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2006 | 53 | 1 |
Tytuł artykułu

Interaction of anthracene and its oxidative derivatives with human serum albumin

Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Binding affinities of ten polycyclic aromatic hydrocarbons to albumin were determined: anthracene, its eight oxy-derivatives: anthraquinone, 9-anthracenemethanol, 9-anthraldehyde, 9-anthracenecarboxylic acid, 1,4-dihydroxyanthraquinone, 1,5-dihydroxyanthraquinone, 1,8-dihydroxyanthraquinone, 2,6-dihydroxyanthraquinone and benzo[a]pyrene. The quenching of albumin fluorescence was used to measure the PAH — protein interaction. The theoretical curve of calculated fluorescence was fitted to experimental data after necessary corrections regarding PAHs fluorescence and inner filter effect. From the numerical fitting the final association constants were calculated. Anthracene and anthraquinone failed to quench the albumin fluorescence. 9-anthracenecarboxylic acid showed the highest, while 9-anthracenemethanol the weakest albumin binding affinity. The affinity constants determined for 9-anthraldehyde and benzo[a]pyrene were of the same magnitude and indicated low-affinity binding to albumin. The constants obtained for the four dihydroxyanthraquinones were higher, but dissimilar, which suggests that the position of the functional group in anthracene molecule influences the binding constant. Moreover, this study suggests that the type of substituent plays a significant role in PAH-albumin complex formation. The carboxylic group increases the binding affinity of the anthracene molecule the most rather than the presence of both carbonyl and hydroxyl groups. The lowest affinity constants were obtained for aldehyde, methyl and carbonyl substituents.
Wydawca
-
Rocznik
Tom
53
Numer
1
Opis fizyczny
p.101-112,fig.,ref.
Twórcy
autor
  • National Institute of Public Health, Warsaw, Poland
autor
autor
Bibliografia
  • Abdel-Mottaleb MSA, Galal HR, Dessouky AFM, El-Naggar M, Mekkawi D, Ali SS, Attya GM (2000) Fluorescence and photostability studies of anthracene-9-carboxylic acid in different media. Int J Photoenergy 2: 47–53.
  • Boysen G, Hecht SS (2003) Analysis of DNA and protein adducts of benzo[a]pyrene in human tissues using structure-specific methods. Mutat Res 543: 17–30.
  • Brunmark P, Harriman S, Skipper PL, Wishnok JS, Amin S, Tannenbaum SR (1997) Identification of subdomain IB in human serum albumin as a major binding site for polycyclic aromatic hydrocarbons epoxides. Chem Res Toxicol 10: 880–886.
  • Dabestani R, Ivanov N (1999) A compilation, spectroscopic and photophysical properties of polycyclic aromatic hydrocarbons. Photochem Photobiol 70: 10–34.
  • Ehrenberg L, Granath F, Tornqvist M (1996) Macromolecule adducts as biomarkers of exposure to environmental mutagens in human populations. Environ Health Perspect 104: 423–428.
  • Epps DE, Raub TJ, Kezdy FJ (1995) A general, wide-range spectrofluorimetric method for measuring the site-specific affinities of drugs toward human serum albumin. Anal Biochem 227: 342–350.
  • Epps DE, Raub TJ, Caiolfa V, Chiari A, Zamai M (1999) Determination of the affinity of drugs toward serum albumin by measurement of the quenching of the intrinsic Tryptophan fluorescence of the protein. J Pharm Pharmacol 51: 41– 48.
  • Fabriciova G, Sanchez-Cortes S, Garcia-Ramos JV, Miskovsky P (2004) Joint application of micro-Raman and surface-enchanced Raman spectroscopy to the interaction study of the antitumoral anthraquinone drugs danthron and quinizarin with albumins. J Raman Spectrosc 35: 384–389.
  • Garner RC (1998) The role of DNA adducts in chemical carcinogenesis. Mut Res 402: 67–75.
  • Guo M, Zou J-W, Yi P-G, Shang Z-C, Hu G-X, Yu Q-S (2004) Binding interaction of gatifloxacin with bovine serum albumin. Anal Sci 20: 465–470.
