• 제목/요약/키워드: 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone

검색결과 11건 처리시간 0.027초

LC-MS/MS를 이용하여 먼지 속의 NNK (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone) 정량 분석법 개발 (Development of a method for the determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in dust using liquld chromatography tandem mass spectrometry)

  • 이원경;강수진;오지은;황상현;이도훈
    • 분석과학
    • /
    • 제28권1호
    • /
    • pp.1-7
    • /
    • 2015
  • 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco specific nitrosamine found only in tobacco products. The ability to monitor biomarker concentrations is very important in understanding environmental tobacco smoke (ETS). In this study, an efficient and sensitive method for the analysis of NNK in dust was developed and validated using liquid chromatography tandem mass spectrometry. Dust was collected with filter paper soaked in methanol. The standard solution and dust sample were diluted with 100 mM ammonium acetate and extracted using dichloromethane. Our calibration curves ranged from 25 to $10^4pg/mL$. Excellent linearity was obtained with correlation coefficient values between 0.9996 and 1.0000. The limit of detection (LOD) was 5 pg/mL ($S/N{\geq}3$) and the retention time was 10 min. The limit of quantification (LOQ) was 25 pg/mL, and the acceptance criteria was the rate of 98-103% (80-120% at levels up to $3{\times}LOQ$). The coefficient of variations (CV) was 2.8%. Accuracies determined from dust samples spiked with four different levels of NNK racurves ranged that from 25 to 104 pg/mL. Excellent linearity was obtained between 92.1% and 114%. The precision of the method was acceptable (5% of CV). The recovery rates of the whole analytical procedure at low, medium, and high levels were 105.7-116.5% for NNK. The carry-over effects during LC-MS/MS analysis were not observed for NNK. This manuscript summarizes the scientific evidence on the use of markers to measure ETS.

Chemopreventive Effect of Saponins Derived from Roots of Platycodon grandiflorum on 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone-Induced Lung Tumorigenesis in A/J Mice

  • Lee, Kyung-Jin;Shin, Dong-Weon;Chung, Young-Chul;Jeong, Hye-Gwang
    • Archives of Pharmacal Research
    • /
    • 제29권8호
    • /
    • pp.651-656
    • /
    • 2006
  • This study examined the chemopreventive effect of saponins that were isolated from the roots of Platycodon grandiflorum A. DC (Campanulaceae), Changkil saponins (CKS), against the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), -on lung tumorigenesis in A/J mice. The mice were treated with a single NNK dose (100 mg/kg b.w., i.p.). CKS (0.5, 1, 4 mg/kg body wt.) was administered orally daily for 3 days/week beginning 1 day after the NNK treatment and was maintained throughout the experiment. The administration of CKS suppressed the NNK-induced increase in the level of proliferating cell nuclear antigen, which are a marker of cell proliferation, in the lungs of the mice 4 weeks after the NNK injection. Twenty-five weeks after the NNK treatment, the mice were sacrificed and the number of surface lung tumors was measured. CKS significantly reduced the number of lung tumors induced by NNK in a dose dependent manner. These results suggest that CKS suppresses the development of lung tumors and has a chemopreventive effect against NNK-induced mouse lung tumorigenesis.

A high-effective method to separate nicotine from the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) mixtures using electrodialysis

  • Ge, Shaolin;Li, Wei;Zhang, Zhao;Li, Chuanrun;Wang, Yaoming
    • Membrane and Water Treatment
    • /
    • 제8권3호
    • /
    • pp.245-257
    • /
    • 2017
  • The separation of nicotine and tobacco-specific N-nitrosamines is a tough problem in tobacco industry. In this study, separation of nicotine from 4-(methylnitrosamino) -1-(3-pyridyl)-1-butanone (NNK) mixtures was investigated using electrodialysis by taking the principle of the protonation status difference between these two components. The results indicated that the solution pH has a dominant impact on the separation process. In a pH range of 5-7, nicotine molecules are existed as mono- and di-protonated ions and can be separated from the uncharged NNK molecules. The acidic electrolyte is conducive to the separation process from the point of flux and energy consumption; while the alkaline electrolyte has negative impact on the separation process. A current density of $10mA/cm^2$ is an appropriate value for the separation process. The lowest energy consumption of the separation process is 0.58 kWh/kg nicotine with the process cost to be estimated at only $0.208 /kg nicotine. Naturally, electrodialysis is a high-efficiency, cost-effective, and environmentally friendly process to separate and purify nicotine from tobacco juice.

