|
|
[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP |
Ying Zhang, Yong-Guang Gao, You-Di Shi, Lian-Qian Tan, Jessica S. Yue, Zhong-Lin Lu |
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China |
|
|
Guide A novel [12]aneN3-based BODIPY sensor 1 can be applied in the sequential recognition of Cu2 and ADP in aqueous solution and living cells with high selectivity and sensitivity |
|
Abstract A new [12]aneN3-based BODIPY sensor 1 showed highly selective and sensitive recognition of Cu2+ ions through fluorescence quenching effect in aqueous solution. The above copper complex solution can further be used as a turn-on fluorescent probe for detecting ADP with high selectivity, and also applied in imaging of living cells.
|
Received: 01 April 2015
Published: 28 May 2015
|
Fund: The authors gratefully acknowledge the financial assistances from the National Natural Science Foundation of China (Nos. 21372032 and 91227109), the Fundamental Research Funds for the Central Universities(2009SC-1), Beijing Municipal Commission of Education, the Program for Changjiang Scholars and Innovative Research Team in University. |
Corresponding Authors:
Zhong-Lin Lu
E-mail: luzl@bnu.edu.cn
|
|
|
|
[1] |
L. Fabbrizzi, A. Poggi, Anion recognition by coordinative interactions: metal-amine complexes as receptors, Chem. Soc. Rev. 42 (2013) 1681-1699.
|
[2] |
J.J. Green, R. Langer, D.G. Anderson, A combinatorial polymer library approach yields insight into nonviral gene delivery, Acc. Chem. Res. 41 (2008) 749-759.
|
[3] |
J.R. Morrow, T.L. Amyes, J.P. Richard, Phosphate binding energy and catalysis by small and large molecules, Acc. Chem. Res. 41 (2008) 539-548.
|
[4] |
F. Liang, S. Wan, Z. Li, et al., Medical applications of macrocyclic polyamines, Curr. Med. Chem. 13 (2006) 711-727.
|
[5] |
B. Le Bon, N.V. Craynest, J.M. Daoudi, et al., AMD3100 conjugates as components of targeted nonviral gene delivery systems: synthesis and in vitro transfection efficiency of cxcr4-expressing cells, Bioconjug. Chem. 15 (2004) 413-423.
|
[6] |
H. Yan, Z.F. Li, Z.F. Guo, et al., Effective and reversible DNA condensation induced by bifunctional molecules containing macrocyclic polyamines and naphthyl moieties, Bioorg. Med. Chem. 20 (2012) 801-808.
|
[7] |
Q.F. Zhang, W.H. Yang, W.J. Yi, et al., TACN-containing cationic lipids with ester bond: preparation and application in gene delivery, Bioorg. Med. Chem. Lett. 21 (2011) 7045-7049.
|
[8] |
B. Liu, Q. Liu, J. Zhang, S. Fan, X. Yu, Transfection of nucleic acids mediated by macrocyclic polyamine-based liposomes, Prog. Chem. 25 (2013) 1237-1245.
|
[9] |
H. Gao, Z. Ke, N.J. DeYonker, et al., Dinuclear Zn(II) complex catalyzed phosphodiester cleavage proceeds via a concerted mechanism: a density functional theory study, J. Am. Chem. Soc. 133 (2011) 2904-2915.
|
[10] |
Z.L. Lu, C.T. Liu, A.A. Neverov, R.S. Brown, Rapid three-step cleavage of RNA and DNA model systems promoted by a dinuclear Cu(II) complex in methanol. Energetic origins of the catalytic efficacy, J. Am. Chem. Soc. 129 (2007) 11642-11652.
|
[11] |
X. Sheng, X.M. Lu, J.J. Zhang, et al., Synthesis and DNA cleavage activity of artificial receptor 1,4,7-triazacyclononane containing guanidinoethyl and hydroxyethyl side arms, J. Org. Chem. 72 (2007) 1799-1802.
|
[12] |
Q. Wang, H. Lönnberg, Simultaneous interaction with base and phosphate moieties modulates the phosphodiester cleavage of dinucleoside 30, 50-monophosphates by dinuclear Zn2+ complexes of di(azacrown) ligands, J. Am. Chem. Soc. 128 (2006) 10716-10728.
|
[13] |
A.S. Delepine, R. Tripier, H. Handel, Cyclen-based bismacrocycles for biological anion recognition. A potentiometric and NMR study of AMP, ADP and ATP nucleotide complexation, Org. Biomol. Chem. 6 (2008) 1743-1750.
|
[14] |
E. Tamanini, K. Flavin, M. Motevalli, et al., Cyclam-based “clickates”: homogeneous andheterogeneousfluorescent sensors forZn(II), Inorg.Chem.49(2010)3789-3800.
|
[15] |
K. Tsuge, F. DeRosa, M.D. Lim, P.C. Ford, Intramolecular reductive nitrosylation: reaction of nitric oxide and a copper(II) complex of a cyclam derivative with pendant luminescent chromophores, J. Am. Chem. Soc. 126 (2004) 6564-6565.
|
[16] |
A.T. Wrobel, T.C. Johnstone, A. Deliz Liang, S.J. Lippard, P. Rivera-Fuentes, A fast and selective near-infrared fluorescent sensor for multicolor imaging of biological nitroxyl (HNO), J. Am. Chem. Soc. 136 (2014) 4697-4705.
