• Bulletin of the Korean Chemical Society
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• 제29권5호
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• pp.948-952
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• 2008

The molecular association of acceptors with electron donors is studied in the highly-polar solvent $CH_3CN$. Tetracyanoquinodimethane (TCNQ) forms a stable charge-transfer complex with donor molecules such as 4- aminobiphenyl (4-AB), benzidine (BD) and 2-aminobiphenyl (2-AB) with high association constants. The complexes of TCNQ with 4-AB or BD show new absorption bands at around 800 and 500 nm, which can be identified as reduced $TCNQ^{{\bullet}-}$ and $TCNQ^{2-}$ species, respectively. These bands grow quickly upon photoirradiation, implying that the charge-transfer complexes are easily formed in an excited state. Conversely, a small spectral manifestation of the charge transfer was observed in the case of 2-AB complex. It is demonstrated that the structural orientation between the geminate ion pairs could play an important role in building a stable complex.

• Toxicological Research
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• 제33권4호
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• pp.265-272
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• 2017

Aryl hydrocarbons such as 3-nitrobenzanthrone (NBA), 4-aminobiphenyl (ABP), acetylaminofluorene (AAF), benzo(a)pyrene (BaP), and 1-nitropyrene (NP) form bulky DNA adducts when absorbed by mammalian cells. These chemicals are metabolically activated to reactive forms in mammalian cells and preferentially get attached covalently to the $N^2$ or C8 positions of guanine or the $N^6$ position of adenine. The proportion of $N^2$ and C8 guanine adducts in DNA differs among chemicals. Although these adducts block DNA replication, cells have a mechanism allowing to continue replication by bypassing these adducts: translesion DNA synthesis (TLS). TLS is performed by translesion DNA polymerases-Pol ${\eta}$, ${\kappa}$, ${\iota}$, and ${\zeta}$ and Rev1-in an error-free or error-prone manner. Regarding the NBA adducts, namely, 2-(2'-deoxyguanosin-$N^2$-yl)-3-aminobenzanthrone (dG-$N^2$-ABA) and N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone (dG-C8-ABA), dG-$N^2$-ABA is produced more often than dG-C8-ABA, whereas dG-C8-ABA blocks DNA replication more strongly than dG-$N^2$-ABA. dG-$N^2$-ABA allows for a less error-prone bypass than dG-C8-ABA does. Pol ${\eta}$ and ${\kappa}$ are stronger contributors to TLS over dG-C8-ABA, and Pol ${\kappa}$ bypasses dG-C8-ABA in an error-prone manner. TLS efficiency and error-proneness are affected by the sequences surrounding the adduct, as demonstrated in our previous study on an ABP adduct, N-(2'-deoxyguanosine-8-yl)-4-aminobiphenyl (dG-C8-ABP). Elucidation of the general mechanisms determining efficiency, error-proneness, and the polymerases involved in TLS over various adducts is the next step in the research on TLS. These TLS studies will clarify the mechanisms underlying aryl hydrocarbon mutagenesis and carcinogenesis in more detail.

• 대한예방의학회:학술대회논문집
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• 대한예방의학회 2000년도 제52차 추계학술대회 연제집
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• pp.314-315
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• 2000

• Toxicological Research
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• 제31권1호
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• pp.41-48
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• 2015

Owing to the increase in price of cigarettes in Korea, herbal cigarettes have received increasing attention as a non-smoking aid; however, its safety has hardly been studied. We analyzed some of the toxic components in the mainstream smoke of herbal cigarettes, performed a mutagenicity test on smoke condensates for safety assessment, and compared the results with the corresponding values of a general cigarette with the same tar content. Herbal cigarette "A" was smoked using automatic smoking machine under ISO conditions in a manner similar to general cigarette "T". The tar content measured was higher than that inscribed on the outside of a package. The mainstream smoke of herbal cigarette "A" did not contain detectable levels of tobacco-specific nitrosamines and nicotine. Carbon monoxide and benzo(${\alpha}$)pyrene contents in herbal cigarette "A" were higher than those in the general cigarette "T". The phenolic contents such as hydroquinone, resorcinol, and catechol in herbal cigarette "A" were higher than those in the general cigarette "T", but cresol contents in herbal cigarette "A" were lower than those in the general cigarette "T". The content of aromatic amines such as 4-aminobiphenyl in herbal cigarette "A" was higher than that in the general cigarette "T"; however, this difference was not statistically significant. On the other hand, 1-aminonaphthalene, 2-aminonaphthalene, and 3-aminobiphenyl contents in herbal cigarette "A" were lower than those in the general cigarette "T". The smoke condensates of herbal cigarette "A" exhibited a higher mutagenic potential than the condensates from the general cigarette "T" at the same concentration. We concluded that the mainstream smoke of herbal cigarette contains some toxic components, the smoke condensates of herbal cigarettes are mutagenic similar to general cigarette because of combustion products, and that the evaluation of the chemical and biological safety of all types of herbal cigarettes available on the market.