  • Hecht SS, Chen M, Yagi H, Jerina DM, Carmella SG (2003) r-1,t-2,3,c-4-Tetrahydroxy-1,2,3,4-tetrahydrophenanthrene in human urine: a potential biomarker for assessing polycyclic aromatic hydrocarbon metabolic activation. Cancer Epidemiol Biomark Prev 12: 1501–1508.
  • Honey S, O’Keefe P, Drahushuk AT, Olson JR, Kumar S, Sikka HC (2000) Metabolism of benzo(a)pyrene by duck liver microsomes. Comp Biochem Physiol C 126: 285–292.
  • Jacob J, Seidel A (2002) Biomonitoring of polycyclic aromatic hydrocarbons in human urine. J Chromatogr B 778: 31–47.
  • Kragh-Hansen U (1990) Structure and ligand binding properties of human serum albumin. Dan Med Bull 37: 57–84.
  • Kumar S, Chang RL, Wood AW, Xie JG, Huang MT, Cui XX, Kole PL, Sikka HC, Balani SK, Conney AH, Jerina DM (2001) Tumorigenicity of racemic and optically pure bay region diol epoxides and other derivatives of the nitrogen heterocycle dibenz[a,h]acridine on mouse skin. Carcinogenesis 22: 951–955.
  • Lecoq S, Chalvet O, Strapelias H, Grover PL, Philips DH, Duquesne M (1991) Microsomal metabolism of dibenz[a,c]anthracene, dibenz[a,h]anthracene and dibenz[a,j]anthracene to bisdihydrodiols and polyhydroxylated products. Chem Biol Interact 80: 261–279.
  • Lee BM, Baoyun Y, Herbert R, Hemminki K, Perera FP, Santella RM (1991) Immunologic measurement of polycyclic aromatic hydrocarbon-albumin adducts in foundry workers and roofers. Scand J Work Environ Health 17: 190–194.
  • Lee W, Shin HS, Hong JE, Pyo H, Kim Y (2003) Studies on the analysis of benzo(a)pyrene and its metabolites in biological samples by using high performance liquid chromatography/fluorescence detection and gas chromatography/ mass spectrometry. Bull Korean Chem Soc 24: 559–565.
  • Levine RL (1977) Fluorescence quenching studies of the binding of bilirubin to albumin. Clin Chem 23: 2292–2301.
  • Lin Z-P, Aue WA (2000) Gas-phase luminescence of aromatic carbonyl compounds in excited nitrogen at atmospheric pressure. Can J Chem 78: 95–117.
  • Ma JK, Fu PP, Luzzi LA (1977) Protein binding of benz[a]anthracene and benzo[a]pyrene. J Pharm Sci 66: 209–213.
  • Mayers RA (2000) Ladokhin Encyclopedia of Analytical Chemistry, pp 5762–5779, John Wiley & Sons LTD Chichester.
  • Morzocchi MP, Mantini AR, Casu M, Smulevich G (1998) Intramolecular hydrogen bonding and excited state proton transfer in hydroxyanthraquinones as studied by electronic spectra, resonance Raman scattering and transform analysis. J Chem Phys 108: 534–549.
  • Niedzwiecka A, Marcotrigiano J, Stepinski J, Jankowska- Anyszka M, Wyslouch-Cieszynska A, Dadlez M, Gingras A-C, Mak P, Darzynkiewicz E, Sonenberg N, Burley SK, Stolarski R (2002) Biophysical studies of eIF4E cap-binding protein: recognition of mRNA 5’ cap structure and synthetic fragments of eIF4G and 4E-BP1 proteins. J Mol Biol 319: 615–635.
  • Nielsen PS, Okkels H, Sigsgaard T, Kyrtopoulos S, Autrup H (1996) Exposure to urban and rural air pollution: DNA and protein adducts and effect of glutathione-Stransferase genotype on adduct levels. Int Arch Environ Health 68: 170–176.
  • Otto S, Bhattacharyya KK, Jefcoate CR (1992) Polycyclic aromatic hydrocarbon metabolism in rat adrenal, ovary and testis microsomes is catalyzed by the same novel cytochrome P450 (P450RAP). Endocrinology 131: 3067–3076.
  • Paal K, Muller J, Hegedus L (2001) High affinity binding of paclitaxel to human serum albumin. Eur J Biochem 268: 2187–2191.
