Comparative studies on the interactions of honokiol and magnolol with human serum albumin

Journal of Pharmaceutical and Biomedical Analysis

Volumn 66, Issue , 2012, Pages 240-251

  Cheng, Zhengjun ^a  

^a CHINA WEST NORMAL UNIVERSITY   (China)

Author keywords

Binding constants; Fluorescence spectroscopy; Honokiol; Human serum albumin; Magnolol

Indexed keywords

BIOPOLYMER; CALCIUM ION; COPPER ION; HONOKIOL; HUMAN SERUM ALBUMIN; MAGNOLOL; MANGANESE; TRYPTOPHAN; TYROSINE; ZINC ION;

ARTICLE; BINDING AFFINITY; BINDING SITE; BIOCHEMISTRY; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG TOXICITY; ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; HUMAN; HYDROPHOBICITY; MICROENVIRONMENT; MOLECULAR INTERACTION; PHARMACOKINETICS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; RADIATION ENERGY; STATIC ELECTRICITY; THERMODYNAMICS; ULTRAVIOLET RADIATION;

BIPHENYL COMPOUNDS; CIRCULAR DICHROISM; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGNANS; PROTEIN BINDING; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STATIC ELECTRICITY;

EID: 84861225927     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.03.010     Document Type: Article

References (47)

