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Schmukler, Frankel and Sergio L. Maze, Schottmuller, C. Razin, A. Auster, Sarah; Gottardi, Piero, Eckhard Hein, Brown, Jeffrey R. Todd D. Stavins, Gerarden, Todd D. Smith, V. Douglas J. Ramon P. DeGennaro, Han, Seungjin, Seungjin Han, Ambec, S. Polemarchakis, Bossler, Mario, Holford, Angus J. Audretsch, David B. Evidence from Local Markets for Fake?

Moschini, GianCarlo, GianCarlo Moschini, Todorova, Tamara, McMillan, John, Lensink, R. Peeters, R. Konrad, Kai A. Rizov, Marian, Lapan, Harvey E. Stam, Kane, Edward J. Edward J. Kane, Haisken-DeNew, John P. Hatemi-J, Abdulnasser, Laffont, J. Francois R. Thomas J.

Miceli, Hoff, Karla, Reito, McGuire, Parry, Ian W. MacLeod, Bentley, Hendrik P. Stiglitz, Joseph E. Stern School of Business, Department of Economics. Kaplan, Kiff, J. Ghatak, M. Guinnane, Department of Economics. Li, Cheng, Avner Ben-Ner, "undated". Luca Lambertini, Jeitschko, Marc T. Libecap, Bonroy, O. Christopher L. Leahy, Huffman, Wallace E. Erber, Georg, Bureau, J. Maths Infor..

Tirole, Jean, Jean Tirole, Nathan Kettlewell, C Wolff, Fischer, Justina A. Eskeland, Gunnar S. Stephen D. Williamson, S. Bradford L. Klemme, Simon Schopohl, Bruce C. Stiglitz, Sylvain Prado, Dur, Timothy Perri, Ben S. Bronwyn H.

Hall, Hall, Bronwyn H. Hall, Bronwyn, Wayne L. Huang, Daisy J. Daisy J. Burke, Paul J. Paul J. Burke, Jorge M. John A. John List, Strausz, Roland, Rodriguez, Elsa M. Ulbricht, Robert, Lubna Hasan, Hasan, Lubna Hasan, Hasan, Lubna, Rothschild, Fortin, B.

Shubik, Stephan Weiler, Perloff, Jeffrey M. Weche Geluebcke, Richard Murphy, Law, Michel Zouboulakis, An econometric analysis of students perceptions in economics courses ," Discussion Papers Series , School of Economics, University of Queensland, Australia. Stulz, Dice Center for Research in Financial Economics. Juan D. Palfrey, Benjamin R. Handel, Benjamin R.

Minh Ha-Duong, Barnes, Paul, Felipe Zurita, McDonald, Guillaume Daudin, John L. Kenneth Baltzer, Shyam Sunder, Fausti, Scott W. Jeffrey V. Butler, Jeffrey V. Mario Pagliero, Sichel, Mark E. Nyborg, Soumyanetra Munshi, Athukorala, Prema-chandra, Joao Correia-da-Silva, Boynton, Robert D. Gallen, School of Economics and Political Science.

Roger H. Lans Bovenberg, Gordon, R. Bovenberg, A. Beuselinck, C. Manigart, Rostam-Afschar, Davud, Davud Rostam-Afschar, Asongu, Markus K. Analysis of the polar dyes isolated from the liver indicated that: the ethyl group was preferentially cleaved, only one methyl of the dimethyl compound was cleaved, and the dye was not bonded to the liver protein through the N-methyl group the latter in confirmation of work by Lin et al The authors considered the azo compound a use- ful tool in the study of the biochemistry of GSH.

DuPlooy and Dijkstra studied the polar extractable metabolites from the liver of rats given 4-dimethylaminoazobenzene. Between one and thirteen hours after dosage six metabolites were present at any one time, but at the fourth hour the amount peaked and consisted mainly of the 0-sulfate esters of 4'-hydroxymethylaminoazobenzene and 4'-hydroxy dimethylaminoazobenzene. If at the time of dosing an i. Henkens and Sturtevant reported that the esterase activity of bovine carbonic anhydrase was completely inhibited by the metal-chelator 4- 8-hydroxyquinolylazo -l-naphthalenesulfonate.

Connors et al compared the ability of various preparations from rats to reductively cleave the azo bond of 2'-cavboxydi 2- chloroethyl aminomethylazobenzene. The preparations were supernatants from homogenates of gut, gut entire homogenate , Walker tumor cells, spleen, kidney, and liver.

The relative rates of cleavage, in the same order, were: 1, 4. Albrecht et al compared the effects on liver functions of medium term feeding to rats of amaranth and 4-dimethylaminoazobenzene. The animals were fed from weaning, up to 2, 3, 4, and 9 months of age, consuming over these periods in grams : 1. The amaranth had no effect on weight gain or liver weight as a percentage of body weight. The carcinogen caused a noticeably lower weight gain at 2 months, but at 9 months the controls were only slightly heavier.

The amaranth had no effect on the percentage of protein in the liver, while the carcinogen caused reductions at 2 and 9, but not 3 and 4 months. The amaranth had no effect on glucosephcsphatase, while the carcinogen lowered it at 2, 4, and 9 months. The amaranth had no effect on glucosephosphate dehydrogenase, while the carcinogen raised it at 2 and 9 months. The amaranth had no effect on 6-phosphogluconate dehydro- genase until 9 months, when a lowering occurred; the carcinogen, on the other hand, raised this enzyme level at 2 and 9 months.