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Induces Retinoic Acid Receptor β Hypermethylation through DNA Methyltransferase 1 Accumulation in Esophageal Squamous Epithelial Cells

  • Wang, Jing;Zhao, Shu-Lei;Li, Yan;Meng, Mei;Qin, Cheng-Yong
    • Asian Pacific Journal of Cancer Prevention
    • /
    • 제13권5호
    • /
    • pp.2207-2212
    • /
    • 2012
  • Overexpression of DNA methyltransferase 1 (DNMT1) has been detected in many cancers. Tobacco exposure is known to induce genetic and epigenetic changes in the pathogenesis of malignancy. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is an important carcinogen present in tobacco smoke; however the detailed molecular mechanism of how NNK induces esophageal carcinogenesis is still unclear. We found that DNMT1 was overexpressed in ESCC tissues compared with paired non-cancerous tissues, the overexpression being correlated with smoking status and low expression of $RAR{\beta}$. The latter could be upregulated by NNK treatment in Het-1A cells, and the increased DNMT1 expression level reflected promoter hypermethylation and downregulation of retinoic acid receptor ${\beta}$($RAR{\beta}$). RNA interference mediated knockdown of DNMT1 resulted in promoter demethylation and upregulation of $RAR{\beta}$ in KYSE30 and TE-1 cells. 3-(4,5-Dimethyl-thiazol-2yl)-2,5-diphenyltetrazolium bromide (MTT) and flow cytometric analysis demonstrated that NNK treatment in Het-1A cells could enhance cell proliferation and inhibit cell apoptosis in a dose-dependent manner. In conclusion, DNMT1 overexpression is correlated with smoking status and low expression of $RAR{\beta}$ in esophageal SCC patients. NNK could induce $RAR{\beta}$ promoter hypermethylation through upregulation of DNMT1 in esophageal squamous epithelial cells, finally leading to enhancement of cell proliferation and inhibition of apoptosis.

Binding Pattern Elucidation of NNK and NNAL Cigarette Smoke Carcinogens with NER Pathway Enzymes: an Onco-Informatics Study

  • Jamal, Qazi Mohammad Sajid;Dhasmana, Anupam;Lohani, Mohtashim;Firdaus, Sumbul;Ansari, Md Yousuf;Sahoo, Ganesh Chandra;Haque, Shafiul
    • Asian Pacific Journal of Cancer Prevention
    • /
    • 제16권13호
    • /
    • pp.5311-5317
    • /
    • 2015
  • Cigarette smoke derivatives like NNK (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone) and NNAL (4-(methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol) are well-known carcinogens. We analyzed the interaction of enzymes involved in the NER (nucleotide excision repair) pathway with ligands (NNK and NNAL). Binding was characterized for the enzymes sharing equivalent or better interaction as compared to +Ve control. The highest obtained docking energy between NNK and enzymes RAD23A, CCNH, CDK7, and CETN2 were -7.13 kcal/mol, -7.27 kcal/mol, -8.05 kcal/mol and -7.58 kcal/mol respectively. Similarly the highest obtained docking energy between NNAL and enzymes RAD23A, CCNH, CDK7, and CETN2 were -7.46 kcal/mol, -7.94 kcal/mol, -7.83 kcal/mol and -7.67 kcal/mol respectively. In order to find out the effect of NNK and NNAL on enzymes involved in the NER pathway applying protein-protein interaction and protein-complex (i.e. enzymes docked with NNK/NNAL) interaction analysis. It was found that carcinogens are well capable to reduce the normal functioning of genes like RAD23A (HR23A), CCNH, CDK7 and CETN2. In silico analysis indicated loss of functions of these genes and their corresponding enzymes, which possibly might be a cause for alteration of DNA repair pathways leading to damage buildup and finally contributing to cancer formation.

흡연특이성 발암물질이 특정 Protein Kinase C Isoform에 미치는 영향 (Effects of Tobacco-Specific Carcinogen on Protein Kinase C Isoforms)

