4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, a Nicotine-derived Carcinogenic Nitrosaminoketone (NNK): Three-dimensional Structure

被引：0

作者：

Amy K. Katz

H. L. Carrell

Carol E. Afshar

Jenny P. Glusker

Dhimant Desai

Shantu Amin

机构：

[1] The Institute for Cancer Research,Fox Chase Cancer Center

[2] American Health Foundation,undefined

来源：

Structural Chemistry | 1999年 / 10卷

关键词：

Nicotine-derived nitrosaminoketone; nitrosamine; crystal structure; molecular dimensions;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The three-dimensional structure of the carcinogenic nicotine-derived nitrosaminoketone, 4-(methyl-nitrosamino)-l-(3-pyridyl)-l-butanone, has been determined by X-ray crystallographic techniques. The molecule is essentially planar except for the methylnitrosamine group which is oriented at a dihedral angle of 68.7° to the pyridine ring. Molecules pack by way of —H⋯O interactions that involve the —NNO group.

引用

页码：439 / 443

页数：4

共 31 条

[1] 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a nicotine-derived carcinogenic nitrosaminoketone (NNK): Three-dimensional structure
Katz, AK
Carrell, HL
Afshar, CE
Glusker, JP
Desai, D
Amin, S
STRUCTURAL CHEMISTRY, 1999, 10 (06) : 439 - 443
[2] Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human placental microsomes
Collazo, NR
Sultatos, LG
BIOCHEMICAL PHARMACOLOGY, 1995, 50 (11) : 1933 - 1941
[3] 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a nicotine derivative, induces apoptosis of endothelial cells
Tithof, PK
Elgayyar, M
Schuller, HM
Barnhill, M
Andrews, R
AMERICAN JOURNAL OF PHYSIOLOGY-HEART AND CIRCULATORY PHYSIOLOGY, 2001, 281 (05): : H1946 - H1954
[4] Rapid quantitation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in rat urine using ultra-fast liquid chromatography mass spectrometry (UFLC/MS/MS)
Sepehr, Estatira
Woodling, Kellie A.
Bryant, Matthew S.
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2018, 41 (08) : 422 - 429
[5] 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone modulation of cytokine release in U937 human macrophages
Rioux, N
Castonguay, A
CANCER IMMUNOLOGY IMMUNOTHERAPY, 2001, 49 (12) : 663 - 670
[6] A possible photo sensitizer:: Tobacco-specific nitrosamine, 4-(N-methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), induced mutations, DNA strand breaks and oxidative and methylative damage with UVA
Arimoto-Kobayashi, Sakae
Sakata, Hiroko
Mitsu, Kanayo
Tanoue, Hiroyuki
MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS, 2007, 632 (1-2) : 111 - 120
[7] Betel quid containing safrole enhances metabolic activation of tobacco specific 4-(methylnitrosamino)-1-(3-pyridy1)-1-butanone (NNK)
Tsou, Han-Hsing
Ko, Hsiao-Tung
Chen, Chia-Tzu
Wang, Tse-Wen
Lee, Chien-Hung
Liu, Tsung-Yun
Wang, Hsiang-Tsui
ENVIRONMENTAL POLLUTION, 2019, 251 : 13 - 21
[8] Genotoxic alterations in murine hepatocytes after short-and long-term exposure to N-nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone, NNK, a component in tobacco cigarette smoke
Miyake-Mizusaka, A. M.
Ikeda, T. L.
Nagamine, M. K.
Araldi, R. P.
Dagli, M. L. Z.
GENETICS AND MOLECULAR RESEARCH, 2021, 20 (03):
[9] Activation of voltage-operated Ca2+-channels in human small cell lung carcinoma by the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
Sheppard, BJ
Williams, M
Plummer, HK
Schuller, HM
INTERNATIONAL JOURNAL OF ONCOLOGY, 2000, 16 (03) : 513 - 518
[10] Coexposure to ethanol with N-nitrosodimethylamine or 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone during lactation of rats:: Marked increase in O6-methylguanine-DNA adducts in maternal mammary gland and in suckling lung and kidney
Chhabra, SK
Anderson, LM
Perella, C
Desai, D
Amin, S
Kyrtopoulos, SA
Souliotis, VL
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2000, 169 (02) : 191 - 200

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