Amaranth had no effect on the ability to cleave the azo bond of amaranth, while the car- cinogen increased this ability at 2, 4, and 9 months on a per mg of protein basis. Liver homogenate supernatant was used for the enzyme studies. Chauveau and Benoit fed weaned rats a diet containing 0.

Metabolic effects 1. Ryan and Welling found that chemically pure Sudan III fed to rats as a suspension in methyl cellulose mucilage, olive oil, or oleic acid showed negligible absorption from the g. Previous reports to the contrary presumably resulted from the use of impure commercial material. Walker reviewed the literature on metabolism of azo compounds, including absorption. His review indicates that in general, highly sufon- ated dyes aren't absorbed.

However, there is a good pjssiblity that they may be cleaved at the azo bond by the intestinal flora, and the metabol- ites may be absorbed. The same "pre-metabolism" interferes with judgments on the extent of absorption of the non-sulfonated, oil soluble dyes. Using C labeled N-methyl groups for ease of detection, they reported the results in Table Copyright hy Cancer Research Inc.

In the 24 hour urine was found o- and p-hydroxyaniline, toluene, p-phenylenediamine, AB, 4-methyl AB; the o-hydroxyaniline pre- dominated. Ryan and Wright examined the biliary excretion of unchanged dye after i. Their results are given in Table 16a, and do not indicate any relationship between structural type and metabolization.

Urinary activity was about the same at 27 days as at 72 hours. There were three more colored metabolites of No. The same experiment on dog and rabbit intestines showed rapid dye destruction in all cases. Attempts to measure the fecal excretion of ad- ministered dye and then run the in vitro study on the intestine of the same rat showed no correlation between in vivo and in vitro results. The in vitro rat, rabbit, and dog studies with No. He was not able to detect thir substance in the urine of dogs similarly dosed.

Radomski and Mellinger found that in oral dosing of rats with amaranth, Ponceau SX, and Sunset Yellow food dyes, increased quantities of unchanged dye in the feces could be generated by dosing with antibiotics to depress the activity of the intestinal flora.

Robinson et al gave rats i. The separate injection of p-phenylenediamirie resulted in enough more of it being excreted in the urine to indicate that the low amounts found above didn't likely result from in situ destruction. Radomski and Harrow administered l- o-tolylazo naphthylamine Yellow OB into the stomachs ligated just beyond the pyloric sphincter of rats.

After six hours they were able to extract material corresponding in UV spectrum to an imidazole, resultant from the reaction of an aldehyde with the dye. Separately the authors administered a single dose of C labeled dye to rats and examined the feces and urine for four days. Of the total activity excreted, Chromatography of the feces extracts revealed unchanged dye, and dye with a hydrory at the 6 position of the naphthyl. In still another test the rats were given the dye orally at the same time an i.

Sato et al investigated the occurrence of N-hydroxy metabolites in the urine of laboratory test animals given parenteral doses of carcino- genic and non-carcinogenic members of the 4-aminoazob3nzene family. There was no excretion of either, or any metabolites, via the bile or urine. From the oral dose of III, was recovered in the feces, unchanged. From the i. When an i. Copyright by Cancer Research Inc. TABLK AAB i p. AAH i p A'! A' llydn. All i. MAB i p. A'-Ilvdroxy-AB s.

AAH i p. A"-lhtfrov; AAB i. AH i p A'-lhdr. A'-Jfydroiy-AAB 0. Ofi 0. TC en-pi i ;! Fore et al found that Brown FK a complex mixture was only decolorized azo linkages reduced or broken by the contents of rat caecum or distal small intestine, and not by stomach or proximal small intestine contents.

The accumulation of the break- down products inhibited further breakdown of the components of the dye. In Table 18 are the results of i. Only traces of the phenazine-like material were actually excreted after intragastric dosing, the ultimate fate after creation in the caecum being unknown.

Prior to the experiment with pigs the authors would not have expected the finding of sulfanilic acid and the phenazine-like material in rats to have had much meaning relative to the toxicity of Brown FK in humans. However, with this finding they considered it of importance to determine just which bac- teria were responsible and how widespread, interspecially, they might be. Hanaki reported that rats fed N-methyl-N-:'. Also, by incubating the N,N-diallyl parent with rat liver homogenate, the methyl group was the one to be cleaved.

However, the polar dye isolatable from the rat liver was shown to be N-methylamino- azobenzene. Walker had a good review of the literature, inclusive of ex- cretion, into Principal Interval after finding? Reprinted with permission from Food Cosmet.

Qualitative findings of the excretory routes of the dye and its metabolites are given in Table The last five columns on the right correspond to: azo metabolite, sulfanilic acid, non-azo metabolite, non-azo metabolite, and non-azo metabolite, respectively all identified. There are two possible azo metabolites as there are two azo linkages in the dye, but only one, apparently, was found.

Residual dye and the azo metabolite were found in the stomach wall and contents. SA and DSA were found in the intestinal contents. None of the azo metab- olite or dye was found in the bladder, intestines, heirt, liver, or stomach after i. In Tables 20, 21, and 22 are the quantitative measure- ments of excreted metabolites.

