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РЖ ВИНИТИ 76 (BI28) 97.03-04Н3.116

The essential role of the functional group in alkyl isothiocyanates for inhibition of tobacco nitrosamine-induced lung tumorigenesis [Text] / Ding Jiao [et al.] // Carcinogenesis. - 1996. - Vol. 17, N 4. - P755-759 . - ISSN 0143-3334
Перевод заглавия: Существенная роль функциональных групп в алкилизотиоцианатах для ингибирования индуцированных нитрозаминами табака опухолей легкого
Аннотация: The importance of the isothiocyanate group in alkyl isothiocyanate for inhibition of tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis was examined in A/J mice. The previous structure-activity relationship study of isothiocyanates showed that 1-dodecyl isothiocyanate [CH[3](CH[2])[11]NCS], a simple alkyl isothiocyanate, is a potent inhibitor of NNK-induced lung tumorigenesis. It was chosen for this study due to its structural features and potency. A single dose of 1-dodecyl isothiocyanate given by gavage at 1 'мю'mol/mouse 2 h prior to NNK administration completely inhibited lung tumorigenesis, while removal of the isothiocyanate group or replacing it with a hydroxyl group abolished the inhibitory activity. These results demonstrate that the isothiocyanate functional group is critical for the inhibitory activity of isothiocyanates in NNK-induced lung tumorigenesis. To gain more insights into the relationship of in vivo inhibition of tumorigenesis with the cytochrome P-450 enzyme inhibitory activity, the effects of these compounds on metabolism of NNK in mouse lung microsomes were studied. 1-Dodecyl isothiocyanate inhibited all three known oxidative pathways of NNK metabolism, with a stronger inhibitory activity toward NNK N-oxidation (IC[50] 430 nM) and keto alcohol formation (IC[50] 500 nM) than keto aldehyde formation (IC[50] 13000 nM). 1-Dodecanol had a similar selectivity in inhibition of these metabolic pathways, but was less potent than 1-dodecyl isothiocyanate. Dodecane showed little or no inhibitory activity in the same concentration range. Thus, isothiocyanate group of 1-dodecyl isothiocyanate is important for inhibition of NNK-induced lung tumorigenesis and also for effective inhibition of cytochrome P-450 enzymes involved in NNK oxidation. Библ. 27

ГРНТИ	76.29.49

ВИНИТИ 761.29.49.55.07.11.11.99
Рубрики: КАНЦЕРОГЕНЕЗ ХИМИЧЕСКИЙ
НИТРОЗАМИНЫ
ТАБАК
ЛЕГКИЕ
АНТИКАНЦЕРОГЕНЫ
АЛКИЛИЗОТИОЦИАНАТЫ
ВЗАИМОСВЯЗЬ СТРУКТУРА-АКТИВНОСТЬ
МЫШИ

Доп.точки доступа:
Jiao, Ding; Smith, Theresa J.; Kim, Sungbin; Yang, Chung S.; Desai, Dhimant; Amin, Shantu; Chung, Fung-Lung

РЖ ВИНИТИ 76 (BI29) 97.04-04Н1.275

The essential role of the functional group in alkyl isothiocyanates for inhibition of tobacco nitrosamine-induced lung tumorigenesis [Text] / Ding Jiao [et al.] // Carcinogenesis. - 1996. - Vol. 17, N 4. - P755-759 . - ISSN 0143-3334
Перевод заглавия: Существенная роль функциональных групп в алкилизотиоцианатах для ингибирования индуцированных нитрозаминами табака опухолей легкого
Аннотация: The importance of the isothiocyanate group in alkyl isothiocyanate for inhibition of tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis was examined in A/J mice. The previous structure-activity relationship study of isothiocyanates showed that 1-dodecyl isothiocyanate [CH[3](CH[2])[11]NCS], a simple alkyl isothiocyanate, is a potent inhibitor of NNK-induced lung tumorigenesis. It was chosen for this study due to its structural features and potency. A single dose of 1-dodecyl isothiocyanate given by gavage at 1 'мю'mol/mouse 2 h prior to NNK administration completely inhibited lung tumorigenesis, while removal of the isothiocyanate group or replacing it with a hydroxyl group abolished the inhibitory activity. These results demonstrate that the isothiocyanate functional group is critical for the inhibitory activity of isothiocyanates in NNK-induced lung tumorigenesis. To gain more insights into the relationship of in vivo inhibition of tumorigenesis with the cytochrome P-450 enzyme inhibitory activity, the effects of these compounds on metabolism of NNK in mouse lung microsomes were studied. 1-Dodecyl isothiocyanate inhibited all three known oxidative pathways of NNK metabolism, with a stronger inhibitory activity toward NNK N-oxidation (IC[50] 430 nM) and keto alcohol formation (IC[50] 500 nM) than keto aldehyde formation (IC[50] 13000 nM). 1-Dodecanol had a similar selectivity in inhibition of these metabolic pathways, but was less potent than 1-dodecyl isothiocyanate. Dodecane showed little or no inhibitory activity in the same concentration range. Thus, isothiocyanate group of 1-dodecyl isothiocyanate is important for inhibition of NNK-induced lung tumorigenesis and also for effective inhibition of cytochrome P-450 enzymes involved in NNK oxidation. Библ. 27

ГРНТИ	76.29.49

ВИНИТИ 761.29.49.21.07.15
Рубрики: КАНЦЕРОГЕНЕЗ ХИМИЧЕСКИЙ
НИТРОЗАМИНЫ
ТАБАК
ЛЕГКИЕ
АНТИКАНЦЕРОГЕНЫ
АЛКИЛИЗОТИОЦИАНАТЫ
ВЗАИМОСВЯЗЬ СТРУКТУРА-АКТИВНОСТЬ
МЫШИ

Доп.точки доступа:
Jiao, Ding; Smith, Theresa J.; Kim, Sungbin; Yang, Chung S.; Desai, Dhimant; Amin, Shantu; Chung, Fung-Lung

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