Interaction Between Baicalein and Amyloid-β Fibrils Studied by Fluorescence Spectroscopy

doi:10.1007/s40242-013-2180-1

Abstract

Abstract:

The interaction between baicalein and amyloid-β(Aβ) polypeptide was investigated by fluorescence and UV-Vis absorbance spectroscopy. The absence of the characteristic peak of tyrosinate(Tyr) in the absorption spectra of Aβ-baicalein complexes provided evidence that the sole Tyr residue in Aβ is not bound to baicalein, but remains close to it. The intrinsic fluorescence of Tyr residues in Aβ_1―42 aggregates was quenched strongly by the excited-state ionization of baicalein. In this complex the hydroxyl group was not ionized, but to ionize immediately upon excitation. Absorbance, fluorescence and synchronous spectroscopies show that the formation of Schiff base between the quinone of baicalein and the lysine(Lys) side chains of Aβ_1―42 is another major reason in the depolymerization of Aβ_1―42 aggregates by baicalein. It is desirable that our research would offer some valuable reference for the application of flavonoid derivants in Alzheimer's disease(AD) treatment.

Key words: Amyloid-β peptide, Baicalein, Depolymerization, Molecular mechanism, Fluorescence spectroscopy

SONG Sheng-mei, WANG Yong-xiang, XIONG Li-min, QU Ling-bo, XU Mao-tian. Interaction Between Baicalein and Amyloid-β Fibrils Studied by Fluorescence Spectroscopy[J]. Chemical Research in Chinese Universities, 2013, 29(1): 20-25.

References

[1] Hebert L. E., Scherr P. A., Bienias J. L., Bennett D. A., Evans D. A., Arch. Neurol., 2003, 60, 1119

[2] Wang Z., Wan L., Zhou C., Fang X., Wang C., Bai C., Chin. Sci. Bull., 2003, 48 , 437

[3] Hardy J. A., Higgins G. A., Science, 1992, 256, 184

[4] Selkoe D. J., Neuron., 1991, 6, 487

[5] Lippa C. F., Schmidt M. L., Nee L. E., Bird T., Nochlin D., Hulette C., Mori H., Lee V. M., Trojanowski J. Q., Neurology, 2000, 54, 100

[6] Selkoe D. J., Science, 1997, 275, 630

[7] Yan L., Kevin M., Noor K., Int. J. Biochem. Cell Biol., 2003, 35, 1505

[8] Ono K., Condron M. M., Teplow D. B., Proc. Natl. Acad. Sci. USA, 2009, 106, 14745

[9] Saraiva A. M., Cardoso I., Pereira M. C., Coelho M. A. N., Saraiva M. J., Möhwald H., Brezesinski G., ChemBioChem, 2010, 11, 1905

[10] de Felice F. G., Houzel J. , Garcia-Abreu J., Louzada P. R. F., Afonso R. C., Meirelles M. N., Lent R., Neto V. M., Ferreira S. T., FASEB J., 2004, 15, 1297

[11] Gestwicki J. E., Crabtree G. R., Graef I. A., Science, 2004, 306, 865

[12] McLaurin J., Cecal R., Kierstead M. E., Tian X., Phinney A. L., Manea M., French J. E., Lambermon M. H. L., Darabie A. A., Brown M. E., Janus C., Chishti M. A., Horne P., Westaway D., Fraser P. E., Mount H. T. J., Przybylski M., St George-Hyslop P., Nat. Med., 2002, 8(11), 1263

[13] Liu R., Yuan B., Emadi S., Zameer A., Schulz P., McAllister C., Lyubchenko Y., Goud G., Sierks M. R., Biochemistry, 2004, 43, 6959

[14] McLaurin J., Kierstead M., Fraser P. E., Neurobiol. Aging, 2002, 23, S432

[15] Tjernberg L. O., Naslund J., Lindqvist F., Johannsson J., Karlstr?m A. R., Thyberg J., Terenius L., Nordstedt C., J. Biol. Chem., 1996, 271, 8545

