Diet-induced endogenous formation of nitroso compounds in the GI tract

Free Radical Biology and Medicine

Volumn 43, Issue 7, 2007, Pages 1040-1047

  Kuhnle, Gunter G C ^a   Story, Giles W ^a   Reda, Torsten ^a   Mani, Ali R ^b   Moore, Kevin P ^b   Lunn, Joanne C ^a   Bingham, Sheila A ^a  

^a WELLCOME TRUST SANGER INSTITUTE   (United Kingdom)

^b ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

Author keywords

Apparent total N nitroso compounds; Colorectal cancer; Free radicals; HemoQuant; Nitrosothiols; Nitrosyl heme

Indexed keywords

HEME; HEMOGLOBIN; IRON COMPLEX; NITROSO DERIVATIVE; NITROSYL IRON; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COLORECTAL CANCER; CONTROLLED STUDY; CORRELATION ANALYSIS; DNA ADDUCT; ELECTRON SPIN RESONANCE; FISH; FOOD ANALYSIS; FOOD INTAKE; GASTROINTESTINAL TRACT; HUMAN; MEAT; NITROSATION; NORMAL HUMAN; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE; STOMACH; VEGETARIAN DIET;

APOPROTEINS; DIET; DIET, VEGETARIAN; ELECTRON SPIN RESONANCE SPECTROSCOPY; FECES; GASTROINTESTINAL TRACT; HEME; HEMOGLOBINS; HUMANS; ILEUM; IRON; KINETICS; MEAT; NITROSO COMPOUNDS; S-NITROSOTHIOLS; SERUM ALBUMIN, BOVINE; STOMACH;

EID: 34548138583     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2007.03.011     Document Type: Article

References (61)

