Human serum albumin stability and toxicity of anthraquinone dye alizarin complexone: An albumin-dye model

Ecotoxicology and Environmental Safety

Volumn 79, Issue , 2012, Pages 238-246

  Ding, Fei ^a,b   Zhang, Li ^a   Diao, Jian Xiong ^a   Li, Xiu Nan ^c   Ma, Lin ^d   Sun, Ying ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b Massachusetts Institute of Technology   (United States)

^c INSTITUTE OF PROCESS ENGINEERING   (China)

^d TSINGHUA UNIVERSITY   (China)

Author keywords

Anthraquinone dye; Circular dichroism; Fluorescence; Human serum albumin; Molecular modeling

Indexed keywords

ALIZARIN; ALIZARIN COMPLEXONE; ANTHRAQUINONE DERIVATIVE; HUMAN SERUM ALBUMIN; TRYPTOPHAN; UNCLASSIFIED DRUG;

DYE; LIGAND; TOXICITY; TOXICOLOGY;

ALPHA HELIX; ARTICLE; CIRCULAR DICHROISM; COMPLEX FORMATION; CONJUGATION; CONTROLLED STUDY; ENERGY TRANSFER; FLUORESCENCE; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; LIGAND BINDING; MOLECULAR MODEL; PROTEIN STABILITY; STEADY STATE;

ANTHRAQUINONES; COLORING AGENTS; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, CHEMICAL; MOLECULAR DYNAMICS SIMULATION; SERUM ALBUMIN;

EID: 84862793090     PISSN: 01476513     EISSN: 10902414     Source Type: Journal    
DOI: 10.1016/j.ecoenv.2012.01.009     Document Type: Article

References (66)

