Crystalline aminoazobenzene tyrosine compound was prepared by hydrolyzing aminoazobenzene dye bound silk fibroin, which was prepared through the Mannich reaction. The chemical structure of the synthetic polar dye thus obtained has been investigated from the UV and IR absorption spectra, elementary analysis, reaction with nitrous acid as well as with Folin-Ciocalteau′s reagent. The unimolecular combination between the 4-position amino group of aminoazobenzene and one of the ortho position of tyrosine through a methylene bridge has been assumed.

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1. The method of isolation and purification of the amino acid bound aminoazobenzene dye (polar dye) from rats liver fed DAB was improved and highly purified preparations having different absorption maxima have been obtained: 514 and 522mμ.
2. Several properties such as optical absorption spectra, Rf, electrophoretic mobility, stability against acid, reaction with nitrous acid, methylation, pH-color dependence, etc. of the natural polar dyes were investigated in comparison with those of non-polar aminoazo dyes as well as the synthetic polar dyes having amino acid substitution at the position 4 amino group.
3. The chemical structure of the natural polar dyes have been assumed tentatively as follows: a substituent containing tyrosine residue is located at the position 3 of aminoazo dye moiety, and the amino group at the position 4 is either primary or secondary, but not tertiary.

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1. The time course change in the amounts of protein bound dyes after 50mg of DAB, MAB, AB or AAT administeration directly into rats′ stomachs was investigated and compared.
2. The protein bound dyes reached its maximum amount in about three days and gradually decreased after that. The maximum amount of protein bound dye was in the order: DAB>MAB>AB.
3. The polar dyes obtained from the DAB and MAB administrations consisted of two types of dyes: one having the secondary amino group (major part) and another having the primary amino group (minor part), while in the polar dye resulting from the AB administration only the presence of primary amino polar dye was shown.
4. The dye binding capacity of the rat liver reaches its maximum in three days after 50mg of DAB has been administered. Further administration of DAB does not seem to increase the dye binding.
5. C₁ compounds, probably formaldehyde, which can be produced in the oxidative metabolism of N-methyl groups of DAB and MAB as well as in the course of the basal liver metabolism was considered to play an important role in the binding between aminoazo dyes and certain liver proteins.

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1. Accumulation of the protein bound dye in the liver of rats fed AAT (orthoaminoazobenzene) has been investigated.
2. Preliminary investigations have revealed that the polar dye from the rat liver fed AAT has some different chemical characteristic from the DAB polar dyes, especially in the stability against the acid treatment.

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1. The production of thiobarbituric acid (TBA) reacting substances (lipid peroxides) was examined in normal rat liver, liver of fibrosarcoma-bearing rat, rat primary hepatoma, and transplanted fibrosarcoma.
2. The capability of such peroxide formation is considerably decreased in livers of tumor-bearing animal, and almost disappeared in tumor tissues.
3. Peroxide formation is accelerated by ascorbic acid and completely inhibited by EDTA. In the presence of EDTA, activating effect of ascorbic acid is no longer observed. This reduced activity by EDTA can be restored only by the addition of zinc.
4. Zinc is the only metal which participates by itself in such peroxide formation, although iron appears to accelerate this reaction in combination with some unknown factor when added to intact homogenates.

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1. Tryptophan peroxidase level and its activity after the injection of tryptophan or histidine were examined in the liver of tumor-bearing mice and hepatic carcinogen fed rats.
2. Tryptophan peroxidase in the liver of tumor-bearing mice increased significantly in its activity, while the catalase activity of the liver was depressed markedly.
3. The adaptive increment of tryptophan peroxidase at 5 hours after the injection of tryptophan was less in tumor-bearing animals than in normal ones.
4. The adaptive increment of tryptophan peroxidase induced by tryptophan injection completed within the period of first 1 hour in tumor-bearing mice, while it was completed at about 5 hours in normal ones. The histidine-induced adaptation occured simultaneously in both tumor-bearing and normal mice.
5. No remarkable changes were found in both the activity of tryptophan peroxidase and the ability to induce the increase of the enzyme between the mice fed hepatic carcinogen and the normal ones.
6. The reduction in the activity of tryptophan peroxidase was significant when the liver was cirrhotic. While the activity was negligible in the liver cancer.
7. The activity of tryptophan peroxidase during the adaptation in the cirrhotic liver retained at the normal degree.
8. The activity of tryptophan peroxidase in liver cancer increased significantly after the injection of tryptophan or histidine.

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1. The effects of allyl-substituted compounds have been tested against a spectrum of 15 tumors of the mouse.
2. Among the series of 85 allyl-substituted compounds tested, 2-allylimino-1, 3, 4-thiadiazoline hydrochloride showed the most anti-tumor activity. At daily doses of 100mg/kg it had a moderate inhibitory effect on Miyono adenocarcinoma, Carcinoma 1025, Wagner and Ridgway osteogenic sarcomas, Gardner lymphosarcoma, and Harding-Passey melanoma. and a slight inhibitory effect on Sarcoma 180, Sarcoma MA 387, Ehrlich carcinoma, Bashford carcinoma 63, Adenocarcinoma E0771, Lewis bladder carcinoma, Lewis lung carcinoma, and Glioma 26.
3. N-Allyl-p-toluene sulfonamide, p-allylaminoazobenzene, and 4-allylthiosemicarbazide had a moderate inhibitory effect on Sarcoma 180; allylguaiacyl ether had a moderate inhibitory effect on Bashford carcinoma 63; 6-allyl-o-aminophenol•HCl had a moderate inhibitory effect on Carcinoma 1025; 4-allylaminophenylacetonitrile and N, N′-diallyl-o-tolidine had a moderate inhibitory effect on Ridgway osteogenic sarcoma; and 2-(γ-chloroallylimino)-1, 3, 4-thiadiazoline had a moderate inhibitory effect on Harding-Passey melanoma.

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The substitution reaction between the nitro-group of various quinoline derivatives with SH-group was investigated under physiological conditions in vitro, and a definite relation was shown to exist between the carcinogenic action and reactivity of the nitro-group of these nitroquinoline N-oxides.
It was also shown that no reaction took place between 4-nitroquinoline N-oxide and amino acids, nucleotides as well as nucleic acid under the same experimental conditions, under which the nitro-group of this quinoline N-oxide so readily reacted with SH-group.

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