|
[17] |
Z.F. Guo, H. Yan, Z.F. Li, Z.L. Lu, Synthesis of mono- and di-[12] aneN3 ligands and study on the catalytic cleavage of RNA model 2-hydroxypropyl-p-nitrophenyl phosphate with their metal complexes, Org. Biomol. Chem. 9 (2011) 6788-6796.
|
[18] |
Z.F. Li, H.L. Chen, L.J. Zhang, Z.L. Lu, Synthesis of [12] aneN3-dipeptide conjugates as metal-free DNA nucleases, Bioorg. Med. Chem. Lett. 22 (2012) 2303-2307.
|
[19] |
Z.F. Li,Z.F.Guo,H.Yan,Z.L. Lu,D.Y.Wu, Synthesesof [12] aneN3-oligopeptide conjugates as effective DNA condensation agents, Bioorg. Med. Chem. 20 (2012) 2897-2904.
|
[20] |
L.J. Zhang, H.L. Chen, Z.F. Li, Z.L. Lu, R. Wang, Click-reaction generated [12] aneN3-based fluorescent sensor for Zn(II) ions, Inorg. Chem. Commun. 23 (2012) 67-69.
|
[21] |
H. Yan, P. Yue, Z. Li, Z. Guo, Z. Lu, Syntheses of bifunctional molecules containing[12] aneN3 and carbazol moieties as effective DNA condensation agents, Sci. China Chem. 57 (2013) 296-306.
|
[22] |
Y. Jeong, J. Yoon, Recent progress on fluorescent chemosensors for metal ions, Inorg. Chim. Acta 381 (2012) 2-14.
|
[23] |
Y.W. Duan, H.Y. Tang, Y. Guo, et al., The synthesis and study of the fluorescent probe for sensing Cu2+ based on a novel coumarin Schiff-base, Chin. Chem. Lett. 25 (2014) 1082-1086.
|
[24] |
J.W. Karr, V.A. Szalai, Role of aspartate-1 in Cu(II) binding to the amyloid-b peptide of Alzheimer's disease, J. Am. Chem. Soc. 129 (2007) 3796-3797.
|
[25] |
B.B. Tewari, Studies on complexation in solution with a paper electrophoretic technique [the system copper(II)/cobalt(II)-methionine-penicillamine], J. Chem. Eng. Data 55 (2010) 1779-1783.
|
[26] |
L. Zhang, J. Lichtmannegger, K.H. Summer, et al., Tracing copper thiomolybdathiomolybdatecomplexes in a prospective treatment for Wilson's disease, Biochemistry 48 (2009) 891-897.
|
[27] |
B. Innocenti, T. Pozzan, C. Fasolato, Intracellular ADP modulates the Ca releaseactivated Ca current in a temperature- and Ca-dependent way, J. Biol. Chem. 271 (1996) 8582-8587.
|
[28] |
J. Kaur, P. Singh, ATP selective acridone based fluorescent probes for monitoring of metabolic events, Chem. Commun. 47 (2011) 4472-4474.
|
[29] |
A.S. Rao, D. Kim, H. Nam, et al., A turn-on two-photon fluorescent probe for ATP and ADP, Chem. Commun. 48 (2012) 3206-3208.
|
[30] |
R.W. Alder, R.W. Mowlam, D.J. Vachon, G.R. Weisman, New synthetic routes to macrocyclic triamines, J. Chem. Soc. Chem. Commun. (1992) 507-508.
|
[31] |
M.R. Rao, S.M. Mobin, M. Ravikanth, Boron-dipyrromethene based specific chemodosimeter for fluoride ion, Tetrahedron 66 (2010) 1728-1734.
|
[32] |
N. Chopin, M. Mé debielle, O. Maury, G. Novitchi, G. Pilet, Quenching of fluorescence in bodipy-derived trifluoromethyl enaminone ligands upon coordination to copper(II), Eur. J. Inorg. Chem. 2014 (2014) 6185-6195.
|
[33] |
X. Xie, Y. Qin, A dual functional near infrared fluorescent probe based on the bodipy fluorophores for selective detection of copper and aluminum ions, Sens. Actuators B 156 (2011) 213-217.
|
[34] |
H.S. Jung, P.S. Kwon, J.W. Lee, et al., Coumarin-derived Cu2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells, J. Am. Chem. Soc. 131 (2009) 2008-2012.
|
[35] |
P.A. Mascaros, C. Bazzicalupi, A. Bianchi, et al., Molecular recognition of ADP over ATP in aqueous solution by a polyammonium receptor containing a pyrimidine residue, Chem. Commun. 47 (2011) 2814-2816.
|
[36] |
P.J. Xie, M.L. Ye, Z.Y. Hu, et al., Determination of levels of adenosine phosphates in blood by ion chromatography, Chin. Chem. Lett. 22 (2011) 1485-1488.
|
[37] |
W. Yu, J. Qiang, J. Yin, et al., Ammonium-bearing dinuclear copper(II) complex: a highly selective and sensitive colorimetric probe for pyrophosphate, Org. Lett. 16 (2014) 2220-2223.
|
|
|
|