1. Abou-Zied O.K. Investigating 2,2'-bipyridine-3,3'-diol as a microenvironment-sensitive probe: its binding to cyclodextrins and human serum albumin. J. Phys. Chem. B 2007, 111:9879-9885.
2. Abou-Zied O.K., Al-Shihi O.I.K. Characterization of subdomain IIA binding site of human serum albumin in its native, unfolded, and refolded states using small molecular probes. J. Am. Chem. Soc. 2008, 130:10793-10801.
3. Abou-Zied O.K., Al-Lawatia N. Exploring the drug-binding site Sudlow I of human serum albumin: the role of water and Trp214 in molecular recognition and ligand binding. ChemPhysChem 2011, 12:270-274.
4. Abou-Zied, O.K., 2011b. Revealing the ionization ability of binding site I in human serum albumin using 2-(2'-hydroxyphenyl)benzoxazole as a pH sensitive probe. Phys. Chem. Chem. Phys., http://10.1039/C2CP23337A.
5. Alarcón E., Aspée A., Abuin E.B., Lissi E.A. Evaluation of solute binding to proteins and intra-protein distances from steady state fluorescence measurements. J. Photochem. Photobiol. B: Biol. 2012, 106:1-17.
6. Bagatolli L.A., Kivatinitz S.C., Aguilar F., Soto M.A., Sotomayor P., Fidelio G.D. Two distinguishable fluorescent modes of 1-anilino-8-naphthalenesulfonate bound to human albumin. J. Fluoresc. 1996, 6:33-40.
7. Beauchemin R., N'soukpoé-Kossi C.N., Thomas T.J., Thomas T., Carpentier R., Tajmir-Riahi H.A. Polyamine analogues bind human serum albumin. Biomacromolecules 2007, 8:3177-3183.
8. Bos O.J.M., Remijn J.P.M., Fischer M.J.E., Wilting J., Janssen L.H.M. Location and characterization of the warfarin binding site of human serum albumin: a comparative study of two large fragments. Biochem. Pharmacol. 1988, 37:3905-3909.
9. Bourassa P., Dubeau S., Maharvi G.M., Fauq A.H., Thomas T.J., Tajmir-Riahi H.A. Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin. Biochimie 2011, 93:1089-1101.
10. Bourassa P., Hasni I., Tajmir-Riahi H.A. Folic acid complexes with human and bovine serum albumins. Food Chem. 2011, 129:1148-1155.
11. Bree F., Nguyen P., Albengres E., Urien S., Riant P., Welling P.G., Tillement J.-P. Evidence for isoxicam binding to site I as a primary site and to site II as a secondary site of human serum albumin. Biochem. Pharmacol. 1989, 38:753-758.
12. Brodersen R., Sjödin T., Sjöholm I. Independent binding of ligands to human serum albumin. J. Biol. Chem. 1977, 252:5067-5072.
13. Carter D.C. Crystallographic survey of albumin drug interaction and preliminary applications in cancer chemotherapy. Burger's Medicinal Chemistry, Drug Discovery and Development 2010, 437-467. John Wiley & Sons, Inc., Hoboken. D.J. Abraham, D.P. Rotella (Eds.).
14. Carter D.C., Ho J.X. Structure of serum albumin. Adv. Protein Chem. 1994, 45:153-203.
15. Cattoni D.I., Kaufman S.B., Flecha F.L.G. Kinetics and thermodynamics of the interaction of 1-anilino-naphthalene-8-sulfonate with proteins. Biochim. Biophys. Acta-Proteins Proteomics 2009, 1794:1700-1708.
16. 0/air process. J. Hazard. Mater. 2009, 166:1127-1133.
17. Clegg R.M. The vital contributions of Perrin and Förster. Biophoton. Int. 2004, 11:42-45.
18. Colmenarejo G., Alvarez-Pedraglio A., Lavandera J.-L. Cheminformatic models to predict binding affinities to human serum albumin. J. Med. Chem. 2001, 44:4370-4378.
19. Dangles O., Dufour C. Flavonoid-protein interactions. Flavonoids: Chemistry, Biochemistry and Applications 2006, 443-469. Chemical Rubber Company Press, Boca Raton. T. Andersen, K.R. Markham (Eds.).
20. De-Llanos R., Sánchez-Cortes S., Domingo C., García-Ramos J.V., Sevilla P. Surface plasmon effects on the binding of antitumoral drug emodin to bovine serum albumin. J. Phys. Chem. C 2011, 115:12419-12429.
21. Endo S., Goss K.-U. Serum albumin binding of structurally diverse neutral organic compounds: data and models. Chem. Res. Toxicol. 2011, 24:2293-2301.
22. Epolito W.J., Yang H., Bottomley L.A., Pavlostathis S.G. Kinetics of zero-valent iron reductive transformation of the anthraquinone dye Reactive Blue 4. J. Hazard. Mater. 2008, 160:594-600.
23. Essemine J., Hasni I., Carpentier R., Thomas T.J., Tajmir-Riahi H.A. Binding of biogenic and synthetic polyamines to Β-lactoglobulin. Int. J. Biol. Macromol. 2011, 49:201-209.
24. Förster T. Zwischenmolekulare Energiewanderung und Fluoreszenz. Ann. Phys. 1948, 437:55-75.
25. Förster T. 10th spiers memorial lecture. Transfer mechanisms of electronic excitation. Discuss. Faraday Soc. 1959, 27:7-17.
26. Ghuman J., Zunszain P.A., Petitpas I., Bhattacharya A.A., Otagiri M., Curry S. Structural basis of the drug-binding specificity of human serum albumin. J. Mol. Biol. 2005, 353:38-52.
27. Gonzàlez-Jimènez J., Frutos G., Cayre I. Fluorescence quenching of human serum albumin by xanthines. Biochem. Pharmacol. 1992, 44:824-826.
28. Greenfield N.J. Using circular dichroism spectra to estimate protein secondary structure. Nat. Protoc. 2006, 1:2876-2890.
29. Gupta V.K., Suhas Application of low-cost adsorbents for dye removal-a review. J. Environ. Manage. 2009, 90:2313-2342.
30. Hage D.S., Anguizola J., Barnaby O., Jackson A., Yoo M.J., Papastavros E., Pfaunmiller E., Sobansky M., Tong Z.H. Characterization of drug interactions with serum proteins by using high-performance affinity chromatography. Curr. Drug Metab. 2011, 12:313-328.
31. Hasni I., Bourassa P., Hamdani S., Samson G., Carpentier R., Tajmir-Riahi H.-A. Interaction of milk α- and Β-caseins with tea polyphenols. Food Chem. 2011, 126:630-639.
32. Hasni I., Bourassa P., Tajmir-Riahi H.-A. Binding of cationic lipids to milk Β-lactoglobulin. J. Phys. Chem. B 2011, 115:6683-6690.