• Toxicological Research
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• 제6권1호
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• pp.63-73
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• 1990

Human exposure to environmental carcinogens can be detected by a number of methods including immunoassay, $^{32}P-postlabeling$ assay, and fluorescence technique. These assays have been applied to measure biological markers of carcinogen-adducts formed with macromolecules such as DNA, RNA and protein. In an attempt to investigate causal relationships between carcinogen exposure and tumor formation, specific carcinogen-adducts have been quantitated from human tissues and body fluids of cancer patients, occupational workers heavily exposed to certain carcinogens, smokers and controls. Carcinogens studied for biological human monitoring include benzo(a)pyrene, aflatoxin B1, UV light, ethylene oxide, 8-methoxypsoralen, 4-aminobiphenyl, vinyl choride, N-nitrosamine, cisplatin and other chemotherapeutic agents. Relevance of human monitoring for cancer research, progress in this field, methods to detect carcinogen-adducts are reviewed here. It is hoped that these approaches will be used for the risk assessment of carcinogen exposure, cancer etiology study and cancer prevention in humans.

• Toxicological Research
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• 제6권1호
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• pp.61-61
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• 1990

Human exposure to environmental carcinogens can be detected by a number of methods including immunoassay, $^{32}P$-postlabeling assay, and fluorescence technique. These assays have been applied to measure biological markers of carcinogen-adducts formed with macromolecules such as DNA, RNA and protein. In an attempt to investigate causal relation ships between carcinogen exposure and tumor formation, specific carcinogen-adducts have been quantitated from human tissues and body fluids of cancer patients, occupational workers heavily exposed to certain carcinogens, smokers and controls. Carcinogens studied for biological human monitoring include benzo(a)pyrene, aflatoxin B1, UV light, ethylene oxide, 8-methoxypsoralen, 4-aminobiphenyl, vinyl chloride, N-nitrosamine, cisplatin and other chemotherapeutic agents. Relevance of human monitoring for cancer research, progress in this field, methods to detect carcinogen-adducts are reviewed here. It is hoped that these approaches will be used for the risk assessment of carcinogen exposure, cancer etiology study and cancer prevention in humans.

• Journal of Preventive Medicine and Public Health
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• 제35권3호
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• pp.229-235
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• 2002

Objectives : To evaluate the effects on the formation of benzidine-hemoglobin, and benzidine metabolite-hemoglobin adducts, caused by pretreatment with the known xenobiotic metabolism effectors, ethanol and phenobarbital, in rats administered Direct Black 38 dye. Methods : The experimental rats were divided into three groups: a control group, an ethanol group and a phenobarbital group. Rats were pretreated with ethanol (1g/kg) or phenobarbital (80mg/kg) 24 hours prior to the oral administration of Direct Black 38 (0.5mmol/kg), with the control group being administered the same amount of distilled water. Blood samples were obtained from the vena cava of 5 rats from each group prior to, and at 30 min, 3h, 5h, 9h, 12h, 24h, 48h, 72h, 96h, and 144h following the oral administration of Direct Black 38. Directly after sampling the blood was separated into hemoglobin and plasma, with the adducts being converted into aromatic amines by basic hydrolysis. Hydrolyzed benzidiene, monoacetylbenzidine and 4-aminobiphenyl were analyzed by reverse-phase liquid chromatography with an electrochemical detector, The quantitative amount of the metabolites was expressed by the hemoglobin binding index (HBI). Results : In the ethanol group, benzidine-, monoacetylbenzidine-, and 4-aminobiphenyl-HBI were increased to a greater extent than those in the control group. These results were attributed to the ethanol inducing N-hydrgxylation, which is related to the formation of the hemoglobin adduct, In the phenobarbital group, all the HBIs, with the exception of the benzidine-HBI, were increased to a greater extent than those of the control group. These results were attributed to the phenobarbital inducing N-hydroxylation related to the formation of the hemoglobin adduct. The N-acetylation ratio was only increased with the phenobarbital pretreatment due to the lower benzidine-HBI of the phenobarbital group compared to these of the control and ethanol groups. The N-acetylation ratios for all groups were higher than f for the duration of the experimental period. Although the azo reduction was unaffected by the ethanol, it was inhibited by the phenobarbital, The ratio of the benzidine-HBI in the phenobarbital group was lower than those of the ethanol the control groups for the entire experiment. Conclusion : Our results indicate that both ethanol and phenobarbital increase the formation of adducts by the induction of N-hydroxylation, but also induced N-acetylation. Phenobarbital decreased the formation of benzidine-HBI due to the decrease of the azo reduction. These results suggest that the effects or ethanol and phenobarbital need to be considered in the biochemical monitoring of Direct Black 38.