  • Pangrekar J, Kole PL, Honey SA, Kumar S, Sikka HC (2003) Metabolism of chrysene by brown bullhead liver microsomes. Toxicol Sci 71: 67–73.
  • Pashko LL, Schwartz AG (1996) Inhibition of 7,12-dimethylbenz[ a]anthracene-induced lung tumorigenesis in A/J mice by food restriction is reversed by adrenalectomy. Carcinogenesis 17: 209–212.
  • Perry JL, Il’ichev YV, Kempf VR, McClendon J, Park G, Manderville RA, Rüker F, Dockal M, Simon JD (2003) Binding of ochratoxin a derivatives to human serum albumin. J Phys Chem B 107: 6644–6647.
  • Philips DH (1999) Polycyclic aromatic hydrocarbons in the diet. Mutat Res 443: 139–247.
  • Prodi G, Grilli S, Mazzullo M, Colacci A, Arfellini G (1984) Comparison between photo-induction and microsomal activation of polycyclic hydrocarbons with different oncogenic potency. Toxicol Pathol 12: 185–188.
  • Qiu Y, Burlingame AL, Benet LZ (1998) Mechanisms for covalent binding of benoxaprofen glucuronide to human serum albumin. Drug Metabol Disp 26: 246–256.
  • Quiming NS, Vergel RB, Nicolas MG, Villanueva JA (2005) Interaction of bovine serum albumin and metallothionein. J Health Sci 51: 8–15.
  • Ruchirawat M, Mahidol Ch, Tangjarukij Ch, Pui-ock S, Jensen O, Kampeerawipakorn O, Tuntaviroon J, Aramphongphan A, Autrup H (2002) Exposure to genotoxins present in ambient air in Bangkok, Thailand – particle associated polycyclic aromatic hydrocarbons and biomarkers. Sci Tot Env 287: 121–132.
  • Santella RM, Perera FP, Young TL, Zhang Y-J, Chiamprasert S, Tang D, Wang LW, Beachman A, Lin J-H, DeLeo VA (1995) Polycyclic aromatic hydrocarbon-DNA and protein adducts in coal tar treated patients and controls and their relationship to glutathione Stransferase genotype. Mutat Res 334: 117–124.
  • Silva D, Cortez CM, Louro SRW (2004) Quenching of the intrinsic fluorescence of bovine serum albumin by chlorpromazine and hemin. Braz J Med Biol Res 37: 963–968.
  • Sram RJ, Binkova B (2000) Molecular epidemiology studies on occupational and environmental exposure to mutagens and carcinogens, 1997–1999. Environ Health Perspect 108: 57–70.
  • Tannenbaum SR, Skipper PL, Wishnok JS, Stillwell WG, Day BW, Taghizadeh K (1993) Characterization of various classes of protein adducts. Environ Health Perspect 99: 51–5.
  • Toulokhonova I, Bjerke-Kroll B, West R (2003) Synthesis and photophysical properties of novel fluorescent silicones. J Organ Chem 686: 101–104.
  • Wang Ch-J, Lee M-J, Chang M-Ch, Lin J-K (1995) Inhibition of tumor promotion in benzo[a]pyrene-initiated CD-1 mouse skin by crocetin. Carcinogenesis 16: 187–191.
  • Willett KL, Gardinali PR, Lienesch LA, Di Giulio RT (2000) Comparative metabolism and excretion of benzo(a)pyrene in 2 species of Ictalurid catfish. Toxicol Sci 58: 68–76.
  • Zuberek J, Wyslouch-Cieszynska A, Niedzwiecka A, Dadlez M, Stepinski J, Augustyniak W, Gingras A-C, Zhang Z, Burley SK, Sonenberg N, Stolarski R, Darzynkiewicz E (2003) Phosphorylation of eIF4E attenuates its interaction with mRNA 5’ cap analogs by electrostatic repulsion: Intein-mediated protein ligation strategy to obtain phosphorylated protein. RNA 9: 52–61.
Typ dokumentu
Bibliografia
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Identyfikator YADDA
bwmeta1.element.agro-article-9faf467d-552a-48a2-bfb2-8e37be0a9c4b
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