Tables reprinted with permission Food Cosmet. Production of sulfanilic acid apparently only occurred in the intestine, as a result of bacterial action. The rat's enzymes did not seem able to reduce the azo bond which would result in this particular metabo- lite, but they did reduce the other azo link. Gingell et al investigated the influence of intestinal bacteria on the reductive cleavage of the azo bonds of Prontosil and Neoprontosil by treating rats with antibiotics prior and subsequent to dosing with the azo compounds.

In Table 23 is the comparison between control and antibiotic treated animals with regard to excretion in urine and feces, and nature of the metabolites, showing the strong effect of the treatments. When biliary-cannulated rats were given an i. When Neoprontosil was dosed orally to these altered rats, 1. Since there was no biliary excretion of the unchanged dye, there must have been diffusion through the peritoneum and intestinal wall. Ozkan showed that 3'-methyldimethylaminoazobenzene could be transported across the placenta in rats, producing changes in the liver of the offspring in line with the amount of dye ingested by the parent.

Golub demonstrated that o- and p-aminoazouoluene could be transferred across mouse placenta. The antibiotic treated rats each received orally ncomycin sulphate mg , b.! The antibiotics were then given 4 h before and 4 and 24 h after the administra- tion of Prontosil.

The urin. The metabolites were determined by cutting out the r. The rats were sacrificed and the homogenized livers centrifuged into nuclear, mitochondrial, and microsome-supernatant. In a different series of otherwise identical feedings, the three fractions were further broken apart by solvent extraction. Tables 25, 26, 27, and 28 present the findings on the distribution in the liver of metabolites of DAB.

Baba gave a rat 15 mg of BAB C labelled in the non-amino ring via stomach tube on two occasions in a single day, followed by a rice diet containing 0. The liver was sectioned, rinsed free of non- protein bound DAB, and then autoradiographed. Very little activity appeared around the bile ducts.

Distribution of the activity was nearly uniform across the peripheral, middle, and central zones, slightly lower in the peripheral. Activity in the two lobes was the same. Slight activity existed in Kupffer's cells. Radomski gave stomach tube doses of Citrus Red No. After 24 hours no unchanged dye could be found in kid- ney, liver, muscle, or spleen tissue. More of the dye was initially incorporated into the fat than with No. Drop off was smooth in the females, zig-zag in the males.

Storey studied the distribution and retention in connective tissues and bones of chlorazol fast pink and related dis- and trisazo dyes i. There was no staining of day fetuses. Noticeable color in the urine persisted six months. Also colored was the cartilage in the nose, ear, and trachea. No staining of the brain, spinal cord, eyes, nails, or hair occurred. At six months coloring had become faint except for the aortas, which were still bright.

Young, but not old animals showed staining at the margins of cranial sutures, dentine, and long bone growing metaphyses. Gingell et al examined the distribution in the bodies of rats after oral dosing with Prontosil S The results have already been dis- played in Table 23 in connection with excretion of metabolites.

Treatment with antibiotics to study the effect on in-gut breakdown did not change the accumulation in the internal organs, but it did increase the amount in the carcass by a factor of 2. TABEK The N" ciiiicenlralion lias liccn corrected for Uic nntural rontent of N" of the pnrtirulnr fractions nsdelcrminedoBral' fed the diet containing nonisolopic DAH. Nuclei: Cold acid-soluble l. Tlic Nlf oinccnlriiliun has been corrected for lie milurnl cant nit of N" of the piirlicuhir fractions ns determined on ruts fed the diet containing nonisotopic Tables reprinted with permission from Cancer Research Physiological effects Danneberg and Schmahl tested the estrus-inhibiting properties in rats of a number of azo compounds.

The compounds which had this property were not necessarily also carcinogenic. Lacassagne et al fed adult rats four derivatives of azobenzene as 0. All four caused considerable weight loss. In order of decreasing damage to the liver, the compounds were: 3',N,N-trimethyaminoazobenzene, 4'-N,N-trimethyaminoazobenzene, 4'-phenyl-N,N-dimethylaminoazobenzene, and 4-hydroxyazobenzene.

Adams and Roe applied to the skin or injected beneath it solu- tions of azo compounds to study the effect on hepatic catalase activity. None of the compounds caused any damage to the liver itself. In decreasing order of ability to depress the enzyme level the compounds tested were: 3',N,N-trimethylaminoazobenzene, 4-N,N-dimethylaminoazobenzene, 2',3'- dimethylaminoazobenzene, m-azotoluene, 2-aminoazotoluene, and azo- benzene no depression.

Doses applied were ym. In both sexes the liver showed higher BI and lower 62 levels than controls. A similar result obtained with vitamin C, but the females were dependent to some extent on the vitamin content of the pre-experiment diet. Akai and Yasumori cultured the fungus Cochliobolus miyabeanus in a nutrient solution containing 10 yM-1 mM Congo Red or 0. Maximal growth occurred at 0.