• 한국연초학회지
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• 제28권2호
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• pp.152-157
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• 2006

A new procedure has been developed for the quantitation of aromatic amines in mainstream cigarette smoke. Two solid-phase extraction (SPE) clean up steps, using a different retention mechanisms, are required to process the samples. The first step used a cation-exchange cartridge, followed by a second step that used a cartridge with a hydrophobic retention character. The aromatic amines eluted from the second SPE cartridge are derivatized with pentafluoropropionic anhydride. This new method have advantages over other reported techniques, being sensitive, robust, and easily automated. The detection limits were ranged from 0.12 ng/mL for 1-aminonaphthalene to 0.16 ng/mL for 3-aminobiphenyl and the recoveries were from 97 to 106%. Compared with other reports for analysis of 2R4F reference cigarette, this method shows a close analytical data and good repeatability.

• 한국식품영양과학회지
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• 제24권6호
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• pp.880-886
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• 1995

감잎 열수 추출물 및 감잎 탄닌의 항돌연변이 효과를 Ames test, spore rec assay 및 SOS chromotest 방법을 이용하여 검토하엿다. Salmonella typhimurium TA100에서 aflatoxin $B_{1}(AFB_{1})$, dimethyl-amino-biphenyl(DMAB)와 같은 간접 돌연변이워에 대해서 뿐만아니라 N-methyl-N'-nitro-N-nitrosoguanidine(MNNG), 4-nitroquinoline-1-oxide(4-NQO)와 같은 직접 돌연변이원에 대해서도 강력한 항돌연변이성을 관찰할 수 있었다. Bacillus subtilis H17($rec^{+}$)와 M45($rec^{-$)를 사용한 spore rec assay에서도 감잎 탄닌은 MNNG에 대한 강한 항돌연변이 효과를 나타내었고, Escherichia coli PQ37을 사용한 SOS chromotest에서도 4-NQO의 돌연변이성이 크게 저해되었다. 또한 감잎차 부터 탄닌을 추출하여 이미 그 효과가 알려진 녹차 탄닌과 함께 항돌연변이 효과를 살펴본 결과 시료의 농도에 비례해서 녹차탄니과 비슷한 수준으로 현저한 항돌연변이 효과를 나타내었다. 이들 항돌연변이 실험계에서 감잎 탄닌이 감잎 열수 추출물에 비해 활성이 크게 나타났다.

• 한국산업보건학회지
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• 제6권1호
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• pp.156-164
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• 1996

Benzidine is recognized as a urinary bladder carcinogen in humans. The use of benzidine in industries was prohibited because of its carcinogenecity, but, production and usage of benzidine-based dye was still permitted in most countries. This study was performed to compare the excretory patterns of urinary metabolites between benzidine-based dye(Direct Black 38) and benzidine in rats Benzidine-based dye was administered orally at the doses of 0.3, 0.5, 0.7 mmol/kg and benzidine was administered orally at the doses of 0.2, 0.4, 0.6 mmol/kg into Sprague-Dawley rats. To analyze benzidine and its metabolites, the high performance liquid chromatography with an electric chemical and ultraviolet detector were used. N-acetylbenzidine, N,N'-diacetylbenzidine and 4-aminobiphenyl were identified in the urine of the rats receiving dye and benzidine. The excreted amount of the urinary benzidine from dye was almost 1/10 of that from benzidine. Excretion rates of metabolites were more prolonged in the dye receiving group than those of the benzidine group. Peak concentration time of urinary N,N'-diacetylbenzidine was more prolonged than other metabolites in both groups. The excreted amount of N-acetylbenzidine was more than the others in both group. These results suggested that N-acetylbenzidine may be an useful Biological exposure index for benzidine-based dye.