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4-甲基亚硝胺基-1-3-吡啶基-1-丁酮

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮用途

NNK是一种尼古丁亚硝化衍生物。NNK通过激活ERK1/2和PKCα,同时仅在Ser70和Thr58和Ser62的c-Myc处刺激Bcl2磷酸化[1]。NNK诱导人肺癌细胞的存活和增殖。NNK可用于肺癌小鼠模型的构建[2]。

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4-甲基亚硝胺基-1-3-吡啶基-1-丁酮名称

[ CAS 号 ]:
64091-91-4

[ 中文名 ]:
4-甲基亚硝胺基-1-3-吡啶基-1-丁酮

[ 英文名 ]:
nnk

[中文别名 ]:

[英文别名 ]:

Nicotine-derived nitrosamine ketone
4-(n-nitrosomethylamino)-1-(3-pyridyl)-1-butanone
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
N-Nitrosonornicotine ketone
NNK
Ozone/NNK
MFCD00274580
1-Butanone, 4-(methylnitrosamino)-1-(3-pyridyl)-

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 癌症

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

NNK(100μm；0-60 min)刺激PKCα和MAPKs ERK1/2的激活,直接诱导c-Myc磷酸化[1]。NNK(100μm；96小时)促进表达WT的细胞增殖,但不促进AA c-Myc突变体的细胞增殖[1]。Western Blot分析细胞系：NCI-H82细胞【1】浓度：100μm孵育时间：0-60 min结果：刺激PKCα和MAPKs ERK1/2的激活,直接诱导c-Myc磷酸化。凋亡分析细胞系：H1299肺癌细胞【1】浓度：100μm孵育时间：96小时结果：表达WT但不表达T58A/S62A c-Myc突变体的细胞增殖增强。

[参考文献]

[1]. Jin Z, Gao F, Flagg T, Deng X. Tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone promotes functional cooperation of Bcl2 and c-Myc through phosphorylation in regulating cell survival and proliferation. J Biol Chem. 2004;279(38):40209-40219.

[2]. Castonguay A, Pepin P, Stoner GD. Lung tumorigenicity of NNK given orally to A/J mice: its application to chemopreventive efficacy studies. Exp Lung Res. 1991;17(2):485-499.

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
423.9±25.0 °C at 760 mmHg

[ 熔点 ]:
63-65ºC

[ 分子式 ]:
C₁₀H₁₃N₃O₂

[ 分子量 ]:
207.229

[ 闪点 ]:
210.2±23.2 °C

[ 精确质量 ]:
207.100784

[ PSA ]:
62.63000

[ LogP ]:
0.09

[ 外观性状 ]:
白色固体

[ 蒸汽压 ]:
0.0±1.0 mmHg at 25°C

[ 折射率 ]:
1.557

[ 储存条件 ]:
Amber Vial, -20°C Freezer

[ 稳定性 ]:
Stable. Incompatible with strong oxidizing agents.

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮MSDS

详细MSDS(安全技术说明书)

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OB6465000

CHEMICAL NAME :: Ketone, 3-pyridyl 3-(N-methyl-N-nitrosamino)propyl

CAS REGISTRY NUMBER :: 64091-91-4

BEILSTEIN REFERENCE NO. :: 3548355

LAST UPDATED :: 199612

DATA ITEMS CITED :: 52

MOLECULAR FORMULA :: C10-H13-N3-O2

MOLECULAR WEIGHT :: 207.26

WISWESSER LINE NOTATION :: T6NJ CV3N1&NO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2156 mg/kg/61W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68396 ug/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 880 mg/kg/95W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Gastrointestinal - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 41452 ug/kg

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 960 mg/kg/95W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Gastrointestinal - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 20 mg/kg female 15 day(s) after conception

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Reproductive - Tumorigenic effects - transplacental tumorigenesis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 1504 mg/kg/25W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 50 ug/kg

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Reproductive - Tumorigenic effects - transplacental tumorigenesis

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 880 mg/kg/7W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 93 mg/kg

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2700 mg/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68396 ug/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2700 mg/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 106 mg/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 166 mg/kg/7W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg/3D-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Reproductive - Tumorigenic effects - transplacental tumorigenesis

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg/3D-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 400 mg/kg/16W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratracheal

DOSE :: 50 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Tumorigenic effects - transplacental tumorigenesis

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Morphological transformation

TYPE OF TEST :: DNA damage

TYPE OF TEST :: DNA adduct

TYPE OF TEST :: DNA adduct

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: DNA damage

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - rabbit Cells - not otherwise specified

DOSE/DURATION :: 2 mmol/L

REFERENCE :: CBTOE2 Cell Biology and Toxicology. (Princeton Scientific Pub., Inc., 301 N. Harrison St., CN 5279, Princeton, NJ 08540) V.1- 1984- Volume(issue)/page/year: 6,399,1990 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 37,209,1985 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 37,209,1985 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987

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4-甲基亚硝胺基-1-3-吡啶基-1-丁酮安全信息

[ 符号 ]:

GHS06, GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301-H317-H351

[ 警示性声明 ]:
P280-P301 + P310

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
Xn

[ 风险声明 (欧洲) ]:
R26/27/28;R45

[ 安全声明 (欧洲) ]:
S45-S53

[ 危险品运输编码 ]:
UN 2811

[ RTECS号 ]:
OB6465000

[ 包装等级 ]:
II

[ 危险类别 ]:
6.1

4-甲基亚硝胺基-1-3-吡啶基-1-丁酮合成路线

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4-甲基亚硝胺基-1-3-吡啶基-1-丁酮文献

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Mechanisms of tumor-promoting activities of nicotine in lung cancer: synergistic effects of cell membrane and mitochondrial nicotinic acetylcholine receptors.

BMC Cancer 15 , 152, (2015)

One of the major controversies of contemporary medicine is created by an increased consumption of nicotine and growing evidence of its connection to cancer, which urges elucidation of the molecular me...

Tobacco-specific N-nitrosamine exposures and cancer risk in the Shanghai Cohort Study: remarkable coherence with rat tumor sites.

Int. J. Cancer 134(10) , 2278-83, (2014)

The tobacco-specific nitrosamines N'-nitrosonornicotine (NNN) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) are potent carcinogens for the rat esophagus and lung, respectively. Consistent w...

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