Transplacental transfer of acrylamide and glycidamide are comparable to that of antipyrine in perfused human placenta

Toxicology Letters

Volumn 182, Issue 1-3, 2008, Pages 50-56

  Annola, Kirsi ^a   Karttunen, Vesa ^a   Keski Rahkonen, Pekka ^a   Myllynen, Päivi ^b   Segerbäck, Dan ^c   Heinonen, Seppo ^d   Vähäkangas, Kirsi ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF OULU   (Finland)

^c KAROLINSKA INSTITUTE   (Sweden)

^d KUOPIO UNIVERSITY HOSPITAL   (Finland)

Author keywords

DNA adducts; Fetal exposure; Food carcinogens; Xenobiotic metabolism

Indexed keywords

ACRYLAMIDE; GLYCIDAMIDE; PHENAZONE;

ARTICLE; CONTROLLED STUDY; DNA ADDUCT; GLUCOSE INTAKE; HUMAN; HUMAN TISSUE; PLACENTA PERFUSION; PLACENTAL TRANSFER; PRENATAL EXPOSURE; PRIORITY JOURNAL; TOXICOKINETICS;

ACRYLAMIDES; ADULT; ANTIPYRINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; EPOXY COMPOUNDS; FEMALE; FETUS; HUMANS; MASS SPECTROMETRY; MATERNAL-FETAL EXCHANGE; MOLECULAR WEIGHT; PERFUSION; PLACENTA; PREGNANCY; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 55049101156     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2008.08.006     Document Type: Article

References (66)

1. Ala-Kokko T.I., Myllynen P., and Vähäkangas K.H. Ex vivo perfusion of the human placental cotyledon: Implications for anesthetic pharmacology. Int. J. Obstet. Anesth. 9 (2000) 26-38
2. Anderson L.M., Diwan B.A., Fear N.T., and Roman E. Critical windows of exposure for children's health: cancer in human epidemiological studies and neoplasms in experimental animal models. Environ. Health Perspect. 108 Suppl. 3 (2000) 573-594
3. Baum M., Fauth E., Fritzen S., Herrmann A., Mertes P., Merz K., Rudolphi M., Zankl H., and Eisenbrand G. Acrylamide and glycidamide: genotoxic effects in V79-cells and human blood. Mutat. Res. 580 (2005) 61-69
4. Besaratinia A., and Pfeifer G.P. Genotoxicity of acrylamide and glycidamide. J. Natl. Cancer Inst. 96 (2004) 1023-1029
5. Bjellaas T., Janak K., Lundanes E., Kronberg L., and Becher G. Determination and quantification of urinary metabolites after dietary exposure to acrylamide. Xenobiotica 35 (2005) 1003-1018
6. Blasiak J., Gloc E., Wozniak K., and Czechowska A. Genotoxicity of acrylamide in human lymphocytes. Chem. Biol. Interact. 149 (2004) 137-149
7. Boettcher M.I., Bolt H.M., Drexler H., and Angerer J. Excretion of mercapturic acids of acrylamide and glycidamide in human urine after single oral administration of deuterium-labelled acrylamide. Arch. Toxicol. 80 (2006) 55-61
8. Boettcher M.I., Schettgen T., Kutting B., Pischetsrieder M., and Angerer J. Mercapturic acids of acrylamide and glycidamide as biomarkers of the internal exposure to acrylamide in the general population. Mutat. Res. 580 (2005) 167-176
9. Brandes J.M., Tavoloni N., Potter B.J., Sarkozi L., Shepard M.D., and Berk P.D. A new recycling technique for human placental cotyledon perfusion: application to studies of the fetomaternal transfer of glucose, insulin, and antipyrine. Am. J. Obstet. Gynecol. 146 (1983) 800-806
10. Challier J.C. Criteria for evaluating perfusion experiments and presentation of results. Contrib. Gynecol. Obstet. 13 (1985) 32-39
11. Challier J.C., D'Athis P., Guerre-Millo M., and Nandakumaran M. Flow-dependent transfer of antipyrine in the human placenta in vitro. Reprod. Nutr. Dev. 23 (1983) 41-50
12. Challier J.C., Dubernard G., Galtier M., Bintein T., Vervelle C., Raison D., Espie M.J., and Uzan S. Junctions and adhesion molecules in first trimester and term human placentas. Cell. Mol. Biol. 51 Suppl. (2005) OL713-OL722
13. Ching M.S., Mihaly G.W., Morgan D.J., Date N.M., Hardy K.J., and Smallwood R.A. Low clearance of cimetidine across the human placenta. J. Pharmacol. Exp. Ther. 241 (1987) 1006-1009
14. Collier A.C., Tingle M.D., Paxton J.W., Mitchell M.D., and Keelan J.A. Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. Hum. Reprod. 17 (2002) 2564-2572
15. Dearfield K.L., Abernathy C.O., Ottley M.S., Brantner J.H., and Hayes P.F. Acrylamide: its metabolism, developmental and reproductive effects, genotoxicity, and carcinogenicity. Mutat. Res. 195 (1988) 45-77
16. Doerge D.R., da Costa G.G., McDaniel L.P., Churchwell M.I., Twaddle N.C., and Beland F.A. DNA adducts derived from administration of acrylamide and glycidamide to mice and rats. Mutat. Res. 580 (2005) 131-141
17. Eisenmann C.J., and Miller R.K. The placental transfer and toxicity of selenite relative to cadmium in the human term perfused placenta. Placenta 15 (1994) 883-895
18. Exon J.H. A review of the toxicology of acrylamide. J. Toxicol. Environ. Health B: Crit. Rev. 9 (2006) 397-412
19. Faber J.J. Review of flow limited transfer in the placenta. Int. J. Obstet. Anesth. 4 (1995) 230-237
20. Fennell T.R., Sumner S.C., Snyder R.W., Burgess J., and Friedman M.A. Kinetics of elimination of urinary metabolites of acrylamide in humans. Toxicol. Sci. 93 (2006) 256-267
21. Fennell T.R., Sumner S.C., Snyder R.W., Burgess J., Spicer R., Bridson W.E., and Friedman M.A. Metabolism and hemoglobin adduct formation of acrylamide in humans. Toxicol. Sci. 85 (2005) 447-459
22. Field E.A., Price C.J., Sleet R.B., Marr M.C., Schwetz B.A., and Morrissey R.E. Developmental toxicity evaluation of acrylamide in rats and mice. Fundam. Appl. Toxicol. 14 (1990) 502-512
23. Fuhr U., Boettcher M.I., Kinzig-Schippers M., Weyer A., Jetter A., Lazar A., Taubert D., Tomalik-Scharte D., Pournara P., Jakob V., Harlfinger S., Klaassen T., Berkessel A., Angerer J., Sörgel F., and Schomig E. Toxicokinetics of acrylamide in humans after ingestion of a defined dose in a test meal to improve risk assessment for acrylamide carcinogenicity. Cancer Epidemiol. Biomarkers Prev. 15 (2006) 266-271
24. Gamboa da Costa G., Churchwell M.I., Hamilton L.P., Von Tungeln L.S., Beland F.A., Marques M.M., and Doerge D.R. DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice. Chem. Res. Toxicol. 16 (2003) 1328-1337
25. Ganapathy V., and Prasad P.D. Role of transporters in placental transfer of drugs. Toxicol. Appl. Pharmacol. 207 (2005) 381-387
26. Ghabrial H., Czuba M.A., Stead C.K., Smallwood R.A., and Morgan D.J. Transfer of acipimox across the isolated perfused human placenta. Placenta 12 (1991) 653-661
27. Ghanayem B.I., McDaniel L.P., Churchwell M.I., Twaddle N.C., Snyder R., Fennell T.R., and Doerge D.R. Role of CYP2E1 in the epoxidation of acrylamide to glycidamide and formation of DNA and hemoglobin adducts. Toxicol. Sci. 88 (2005) 311-318
28. Glover D.D., McRobie D.J., and Tracy T.S. Effects of gestational and overt diabetes on placental cytochromes P450 and glutathione S-transferase. Prim. Care Update Obstet. Gyns. 5 (1998) 189
29. Gupta R.C. Nonrandom binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl. Acad. Sci. U.S.A. 81 (1984) 6943-6947
30. Hakkola J., Pasanen M., Hukkanen J., Pelkonen O., Mäenpää J., Edwards R.J., Boobis A.R., and Raunio H. Expression of xenobiotic-metabolizing cytochrome P450 forms in human full-term placenta. Biochem. Pharmacol. 51 (1996) 403-411
31. Hakkola J., Raunio H., Purkunen R., Pelkonen O., Saarikoski S., Cresteil T., and Pasanen M. Detection of cytochrome P450 gene expression in human placenta in first trimester of pregnancy. Biochem. Pharmacol. 52 (1996) 379-383
32. International Agency for Research on Cancer (IARC). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans; Some Industrial Chemicals vol. 60 (1994), IARC, Lyon, France
33. Karl P.I., Gordon B.H., Lieber C.S., and Fisher S.E. Acetaldehyde production and transfer by the perfused human placental cotyledon. Science 242 (1988) 273-275
34. Koyama N., Sakamoto H., Sakuraba M., Koizumi T., Takashima Y., Hayashi M., Matsufuji H., Yamagata K., Masuda S., Kinae N., and Honma M. Genotoxicity of acrylamide and glycidamide in human lymphoblastoid TK6 cells. Mutat. Res. 603 (2006) 151-158
35. Leiser R., and Kaufmann P. Placental structure: in a comparative aspect. Exp. Clin. Endocrinol. 102 (1994) 122-134
36. McRobie D.J., Glover D.D., and Tracy T.S. Effects of gestational and overt diabetes on human placental cytochromes P450 and glutathione S-transferase. Drug Metab. Dispos. 26 (1998) 367-371
37. Miller M.S. Transplacental lung carcinogenesis: molecular mechanisms and pathogenesis. Toxicol. Appl. Pharmacol. 198 (2004) 95-110
38. Mose T., Knudsen L.E., Hedegaard M., and Mortensen G.K. Transplacental transfer of monomethyl phthalate and mono(2-ethylhexyl) phthalate in a human placenta perfusion system. Int. J. Toxicol. 26 (2007) 221-229
39. Myllynen P., Kurttila T., Vaskivuo L., and Vähäkangas K. DNA damage caused by benzo(a)pyrene in MCF-7 cells is increased by verapamil, probenecid and PSC833. Toxicol. Lett. 169 (2007) 3-12
40. Myllynen P., Pasanen M., and Pelkonen O. Human placenta: a human organ for developmental toxicology research and biomonitoring. Placenta 26 (2005) 361-371
41. Myllynen P., Pasanen M., and Vähäkangas K. The fate and effects of xenobiotics in human placenta. Expert Opin. Drug Metab. Toxicol. 3 (2007) 331-346
42. Myllynen P.K., Pienimäki P.K., and Vähäkangas K.H. Transplacental passage of lamotrigine in a human placental perfusion system in vitro and in maternal and cord blood in vivo. Eur. J. Clin. Pharmacol. 58 (2003) 677-682
43. Mölsä M., Heikkinen T., Hakkola J., Hakala K., Wallerman O., Wadelius M., Wadelius C., and Laine K. Functional role of P-glycoprotein in the human blood-placental barrier. Clin. Pharmacol. Ther. 78 (2005) 123-131
44. Parzefall W. Minireview on the toxicity of dietary acrylamide. Food Chem. Toxicol. 46 (2008) 1360-1364
45. Pastrakuljic A., Schwartz R., Simone C., Derewlany L.O., Knie B., and Koren G. Transplacental transfer and biotransformation studies of nicotine in the human placental cotyledon perfused in vitro. Life Sci. 63 (1998) 2333-2342
46. Pienimäki P., Hartikainen A.L., Arvela P., Partanen T., Herva R., Pelkonen O., and Vähäkangas K. Carbamazepine and its metabolites in human perfused placenta and in maternal and cord blood. Epilepsia 36 (1995) 241-248
47. Pienimäki P., Lampela E., Hakkola J., Arvela P., Raunio H., and Vähäkangas K. Pharmacokinetics of oxcarbazepine and carbamazepine in human placenta. Epilepsia 38 (1997) 309-316
48. 6-substituted adenine and 3-substituted cytosine/uracil: formation and persistence in vitro and in vivo. Carcinogenesis 20 (1999) 2025-2032
49. Rasheed A., Hines R.N., and McCarver-May D.G. Variation in induction of human placental CYP2E1: possible role in susceptibility to fetal alcohol syndrome?. Toxicol. Appl. Pharmacol. 144 (1997) 396-400
50. Rurak D.W., Wright M.R., and Axelson J.E. Drug disposition and effects in the fetus. J. Dev. Physiol. 15 (1991) 33-44
51. Sakamoto J., and Hashimoto K. Reproductive toxicity of acrylamide and related compounds in mice-effects on fertility and sperm morphology. Arch. Toxicol. 59 (1986) 201-205
52. Sawada M., Kitamura R., Norose T., Kitada M., Itahashi K., and Kamataki T. Metabolic activation of aflatoxin B1 by human placental microsomes. J. Toxicol. Sci. 18 (1993) 129-132
53. Schenker S., Johnson R.F., Mahuren J.D., Henderson G.I., and Coburn S.P. Human placental vitamin B6 (pyridoxal) transport: normal characteristics and effects of ethanol. Am. J. Physiol. 262 (1992) R966-R974
54. Schettgen T., Kutting B., Hornig M., Beckmann M.W., Weiss T., Drexler H., and Angerer J. Trans-placental exposure of neonates to acrylamide--a pilot study. Int. Arch. Occup. Environ. Health 77 (2004) 213-216
55. Segerbäck D., Calleman C.J., Schroeder J.L., Costa L.G., and Faustman E.M. Formation of N-7-(2-carbamoyl-2-hydroxyethyl)guanine in DNA of the mouse and the rat following intraperitoneal administration of [14C]acrylamide. Carcinogenesis 16 (1995) 1161-1165
56. Sörgel F., Weissenbacher R., Kinzig-Schippers M., Hofmann A., Illauer M., Skott A., and Landersdorfer C. Acrylamide: increased concentrations in homemade food and first evidence of its variable absorption from food, variable metabolism and placental and breast milk transfer in humans. Chemotherapy 48 (2002) 267-274
57. Sumner S.C., MacNeela J.P., and Fennell T.R. Characterization and quantitation of urinary metabolites of [1,2,3-13C]acrylamide in rats and mice using 13C nuclear magnetic resonance spectroscopy. Chem. Res. Toxicol. 5 (1992) 81-89
58. Sumner S.C., Williams C.C., Snyder R.W., Krol W.L., Asgharian B., and Fennell T.R. Acrylamide: a comparison of metabolism and hemoglobin adducts in rodents following dermal, intraperitoneal, oral, or inhalation exposure. Toxicol. Sci. 75 (2003) 260-270
59. Tareke E., Rydberg P., Karlsson P., Eriksson S., and Törnqvist M. Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J. Agric. Food Chem. 50 (2002) 4998-5006
60. Tyl R.W., and Friedman M.A. Effects of acrylamide on rodent reproductive performance. Reprod. Toxicol. 17 (2003) 1-13
61. Urbach J., Boadi W., Brandes J.M., Kerner H., and Yannai S. Effect of inorganic mercury on in vitro placental nutrient transfer and oxygen consumption. Reprod. Toxicol. 6 (1992) 69-75
62. Vieira I., Pasanen M., Raunio H., and Cresteil T. Expression of CYP2E1 in human lung and kidney during development and in full-term placenta: a differential methylation of the gene is involved in the regulation process. Pharmacol. Toxicol. 83 (1998) 183-187
63. Vähäkangas K., and Myllynen P. Experimental methods to study human transplacental exposure to genotoxic agents. Mutat. Res. 608 (2006) 129-135
64. Wirfält E., Paulsson B., Törnqvist M., Axmon A., and Hagmar L. Associations between estimated acrylamide intakes, and hemoglobin AA adducts in a sample from the malmö diet and cancer cohort. Eur. J. Clin. Nutr. 62 (2007) 314-323
65. Xie Q., Sun H., Liu Y., Ding X., Fu D., and Liu K. Adduction of biomacromolecules with acrylamide (AA) in mice at environmental dose levels studied by accelerator mass spectrometry. Toxicol. Lett. 163 (2006) 101-108
66. Zenick H., Hope E., and Smith M.K. Reproductive toxicity associated with acrylamide treatment in male and female rats. J. Toxicol. Environ. Health 17 (1986) 457-472