1. Berde C.B., Hudson B.S., Simoni R.D., Sklar L.A. Human serum albumin: spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin. J. Biol. Chem. 1979, 254:391-400.
2. He X.M., Carter D.C. Atomic structure and chemistry of human serum albumin. Nature 1992, 358:209-215.
3. 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.
4. Sudlow G., Birkett D.J., Wade D.N. Further characterization of specific drug binding sites on human serum albumin. Mol. Pharmacol. 1976, 12:1052-1061.
5. Hou H.N., Qi Z.D., OuYang Y.W., Liao F.L., Zhang Y., Liu Y. Studies on interaction between Vitamin B12 and human serum albumin. J. Pharm. Biomed. Anal. 2008, 47:134-139.
6. Hu Y.J., Liu Y., Xiao X.H. Investigation of the interaction between berberine and human serum albumin. Biomacromolecules 2009, 10:517-521.
7. Neelam S., Gokara M., Sudhamalla B., Amooru D.G., Subramanyam R. Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. J. Phys. Chem. B 2010, 114:3005-3012.
8. Yue Y.Y., Liu J.M., Fan J., Yao X.J. Binding studies of phloridzin with human serum albumin and its effect on the conformation of protein. J. Pharm. Biomed. Anal. 2011, 56:336-342.
9. Matei I., Ionescu S., Hillebrand M. Interaction of fisetin with human serum albumin by fluorescence, circular dichroism spectroscopy and DFT calculations: binding parameters and conformational changes. J. Lumin. 2011, 131:1629-1635.
10. Wang Y.L., Zhang T., Xu J., Du W.H. Comparison of the binding affinity of chlorogenic acid with two serum albumins. Int. J. Biol. Macromol. 2011, 48:81-86.
11. Bourassa P., Hasni I., Tajmir-Riahi H.A. Folic acid complexes with human and bovine serum albumins. Food Chem. 2011, 129:1148-1155.
12. Zhou X.M., Yang Q., Xie X.Y., Hu Q., Qi F.M., Rahman Z.U., Chen X.G. NMR, multi-spectroscopic and molecular modeling approach to investigate the complexes between C.I. Acid Orange 7 and human serum albumin in vitro. Dyes and Pigments 2012, 92:1100-1107.
13. Shen C.C., Ni C.L., Shen Y.C., Huang Y.L., Kuo C.H., Wu T.S., Chen C.C. Phenolic constituents from the stem bark of Magnolia officinalis. J. Nat. Prod. 2009, 72:168-171.
14. Lin Y.R., Chen H.H., Ko C.H., Chan M.H. Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage. Eur. J. Pharmacol. 2006, 537:64-69.
15. Lin Y.R., Chen H.H., Ko C.H., Chan M.H. Effects of honokiol and magnolol on acute and inflammatory pain models in mice. Life Sci. 2007, 81:1071-1078.
16. Zhao C., Liu Z.Q. Comparison of antioxidant abilities of honokiol and magnolol to scavenge radicals and to protect DNA. Biochimie 2011, 93:1755-1760.
17. 2+ mobilization in rat cortical neurons and human neuroblastoma SH-SY5Y cells. Eur. J. Pharmacol. 2003, 474:199-204.
18. Fukuyama Y., Nakade K., Minoshima Y., Yokoyama R., Zhai H., Mitsumoto Y. Neurotrophic activity of honokiol on the cultures of fetal rat cortical neurons. Bioorg. Med. Chem. Lett. 2002, 12:1163-1166.
19. Alonso-Castro A.J., Zapata-Bustos R., Domínguez F., García-Carrancá A., Salazar-Olivo L.A. Magnolia dealbata Zucc and its active principles honokiol and magnolol stimulate glucose uptake in murine and human adipocytes using the insulin-signaling pathway. Phytomedicine 2011, 18:926-933.
20. Matsui N., Takahashi K., Takeichi M., Kuroshita T., Noguchi K., Yamazaki K., Tagashira H., Tsutsui K., Okada H., Kido Y., Yasui Y., Fukuishi N., Fukuyama Y., Akagi M. Honokiol and magnolol prevent learning and memory impairment and cholinergic deficit in SAMP8 mice. Brain Res. 2009, 1305:108-117.
21. Chuang T.C., Hsu S.C., Cheng Y.T., Shao W.S., Wu K.H., Fang G.S., Ou C.C., Wang V.C. Magnolol down-regulates HER2 gene expression, leading to inhibition of HER2-mediated metastatic potential in ovarian cancer cells. Cancer Lett. 2011, 311:11-19.
22. Park E.J., Min H.Y., Chung H.J., Hong J.Y., Kang Y.J., Hung T.M., Youn U.J., Kim Y.S., Bae K., Kang S.S., Lee S.K. Down-regulation of c-Src/EGFR-mediated signaling activation is involved in the honokiol-induced cell cycle arrest and apoptosis in MDA-MB-231 human breast cancer cells. Cancer Lett. 2009, 277:133-140.
23. Wang X.H., Cai L.L., Zhang X.Y., Deng L.Y., Zheng H., Deng C.Y., Wen J.L., Zhao X., Wei Y.Q., Chen L.J. Improved solubility and pharmacokinetics of PEGylated liposomal honokiol and human plasma protein binding ability of honokiol. Int. J. Pharm. 2011, 410:169-174.
