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
收藏
页码:439 / 443
页数:4
相关论文
共 50 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] Detoxification of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by glucuronidation
    Murphy, SE
    Spina, DA
    Pullo, DA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 62 - TOXI
  • [3] The effect of methoxsalen on nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in vivo
    Sellers, EM
    Ramamoorthy, Y
    Zeman, MV
    Djordjevic, MV
    Tyndale, RF
    NICOTINE & TOBACCO RESEARCH, 2003, 5 (06) : 891 - 899
  • [4] Enhancements of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism and carcinogenic risk via NNK/arsenic interaction
    Lee, Hui-Ling
    Chang, Louis W.
    Wu, Jui-Pin
    Ueng, Yune-Fang
    Tsai, Ming-Hsien
    Hsieh, Dennis Paul Hsientang
    Lin, Pinpin
    TOXICOLOGY AND APPLIED PHARMACOLOGY, 2008, 227 (01) : 108 - 114
  • [5] Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in rhesus monkeys
    Meger, MHE
    Richter, E
    Zwickenpflug, W
    Hargaden, MB
    ARahim, YI
    Vesell, ES
    NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1997, 355 (04) : 619 - 619
  • [6] Biomonitoring of the exposure to 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in nonsmokers
    Meger, M
    Meger-Kossien, I
    Scherer, G
    NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1998, 357 (04) : R126 - R126
  • [7] Metabolism and disposition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in rhesus monkeys
    Meger, M
    Richter, E
    Zwickenpflug, W
    Oehlmann, C
    Hargaden, MB
    A-Rahim, YI
    Vesell, ES
    DRUG METABOLISM AND DISPOSITION, 1999, 27 (04) : 471 - 478
  • [8] 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
  • [9] Does smoking mentholated cigarettes inhibit the metabolism of nicotine or 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)?
    Sarkar, M.
    Wang, J.
    Liang, Q.
    JOURNAL OF CLINICAL PHARMACOLOGY, 2010, 50 (09): : 1095 - 1095
  • [10] 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) regulates CTL activation and memory programming
    Sun, Zhifeng
    Xiao, Zhengguo
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2013, 435 (03) : 472 - 476