At the highest concentrations of both, growth was less than that of the control, the Chrysoidin being the more toxic. Optimal usage of glucose and nitrate occurred at the lowest dye concentration, not at that concentration which gave highest growth. Innoculation of the dye-grown fungus on rice plant leaves showed that there was decreased toxicity to the plant; the decrease was independent of the Chrysoidin concentration, but correlated with the Congo Red concentration the lower the concentration the higher the toxicity.

The same figures applied fcr 2,2 '-dimethyl- 4,4'-dihydroxyazobenzene. In the case of 2 ,4,4'-trihydroxya;jobenzene or 2-methyl-4,4'-dihydroxyazobenzene, a yg dose had no effect. Doi fed rats 0. Examination of the liver showed increases over normal in haemosiderin, ferritin, and ascorbic acid, decreases in catalase, copper, and riboflavin. Okuda fed rats a diet containing the usual amount probably 0.

No reliable change in thiamine resulted. Nicotinic acid increased slightly. Pyridoxic acid decreased noticeably. Riboflavin increased considerably. Guinea pigs did not show the increase in riboflavin. Neish gave single i. Methaemoglobin from tail blood was then determined at 3, 7, 22, and 28 hours. Table 29 sums these four values and presents them as methaemoglobinemia. It may be seen that there was no correlation with carcinogenicity. Natur- Copy right Mascitelli-Coriandoli fed rats a diet containing 0.

Yamada gave rats i. Radio-iodine was given s. Testis weight was of control. Total iodine and protein-bound iodine in the serum were 62 ' On average, a single in jection of trypan blue inhibited thyroid hormone secretion for 14 hours. Neish and Rylett gave rats i. Neish and Rylett , pp. Kizer and Howell reported a study on the effect of 3'- and 4'- methyl butter yellow on rat hepatic kynurenine hydroxylase activity. Ax- though the control diet seemed to be deficient in something which also affected the enzyme in the same direction as the azo compounds, the latter's effect was still noticeable.

The results are in Table The reduction in activity did not become significant until the livers had shown signs of cirrhosis for three weeks. Continuing the feeding until tumors appeared in the liver revealed that the tumors had far less activity than surrounding tissue.

Furlong and Thomann fed rats 0. After six days the activity had nearly doubled. After seven weeks the activity was only slightly higher than normal. Dijkstra gave rats a single intragastric dose of 2,N,N- or 3',N,N-trimethylaminoazobenzene and measured the hepatic ascorbic acid level.

The levels were still below normal after two weeks. Over an entire 20 week period hepatic ascorbic acid was above the normal range with the 3'N,N compound, especially from the third week. With che 2,N,N compound the level was at the normal upper limit or slightly above. Omission of all B2 from the diet resulted in death however. Mel'nikova and Selikhova found that mice given azobisformamide produced less serum pseudocholinesterase and acetylcholinesterase, and less hepatic cholinesterase. Mulay fed normal, three month old rats a low-protein, low- riboflavin diet containing 0.

Each 7. Hepatic steroids and fat were considerably lower than this control. The author claimed that hepatic ascorbic acid and ratio to whole body were the same as controls, but did not specify which controls. The protein level was fully recovered within one month.

Hepatic hexokinase was unchanged. Arginase was unchanged. In a separate experiment the rats were given 5 mg of the azo compound daily for days. Relative liver weight was about doubled for 80 and day treatments, but pentupled after days. All of the changes from 80 day treatment were at least partially reversiMe as seen from weeks on a normal diet.

After six weeks normal diet after days on treatment relative liver weight was returning to normi. Doctor et al showed that rats fed 0. Both treatments resulted in myofibrillo- lysis and lysosomal damage followed by lipofuscin deposition. The lysis is rapid and extensive after the forced feeding, occasionally not appearing after dietary treatment.

Gaunt et al fed rats Brown FK at 0. Unchanged were growth rate and food consumption, kidney and liver weights and function. Hematology was normal. Apart from the follow- ing, histopathology was normal. In the pigs the principal change was deposition of lipofuscin in the liver in both sexes at all dosage levels, accompanied by higher lysosomal enzyme activity. The lipofuscin also de- posited in male, but not female, hearts.

The only effect noted was a slight decrease in erythrocytes in males after six weeks at the highest dose. Gaunt et al , pp. Beaudoin gave i. Reprinted with permission from Teratology Copyright by WTstar Institute Press. Blood samples were taken just before Injection, 48 hours after and 12 days after injection.

Table 32 presents the findings on the protein content of the serum. In Section X. Reuber gave rats five weekly s. Those animals which developed thyroiditis also weighed less than controls or normal-thyroid experimentals; a greater percentage of females developed thyroiditis, but those which did were closer in weight to "normals" than the corresponding males. Poirier and Pitot fed rats 0.

The 3',N,N ani- mals after weeks showed a loss of ability to produce ornithine transaminase and histidase after casein hydrolyzate force feeding , and also serine dehydratase. The 2,N,N animals after weeks showed a loss of ability to produce tyrosine-a-ketoglutarate-trnnsaminase and serine dehydratase. Decloitre and Meunier fed 0. The hamsters showed no hepatic cellular alterations.

The C3H mice showed glycogen and fat deposits in the hepatic cells after six weeks; cellular damage became severe after three months, and continued to increase. The 1C mice showed no hepatic alterations until five months. The glycogen and fat deposits appeared at six months along with inflammation. In the 1C mice the maximum slightly greater than in the ham- sters was reached in two weeks, then gradually decreased lower than the hamster level at six weeks.

