Abstract
A sulfonated 9,10-distyrylanthracene derivative with aggregation-induced emission (AIE) property is designed and synthesized. It shows a highly sensitive and selective fluorescence enhancement property for bovine serum albumin (BSA) protein detection and quantification. Analysis on the interaction between the probe molecule and BSA reveals the essential role of the hydrophobic cavities of the protein folding structure.
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References
Royer CA. Probing protein fording and conformational transitions with fluorescence. Chem Rev, 2006, 106:1769–1784
Wang Y, Li ZH, Zhong WY, Li H, Xu DK, Chen HY. Rhodamine B doped silica nanoparticle labels for protein microarray detection. Sci Chi Chem, 2010, 53:747–751
Xu Y, Dong P, Zhang XY, He PG, Fang YZ. Solid-state electrochemiluminescence protein biosensor with aptamer substitution strategy. Sci Chi Chem, 2011, 54:1109–1115
Hu CH, Zou CL. Effect of native disulfide bonds on the denaturation of proteins in 6 mol/L guanidnium chloride-A fourier transformed infrared study. Sci Chi Chem, 1993, 36:568–574
Shi H, He XX, Yang XH, Wang KM, Wang Q, Guo QP, Huo XQ. Protein analysis based on molecular beacon probes and biofunctionalized nanoparticles. Sci Chi Chem, 2010, 53:704–719
Berggren K, Steinberg TH, Lauber WM, Carroll JA, Lopez MF, Chernokalskaya E, Zieske L, Diwu ZJ, Haugland RP, Patton WF. A luminescent ruthenium complex for ultrasensitive detection of proteins immobilized on membrane supports. Anal Biochem, 1999, 276:129–143
Suzuki Y, Yokoyama K. Design and synthesis of intramolecular charge transfer-based fluorescent reagents for the highly-sensitive detection of proteins. J Am Chem Soc, 2005, 127:17799–17802
Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40:5361–5388
Luo JD, Xie ZL, Lam JWY, Cheng L, Chen HY, Qiu CF, Kwok HS, Zhan XW, Liu YQ, Zhu DB, Tang BZ. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun, 2001:1740–1741
Tong H, Hong Y, Dong YQ, Haussler M, Lam JWY, Li Z, Guo ZF, Guo ZH, Tang BZ. Fluorescent “light-up” bioprobes based on tetrapheny ethylene derivatives with aggregation-induced emission characteristics. Chem Commun, 2006:3705–3707
Tong H, Dong YQ, Hong Y, Haussler M, Lam JWY, Sung HHY, Yu XM, Sun JX, Williams ID, Kwok HS, Tang BZ. Aggregationinduced emission: Effects of molecular structure, solid-state conformation, and morphological packing arrangement on light-emitting behaviors of diphenyldibenzofulvene derivatives. J Phys Chem C, 2007, 111:2287–2294
Mi BX, Dong YQ, Li Z, Lam JWY, Haussler M, Sung HHY, Kwok HS, Dong YP, Williams ID, Liu YQ, Luo Y, Shuai ZG, Zhu DB, Tang BZ. Making silole photovoltaically active by attaching carbazolyl donor groups to the silolyl acceptor core. Chem Commun, 2005:3583–3585
Yu G, Yin SW, Liu YQ, Chen JS, Xu XJ, Sun XB, Ma DG, Zhan XW, Peng Q, Shuai ZG, Tang BZ, Zhu DB, Fang WH, Luo Y. Structures, electronic states, photoluminescence, and carrier transport properties of 1,1-disubstituted 2,3,4,5-tetraphenylsiloles. J Am Chem Soc, 2005, 127:6335–6346
Shi HB, Liu JL, Tang BZ, Liu B. Specific detection of integrin αvβ3 by light-up bioprobe with aggregation-induced emission characteristics. J Am Chem Soc, 2012, 134:9569–9572
