phenanthrenes and Papilloma

Topics: Animals; Carcinogens; Carcinoma, Squamous Cell; Chemical Phenomena; Chemistry; Hydrocarbons; Ketones; Methylcholanthrene; Mice; Neoplasms, Experimental; Papilloma; Phenanthrenes; Sarcoma, Experimental; Skin Neoplasms; Steroids

Fibropapillomatosis (FP) poses a significant threat to the conservation of green sea turtles (Chelonia mydas). Polycyclic aromatic hydrocarbons-PAHs are considered mutagenic, carcinogenic and toxic, and can act as cofactor of this disease. In order to evaluate possible differences between green sea turtles with and without FP, we monitored 15 PAHs in liver samples of 44 specimens (24 with FP) captured in Brazil. We detected eight PAHs and quantified phenanthrene in all green sea turtles with FP. Specimens without FP presented lower values than the tumored ones (1.48 ng g

Topics: Animals; Brazil; Case-Control Studies; Liver; Papilloma; Phenanthrenes; Polycyclic Aromatic Hydrocarbons; Turtles

Natural resin acids present in rosin of Pinus spez., including isopimaric acid (1), mercusic acid (2), neoabietic acid (3), dehydroabietic acid (4), and podocarpic acid (8), as well as resin acid derivatives 8β,9α,13α-H-tetrahydroabietic acid (5), 8α,9α,13α-H-tetrahydroabietic acid (6), 13α-H-Δ(8)-dihydroabietic acid (7), maleopimaric acid (9), and fumaropimaric acid (10), were studied for their possible inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Compounds 1, 3, 4, 7, and 10 (IC(50): 352, 330, 311, 340, and 349, respectively) exhibited strong inhibitory effects compared to the other compounds. Among these, 1, 4, and 7 were selected to examine their effects on in vivo two-stage mouse skin carcinogenesis induced by 7,12-dimethylbenz[a]anthracene (DMBA) as initiator and TPA as promoter. Treatment with compounds 4 and 7 (85 nmol) along with DMBA/TPA inhibited papilloma formation up to week 8 and the percentage of papilloma bearers in these two groups was approximately 80% at week 20. The average number of papillomas formed per mouse was 4.4 and 4.2 even at week 20 (p>0.05). Compounds 4 and 7 exhibited high activity in the in vivo anti-tumor-promoting test. In addition, rosin was examined in vivo for its chemopreventive effect. Treatment with rosin (50 μmol) along with DMBA (100 μg)/TPA (1 μg) inhibited papilloma formation up to week 8 and the percentage of papilloma bearers in this group was less than 80% at week 20. The average number of papillomas formed per mouse in the rosin-treated group was 3.8 even at week 20 (p>0.05). The in vivo two-stage mouse skin carcinogenesis test revealed that rosin possessed a pronounced anticarcinogenetic effect, and its high activity is due to the synergism of the diterpenes contained in it.

Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Anticarcinogenic Agents; Antigens, Viral; Carboxylic Acids; Carcinogenicity Tests; Drug Screening Assays, Antitumor; Humans; Mice; Mice, Inbred ICR; Papilloma; Phenanthrenes; Pinus; Resins, Plant; Skin Neoplasms; Tetradecanoylphorbol Acetate

Salvia miltiorrhiza is a traditional Chinese medicine which has been well documented for its anti-cancer effects. Based on the structure of danshinone, one of the active compounds derived from Salvia miltiorrhiza, we synthesized a simplified phenolic analog, S-3-1, and tried to explore its possible actions in preventing the development of cancer. With the Ames test, S-3-1 was found to efficiently suppress the mutagenicity of benzo[alpha]pyrene. This result is consistent with the inhibitory effect of S-3-1 on the activation of benzo[alpha]pyrene by hepatic microsomal enzymes. Besides the anti-initiation effects, S-3-1 could significantly inhibit the croton oil-induced increase of mouse skin epithermal ornithine decarboxylase activity. Moreover, S-3-1 quenched both superoxide and hydroxyl free radicals whereas it inhibited lipid peroxidation in the in vitro model. These results suggest that S-3-1 might act as anti-initiation and anti-promotion agents through reversing the biochemical alterations induced by carcinogen during carcinogenesis. Therefore, we further investigated the effects of S-3-1 on carcinogenesis. In vitro, S-3-1 inhibited the benzo[alpha]pyrene-induced transformation of V79 Chinese hamster lung fibroblasts. At 10-40 mg/kg, S-3-1 was found to inhibit the development of DMBA/croton oil-induced skin papilloma in mice through decreasing the incidence of papilloma, prolonging the latent period of tumor occurrence and reducing tumor number per mouse in a dose-dependent manner. We concluded from this study that S-3-1 might be developed as a new chemopreventive drug.

Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Anticarcinogenic Agents; Benzo(a)pyrene; Benzofurans; Bepridil; Biphenyl Compounds; Cell Transformation, Neoplastic; Cells, Cultured; Cricetinae; Croton Oil; Cysteine; Disease Models, Animal; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Epithelial Cells; Fibroblasts; Free Radical Scavengers; Hypoxanthine; In Vitro Techniques; Iron; Lipid Peroxidation; Lung; Male; Medicine, Chinese Traditional; Mice; Mice, Inbred ICR; Microsomes, Liver; Molecular Structure; Mutagens; Ornithine; Ornithine Decarboxylase; Papilloma; Pentetic Acid; Phenanthrenes; Picrates; Plants, Medicinal; Rats; Salmonella; Skin; Skin Neoplasms; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; Xanthine Oxidase

The histopathogenesis of rat forestomach carcinoma induced experimentally with aristolochic acid was investigated. The intragastric administration of 10 mg/kg/day caused extensive necrosis of the squamous epithelium, followed by regeneration and hyperplasia, papilloma formation and ultimately by invasive squamous cell carcinoma.

Topics: Animals; Antineoplastic Agents; Aristolochic Acids; Hyperplasia; Male; Neoplasms, Experimental; Papilloma; Phenanthrenes; Rats; Rats, Inbred Strains; Stomach; Stomach Neoplasms

The major dihydrodiols formed from 5-methylchrysene by rat liver 9000 X g supernatant were tested for tumor-initiating activity on mouse skin. The compounds tested were 1,2-dihydro-1,2-dihydroxy-5-methylchrysene, 7,8-dihydro-7,8-dihydroxy-5-methylchrysene, 9,10-dihydro-9,10-dihydroxy-5-methylchrysene, and 5-methylchrysene. Each compound was applied in a total initiating dose of 30 microgram and was followed by promotion with tetradecanoylphorbol acetate. 1,2-Dihydro-1,2-dihydroxy-5-methylchrysene was the most powerful tumor initiator, inducing tumors in 95% of the animals and 7.3 tumors per animal. 5-Methylchrysene and 7,8-dihydro-7,8-dihydroxy-5-methylchrysene induced tumors in 75 and 50% of the animals and gave 3.0 and 1.1 tumors per animal, respectively. 9,10-Dihydro-9,10-dihydroxy-5-methylchrysene was not tumorigenic. The results indicate that 1,2-dihydro-1,2-dihydroxy-5-methylchrysene is a major proximate carcinogen of 5-methylchrysene. Both 1,2-dihydro-1,2-dihydroxy-5-methylchrysene and 7,8-dihydro-7,8-dihydroxy-5-methylchrysene can theoretically form bay-region dihydrodiol epoxides, but the former was more tumorigenic than the latter. The high activity of 1,2-dihydro-1,2-dihydroxy-5-methylchrysene is typical of hydrocarbon derivatives with a methyl group in the bay region adjacent to an unsubstituted angular ring.

Topics: Animals; Biotransformation; Carcinogens; Carcinoma; Chrysenes; Dose-Response Relationship, Drug; Female; Mice; Neoplasms, Experimental; Papilloma; Phenanthrenes; Skin Neoplasms; Structure-Activity Relationship

5,6-Dihydro-5-oxo-7,12-dimethylbenz(a)anthracene and 5,6-dihydro-6-oxo-7,12-dimethylbenz(a)anthracene are described. These compounds, which are isomeric with 7,12-dimethylbenz(a)anthracene-5,6-oxide (the K-region epoxide), were inactive in tests for tumor-initiating activity in mouse skin and tumor production in the s.c. tissue of the mouse.

Topics: Animals; Benz(a)Anthracenes; Carcinogens; Chemical Phenomena; Chemistry; Chromatography; Embryo, Mammalian; Isomerism; Ketones; Male; Mice; Mice, Inbred C57BL; Mice, Inbred Strains; Neoplasms, Experimental; Papilloma; Phenanthrenes; Spectrum Analysis

Topics: Administration, Oral; Administration, Topical; Animals; Female; Liver Neoplasms; Lung Neoplasms; Lymphoma; Male; Mice; Mice, Inbred Strains; Neoplasm Metastasis; Neoplasms, Experimental; Papilloma; Phenanthrenes; Sex Factors; Skin Neoplasms

Topics: Acids; Alkylating Agents; Animals; Biological Assay; Carcinogens; Carcinoma; Chemical Phenomena; Chemistry; Chromatography; Chromatography, Gas; Esters; Female; Fluorenes; Hydrocarbons; Hydrocarbons, Halogenated; Hydrogen-Ion Concentration; Insecticides; Mice; Neoplasms, Experimental; Nicotiana; Nicotine; Papilloma; Phenanthrenes; Plant Extracts; Plants, Toxic; Quinones; Skin Neoplasms; Smoke; Tars; Terpenes

Topics: Animals; Carcinogens; Carcinoma, Squamous Cell; Cyclopentanes; Neoplasms, Experimental; Papilloma; Phenanthrenes; Sarcoma, Experimental

Topics: Benzo(a)pyrene; Benzopyrenes; Croton Oil; Papilloma; Phenanthrenes