This decreased at a rapid linear pace until three months, when it was between the IC's and hamsters. Then it rose slightly at four months, and then dropped quickly to zero at five months at which point the IC's were slightly above zero, the hamsters considerably above. Over a five month period the hepatic azoreductase and NADPH-cytochrome c reductase activities were measured. Although C3H mice were known to spontaneously develop hepatomas after one year on the control diet used, none of the control mice showed the, apparently, irreversible cell changes occurring in the livers of the dye- fed mice at six months.

Endo et al fed rats 0. The former did not increase the level of hepatic muscle type aldolase, but the latter did, even after only 15 days of feeding. If the diet were maintained for 60 days, then the increased level of activity was maintained for an additional days. The livers were then examined for various induced enzyme activities.

The 3',1I,N dye resulted in zero or diminished responses of glucokinase, glucose phosphate dehydrogenase, 6-phosphogluconate dehydrogenase, malic enzyme, and citrate cleavage. The 2,N,N dye lowered the 6-phosphogluconate de- hydrogenase and glucosephosphate dehydrogenase, without affecting the others.

Gaunt et al fed male and female immature rats No effects on food or water consumption or weight gain were seen. Hemoglobin was low at the ppm level after two weeks in the females, in both sexes after six weeks. Methemoglobin was considerably higher as percentage of hemoglobin in both sexes after two weeks at ppm. The only significant change at t. Packed cell volume decreased at ppm in females after two weeks, and at ppm in males after six weeks.

Reticulocytes as percentage of red blood cells increased con- siderably at ppm in both sexes after two weeks, in both at ppm after six weeks. The only significant compositional changes in the leukocytes occurred in males at six weeks when the neutrophils showed a large increase at and ppm, and the lymphocytes showed a small decrease at the same levels. There were no significant changes in blood chemistry. An i ru iejse in urine vo Limit- w,i. The changes in white blood cells and decreased relative brain weights were not considered related to the dye feeding.

Yen et al gave i. The lower two doses had no effect on dentin forma- tion, while the high dose completely inhibited it for eight days. Tschopp et al gave i. The middle dose had a similar effect on leukocyte count, but recovery was complete in about 20 minutes, followed by attainment of a long lasting plateau of ex- cess leukocytes 3 times normal in 30 minutes. The immediate effect on leukocytes of the high dose was not clear, but a gradual increase to well above normal followed.

Remaining platelets showed extensive swelling and pseudo- pod formation. Within two hours the lungs showed alveolar edema and capillary obstruction, with larger vessels containing Isrge numbers of leukocytes and platelet aggregates. Popa et al reported that 0. Some lesions were found in the stomach, liver, and kidneys which seemed to be reversible.

These correlated in intensity with decreases in serum glycoprotein and albumin, and increases in leucine aminopeptidase, glutamic-oxalacetic transaminase, glutamic-pyruvi. Iga et al gave adult male rats 30 umole i. The authors examined the ability of the plasma protein to bind with the dyes, and decided the difference could account for only a small part of the biliary excretion spread.

Holland and Spain fed immature male rats 0. Examination of the shorter period feces for bile acids showed normal amounts of Lithocholic, deoxycholic, chenodeoxycholic, somewhat lesser amounts of keto- lithocholic and hyodeoxycholic, and considerably less cholic. The urine collected from the controls showed the bile acids hyodeoxycholic day 15 and lithocholic day66 ; the dye-fed animals' urine also showed these two, but considerably more cholic, hyodeoxycholic and ursodeoxycholic.

Urinary bile acids peaked at 26 and lower 53 days. One day prior to sacrifice each rat was given radioiodine, i. Gaunt et al gave immature male and female rats ppm of Black PN for up to two years. Mortality was considered equivalent to the controls. Body weight of controls and dye-fed animals was equivalent. Hemoglobin was lower in 82 week females at ppm, and week males at all levels.

Packed cell volume was lower in the and ppm groups of these males. Red blood cells were higher in 82 week females at ppm. Total leukocytes were lower in week females at ppm. Serum and urinary biochemical analyses were normal at 52 and weeks. Absolute organ weights were all normal at weeks. Relative organ weights were normal except for male liver which was heavier at all levels. Histological examination of lungs, kidneys, pancreas, liver, and testes showed no abnormal occurrences in dye-fed animals.

Incidence of tumors in the mammary, pancreas, thyroid, and adrenal glands was normal, likewise that in the ovary and subcutaneous tissue. Lin et al gave i. Analysis of the blood for methemoglobin as percentage of hemoglobin showed a rapid rise to 70, followed by a linear drop to 10 at 7 hours for 4-amino-, a rapid rise to 50, followed by a plateaued drop to 10 at. Examination of possible metabolites implicated N-hydroxylation as a highly likely preliminary step.

Singh and Khanna gave rats a single injection into one testis of 0. Acid yellow Exam- ination of the testis was conducted at hours, days. At four hours there were signs of edema and inflammation. An eight hours both had increased in intensity and were accompanied by seminiferous tubule degen- eration, Leydig cell degeneration, and engorgement of blood vessels.