[16] Li B. Q., Fu T., Gong W. H., Dunlop N., Kung H., Yan Y., Kang J., Wang J. M., Immunopharmacology, 2000, 49, 295

[17] Wu J. A., Attele A. S., Zhang L., Yuan C. S., Am. J. Chin. Med., 2001, 29, 69

[18] van Leyen K., Kim H. Y., Lee S. R., Jin G., Arai K., Lo E. H., Stroke, 2006, 37, 3014

[19] Lebeau A., Esclaire F., Rostene W., Pelaprat D., Neuroreport, 2001, 12, 2199

[20] Wang S. Y., Wang H. H., Chi C. W., Chen C. F., Liao J. F., Eur. J. Pharmacol., 2004, 506, 55

[21] Heo H. J., Kim D. O., Choi S. J., Shin D. H., Lee C. Y., J. Agr. Food Chem., 2004, 52, 4128

[22] Zhu J. T. T., Choi R. C. Y., Chu G. K.Y., Cheung A. W. H., Gao Q. T., Li J., Jiang Z. Y., Dong T. T. X., Tsim A. W. K., J. Agric. Food Chem., 2007, 55, 2438

[23] Song S. M., Wang Y. X., Xiong L. M., Qu L. B., Xu M. T., Chin. Chem. Lett., 2012, 23, 595

[24] Zhu M., Rajamani S., Kaylor J., Han S. B., Zhou F. M., Fink A. L., J. Bio. Chem., 2004, 279, 26846

[25] Steiner R. F., Weinryb I., Excited States of Proteins and NucleicAcids, Plenum Press, New York, 1971, 319

[26] Sun Y., Bi S., Song D., Qiao C., Mu D., Zhang H., Sensor Actuat. B, Chem., 2008, 129, 799

[27] Lakowicz J. R., Principles of Fluorescence Spectroscopy., 3rd Ed., Springer Press, Berlin, 2006, 278

[28] Sharma A., Schulman S. G., Introduction to Fluorescence Spectro- scopy, Wiley Press, New York, 1999, 129

[29] Westlind-Danielsson A., Arnerup G., Biochemistry, 2001, 40, 14736

[30] Petkova A. T., Ishii Y., Balbach J. J., Antzutkin O. N., Leapman R., Delaglio D. F., Tycko R., Proc. Natl. Acad. Sci. USA, 2002, 99, 16742

[31] Wang J., Zhu S., Xu C., Biochemistry, Higher Education Press, Beijing, 2007, 137

[32] Naskar J., Drew M. G. B., Deb I., Das S., Banerjee A., Org. Lett., 2008, 10, 2625

[33] Selenica M. L., Wang X., Ostergaard-Pedersen L., Westlind- Danielsson A., Grubb A., Scand. J. Clin. Lab. Invest., 2007, 67, 179

[34] Barrow C. J., Zagrski M. G., Science, 1991, 253, 179

[35] Zhu M., Han S., Zhou F., Carter S. A., Fink A. L., J. Biol. Chem., 2004, 279, 24452

[36] Lührs T., Ritter C., Adrian M., Riek-Loher D., Bohrmann B., Döbeli H., Schubert D., Riek R., Proc. Natl. Acad. Sci. USA, 2005, 102, 17342

[37] Petkova A.T., Buntkowsky G., Dyda F., Leapman R. D., Yau W. M., Tycko R., J. Mol. Biol., 2004, 335, 247

[38] Gazit E., FASEB J., 2002, 16, 77

[39] Wang N., Liu Z. Y., Hu X. L., Bu F. Q, Zhao X. Z., Chem. J. Chinese Universities, 2011, 32(2), 241

[40] Zhang W., Zhao Y., Bai X. Y., Hui G., Zhao D. Q., Zhai B., Chem. J. Chinese Universities, 2010, 31(9), 1834

[41] Zhang B. L., Wang W. Q., Bao F. L., Chem. J. Chinese Universities, 1994, 15(3), 373