1. Norat T., et al. Meat, fish, and colorectal cancer risk: the European Prospective Investigation into cancer and nutrition. J. Natl. Cancer Inst. 97 (2005) 906
2. Bingham S.A., et al. Does increased endogenous formation of N-nitroso compounds in the human colon explain the association between red meat and colon cancer?. Carcinogenesis 17 (1996) 515
3. Hughes R., et al. Dose-dependent effect of dietary meat on endogenous colonic N-nitrosation. Carcinogenesis 22 (2001) 199
4. Bingham S.A., et al. Effect of white versus red meat on endogenous N-nitrosation in the human colon and further evidence of a dose response. J. Nutr. 132 (2002) 3522S
5. Schwartz S., et al. Quantitative fecal recovery of ingested hemoglobin heme in blood: comparisons by HemoQuant assay with ingested meat and fish. Gastroenterology 89 (1985) 19
6. Cross A.J., et al. Haem, not protein or inorganic iron, is responsible for endogenous intestinal N-nitrosation arising from red meat. Cancer Res. 63 (2003) 2358
7. Bonnett R., et al. Reactions of nitrous acid and nitric oxide with porphyrins and haems: nitrosylhaems as nitrosating agents. J. Chem. Soc. Chem. Commun. (1975) 884
8. Wade R.S., et al. Redox reactivity of iron(III) porphyrins and heme proteins with nitric oxide: nitrosyl transfer to carbin, oxygen, nitrogen and sulfur. Chem. Res. Toxicol. 3 (1990) 289
9. Lakshmi V.M., et al. Hemin potentiates nitric oxide-mediated nitrosation of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to 2-nitrosoamino-3-methylimidazo[4,5-f]quinoline. Chem. Res. Toxicol. 18 (2005) 528
10. Lakshmi V.M., et al. Myeloperoxidase potentiates nitric oxide-mediated nitrosation. J. Biol. Chem. 280 (2005) 1746
11. Magee P.N., et al. The production of malignant primary hepatic tumours in the rat by feeding dimethylnitrosamine. Br. J. Cancer 10 (1956) 114
12. Bogovski P., et al. Animal species in which N-nitroso compounds induce cancer. Int. J. Cancer 27 (1981) 471
13. Lijinsky W. Chemical structure of nitrosamines related to carcinogens. In: Loeppky R.N., and Michejda C.J. (Eds). Nitrosamines and Related N-nitroso Compounds: Chemistry and Biochemistry (1994), Am. Chem. Soc., Washington, DC 250
14. Mirvish S.S. Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Lett. 93 (1995) 17
15. Saffhill R., et al. Mechanisms of carcinogenesis induced by alkylating agents. Biochim. Biophys. Acta 823 (1985) 111
16. 6-(carboxymethyl)-2′-deoxyguanosine: a DNA adduct formed by nitrosated glycine derivatives. Chem. Res. Toxicol. 10 (1997) 652
17. Bos J.L. ras oncogenes in human cancer: a review. Cancer Res. 49 (1989) 4682
18. 6-carboxymethyl-2′-deoxyguanosine in DNA following reaction of nitric oxide with glycine and in human blood DNA using a quantitative immunoslot blot assay. Chem. Res. Toxicol. 17 (2004) 294
19. 6-methylguanine in DNA. Cancer Res. 57 (1997) 366
20. 6-carboxymethyl guanine: implications for colorectal cancer risk. Cancer Res. 66 (2006) 1859
21. 6-methyl-2′-deoxyguanosine DNA adducts-relevance for gastrointestinal cancer. Carcinogenesis 28 2 (2007) 356
22. Al-Kaabi S.S., et al. A kinetic investigation of the thionitrite from (±)-2-acetylamino-2-carboxy-1,1-dimethylethanethiol as a possible nitrosating agent. J. Chem. Soc. (Perkin 2) (1982) 227
23. Butler A.R., et al. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal. Biochem. 249 (1997) 1
24. Williams D.L.H. Nitrosation mechanisms. Adv. Phys. Org. Chem. 19 (1983) 381
25. Fischer O., et al. Chem. Ber. 1886 (1886) 2291
26. Neber P.W., et al. Justus Liebigs Ann. Chem. 550 (1942) 182
27. Eisenbrand G., et al. Eine neue Methode zur kolorimetrischen Bestimmung von Nitrosaminen nach Spaltung der N-Nitrosogruppe mit Bromwasserstoff in Eisessig. Arzneimittelforschung 20 (1970) 1512
28. Downes M.J., et al. Determination of a non-volatile nitrosamine by using denitrosation and a chemiluminescence analyser. Analyst (London) 101 (1976) 742
29. Walters C.L., et al. Determination of a non-volatile N-nitrosamine on a food matrix. Analyst (London) 103 (1978) 1127
30. Pignatelli B., et al. An improved method for analysis of total N-nitroso compounds in gastric juice. IARC Sci. Publ. 209 (1987)
31. Pignatelli B., et al. Group-selective determination of total N-nitroso compounds in nitrate-containing human urine samples. Analyst (London) 114 (1989) 1103