At 16 hours the edema had decreased, but now the interstitiam had begun to de- generate where associated with the tubules also degenerating. After one day no increase in magnitude of changes had occurred, but in half of the specimens the seminiferous and interstitial elements had totally degen- erated. After two days massive degenerative changes showed in the gameto- genic and endocrine elements.

Spermatozoa had decomposed here and there. After seven days the tubules were totally necrosed along with the inter- stitial elements. After 15 days the interstitium shows signs of regenera- tion, but the tubules did not. At the highest dose there was severe hepatic interstitial fibrosis and multiple mdular hyperplasias of the parenchyma. All dosages caused proliferation of hepatic bile duc- tule epithelium cells along the triads and the interlobular septa, some- times intrahepatically also.

They incubated a variety of azoben- zene derivatives with fresh baker's yeast and determined the extent of decolorization - possibly synonymous with azo cleavage. Azobenzene did not decolorize, nor did the 2-, 3-, or 4-methyl-, or the 4, 4'-bis di- me thylamino - derivative. Also not decolorizing were phenylazo N- methyl naphthylamine, o-tolylazonaphthylamine, and anisidineazonaph- thol.

Solubility in water apparently was not a factor. Walker et al removed azoreductases from various rat gut bacteria and compared their ability to reduce Red 2G. The most proficient came from Streptococcus faecalis. The following activities relative to S. Environmental Transport No specific information was found. The azo dyes and foaming agents investigated are not notably volatile, so their ability to move once released into the environment is dependent upon water solubility and specific gravity for the non-water solubles.

Bioaccumulation No specific information was found. Intestinal bacteria seem able to destroy the azo bond in many compounds. Some, metabolism tests indicated "storage" of various azo dyes in skin and fur on prolonged forced feeding, but to no obvious detriment of the animal. Human-Occupational experience, Other 1. On the first, seven doses over five hours totalled mg in the first three hours and mg in the last two.

On the second, at nine-minute intervals doses of 40, 48, 78, , , and mg were given; maximum blood level reached On the third, at nine-minute intervals doses of 40, 36, 72, , , , and mg were given; maximum blood level was All symptoms subsided after hours. Accidental perivenous administration produced severe pain after hours. Hb'rstensmeyer reported a fatal reaction after i.

Cohen and Bovasso, Jr. Apart from cyanosis of the lips, the only outward symptom was lethargy. After another 14 hours this had dropped to Normal methylene blue treatment for methemoglobinemia proved inadequate, but transfusion corrected the situation. Foussereau et al discussed the rather common skin allergy to Disperse Yellow 3, apparently known for many years. They showed that any impurities present in commercial material were no more allergenic than the dye itself.

Birds and Mammals 1. Chadwick et al reported LD's in mice after i. Grasso et al studied the toxicity of Brown FK in laboratory animals; chronic results are given in the next section. Results of the acute study are in Table 33, on rats and mice, 14 and 7 day observation periods, respectively.

LD's of 1. LD as females, after 48 hours, but after seven days the male value dropped to 0. On autopsy, renal tubular necrosis was found. Gaunt et al pp. In the earlier Gaunt report i. LD's of 0. The Toxic Substances List Edition provided the following compilation of acute toxicities, including the year of publi- cation of their source.

The parenthetical chronologies refer to obser- vation periods. Acid Red 26 LD, mice, i. This treatment resulted in death of the rats in three weeks. The i. LDLo for Trypan Blue in rats, above, corresponds to 60 mg per g rat, an interesting, though not directly comparable, comparison. Davis and Fitzhugh fed male and female rats 0.

There was no effect on growth. Survivors' splenic weight relative increased times in both sexes at the 0. Slight to moderate bone marrow hyperplasia was noted in the 0. Frequency of occurrence of the wide variety of tumors found was not significantly different from that in the controls. Oser et al treated for two years male and female dogs and rats with a diet composed mainly of bread overall nutritionally balanced for each animal which had been made with ppm of azobis- formamide. This level was ten times the proposed use level, about twice the maximally permitted level, and was all that could be incorporated without interfering with the baking process.

There were no adverse effects on the original animals, or on three subsequent generations of rats. Chadwick et al , in an anti-tumor study, gave rats i. Ikeda fed rats 0. Mortality was the same as the control group. All levels produced heavier than normal livers and thyroids from at least the third month. Liver cell adenomas were seen in dead animals as early as 10 months, the incidence increasing with amount of dye fed.

Obvious renal tubular degeneration had occurred by three months at even the 0. By the 15th month all groups including the control showed glomerulo- nephritic and nephrotic changes, also interstitial cell infiltration. Incidence and severity were greater in the dye-fed animals than the controls.

In an in-progress study on feeding the same range of this dye to mice for up to 12 months, liver tumors were found at the 0. Grasso et al did a chronic toxicity study on various laboratory animals of Brown FK and some of its isolated azo components.

Rats and mice were given in their diet for up to 43 days 0. The observed symptoms were, sequentially, growth retardation, heavy weight loss, lethargy, piloerec- tion, hypothermia, difficult breathing, death. Sacrifice of the animals just after weight loss was noticed revealed greyish-white areas in the ventricular myocardium, conjested liver and lungs. Lesions were found in the heart and skeletal muscles. Of the rats given 1. The following tables condense the muscle damage information obtained from stomach tube dosing.

