Synthesis, structure-activity relationships and a reaction mechanism for mutagenic N-nitroso derivatives of glycosylamines and Amadori compounds-Model substances for N-nitrosated early Maillard reaction products

B. Pignatelli, C. Malaveille, M. Friesen, A. Hautefeuille, H. Bartsch, D. Piskorska, G. Descotes

Research output: Contribution to journalArticle

Abstract

A series of nine glycosylamines and an Amadori compound were synthesized, together with their N-nitroso derivatives. Their structures were established by physico-chemical and spectroscopic data and elemental analyses. The N-nitroso compounds were further characterized by denitrosation with hydrogen bromide-acetic acid, followed by detection of the liberated NO by a chemiluminescence detector. N-Nitroso derivatives of N-p-nitrophenyl/p-methylphenyl/p-carboxyphenyl pentopyranosylamines, N-p-methylphenyl-I-deoxy-d-fructosylamine (the Amadori compound) and N-3-thylindole-d-xylopyranosylamine were shown to be direct-acting mutagens in Salmonella typhimurium TA100. The activity of some of the compounds was similar to that of N-ethyl-N-nitrosourea. Their mutagenic activity was shown to depend on the structure of the amine and the sugar moieties and to require the presence of free hydroxyl groups in the sugar. The mutagenicity of N-nitrosoglycosylamines was attributed to their hydrolysis to arenediazonium cations. The formation of these compounds was detected by azo-coupling with N-ethyl-1-naphthylamine, using spectrophotometric and mass spectrometric analyses. These data implicate arene(alkyl)diazonium cations as the ultimate mutagens of N-nitrosoglycosylamines (and possibly of N-nitroso Amadori compounds), a little-explored class of N-nitroso compounds that may be formed in vivo.

Original languageEnglish (US)
Pages (from-to)669-680
Number of pages12
JournalFood and Chemical Toxicology
Volume25
Issue number9
DOIs
StatePublished - 1987
Externally publishedYes

Fingerprint

nitroso compounds
Nitroso Compounds
Maillard Reaction
Maillard reaction products
reaction mechanisms
Mutagens
structure-activity relationships
Structure-Activity Relationship
Reaction products
Sugars
Cations
cations
Hydrobromic Acid
1-Naphthylamine
N-ethyl-N-nitrosourea
chemical derivatives
Ethylnitrosourea
Derivatives
sugars
Salmonella

ASJC Scopus subject areas

  • Food Science
  • Toxicology

Cite this

Synthesis, structure-activity relationships and a reaction mechanism for mutagenic N-nitroso derivatives of glycosylamines and Amadori compounds-Model substances for N-nitrosated early Maillard reaction products. / Pignatelli, B.; Malaveille, C.; Friesen, M.; Hautefeuille, A.; Bartsch, H.; Piskorska, D.; Descotes, G.

In: Food and Chemical Toxicology, Vol. 25, No. 9, 1987, p. 669-680.

Research output: Contribution to journalArticle

@article{3ada37daa857486990019fb9e914f069,
title = "Synthesis, structure-activity relationships and a reaction mechanism for mutagenic N-nitroso derivatives of glycosylamines and Amadori compounds-Model substances for N-nitrosated early Maillard reaction products",
abstract = "A series of nine glycosylamines and an Amadori compound were synthesized, together with their N-nitroso derivatives. Their structures were established by physico-chemical and spectroscopic data and elemental analyses. The N-nitroso compounds were further characterized by denitrosation with hydrogen bromide-acetic acid, followed by detection of the liberated NO by a chemiluminescence detector. N-Nitroso derivatives of N-p-nitrophenyl/p-methylphenyl/p-carboxyphenyl pentopyranosylamines, N-p-methylphenyl-I-deoxy-d-fructosylamine (the Amadori compound) and N-3-thylindole-d-xylopyranosylamine were shown to be direct-acting mutagens in Salmonella typhimurium TA100. The activity of some of the compounds was similar to that of N-ethyl-N-nitrosourea. Their mutagenic activity was shown to depend on the structure of the amine and the sugar moieties and to require the presence of free hydroxyl groups in the sugar. The mutagenicity of N-nitrosoglycosylamines was attributed to their hydrolysis to arenediazonium cations. The formation of these compounds was detected by azo-coupling with N-ethyl-1-naphthylamine, using spectrophotometric and mass spectrometric analyses. These data implicate arene(alkyl)diazonium cations as the ultimate mutagens of N-nitrosoglycosylamines (and possibly of N-nitroso Amadori compounds), a little-explored class of N-nitroso compounds that may be formed in vivo.",
author = "B. Pignatelli and C. Malaveille and M. Friesen and A. Hautefeuille and H. Bartsch and D. Piskorska and G. Descotes",
year = "1987",
doi = "10.1016/0278-6915(87)90100-1",
language = "English (US)",
volume = "25",
pages = "669--680",
journal = "Food and Chemical Toxicology",
issn = "0278-6915",
publisher = "Elsevier Limited",
number = "9",

