Ratiometric fluorescent probe based on novel red-emission BODIPY for determination of bovine serum albumin

Abstract

A novel red-emission boron-dipyrromethene(BODIPY) dye with a pyrrole ring was synthesized simply via one-pot reaction. The spectral properties of it were investigated under the conditions of different solvents. The results show that the as-prepared BODIPY dye is extremely sensitive to solvent polarity, and the fluorescent emission enhances with the decrease of solvent polarity. In aqueous buffer, the addition of bovine serum albumin leads to a ratiometric change in absorption spectra with an association constant of 1.16×10⁶ L/mol. Meanwhile, the fluorescence emission increases greatly at 622 nm but changes slightly at 575 nm. The response time is very short(less than 3 min), and the changes of color can be noticed by naked eyes. Bovine serum albumin can be detected by this ratiometric fluorescence probe, but other proteins or enzymes cannot be detected by this method, which indicates that this novel dye has high selectivity towards bovine serum albumin. The reason is that bovine serum albumin has suitable hydrophobic cavities for binding with the dye. In addition, the dye molecule can penetrate cell membrane easily and make a fast fluorescent stain, which makes it a potential probe for living-cell fluorescence imaging.

Keywords

Fluorescent dye / Boron-dipyrromethene(BODIPY) / Bovine serum albumin / Ratiometric / High selectivity

References

[1] Carter D C, Ho J X. Adv. Protein Chem., 1994, 45: 153.

[2] Pu L. Chem. Rev., 2004, 104(3): 1687.

[3] Wang W, Zhang Y M, Li Y X, Zhao Q. Chem. Res. Chinese Universities, 2013, 29(4): 632.

[4] Su W Q, Yang B Q. Chem. Res. Chinese Universities, 2013, 29(4): 657.

[5] Zheng A H, Zhu Q, Xiang D S, He Z K. Chin. J. Anal. Chem., 2013, 41(3): 325.

[6] Chang W, Shen Y, Xie A, Zhang H, Wang J, Lu W. J. Colloid Interface Sci., 2009, 335(2): 257.

[7] Chen X T, Xiang Y, Tong A J. Talanta, 2010, 80(5): 1952.

[8] Cui F, Wang J, Cui Y, Li J. Anal. Chim. Acta, 2006, 571(2): 175.

[9] Cui F L, Fan J, Li J P, Hu Z D. Biorg. Med. Chem., 2004, 12(1): 151.

[10] Cui J, Fan J, Peng X, Sun S. Dyes Pigments, 2011, 89(3): 330.

[11] Ojha B, Das G. Chem. Commun., 2010, 46(12): 2079.

[12] Jisha V S, Arun K T, Hariharan M, Ramaiah D. J. Am. Chem. Soc., 2006, 128: 6024.

[13] Wang B, Fan J, Sun S, Wang L, Song B, Peng X. Dyes Pigments, 2010, 85(1/2): 43.

[14] Wen J, Geng Z, Yin Y, Wang Z. Dalton Trans., 2011, 40: 9737.

[15] Yu Y, Lai Y, Zheng X, Wu J, Long Z, Liang C. Spectrochim Acta A, 2007, 68(5): 1356.

[16] Zeng X, Zhang X, Zhu B, Jia H, Li Y, Xue J. Analyst, 2011, 136(19): 4008.

[17] Tremblay M S, Halim M, Sames D. J. Am. Chem. Soc., 2007, 129(24): 7570.

[18] Xu Z, Singh N J, Lim J, Pan J, Kim H N, Park S, Kim K S, Yoon J. J. Am. Chem. Soc., 2009, 131(42): 15528.

[19] Hu M, Fan J, Li H, Song K, Wang S, Cheng G, Peng X. Org. Biomol. Chem., 2011, 9: 980.

[20] Peng X J, Du J J, Fan J L, Wang J Y, Wu Y K, Zhao J Z, Sun S G, Xu T. J. Am. Chem. Soc., 2007, 129(6): 1500.

[21] Wang D, Fan J, Gao X, Wang B, Sun S, Peng X. J. Org. Chem., 2009, 74(20): 7675.

[22] Wu Y K, Peng X J, Guo B C, Fan J L, Zhang Z C, Wang J Y, Cui A J, Gao Y L. Org. Biomol. Chem., 2005, 3(8): 1387.

[23] Jiao L, Yu C, Liu M, Wu Y, Cong K, Meng T, Wang Y, Hao E. J. Org. Chem., 2010, 75(17): 6035.

[24] Loudet A, Burgess K. Chem. Rev., 2007, 107(11): 4891.

[25] Peng X J, Song F L, Lu E, Wang Y N, Zhou W, Fan J L, Gao Y L. J. Am. Chem. Soc., 2005, 127(12): 4170.

[26] Bonnett R, McManus K A. J. Chem. Soc. Chem. Comm., 1994, 1129.

[27] Velapoldi R A, Tonnesen H H. J. Fluoresc., 2004, 14(4): 465.

[28] Urien S, Nguyen P, Berlioz S, Bree F, Vacherot F, Tillement J P. Biochem. J., 1994, 302: 69.

[29] Wolfe A, Shimer G H, Meehan T. Biochemistry, 1987, 26(20): 6392.

[30] Bhattacharya M, Jain N, Bhasne K, Kumari V, Mukhopadhyay S. J. Fluoresc., 2011, 21(3): 1083.