VI I, i! Joscs ,ibov:! JO 90 90 Tor. Tables reprinted with permission from Food Cosmet. Although the 0. The renal tubules were dilated, vacuolated, and pigmented with FK not pigmented at all after oral dosing. It was suggested that, since some animals were unaffected by even the highest doses, there was intraspecies variation in the gut microflora apparently responsible for the metabolizing of the azo linkages. Grasso and Golberg reviewed the rather extensive literature on metabolism and toxicity of Brown FK, using some lessons learned to comment on the nature of the testing procedures for food dye toxicity.

There was no effect on weight gain. Urine and serum chemical analyses were normal. Relative internal organ weights were also considered normal. Grasso et al fed male and female rats 0. The 0. Examination of food eaten at consecu- tive three-month intervals showed decreases by females only over the three intervals covering weeks at the 0.

The animals didn't care for the taste of the dye even at the 0. Hematology revealed decreases in hemoglobin in males by week 14 at the 0. By week 61 males were showing lower hemoglobin at 0. At week 79 only hemoglobin was low at the highest level in both sexes, except that males showed a higher total leukocyte count at 0.

At week hemoglobin was low in both sexes at 0. Chemical analysis of the blood was normal after two years. Urine analysis showed higher ascorbic acid after one year at 0. Relative internal organ weights after two years showed increases in the brain of both sexes at 0. Incidence and severity of pathological hepatic changes were directly related to dose level, but there was nothing to suggest carcinogenicity. There was no effect on body weight. Relative internal organ weights were normal.

Gafford et al gave male rats daily i. The deaths were preceeded by days of bloody urine. Between 60 and days weight began to lag behind the controls, but the absolute difference didn't in- crease between and days. Apparently there was considerable mortality in the dosed animals, but inconsistencies in the paper obscured the results. Shtenberg and Gavrilenko fed male and pregnant female rats a daily dose of 1.

The 1. Collins et al gave pregnant rats 7. They found no change in the number of corpora lutea, nor any adverse effect on implantation. Weight of live young was not affected. Percentage of resorptions increased with dose. Skeletal and soft-tissue abnormalities were not dose related. The Toxic Substances List Edition provided the follow- ing compilation of chronic toxicities; see the last entry under Section X.

I, for elaboration of terms. In column 2, the higher the number the higher the carcinogenicity in rats not necessarily the same in the guinea pigs used here. The cross-reaction test was run at the same time as the confirmation of sensitivity test; it indicated that an animal sensitized by one of the azo compounds was likely to be sensitized by all. The desired correlation was not achieved. Us in cjieh experiment. Vickerstaff, , from The Physical Chemistry of Dyeing: "It is virtually impossible to synthesize a pure disazo dye and only slightly easier to purify a given sample.

Hamburgh injected female mice with about 1. The experiment was repeated, but the mice were sacrificed days after fertilization. The latter probably resulted in failure to survive to term. Waddington and Carter injected female mice in the seventh day of fertilization with 5 mg of trypan blue. Mortality embryo rose sharply on the llth day of gestation. Abnormalities were notably high one day after injection, but decreased sharply on the llth day.

Of the full term animals, litter size was half the normal and males predominated. Head and tail abnormalities predominated. Hamburgh reported on a follow-up study in which pregnant mice were injected with 5 mg of Trypan Blue on the 7th day of gestation, and then sacrificed on the days of gestation. The chronology of the malformations is presented in Table AD MnI? Wilson gave s. On the 20th day all were sacrificed. Copyright by" Wistar Institute Press. Table 40 breaks down the malformations according to most frequent type.

In the last column of this table, "other" consisted of gastroschisis, short snout, and clubfoot, about equally. Ocular effects included monolateral usually anopthalmia, microphthalmia, and retinal coloboma. Cataract of the lens was also seen, and deemed to be degenerative rather than developmental in nature; its incidence was not known as few animals were examined for it.

Cardiovascular effects were decreasingly : aortal-pulmonary trunk transposition, aortal right-sided arch, aortal double arch, absence of ductus arterio- sus, and trunkus arteriosus communis. Vertebral colunnar effects were rudimentary-absent lumbar, sacral and caudal vertebrae, absence of entire sacrum, medially displaced ilia.

There was no evidence for the dyes having crossed the placenta. This, together with the occurrence in the same litter of normal appearing inside and out embryos at term, did not allow for even an intelligent guess as to the reason for the malformations. Langman and van Drunen injected s. The uterus was excised on the 28th day of gestation. Serum proteins were analyzed at pre- and post- fertilization intervals.

Table 41 contains the overall teratogenic statistics. Malformations were found in the spine, tail none , gut eventrated , and brain hydrocephalus. The eyes were normal. Control rabbits showed a decrease in total serum protein and albumin during gestation, but dye-dosed ones showed an increase in both, especially during the first 14 days, followed by a decrease to non-pregnant levels.

Embryos were sacrificed on 10th day. The same was done using trypan blue at hours of incubation to test the time span effectiveness of the teratogenicity. The dyes tested in the first study and results are given in Tables 43 and Congo red Saline controls. Untreated controls. Evans blue Niagara blue 4B Niagara blue 28 Azo b!

Eiabryol Exptl. Copy- right by Cambridge University Press. The eye defects were anophthalmia and microphthalmia; beak defects were cross-beak and small beak. The separate trypan blue study indicated insignificant mortality after 48 hours from eubgerminal, and 72 hours Percentage of malformed survivors was unaf- fected after 72 hours from subgerminal or yolk sac injection.

The percentage of malformations regardless of survival peaked at 36 hours after yolk sac, and at hours after subgerminal injection. Beck obtained three commercial samples of trypan blue and made up solutions of each, 0. Pregnant rats were given s. One of the samples of trypan blue failed to produce any abnormalities, and caused a statistically insignificant increase in percentage of resorptions.

The other two samples produced resorptions and abnormalities typical for this rat strain, but in differing amounts. An attempt to see if there was a difference in toxicity between the samples by determining the LD values on non-pregnant females somewhat equivocally indicated that the non-teratogenic sample was also less toxic than the one of the others which was used for comparison.

The litters were sacrificed or. There wasn't any pattern during this time span to the reduced weight and reduced crown- rump length seen. Resorptions were highest when the dose was given on day 12 or 13, next highest on day 7. Gross malformations were highest when the dose was given on day 11, day 9 being next. Kn: malformation of knee joint, Pd: polydactyly of tee. J of survived.

Table IS- Effects of 4'-methy! H13 1 Cp, 2 Dt. Olu 1 Ct. Dt: deviation of toe or finger, Kn: malformation of knee joint. Pd: polydactyly of tee. IDt, 1HI. IPd 2An. IKn, IPd! An: malformation of ankle joint, Cp: clef palate, Dt: deviation of toe or finger. HI: harelip, Kn: malformation of knee joint, Md: macrodnctyly of tee, Pd: polydactyly of toe, St: short tail. Table fl- Comparison of teratogenicity between the fetuses treated by various derivatives on the 10th to llth day Denvat- 3'-tnftuoro ' ives tre-' methyl- 1-d ated imethylam inonzoben.

Table tfc. Occurrence of malformed ribs in the offspring of control mice tr- eated with peanut oil Liay 01 injection No. Table fcl Classification of fetuses according to No. Classification of fetuaes according to No. Table "ft No, of fetuses with not ossified 13th rib in mice treated with rronometbylamino- azobenzene ro. Table 1i 0, No. Table n. Classification of fetuses according.

Half gram units of the as-received dye were made up to 50 ml in 0. No attempt was made to adiust the whole, blue, or red solutions from the various suppliers to the same "concen- tration. They were sacrificed on day Resorption and malformation statistics are given in Table The malformed fetuses showed reduced body size, edema, exencephaly, spina bifida, but rare caudal defects. Rats were given s.

Variations of treatment involved sacrifice of Niagara blue 4B-treated rats at A number of male rats were given s. TABLI-; S 10X AnoiiiiiliMis individuals No. Table 9i Teratogcnic response to four bisazo dyes injected subcutdneously at days of pregnancy No. Niagara blue 28 Afridol blue Tryp. Trypan blue Fig. The results of killing the mothers at Autopsy samples of the maternal macrophage system, kidneys, placenta, and yolk sac were examined for the presence of the injected dye. Table 94 presents dose-comparable literature results on some highly relevant compounds.

Table 95 presents the five compounds most closely related to trypan blue structurally, and results. Table 96 presents the tissue distribution of the compounds whose structures were given. The authors disclaimed Compound 1 as a teratogen, and were reluctant to so label Compound 8, pending further study. Effects of synthesized disazo compounds on rat gesl. HO OH M. From the PEG injection all of the surviving chicks had shortened leg bones, and half had deformed feathers.

Stein et al injected 10 ug of Janus green B into the amniotic fluid of incubated eggs at the 29 Hamburger-Hamilton stage. All of the survivors exhibited syndactylism. Reports dealing with anti-cancer testing of azo compounds, and any metabolic-physiologic information contained therein have been incorporated into this carcinogenic reports section. Seligman et al found that growth of sarcoma 37 in mice and Walker carcinoma in rats was inhibited by l-methyl phenylazo naph- thalene and l,4-dimethyl phenylazo naphthalene.

Sarcoma 37, only, was inhibited by 3-phenylazophenanthrene, 2,2',5,5'- and 3,4,4',5- tetramethoxyazobenzene. Walker carcinoma, only, was inhibited by 3-phenylazoacenaphthene, 3,3'-dimethylazobenzene, and 3,3',4,4',5,5'- hexamethoxyazobenzene.

Simpson gave rats s. Of those given 14 doses in days and surviving days, 3 of 5 had tumors. Miller et al fed rats 4-dimethylaminoazobenzene DAB with 1, 2, or 3 fluoro groups in the non-amino benzene ring for comparison oT carcinogenicity with DAB itself. Also tested, ai. Group 6. TABLE 9? CMIf O. OOi 0. Series V was an attempt to determine the carcinogenicity of a possible metabolite of the fluoro groups, fluoroacetate, but it was too toxic to be given at the maximum potential level; it didn't show any carcinogenicity at the maximum level tolerable to the rats.

The same dose of DAB produced no tumors in six dogs in 63 months.

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