33. Hassler N., Baurecht D., Reiter G., Fringeli U.P. In situ FTIR ATR spectroscopic study of the interaction of immobilized human serum albumin with cholate in aqueous environment. J. Phys. Chem. C 2011, 115:1064-1072.
34. He X.M., Carter D.C. Atomic structure and chemistry of human serum albumin. Nature 1992, 358:209-215.
35. Ibrahim N., Ibrahim H., Kim S., Nallet J.-P., Nepveu F. Interactions between antimalarial indolone-N-oxide derivatives and human serum albumin. Biomacromolecules 2010, 11:3341-3351.
36. Kalanur S.S., Seetharamappa J., Kalalbandi V.K.A. Characterization of interaction and the effect of carbamazepine on the structure of human serum albumin. J. Pharm. Biomed. Anal. 2010, 53:660-666.
37. Khan M.K., Rakotomanomana N., Dufour C., Dangles O. Binding of citrus flavanones and their glucuronides and chalcones to human serum albumin. Food Funct. 2011, 2:617-626.
38. Kobori Y., Fuki M. Protein-ligand structure and electronic coupling of photoinduced charge-separated state: 9,10-Anthraquinone-1-sulfonate bound to human serum albumin. J. Am. Chem. Soc. 2011, 133:16770-16773.
39. Kratochwil N.A., Huber W., Müller F., Kansy M., Gerber P.R. Predicting plasma protein binding of drugs: a new approach. Biochem. Pharmacol. 2002, 64:1355-1374.
40. Lakowicz J.R. Principles of Fluorescence Spectroscopy 2006, Springer Science+Business Media, New York. third ed.
41. Langham J.J., Cleves A.E., Spitzer R., Kirshner D., Jain A.N. Physical binding pocket induction for affinity prediction. J. Med. Chem. 2009, 52:6107-6125.
42. Leggio C., Galantini L., Pavel N.V. About the albumin structure in solution: cigar Expanded form versus heart normal shape. Phys. Chem. Chem. Phys. 2008, 10:6741-6750.
43. Li Q., Seeger S. Multidonor deep-UV FRET study of protein-ligand binding and its potential to obtain structure information. J. Phys. Chem. B 2011, 115:13643-13649.
44. Liu Z.J., Zheng X.L., Yang X.R., Wang E.K., Wang J. Affinity and specificity of levamlodipine-human serum albumin interactions: insights into its carrier function. Biophys. J. 2009, 96:3917-3925.
45. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193:265-275.
46. Mahmoudi M., Lynch I., Ejtehadi M.R., Monopoli M.P., Bombelli F.B., Laurent S. Protein-nanoparticle interactions: opportunities and challenges. Chem. Rev. 2011, 111:5610-5637.
47. Mandeville J.S., Tajmir-Riahi H.A. Complexes of dendrimers with bovine serum albumin. Biomacromolecules 2010, 11:465-472.
48. Miller J.N. Recent advances in molecular luminescence analysis. Proc. Anal. Div. Chem. Soc. 1979, 16:203-208.
49. Novotný č., Dias N., Kapanen A., Malachová K., Vándrovcová M., Itävaara M., Lima N Comparative use of bacterial, algal and protozoan tests to study toxicity of azo- and anthraquinone dyes. Chemosphere 2006, 63:1436-1442.
50. Patel S., Datta A. Steady state and time-resolved fluorescence investigation of the specific binding of two chlorin derivatives with human serum albumin. J. Phys. Chem. B 2007, 111:10557-10562.
51. Peters T. All about Albumin: Biochemistry, Genetics, and Medical Applications 1995, Academic Press, San Diego.
52. Petitpas I., Bhattacharya A.A., Twine S., East M., Curry S. Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I. J. Biol. Chem. 2001, 276:22804-22809.
53. Rohacova J., Sastre G., Marin M.L., Miranda M.A. Dansyl labeling to modulate the relative affinity of bile acids for the binding sites of human serum albumin. J. Phys. Chem. B 2011, 115:10518-10524.
54. Sahoo B.K., Ghosh K.S., Dasgupta S. Molecular interactions of isoxazolcurcumin with human serum albumin: spectroscopic and molecular modeling studies. Biopolymers 2009, 91:108-119.
55. Salvalaglio M., Muscionico I., Cavallotti C. Determination of energies and sites of binding of PFOA and PFOS to human serum albumin. J. Phys. Chem. B 2010, 114:14860-14874.
56. Seedher N., Agarwal P. Complexation of fluoroquinolone antibiotics with human serum albumin: a fluorescence quenching study. J. Lumin. 2010, 130:1841-1848.
57. Seidel C.A.M., Schulz A., Sauer M.H.M. Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies. J. Phys. Chem. 1996, 100:5541-5553.
58. Shakeri M., Shoda M. Efficient decolorization of an anthraquinone dye by recombinant dye-decolorizing peroxidase (rDyP) immobilized in silica-based mesocellular foam. J. Mol. Catal. B: Enzym. 2010, 62:277-281.
59. Stryer L. The interaction of a naphthalene dye with apomyoglobin and apohemoglobin: a fluorescent probe of non-polar binding sites. J. Mol. Biol. 1965, 13:482-495.
60. Stryer L. Fluorescence spectroscopy of proteins. Science 1968, 162:526-533.
61. Sudlow G., Birkett D.J., Wade D.N. The characterization of two specific drug binding sites on human serum albumin. Mol. Pharmacol. 1975, 11:824-832.
62. Takahashi D., Yamashita S., Prakash O., Nishimoto E. Rotational diffusion analysis of polyethylene glycol induced protein interactions. J. Phys. Chem. B 2011, 115:11786-11792.
63. Venturini S., Tamaro M. Mutagenicity of anthraquinone and azo dyes in Ames' Salmonella typhimurium test. Mutat. Res./Genet. Toxicol. 1979, 68:307-312.
64. Vuignier K., Schappler J., Veuthey J.-L., Carrupt P.-A., Martel S. Drug-protein binding: a critical review of analytical tools. Anal. Bioanal. Chem. 2010, 398:53-66.
65. Wasylewski M., Małecki J., Wasylewski Z. Fluorescence study of Escherichia coli cyclic AMP receptor protein. J. Protein Chem. 1995, 14:299-308.
66. Xu M.Y., Guo J., Zeng G.Q., Zhong X.Y., Sun G.P. Decolorization of anthraquinone dye by Shewanella decolorationis S12. Appl. Microbiol. Biotechnol. 2006, 71:246-251.