  • 강형석;고무성;박기성;이섭;전상훈;권오춘
    • Journal of Chest Surgery
    • /
    • 제36권9호
    • /
    • pp.666-673
    • /
    • 2003
  • 폐암의 주된 원인으로 알려진 흡연은 그 악성세포 발현기전이 아직 정확히 규명된 바 없다. 이에 저자들은 흡연에 의한 발암성의 지표로 흡연 중에 특이적으로 존재하는 강력한 발암물질인 NNK(4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone)를 이용하여 흡연에 따른 폐암의 발생과 그 Protein kinase C (PKC) isoform과 관련된 기전에 관한 연구를 시도하였다. 대상 및 방법: 인체 상피세포를 NNK에 노출시킨 후 saturation density, soft agar colony formation, cell aggregation 및 foci의 출현 등의 양상을 파악하여 세포 발암성 여부를 관찰하였으며 NNK를 15분간 노출시킨 후 PKC의 변화는 세포 내 PKC isoform의 양을 cytosolic fraction과 membrane fraction으로 분리하여 측정하여 분석하였다. 결과: NNK 투여군에서 saturation density, soft agar colony formation, cell aggregation 및 foci의 출현 시기 등의 세포 발암성을 뚜렷이 나타내었으며 PKC isoform분석의 경우 PKC-$\alpha$의 membrane fraction의 뚜렷한 증가를 보였으며 이러한 활성은 용량-의존적인 형태를 유지하였다. PKC-$\varepsilon$은 NNK 처리 시 용량-의존적으로 cytosol fraction의 감소 및 membrane fraction의 증가를 뚜렷하게 보였고 NNK에 의한 PKC-λ의 변화는 감지되지 않았다. 결론: 본 연구는 화학적 발암물질인 NNK가 인체발암화에 관여함을 재차 확인하면서 초기 과정에 관여하는 PKC isoform의 변화를 분석함으로써 total PKC활성이 아닌 isoform 각각에 대한 변화를 확인하였다는 점에서 앞으로 인체상피세포 기원의 폐암 생성 기전 연구에 기여할 것으로 생각한다.

녹차 추출물에 의한 니코틴의 코티닌으로 전이 촉진 (Enhanced conversion to cotinine from nicotine by green tea extract)

  • 경윤주;이동희
    • 한국환경농학회지
    • /
    • 제19권2호
    • /
    • pp.147-153
    • /
    • 2000
  • 흡연은 직접 또는 environmental tobacco smoke를 통하여 많은 위해성 물질을 인체에 유입시킨다. 이러한 위해 물질중 니코틴을 인체내의 대사에 따라서 암을 유발시키는 물질로 전이되기도 한다. 니코틴의 대사산물로 대표적인 발암물질인 nitrosamine-4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone (NNK)가 있다. 많은 연구는 녹차의 추출물이 암을 예방하는데 탁월한 효능이 있음을 보고하고 있다. 그러나, 녹차의 암예방 효과에 대한 기작은 거의 알려져 있지 않다. 최근의 보고는 니코틴의 주요대사 산물인 코니틴이 안정한 물질임과 동시에 NNK의 활성 및 형성을 억제하는 것으로 알려져 있다. 본 연구는 세포내의 니코틴의 대사에 있어, 코티닌으로의 전이도에 녹차의 추출물이 미치는 영향에 대하여 연구하였다. 녹차의 추출물은 시험관에서 직접 혼합한 경우와 세포주를 이용한 실험에서, 니코틴이 코티닌으로 전이하는 데 긍정적 영향을 주었다. 이 결과는 녹차의 성분 중에 니코틴의 여러 대사경로중에서 코티닌의 대사를 촉진하는 물질이 함유되어 있음을 의미한다. 이 결과는 아울러, 녹차의 암 예방의 가능성에 대하여 설명할 수 있는 기전을 제시한다.

  • PDF

Effect of Tea Polyphenols on Conversion of Nicotine to Cotinine

  • Lee, Dong-Hee;Kim, Ha-Won
    • Biomolecules & Therapeutics
    • /
    • 제11권4호
    • /
    • pp.238-244
    • /
    • 2003
  • Nicotine is one of the major hazardous components in cigarettc smoke. Nicotine deals a harmful effect to smokers and passive smokers due to its rapid conversion to various carcinogenic metabolites. Nitrosamine-4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is believed to cause lung cancers among the nicotine-derived carcinogens. Recent studies report that NNK synthesis can be inhibited by the metabolism pathway to produce a stable metabolite cotinine from nicotine. Tea polyphenols have been known to contain factors to prevent cancers and to retard progression of cancers. This study aims to correlate tea polyphenol's potential for cancer prevention with an accelerated formation of cotinine. The conversion from nicotine to cotinine in the presence of tea extracts or three polyphenols (Catechin, epicatechin gallate, epigallocatechin gallate) was measured in established cell lines and in Xenopus oocytes. Among three lines of cell used, PLC/PRF5 and HEK293 cells showed a fast turnover from nicotine to cotinine while HepG2 cell line showed a marginal difference between groups treated and non-treated with tea polyphenols. When Xenopus oocytes were microinjected with nicotine, tea polyphenols appear to accelerate the conversion of nicotine to cotinine. Among the polyphenols tested in this study, (+)-catechin showed the best efficiency overall in accelerating conversion from nicotine to cotinine both in the cell lines and in the oocytes. In summary, the present study indicated that tea polyphenols have a positive effect on conversion of nicotine to cotinine.