}

TY - JOUR

T1 - Synthesis, structure-activity relationships and a reaction mechanism for mutagenic N-nitroso derivatives of glycosylamines and Amadori compounds-Model substances for N-nitrosated early Maillard reaction products

AU - Pignatelli, B.

AU - Malaveille, C.

AU - Friesen, M.

AU - Hautefeuille, A.

AU - Bartsch, H.

AU - Piskorska, D.

AU - Descotes, G.

PY - 1987

Y1 - 1987

N2 - A series of nine glycosylamines and an Amadori compound were synthesized, together with their N-nitroso derivatives. Their structures were established by physico-chemical and spectroscopic data and elemental analyses. The N-nitroso compounds were further characterized by denitrosation with hydrogen bromide-acetic acid, followed by detection of the liberated NO by a chemiluminescence detector. N-Nitroso derivatives of N-p-nitrophenyl/p-methylphenyl/p-carboxyphenyl pentopyranosylamines, N-p-methylphenyl-I-deoxy-d-fructosylamine (the Amadori compound) and N-3-thylindole-d-xylopyranosylamine were shown to be direct-acting mutagens in Salmonella typhimurium TA100. The activity of some of the compounds was similar to that of N-ethyl-N-nitrosourea. Their mutagenic activity was shown to depend on the structure of the amine and the sugar moieties and to require the presence of free hydroxyl groups in the sugar. The mutagenicity of N-nitrosoglycosylamines was attributed to their hydrolysis to arenediazonium cations. The formation of these compounds was detected by azo-coupling with N-ethyl-1-naphthylamine, using spectrophotometric and mass spectrometric analyses. These data implicate arene(alkyl)diazonium cations as the ultimate mutagens of N-nitrosoglycosylamines (and possibly of N-nitroso Amadori compounds), a little-explored class of N-nitroso compounds that may be formed in vivo.

AB - A series of nine glycosylamines and an Amadori compound were synthesized, together with their N-nitroso derivatives. Their structures were established by physico-chemical and spectroscopic data and elemental analyses. The N-nitroso compounds were further characterized by denitrosation with hydrogen bromide-acetic acid, followed by detection of the liberated NO by a chemiluminescence detector. N-Nitroso derivatives of N-p-nitrophenyl/p-methylphenyl/p-carboxyphenyl pentopyranosylamines, N-p-methylphenyl-I-deoxy-d-fructosylamine (the Amadori compound) and N-3-thylindole-d-xylopyranosylamine were shown to be direct-acting mutagens in Salmonella typhimurium TA100. The activity of some of the compounds was similar to that of N-ethyl-N-nitrosourea. Their mutagenic activity was shown to depend on the structure of the amine and the sugar moieties and to require the presence of free hydroxyl groups in the sugar. The mutagenicity of N-nitrosoglycosylamines was attributed to their hydrolysis to arenediazonium cations. The formation of these compounds was detected by azo-coupling with N-ethyl-1-naphthylamine, using spectrophotometric and mass spectrometric analyses. These data implicate arene(alkyl)diazonium cations as the ultimate mutagens of N-nitrosoglycosylamines (and possibly of N-nitroso Amadori compounds), a little-explored class of N-nitroso compounds that may be formed in vivo.

UR - http://www.scopus.com/inward/record.url?scp=0023181185&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023181185&partnerID=8YFLogxK

U2 - 10.1016/0278-6915(87)90100-1

DO - 10.1016/0278-6915(87)90100-1

M3 - Article

C2 - 3308660

AN - SCOPUS:0023181185

VL - 25

SP - 669

EP - 680

JO - Food and Chemical Toxicology

JF - Food and Chemical Toxicology

SN - 0278-6915

IS - 9

ER -