32. Xu G., et al. Method for group determination of total N-nitroso compounds and nitrite in fresh gastric juice by chemical denitrosation and thermal energy analysis. Analyst (London) 118 (1993) 877
33. Fine D.H., et al. Description of the thermal energy analyzer (TEA) for trace determination of volatile and nonvolatile N-nitroso compounds. Anal. Chem. 47 (1975) 1188
34. Walters C.L., et al. Breakdown into nitric oxide of compounds potentially derived from nitrite in a biological matrix. Z. Lebensm. Unters Forsch. 167 (1978) 315
35. Smith P.L.R., et al. Importance of selectivity in the determination of N-nitroso compounds as a group. Analyst (London) 108 (1983) 896
36. Feelisch M., et al. Concomitant S-, N-, and heme-nitros(yl)ation in biological tissues and fluids: implications for the fate of NO in vivo. FASEB J. 16 (2002) 1775
37. Rowland I.R., et al. Endogenous N-nitrosation in man assessed by measurement of apparent total N-nitroso compounds in faeces. Carcinogenesis 12 (1991) 1395
38. Saville B. A scheme for the colorimetric determination of microgram amounts of thiols. Analyst (London) 83 (1958) 670
39. Gladwin M.T., et al. Role of circulating nitrite and S-nitrosohemoglobin in the regulation of regional blood flow in humans. Proc. Natl. Acad. Sci. USA 97 (2000) 11482
40. Mani A.R., et al. Metalloprotein-dependent decomposition of S-nitrosothiols: studies on the stabilization and measurement of S-nitrosothiols in tissues. J. Free Radic. Biol. Med. 40 (2006) 1654
41. Sharma V.S., et al. Reaction of nitric oxide with heme proteins and model compounds of hemoglobin. Biochemistry 26 (1987) 3837
42. Eich R.F., et al. Mechanism of NO-induced oxidation of myoglobin and hemoglobin. Biochemistry 35 (1996) 6976
43. Boccini F., et al. Pulse radiolysis studies of the reactions of CO3*- and NO2* with nitrosyl(II)myoglobin and nitrosyl(II)hemoglobin. J. Phys. Chem., A Mol. Spectrosc. Kinet. Environ. Gen. Theory 110 (2006) 3927
44. Lunn J.C., et al. The effect of haem in red and processed meat on the effect of N-nitroso compounds in the upper gastrointestinal tract. Carcinogenesis 28 3 (2007) 685
45. Ascoli F., et al. Preparation and properties of apohemoglobin and reconstituted hemoglobins. Methods Enzymol. 76 (1981) 72
46. Drabkin D.L., et al. Spectrophotometric studies. II. Preparations from washed blood cells; nitric oxide hemoglobin and sulfhemoglobin. J. Biol. Chem. 112 (1935) 51
47. Gornall A.G., et al. Determination of serum proteins by means of the biuret reaction. J. Biol. Chem. 177 (1949) 751
48. Moore K.P., et al. Measurement of protein nitration and S-nitrosothiol formation in biology and medicine. Methods Enzymol. 359 (2002) 256
49. Ingram D.J.E., et al. Paramagnetic resonance in phtalocyanine, haemoglobin and other organic derivatives. Discuss. Faraday Soc. 19 (1955) 140
50. Hille R., et al. Spectral transitions of nitrosyl hemes during ligand binding to hemoglobin. J. Biol. Chem. 254 (1979) 12110
51. Kosaka H., et al. ESR spectral transition by arteriovenous cycle in nitric oxide hemoglobin of cytokine-treated rats. Am. J. Physiol. 266 (1994) C1400
52. Reed G.H., et al. In: Berliner L.J., and Reuben J. (Eds). Biological Magnetic Resonance, 6 6 (1984), Plenum Press, New York 73
53. Fee J.A., et al. Direct evidence for manganese(III) binding to the manganosuperoxide dismutase of Escherichia coli B. J. Biol. Chem. 251 (1976) 6157
54. Bartsch H., and O'Neill I.K. The relevance of N-nitroso compounds to human cancer: exposures and mechanisms (1987), IARC, Lyons
55. Cross A.J., et al. Variability in fecal water genotoxicity, determined using the Comet assay, is independent of endogenous N-nitroso compound formation attributed to red meat consumption. Environ. Mol. Mutagen. 47 (2006) 179
56. Williams D.L.H. Nitrosation Reactions and the Chemistry of Nitric Oxide (2004), Elsevier, Amsterdam
57. Chan N.-L., et al. Crystal structure of the S-nitroso form of liganded human hemoglobin. Biochemistry 37 (1998) 16459
58. Evans D.F., et al. Measurement of gastrointestinal pH profiles in normal ambulant human subjects. Gut 29 (1988) 1035
59. 2+ sources. Chem. Biol. 3 (1996) 655
60. Chiodi H., et al. Effects of exposure of blood hemoglobin to nitric oxide. Environ. Res. 37 (1985) 355
61. Rao C.V. Nitric oxide signaling in colon cancer chemoprevention. Mutat. Res. 555 (2004) 107