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Chemical Compound Review

NPRO     1-nitrosopyrrolidine-2- carboxylic acid

Synonyms: Nitrosoproline, NO-Pro, CHEMBL75995, LS-7618, NSC-109545, ...
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Disease relevance of NO-Pro


High impact information on NO-Pro

  • Extracts of betel nut (Areca catechu) were tested for their capacity to inhibit the endogenous formation of nitrosamines by measurement of the amount of urinary N-nitroso-L-proline (NPRO) following ingestion of sodium nitrate (300 mg) and L-proline (300 mg) by 2 volunteers [5].
  • Excretion of N-nitrosoproline in 12-h overnight urine after intake of 500-mg L-proline was used to quantify the rate of endogenous nitrosation in 285 individuals in an area in northern Denmark with large variation in nitrate concentration of the drinking water [6].
  • Gas chromatography-high resolution mass spectrometry methods were developed for quantifying nitrosodimethylamine (NDMA) and nitrosoproline (NPRO) in human urine [7].
  • Endogenous formation of N-nitrosoproline using the NPRO-test was determined in two groups with low (healthy control and proximal gastral vagotomy patients) and high (Billroth I and II patients) gastric nitrite concentrations [8].
  • In this group, nitrosoproline excretion was highly correlated with nitrate excretion in the subpopulation with advanced gastric pathology, but not in control subpopulations with more normal stomachs [9].

Chemical compound and disease context of NO-Pro


Biological context of NO-Pro


Anatomical context of NO-Pro


Associations of NO-Pro with other chemical compounds


Gene context of NO-Pro


Analytical, diagnostic and therapeutic context of NO-Pro


  1. Urinary excretion of nitrate, N-nitrosoproline, 3-methyladenine, and 7-methylguanine in a Colombian population at high risk for stomach cancer. Stillwell, W.G., Glogowski, J., Xu, H.X., Wishnok, J.S., Zavala, D., Montes, G., Correa, P., Tannenbaum, S.R. Cancer Res. (1991) [Pubmed]
  2. Metabolic fate of nitrosoproline in the rat. Chu, C., Magee, P.N. Cancer Res. (1981) [Pubmed]
  3. N-nitrosoproline excretion in the presence and absence of gastric disease. Knight, T.M., Leach, S., Forman, D., Vindigni, C., Packer, P., Venitt, S., Minacci, C., Lorenzini, L., Tosi, P., Frosini, G. Eur. J. Cancer (1991) [Pubmed]
  4. Hunting for electrophiles that harm human DNA: Frits Sobels Award Lecture. Bartsch, H. Mutagenesis (2002) [Pubmed]
  5. Inhibitory effect of betel nut extracts on endogenous nitrosation in humans. Stich, H.F., Ohshima, H., Pignatelli, B., Michelon, J., Bartsch, H. J. Natl. Cancer Inst. (1983) [Pubmed]
  6. Endogenous nitrosation in relation to nitrate exposure from drinking water and diet in a Danish rural population. Møller, H., Landt, J., Pedersen, E., Jensen, P., Autrup, H., Jensen, O.M. Cancer Res. (1989) [Pubmed]
  7. Urinary excretion of nitrosodimethylamine and nitrosoproline in humans: interindividual and intraindividual differences and the effect of administered ascorbic acid and alpha-tocopherol. Garland, W.A., Kuenzig, W., Rubio, F., Kornychuk, H., Norkus, E.P., Conney, A.H. Cancer Res. (1986) [Pubmed]
  8. Proline is not useful as a chemical probe to measure nitrosation in the gastrointestinal tract of patients with gastric disorders characterised by anacidic conditions. Adam, B., Schlag, P., Friedl, P., Preussmann, R., Eisenbrand, G. Gut (1989) [Pubmed]
  9. Urinary markers for exposures to alkylating or nitrosating agents. Wishnok, J.S., Tannenbaum, S.R., Stillwell, W.G., Glogowski, J.A., Leaf, C.D. Environ. Health Perspect. (1993) [Pubmed]
  10. N-nitrosamine formation in urinary-tract infections. Ohshima, H., Calmels, S., Pignatelli, B., Vincent, P., Bartsch, H. IARC Sci. Publ. (1987) [Pubmed]
  11. Comparison of urinary nitrate, N-nitrosoproline, 7-methylguanine and 3-methyladenine levels in a human population at risk for gastric cancer. Stillwell, W.G., Xu, H.X., Glogowski, J., Wishnok, J.S., Tannenbaum, S.R., Correa, P. IARC Sci. Publ. (1991) [Pubmed]
  12. Quantitative estimation of endogenous nitrosation in humans by monitoring N-nitrosoproline excreted in the urine. Ohshima, H., Bartsch, H. Cancer Res. (1981) [Pubmed]
  13. Human exposure to endogenous N-nitroso compounds: quantitative estimates in subjects at high risk for cancer of the oral cavity, oesophagus, stomach and urinary bladder. Bartsch, H., Ohshima, H., Pignatelli, B., Calmels, S. Cancer Surv. (1989) [Pubmed]
  14. The analysis and significance of bound N-nitrosoproline in nitrite-cured meat products. Sen, N.P., Baddoo, P.A., Seaman, S.W. Food additives and contaminants. (1989) [Pubmed]
  15. Nitrosoproline formation in control and antibiotic-treated rats given nitrate and proline. Mallett, A.K., Rowland, I.R., Cottrell, R.C., Gangolli, S.D. Cancer Lett. (1984) [Pubmed]
  16. Endogenous formation of N-nitrosoproline upon cigarette smoke inhalation. Brunnemann, K.D., Scott, J.C., Haley, N.J., Hoffmann, D. IARC Sci. Publ. (1984) [Pubmed]
  17. Urinary N-nitrosoproline excretion: a further evaluation of the nitrosamine hypothesis of gastric carcinogenesis in precancerous conditions. Hall, C.N., Kirkham, J.S., Northfield, T.C. Gut (1987) [Pubmed]
  18. Exposure of humans to endogenous N-nitroso compounds: implications in cancer etiology. Bartsch, H., Ohshima, H., Shuker, D.E., Pignatelli, B., Calmels, S. Mutat. Res. (1990) [Pubmed]
  19. Metabolic studies of 15N-labeled N-nitrosoproline in isolated rat hepatocytes and subcellular fractions. Koepke, S.R., Tondeur, Y., Farrelly, J.G., Stewart, M.L., Michejda, C.J., Kroeger-Koepke, M.B. Cancer Lett. (1985) [Pubmed]
  20. Nitrate and N-nitrosoproline excretion in two Italian regions with contrasting rates of gastric cancer: the role of nitrate and other factors in endogenous nitrosation. Knight, T., Pirastu, R., Palli, D., Cocco, P., Leach, S., Packer, P., Iannarilli, R., Manca, P., Møller, H., Forman, D. Int. J. Cancer (1992) [Pubmed]
  21. Effect of ascorbic acid and green tea on endogenous formation of N-nitrosodimethylamine and N-nitrosopiperidine in humans. Vermeer, I.T., Moonen, E.J., Dallinga, J.W., Kleinjans, J.C., van Maanen, J.M. Mutat. Res. (1999) [Pubmed]
  22. Chromatographic separation of conformers of substituted asymmetric nitrosamines. Iwaoka, W.T., Hansen, T., Hsieh, S.T., Archer, M.C. J. Chromatogr. (1975) [Pubmed]
  23. Determination of N-nitrosoproline at the nanogram level. Wolfram, J.H., Feinberg, J.I., Doerr, R.C., Fiddler, W. J. Chromatogr. (1977) [Pubmed]
  24. Acute cytogenetic effects of tyramine, MTCAs, NaCl and soy sauce on rat bone marrow cells in vivo. Fujie, K., Nishi, J., Wada, M., Maeda, S., Sugiyama, T. Mutat. Res. (1990) [Pubmed]
  25. Activation of N-nitrosodialkylamines by near-ultraviolet irradiation: formation of directly-acting mutagens and DNA-damaging products. Shimada, H., Yakushi, K., Ikarashi, A., Mochizuki, M., Suzuki, E., Okada, M., Yokoyama, S., Miyazawa, T., Hayatsu, H. IARC Sci. Publ. (1987) [Pubmed]
  26. Effects of N-nitrosopyrrolidine and N-nitrosoproline on the incorporation of 3H-thymidine into the DNA of various organs of the mouse: tissue specificity and effects of ethanol consumption. Hellman, B., Tjälve, H. Acta pharmacologica et toxicologica. (1986) [Pubmed]
  27. Effects of ascorbic acid and thiocyanate on nitrosation of proline in the dog stomach. Licht, W.R., Fox, J.G., Deen, W.M. Carcinogenesis (1988) [Pubmed]
  28. High-performance liquid chromatography of N-nitrosoproline in urine. Walters, D.G., Mallett, A.K., Cottrell, R.C. J. Chromatogr. (1982) [Pubmed]
  29. Dietary fat and N-nitrosation in the rat. Ward, F.W., Coates, M.E. Br. J. Nutr. (1987) [Pubmed]
  30. Evaluation of the nitrosamine hypothesis of gastric carcinogenesis in man. Hall, C.N., Darkin, D., Viney, N., Cook, A., Kirkham, J.S., Northfield, T.C. IARC Sci. Publ. (1987) [Pubmed]
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