at 23 days of age, and the OH Oh experiment was terminated by killing the animals when they 0 ‘@ 0 : were 38 to 42 weeks old. At autopsy, the major organs of each 0 0 0 0 0 -@5 animal were examined grossly, tumors were counted, and CHRYSENE 1,2-DIOL- CHRYSENE 1,2-DIOL- tissues were fixed in 1 0% buffered formalin. A representative 3,4-EPOXIDE-I 3,4-EPOXIDE-2 number of pulmonary tumors, all hepatic tumors, and all other tissues with suspected pathology were examined histologically. 0 ..- 0 Pathology of the lung tumors was the same as has been 0 0 0 described previously (13). 1,2-H2 PHENANTHR(N( PHENANTHRENE H4'3,4-EPOXIDE RESULTS Because of the weak tumonigenic activity of chrysene, we PHENANTHRENE @,,OH @1:@oH administered the maximum dose that could be given to newborn mice with our experimental protocol. The dose was limited by PHENANTHRENE 1,2-DIOL- PHENANTHRENE the solubility of chrysene in DMSO and by the toxicity of DMSO 3,4-EPOXIDE-i 3,4-EPOxIDE-2 to the newborn mice. The limit of solubility of chrysene in Chart 1. Structures of chrysene, phenanthrene, and their derivatives, tested DMSO is about 20 mM, and we therefore doubled the volume for tumorigenic activity in newborn mice. Stereochemistry is relative. of the injections from the amount used in previous experiments (2, 7, 21). Although the phenanthrene derivatives are more In recent studies (23), the diastereomenic 1,2-diol-3,4-epox soluble in DMSO, we chose to use a dose equimolamto the ides of chrysene were 5 to 60 times more mutagenic than was chrysene derivatives so that the biological activities of the 2 the K-region chrysene 5,6-oxide in strains TA 98 and TA 100 hydrocarbons could be compared directly.
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