24. 3+ by spectroscopic approaches. Eur. J. Med. Chem. 2011, 46:588-599.
25. Liu R.H., Yu X.Y., Gao W., Ji D.H., Yang F.X., Li X.F., Chen J., Tao H.W., Huang H.W., Yi P.G. Study on the interaction between salvianic acid A sodium and bovine serum albumin by spectroscopic methods. Spectrochim. Acta A 2011, 78:1535-1539.
26. Zhang J., Wang X.J., Yan Y.J., Xiang W.S. Comparative studies on the interaction of genistein, 8-chlorogenistein, and 3',8-dichlorogenistein with bovine serum albumin. J. Agric. Food Chem. 2011, 59:7506-7513.
27. Cheng Z.J., Zhang Y.T. Spectroscopic investigation on the interaction of salidroside with bovine serum albumin. J. Mol. Struct. 2008, 889:20-27.
28. Lakowicz J.R., Weber G. Quenching of fluorescence by oxygen: a probe for structural fluctuation in macromolecules. Biochemistry 1973, 12:4161-4170.
29. Eftink M.R., Ghiron C.A. Fluorescence quenching studies with proteins. Anal. Biochem. 1981, 114:199-212.
30. Xie M.X., Xu X.Y., Wang Y.D. Interaction between hesperetin and human serum albumin revealed by spectroscopic methods. Biochim. Biophys. Acta 2005, 1724:215-224.
31. Chipman D.M., Grisaro V., Sharon N. The binding of oligosaccharides containing N-acetylplucosamine and N-acetylmuramic acid to lysozyme. J. Biol. Chem. 1967, 242:4388-4394.
32. Gao H., Lei L.D., Liu J.Q., Kong Q., Chen X.G., Hu Z.D. The study on the interaction between human serum albumin and a new reagent with antitumor activity by spectrophotometric methods. J. Photochem. Photobiol. A 2004, 167:213-221.
33. Carter D.C., Ho J.X. Structure of serum albumin. Adv. Protein Chem. 1994, 45:153-203.
34. Chi Z., Liu R., Teng Y., Fang X., Gao C. Binding of oxytetracycline to bovine serum albumin: Spectroscopic and molecular modeling investigations. J. Agric. Food Chem. 2010, 58:10262-10269.
35. Kumar R.S., Paul P., Riyasdeen A., Wagniéres G., van den Bergh H., Akbarsha M.A., Arunachalam S. Human serum albumin binding and cytotoxicity studies of surfactant-cobalt(III) complex containing 1,10-phenanthroline ligand. Colloid Surface B 2011, 86:35-44.
36. Ross D.P., Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 1981, 20:3096-3102.
37. Forster T., Sinanoglu O. Modern Quantum Chemistry 1965, Academic Press, New York, pp. 93-137.
38. Sandhya B., Hegde A.H., Kalanur S.S., Katrahalli U., Seetharamappa J. Interaction of triprolidine hydrochloride with serum albumins: Thermodynamic and binding characteristics, and influence of site probes. J. Pharm. Biomed. Anal. 2011, 54:1180-1186.
39. Jiang C.Q., Gao M.X., Meng X.Z. Study of the interaction between daunorubicin and human serum albumin, and the determination of daunorubicin in blood serum samples. Spectrochim. Acta A 2003, 59:1605-1610.
40. Cheng Z.J., Zhang Y.T. Fluorometric investigation on the interaction of oleanolic acid with bovine serum albumin. J. Mol. Struct. 2008, 879:81-87.
41. Witold K.S., Henry H.M., Dennis C. De-termination of protein secondary structure by transform infrared spectroscopy: a critical assessment. Biochemistry 1993, 32:389-394.
42. Llody J.B.F. Synchronized excitation of fluorescence emission spectra. Nat. Phys. Sci. 1971, 231:64-65.
43. Chi Z.X., Liu R.T., Yang B.J., Zhang H. Toxic interaction mechanism between oxytetracycline and bovine hemoglobin. J. Hazard. Mater. 2010, 180:741-747.
44. Li D.J., Wang Y., Chen J.J., Ji B.M. Characterization of the interaction between farrerol and bovine serum albumin by fluorescence and circular dichroism. Spectrochim. Acta A 2011, 79:680-686.
45. Dubeau S., Bourassa P., Thomas T.J., Tajmir-Riahi H.A. Biogenic and synthetic polyamines bind bovine serum albumin. Biomacromolecules 2010, 11:1507-1515.
46. Bourassa P., Kanakis C.D., Tarantilis P., Pollissiou M.G., Tajmir-Riahi H.A., Resveratrol Genistein, and curcumin bind bovine serum albumin. J. Phys. Chem. B 2010, 114:3348-3354.
47. Cui F.L., Fan J., Li J.P., Hu Z.D. Interactions between 1-benzoyl-4-p-chlorophenyl thiosemicarbazide and serum albumin: investigation by fluorescence spectroscopy. Bioorg. Med. Chem. 2004, 12:151-157.