Rhodamine based colorimetric and fluorescent probe for recognition of nucleoside polyphosphates through multi-hydrogen bond

Dyes and Pigments

Volumn 101, Issue , 2014, Pages 254-260

  Kong, Jichuan ^a,b   He, Cheng ^a   Zhang, Xiaolin ^a   Meng, Qingtao ^a   Duan, Chunying ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b HENAN POLYTECHNIC UNIVERSITY   (China)

Author keywords

Cell imaging; Chemosensor; Colorimetric and fluorescent; Naphthyridine; Nucleoside; Rhodamine B

Indexed keywords

CELL IMAGING; CHEMOSENSOR; COLORIMETRIC AND FLUORESCENT; NAPHTHYRIDINE; NUCLEOSIDE; RHODAMINE B;

BIOMOLECULES; COLOR; COLORIMETRY; FLUORESCENCE; HYDRATES; PHOSPHATES; PHYSIOLOGY;

HYDROGEN BONDS;

EID: 84886739030     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.10.002     Document Type: Article

References (31)

1. H. Zimmermann Purinergic signaling in neural development Semin Cell Dev Biol 22 2011 194 204
2. G.G. Yegutkin Nucleotide- and nucleoside-converting ectoenzymes: important modulators of purinergic signalling cascade Biochim Biophys Acta Mol Cell Res 1783 2008 673 694
3. A. Kobori, S. Horie, H. Suda, I. Saito, and K. Nakatani The SPR sensor detecting cytosine-cytosine mismatches J Am Chem Soc 126 2004 557 562
4. K. Yoshimoto, S. Nishizawa, M. Minagawa, and N. Teramae Use of abasic site-containing DNA strands for nucleobase recognition in water J Am Chem Soc 125 2003 8982 8983
5. T. Peng, C. Dohno, and K. Nakatani Bidirectional control of gold nanoparticle assembly by turning on and off DNA hybridization with thermally degradable molecular glue Chem Bio Chem 8 2007 483 485
6. K. Nakatani, S. Horie, and I. Saito Affinity labeling of a single guanine bulge J Am Chem Soc 125 2003 8972 8973
7. L.R. Squire Encyclopedia of neuroscience 2009 Academic Press New York
8. Y. Zhou, Zh Xu, and J. Yoon Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004-2010 Chem Soc Rev 40 2011 2222 2235
9. X. Chen, T. Pradhan, F. Wang, J.S. Kim, and J. Yoon Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives Chem Rev 112 2012 1910 1956
10. Y. Yang, Q. Zhao, W. Feng, and F. Li Luminescent chemodosimeters for bioimaging Chem Rev 113 2013 192 270
11. H.N. Kim, M.H. Lee, H.J. Kim, J.S. Kim, and J. Yoon A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions Chem Soc Rev 37 2008 1465 1472
12. M. Beija, C.A.M. Afonsoa, and J.M.G. Martinhoa Synthesis and applications of rhodamine derivatives as fluorescent probes Chem Soc Rev 38 2009 2410 2433
13. H. Zheng, X. Zhan, Q. Bian, and X. Zhang Advances in modifying ïuorescein and rhodamine ïuorophores as fluorescent chemosensors Chem Commun 49 2013 429 447
14. E.V. Brown 1,8-Naphthyridines. I. Derivatives of 2- and 4-methyl-1,8-naphthyridines J Org Chem 30 1965 1607 1610
15. F. Herranz, M.D. Santa Maria, and R.M. Claramunt Molecular recognition: improved binding of biotin derivatives with synthetic receptors J Org Chem 71 2006 2944 2951
16. J. Folling, V. Belov, R. Kunetsky, R. Medda, A. Schonle, and A. Egner Photochromic rhodamines provide nanoscopy with optical sectioning Angew Chem Int Ed 46 2007 6266 6270
17. V.N. Belov, M.L. Bossi, J. Folling, V.P. Boyarskiy, and S.W. Hell Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy Chem Eur J 15 2009 10762 10776
18. M.E. Jun, and K.H. Ahn Fluorogenic and chromogenic detection of palladium species through a catalytic conversion of a rhodamine B derivative Org Lett 12 2010 2790 2793
19. K. Zhou, H. Liu, S. Zhang, X. Huang, Y. Wang, and G. Huang Multicolored pH-tunable and activatable fluorescen nanoplatform responsive to physiologic pH stimuli J Am Chem Soc 134 2012 7803 7811
20. H. Zhu, J. Fan, Q. Xu, H. Li, J. Wang, and P. Gao Imaging of lysosomal pH changes with a fluorescent sensor containing a novel lysosome-locating group Chem Commun 48 2012 11766 11768
21. M.H. Lee, J.H. Han, J.H. Lee, N. Park, R. Kumar, and C. Kang Two-color probe to monitor a wide range of pH values in cells Angew Chem Int Ed 52 2013 6206 6209
22. W.L. Jorgensen, and J. Pranata Importance of secondary interactions in triply hydrogen bonded complexes: guanine-cytosine vs uracil-2,6-diaminopyridine J Am Chem Soc 112 1990 2008 2010
23. C.F. Guerra, F.M. Bickelhaupt, J.G. Snijders, and E.J. Baerends Hydrogen bonding in DNA base pairs: reconciliation of theory and experiment J Am Chem Soc 122 2000 4117 4128
24. J. Sponer, J. Leszczynski, and P. Hobza Structures and energies of hydrogen-bonded DNA base pairs. A nonempirical study with inclusion of electron correlation J Phys Chem 100 1996 1965 1974
25. J. Sponer, J. Leszczynski, and P. Hobza Nature of nucleic acid-base stacking: nonempirical ab initio and empirical potential characterization of 10 stacked base dimers. Comparison of stacked and H-bonded base pairs J Phys Chem 100 1996 5590 5596
26. P.S. Corbin, and S.C. Zimmerman Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers J Am Chem Soc 120 1998 9710 9711
27. D. QuiÊonero, C. Garau, C. Rotger, A. Frontera, P. Ballester, and A. Costa Anion-π interactions: do they exist? Angew Chem Int Ed 41 2002 3389 3391
28. K. Nakatani, S. Sando, and I. Saito Recognition of a single guanine bulge by 2-acylamino-1,8-naphthyridine J Am Chem Soc 122 2000 2172 2177
29. Y. Sato, S. Nishizawa, K. Yoshimoto, T. Seino, T. Ichihashi, and K. Morita Influence of substituent modifications on the binding of 2-amino-1,8-naphthyridines to cytosine opposite an AP site in DNA duplexes: thermodynamic characterization Nucleic Acids Res 37 2009 1411 1422
30. S. Nishizawaa, K. Yoshimotoa, T. Seinoa, C. Xu, M. Minagawaa, and H. Satake Fluorescence detection of cytosine/guanine transversion based on a hydrogen bond forming ligand Talanta 63 2004 175 179
31. A. Bencini, S. Biagini, C. Giorgi, H. Handel, M.L. Baccon, and P. Mariani A Tris-macrocycle with proton sponge characteristics as efficient receptor for inorganic phosphate and nucleotide anions Eur J Org Chem 32 2009 5610 5621