Mei J, Tong JQ, Wang J, Qin AJ, Sun JZ, Tang BZ. Discriminative fluorescence detection of cysteine, homocysteine and glutathione via reaction-dependent aggregation of fluorophore-analyte adducts. J Mater Chem, 2012, 22:17063–17070
Gu XG, Zhang GX, Zhang DQ. A new ratiometric fluorescence detection of heparin based on the combination of the aggregationinduced fluorescence quenching and enhancement phenomena. Analyst, 2012, 137:365–369
Yu Y, Hong YN, Feng C, Liu JZ, Lam WY, Faisal M, NG KM, Luo KQ, Tang BZ. Synthesis of an AIE-active fluorogen and its application in cell imaging. Sci Chi Chem, 2009, 52:15–19
Qin A J, Zhang Y, Han N, Mei J, Sun JZ, Fan WM, Tang BZ. Preparation and self-assembly of amphiphilic polymer with aggregation-induced emission characteristics. Sci Chi Chem, 2012, 55:772–778
He JT, Xu B, Chen FP, Xia HJ, Li KP, Ye L, Tian WJ. Aggregation-induced emission in the crystals of 9,10-distyrylanthracene derivatives: The essential role of restricted intramolecular torsion. J Phys Chem C, 2009, 113:9892–9899
Xu B, Fang HH, Dong YJ, Chen FP, Chen QD, Sun HB, Tian WJ. Solid state emission enhancement of 9,10-distyrylanthracene derivatives and amplified spontaneous emission from a large single crystal. New J Chem, 2010, 34:1838–1842
Xu B, He JT, Dong YJ, Chen FP, Yu WL, Tian WJ. Aggregation emission properties and self-assembly of conjugated oligocarbazoles. Chem Commun, 2011, 47:6602–6604
Wang ZL, Xu B, Zhang L, Zhang JB, Ma TH, Zhang JB, Fu XQ, Tian WJ. Folic acid-functionalized mesoporous silica nanospheres hybridized with AIE luminogens for targeted cancer cell imaging. Nanoscale, 2013, 5:2065–2072
Li X, Xu B, Lu HG, Wang ZL, Zhang JB, Zhang Y, Dong YJ, Ma K, Wen SP, Tian WJ. Label-free fluorescence turn-on detection of Pb2+ based on AIE-active quaternary ammonium salt of 9,10-distyrylan-thrancene. Anal Meth, 2013, 5:438–441
Dong YJ, Xu B, Zhang JB, Tan X, Wang LJ, Chen JL, Lv HG, Wen SP, Li B, Ye L, Zou B, Tian WJ. Piezochromic luminescence based on the molecular aggregation of 9,10-bis((E)-2-(pyrid-2-yl)vinyl) anthracene. Angew Chem Int Ed, 2012, 51:10782–10785
Lu HG, Su FY, Mei Q, Zhou XF, Tian YQ, Tian WJ, Johnson RH, Meldrum DR. A series of poly[N-(2-hydroxy-propyl)methacrylamide] copolymes with anthracene-derived fluorophores showing aggregation-induced emission properties for bioimaging. J Polym Sci Part A: Polym Chem, 2012, 50:890–899
Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009:4332–4353
Eisen HN, Karush F. The interaction of purified antibody with homologous hapten; Antibody valence and binding constant. J Am Chem Soc, 1949, 71:363–364
Gonzalez-Jimenez J, Jacquotte H, Cayre I. Fluorescence quenching studies on binding fluoreno-9-spiro-oxazolidinedione to human serum albumin. Chem Biol Interactions, 1992, 84:221–228
Alain M, Michel B, Michel D. How to illustrate ligand-protein binding in a class experiment. J Chem Ed, 1986, 63:365–366
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Wang, Z., Ma, K., Xu, B. et al. A highly sensitive “turn-on” fluorescent probe for bovine serum albumin protein detection and quantification based on AIE-active distyrylanthracene derivative. Sci. China Chem. 56, 1234–1238 (2013). https://doi.org/10.1007/s11426-013-4917-6
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DOI: https://doi.org/10.1007/s11426-013-4917-6