HOMEPRODUCTSSERVICESCOMPANYCONTACTFAQResearchDictionaryPharmaMobileSign Up FREE or Login

Metabolic transformation and mechanism of action of mononitroso caffeidine- a new interpretation.

Abstract
Although caffeine is not carcinogenic, its hydrolysed product, caffeidine causes human cancer, possibly through endogenous nitrosation to form mononitroso caffeidine (MNC). MNC undergoes enzymatic demethylation and reacts with cellular nucleophiles, notably DNA, via the formation of a putative imidazole diazonium ion. Its interaction with proteins has not been reported. The present work is based on the hypothesis that some active metabolites of MNC covalently interact with cellular DNA and/or proteins to initiate carcinogenesis. We report here the synthesis of a possible reactive metabolite of MNC, viz., N, 1-methyl-4(N-methyl-N-nitrosamino)-imidazole-5-carboxylic acid (MNIC). Its structure has been determined by uv, ir, nmr and mass spectral analyses and its interaction with egg albumin and human serum protein has been examined by uv and CD spectroscopy. We concluded that metabolic activation of MNC occurs through the formation of MNIC. Avoiding consumption of salted tea or coffee that prevents the intake of caffeidine will possibly eliminate the risk of MNC carcinogenicity.
AuthorsG S Panda, R K Bhattacharya, S K Choudhuri
JournalEndocrine, metabolic & immune disorders drug targets (Endocr Metab Immune Disord Drug Targets) Vol. 6 Issue 1 Pg. 1-6 (Mar 2006) ISSN: 1871-5303 [Print] United Arab Emirates
PMID16611159 (Publication Type: Journal Article)
Chemical References
  • Amino Acids
  • Anticarcinogenic Agents
  • Blood Proteins
  • Carcinogens
  • Coffee
  • Nitroimidazoles
  • Tea
  • 1-methyl-4-nitro-5-imidazolyl-2-chloro-6-methylphenyl sulfone
  • caffeidine
  • Caffeine
Topics
  • Amino Acids (chemistry)
  • Animals
  • Anticarcinogenic Agents
  • Biotransformation
  • Blood Proteins (chemistry)
  • Caffeine (analogs & derivatives, pharmacokinetics, pharmacology)
  • Carcinogens (toxicity)
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Coffee (chemistry)
  • Humans
  • Magnetic Resonance Spectroscopy
  • Male
  • Mass Spectrometry
  • Mice
  • Nitroimidazoles (antagonists & inhibitors, toxicity)
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Tea (chemistry)

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research network!


Choose Username:
Email:
Password:
Verify Password: