Absorption of nitro-polycyclic aromatic hydrocarbons by biomembrane models: Effect of the medium lipophilicity

Chemosphere

Volumn 73, Issue 7, 2008, Pages 1108-1114

  Castelli, Francesco ^a   Micieli, Dorotea ^a   Ottimo, Sara ^a   Minniti, Zelica ^a   Sarpietro, Maria Grazia ^a   Librando, Vito ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

2,7 Dinitrofluorene; 2 Nitrofluorene; 3 Nitrofluoranthene; Biomembrane models; Differential scanning calorimetry

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; ARSENIC COMPOUNDS; CHLORINE COMPOUNDS; DIFFERENTIAL SCANNING CALORIMETRY; HYDROCARBONS; ION EXCHANGE MEMBRANES; LASER INTERFEROMETRY; ORGANIC COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS;

2,7-DINITROFLUORENE; 2-NITROFLUORENE; 3-NITROFLUORANTHENE; AB SORPTION PROCESSES; AQUEOUS MEDIUM; BIOMEMBRANE MODELS; BIOMEMBRANES; DIMYRISTOYL PHOSPHATIDYLCHOLINE; LIPOPHILICITY; MULTI LAMELLAR VESICLES; NITRO-POLYCYCLIC AROMATIC HYDROCARBONS; PHASE TRANSITIONS; SCANNING CALORIMETRY;

AROMATIC HYDROCARBONS;

2 NITROFLUORENE; 2,7 DINITROFLUORENE; 3 NITROFLUORANTHENE; AROMATIC NITRO COMPOUND; FLUORENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ABSORPTION; CALORIMETRY; MEMBRANE; MODELING; PAH;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; LIPOPHILICITY; MEMBRANE; TEMPERATURE SENSITIVITY;

ABSORPTION; CALORIMETRY, DIFFERENTIAL SCANNING; CELL MEMBRANE; DIMYRISTOYLPHOSPHATIDYLCHOLINE; MEMBRANES, ARTIFICIAL; MODELS, BIOLOGICAL; PHASE TRANSITION; POLYCYCLIC HYDROCARBONS, AROMATIC; TEMPERATURE;

EID: 53049096063     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2008.07.023     Document Type: Article

References (29)

1. Beije B., and Moller L. 2-Nitrofluorene and related compounds: prevalence and biological effects. Mutat. Res. 196 (1988) 177-209
2. Campbell J., Crumplin G.C., Garner J.V., Garner R.C., Martin C.N., and Rutter A. Nitrated polycyclic aromatic hydrocarbons: potent bacterial mutagens and stimulators of DNA repair synthesis in cultured human cells. Carcinogenesis 2 (1981) 599-606
3. Castelli F., Librando V., and Sarpietro M.G. A calorimetric evidence of the interaction and transport of environmentally carcinogenic compounds through biomembranes. Thermochim. Acta 373 (2001) 133-140
4. Castelli F., Librando V., and Sarpietro M.G. Calorimetric approach of the interaction and absorption of polycyclic aromatic hydrocarbons with model membranes. Environ. Sci. Technol. 36 (2002) 2717-2723
5. Castelli F., Puglisi G., Giammona G., and Ventura C.A. Effect of the complexation of some non steroidal anti-inflammatory drugs with β-cyclodextrin on the interaction with phosphatidylcholine liposomes. Int. J. Pharm. 88 (1992) 1-8
6. Cerniglia C.E., and Somerville C.C. Reductive metabolism of nitroaromatic and nitropolycyclic aromatic hydrocarbons. In: Spain G.C. (Ed). Biodegradation of Nitroaromatic Compounds (1995), Plenum Press, New York 99-115
7. Cui X.-S., Torndal U.-B., Eriksson L.C., and Möller L. Early formation of DNA adducts compared with tumor formation in a long-term tumor study in rats after administration of 2-nitrofluorene. Carcinogenesis 16 (1995) 2135-2141
8. Farkas N., Lorinczy D., Dergez T., Kilar F., and Belagyi J. Effect of polycyclic aromatic hydrocarbons on erythrocyte membranes by DSC and EPR. Environ. Toxicol. Pharm. 16 (2004) 163-168
9. Fu P.P. Metabolism of nitro-polycyclic aromatic hydrocarbons. Drug Metab. Rev. 22 (1990) 209-268
10. IARC (International Agency for Research on Cancer). Monographs on the evaluation of the carcinogenic risks to humans. Diesel and Gasoline Engine Exhausts and Some Nitroarenes vol. 46 (1989), International Agency for Research on Cancer, Lyon, France
11. IPCS, Environmental Health Criteria 229. Selected nitro- and nitro-oxy-polycyclic aromatic hydrocarbons. International Programme on Chemical Safety. World Health Organization, Geneva, Switzerland, 2003.
12. Jorgensen K., Ipsen J.H., Mouritsen O.G., Bennet D., and Zuckermann M.J. The effects of density fluctuations on the partitioning of foreign molecules into bilayers: application to anaesthetics and insecticides. Biochim. Biophys. Acta 1067 (1991) 241-253
13. 14C]pyrene to DNA and protein in cultured lung macrophages and respiratory tissues. Cancer Lett. 19 (1983) 241-246
14. Landvik N.E., Gorria M., Arlt V.M., Asare N., Solhaug A., Lagadic-Gossmann D., and Holme J.A. Effects of nitrated-polycyclic aromatic hydrocarbons and diesel exhaust particle extracts on cell signalling related to apoptosis: possible implications for their mutagenic and carcinogenic effects. Toxicology 231 (2007) 159-174
15. Lewtas J. Air pollution combustion emissions: characterization of causative agents and mechanisms associated with cancer, reproductive, and cardiovascular effects. Mutat. Res. 636 (2007) 95-133
16. Li Y.S., Fu P.P., and Church J.S. The conformation of some nitro-polycyclic aromatic hydrocarbons. J. Mol. Struct. 550-551 (2000) 217-223
17. Librando V., Castelli F., and Sarpietro M.G. Role of lipophilic medium in the absorption of polycyclic aromatic compounds by biomembranes. Environ. Toxicol. Pharm. 14 (2003) 25-32
18. Librando V., Sarpietro M.G., Cascone C., Minniti Z., and Castelli F. Time dependent absorption evidence of phenylurea derivatives herbicides on biomembrane models: a DSC study. Environ. Chem. 2 (2005) 63-70
19. Librando V., Sarpietro M.G., Minniti Z., Micieli D., and Castelli F. Biomimetic approach to biomembrane models studies: medium influence on the interaction kinetics of some phenylurea derivatives herbicides. Environ. Sci. Technol. 40 (2006) 2462-2468
20. Malejka-Giganti D., Niehans G., Reichert M.A., Bennett K.K., and Bliss R.L. Potent carcinogenicity of 2,7-dinitrofluorene, an environmental pollutant, for the mammary gland of female Sprague-Dawley rats. Carcinogenesis 20 (1999) 2017-2023
21. Marsh D. Physical characterization of liposomes for understanding structure-function relationships in biological membranes. In: Barenholz Y., and Lasic D.D. (Eds). Handbook of Nonmedical Applications of Liposomes (1995), CRC Press Inc., Boca Raton, FL 1-19
22. Marshall J.C., Royer R.E., Li A.P., Kusewitt D.F., and Brooks A.L. Acute genetic toxicity of 1-nitropyrene and its fate after single oral doses to rats. J. Toxicol. Environ. Health 10 (1982) 373-384
23. Ohnishi Y., Kinouchi T., Manabe Y., Tsutsui H., Otsuka H., Tokiwa H., and Otofuji T. Nitro compounds in environmental mixtures and food. In: Waters M.D., Shandhu S.S., Lewtas J., Claxton L., Strauss G., and Nesnow S. (Eds). Short-Term Genetics Bioassays in the Evaluation of Complex Environmental Mixtures (1985), Plenum Press, New York 195-204
24. Pedersen D.U., Durant J.L., Taghizadeh K., Hemond H.F., Lafleur A.L., and Cass G.R. Human cell mutagens in respirable airbone particles from the Northeastern United States. 2. Quantification of mutagens and other organic compounds. Environ. Sci. Technol. 39 (2005) 9547-9560
25. Pitts Jr. J.N., Van Cauwenberghe K.A., Grosjean D., Schmid J.P., Fits D.R., Belser Jr. W.L., Knudson G.B., and Hynds E.M. Atmospheric reactions of polycyclic aromatic hydrocarbons: facile formation of mutagenic nitro derivatives. Science 202 (1978) 515-519
26. Purohit V., and Basu A.K. Mutagenicity of nitroaromatic compounds. Chem. Res. Toxicol. 13 (2000) 673-692
27. Rouser G., Fleicher S., and Yamamoto A. Two dimensional thin-layer chromatographic separation of polar lipids and determination of phospholipids by phosphorous analysis of spots. Lipids 5 (1970) 494-496
28. Tenchov B. On the reversibility of phase transitions in lipidwater systems. Chem. Phys. Lipids 57 (1991) 165-177
29. Walde P. Preparation of Vesicles (Liposomes). In: Nalwa H.S. (Ed). ASP Encyclopedia of Nanoscience and Nanotechnology (2004), American Scientific Publishers, Stevenson Ranch, Calif 43-79