Inhibition of Carcinogen-Activating Cytochrome P450 Enzymes by Xenobiotic Chemicals in Relation to Antimutagenicity and Anticarcinogenicity

  • Shimada, Tsutomu
    • Toxicological Research
    • /
    • 제33권2호
    • /
    • pp.79-96
    • /
    • 2017
  • A variety of xenobiotic chemicals, such as polycyclic aromatic hydrocarbons (PAHs), aryl- and heterocyclic amines and tobacco related nitrosamines, are ubiquitous environmental carcinogens and are required to be activated to chemically reactive metabolites by xenobiotic-metabolizing enzymes, including cytochrome P450 (P450 or CYP), in order to initiate cell transformation. Of various human P450 enzymes determined to date, CYP1A1, 1A2, 1B1, 2A13, 2A6, 2E1, and 3A4 are reported to play critical roles in the bioactivation of these carcinogenic chemicals. In vivo studies have shown that disruption of Cyp1b1 and Cyp2a5 genes in mice resulted in suppression of tumor formation caused by 7,12-dimethylbenz[a]anthracene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, respectively. In addition, specific inhibitors for CYP1 and 2A enzymes are able to suppress tumor formation caused by several carcinogens in experimental animals in vivo, when these inhibitors are applied before or just after the administration of carcinogens. In this review, we describe recent progress, including our own studies done during past decade, on the nature of inhibitors of human CYP1 and CYP2A enzymes that have been shown to activate carcinogenic PAHs and tobacco-related nitrosamines, respectively, in humans. The inhibitors considered here include a variety of carcinogenic and/or non-carcinogenic PAHs and acethylenic PAHs, many flavonoid derivatives, derivatives of naphthalene, phenanthrene, biphenyl, and pyrene and chemopreventive organoselenium compounds, such as benzyl selenocyanate and benzyl selenocyanate; o-XSC, 1,2-, 1,3-, and 1,4-phenylenebis(methylene)selenocyanate.

Nicotine 및 Tobacco-Specific Nitrosamine이 발암과정에 미치는 영향 (Effects of Nicotine and Tobacco-Specific Nitrosamine on Carcinogenesis)

  • 강호일;박미선;김옥희
    • 한국환경성돌연변이발암원학회지
    • /
    • 제25권3호
    • /
    • pp.118-123
    • /
    • 2005
  • Nicotine has been implicated as a potential factor in the pathogenesis of human lung cancer, however its mechanism of action in the development of lung cancer remains largely unknown. To explore the role of nicotine in the development of lung cancer, we first investigated the effects of nicotine on the expression of tumor associated genes by treating Sprague-Dawley rats with nicotine (10 mg/kg) by gavage once daily for 10 days. We determined the expression of proteins and mRNAs of the ras, raf, myc, jun, fos oncogenes and p53, Rb tumor suppressor genes by Western and Northern blotting, respectively. We did not detect any changes on the levels of proteins and mRNAs of these tumor associated genes in the lung of Sprague-Dawley rats from 3 days to 12 weeks after the last treatment of nicotine, indicating that nicotine appears to have no effect on expression of these oncogenes and tumor suppressor genes at an early stage in multistage chemical carcinogenesis. In a second experiment, we investigated the possibility that 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) could be formed endogenously by treating with nicotine and sodium nitrite. We treated groups of Fischer 344 rats with nicotine ($60{\mu}mol/kg$) and sodium nitrite ($180{\mu}mol/kg$), nicotine, sodium nitrite and NNK (120 nmol/kg) alone by gavage once daily for 7 days, respectively and determined the 8-hydroxydeoxyguanosine (8-OHdG), as an indicator of NNK formation, in the lungs of rats 24 hours and 48 hours after the last treatment by HPLC/ECD method. We detect increased level of 8-OHdG in the lungs of rats treated with NNK, but in the case of nicotine plus sodium nitrite, nicotine and sodium nitrite alone we could not detected any changes of 8-OHdG, respectively.

  • PDF