Substitution pattern reverses the fluorescence response of coumarin glycoligands upon coordination with silver (I)

Scientific Reports

Volumn 4, Issue , 2014, Pages

  Shi, De Tai ^a   Wei, Xiao Li ^a,b   Sheng, Yayun ^a   Zang, Yi ^b   He, Xiao Peng ^a   Xie, Juan ^c   Liu, Guixia ^a   Tang, Yun ^a   Li, Jia ^b   Chen, Guo Rong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c Ecole Normale Superieure de Cachan   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONTRAST MEDIUM; COUMARIN; COUMARIN DERIVATIVE; DIAGNOSTIC AGENT; GLYCOGEN; LIGAND; SILVER;

ARTICLE; CELL FRACTIONATION; CHEMISTRY; FLUORESCENCE MICROSCOPY; HEPG2 CELL LINE; HUMAN; METHODOLOGY; SYNTHESIS; ULTRASTRUCTURE;

CONTRAST MEDIA; COUMARINS; GLYCOGEN; HEP G2 CELLS; HUMANS; LIGANDS; MICROSCOPY, FLUORESCENCE; SILVER; SUBCELLULAR FRACTIONS;

EID: 84897639621     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep04252     Document Type: Article

References (41)

1. Bellot, F., Hardré, R., Pelosi, G., Thérisod, M. & Policar, C. Superoxide dismutaselike activity of cobalt(II) complexes based on a sugar platform. Chem. Commun. 41, 5414-5416 (2005). (Pubitemid 41689374)
2. Yuasa, R. H. et al. Hinge sugar as amovable component of an excimer fluorescence sensor. Org. Lett. 6, 1489-1492 (2004).
3. Yuasa, H., Miyagawa, N., Nakatani, M., Izumi, M. & Hashimoto, H. A tongs-like fluorescence sensor for metal ions: perfect conformational switch of hinge sugar by a pyrene stacking. Org. Biomol. Chem. 2, 3548-3556 (2004). (Pubitemid 40010628)
4. 2+ ion in natural water. Chem. Commun. 42, 4392-4394 (2006). (Pubitemid 44611700)
5. II complexes. Chem. Eur. J. 13, 2774-2782 (2007). (Pubitemid 46941852)
6. Xie, J., Ménand, M., Maisonneuve, S. & Métivier, R. Synthesis of bispyrenyl sugaraza-crown ethers as new fluorescent molecular sensors for Cu(II). J. Org. Chem. 72, 5980-5985 (2007). (Pubitemid 47205967)
7. Yang, Y.-K., Shim, S. & Tae, J. Rhodamine-sugar based turn-on fluorescent probe for the detection of cysteine and homocysteine in water. Chem. Commun. 46, 7766-7768 (2010).
8. Garcia, L. et al. Sugars to control ligand shape in metal complexes: conformationally constrained glycoligands with a predetermination of stereochemistry and a structural control. Inorg. Chem. 49, 7282-7288 (2010).
9. Mitra, A., Mittal, A. K. & Rao, C. P. Carbohydrate assisted fluorescence turn-on gluco-imino-anthracenylconjugate as a Hg(II) sensor in milk and blood serum milieu. Chem. Commun. 47, 2565-2567 (2011).
10. Garcia, L. et al. Intrinsically fluorescent glycoligands to study metal selectivity. Inorg. Chem. 50, 11353-11362 (2011).
11. Hsieh, Y.-C. et al. A sugar-aza-crown ether-based fluorescent sensor for Cu21 and Hg21 ions. Carbohydr. Res. 346, 978-981 (2011).
12. Pujol, A. M. et al. Hepatocyte targeting and intracellular copper chelation by a thiol-containing glycocyclopeptide. J. Am. Chem. Soc. 133, 286-296 (2011).
13. Lee, M. H. et al. Hepatocyte-targeting single galactose-appended naphthalimide: a tool for intracellular thiol imaging in vivo. J. Am. Chem. Soc. 134, 1316-1322 (2012).
14. Singhal, N. K., Ramanujam, B., Mariappanadar, V. & Rao, C. P. Carbohydratebased switch-onmolecular sensor for Cu(II) in buffer: asorption and fluorescence study of the selective recognition of Cu(II) ions by galactosyl derivatives in HEPES buffer. Org. Lett. 8, 3525-3527 (2006).
15. He, X.-P. et al. Creation of 3,4-bis-triazolocoumarian-sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media. Tetrahedron 67, 3343-3347 (2011).
16. 2+ detection. Analyst 137, 1436-1439 (2012).
17. Ke, B. et al. A fluorescent probe for rapid aqueous fluoride detection and cell imaging. Chem. Commun. 49, 2494-2496 (2013).
18. Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew. Chem. Int. Ed. 41, 2596-2599 (2002). (Pubitemid 34803480)
19. Tornøe, C. W., Christensen, C. & Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064 (2002). (Pubitemid 34457265)
20. Wang, Q. & Hawker, C. Toward a few good reactions: Celebrating click chemistry s first decade. Chem. Asian J. 6, 2568-2569 (2011).
21. Holb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021 (2001).
22. Struthers, H., Mindt, T. L. & Schibli, R. Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition. Dalton Trans. 39, 675-696 (2010).
23. Shi, D.-T. et al. K. Bis-triazolyl indoleamines as unique "off-approach-on" chemosensors for copper and fluorine. Analyst 138, 2808-2811 (2013).
24. Zhang, Y.-J. et al. Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone. Dyes Pigm. 88, 391-395 (2011).
25. Song, Z. et al. 'Click' to bidentate bis-triazolyl sugar derivatives with promising biological and optical features. Tetrahedron Lett. 52, 894-898 (2011).
26. Tang, Y.-H. et al. Discovery of a sensitive Cu(II)-cyanide "off-on" sensor based on new C-glycosyl triazolyl bis-amino acid scaffold. Org. Biomol. Chem. 10, 555-560 (2012).
27. He, X.-P., Xie, J., Chen, G. & Chen, K. Pyrene excimer-based bis-triazolyl pyranoglycoligands as specific mercury sensors. Chin. J. Chem. 30, 2874-2878 (2012).
28. Cisnetti, F., Guillot, R., Thérisod, M., Desmadril, M. & Policar, C. Stereocontrol by a pair of epimeric sugar-derived ligands of the coordination sphere of copper(II) Complexes. Inorg. Chem. 47, 2243-2245 (2008).
29. Cisnetti, F. et al. Metal complexation of a D-ribose-based ligand decoded by experimental and theoretical studies. Eur. J. Inorg. Chem. 2012, 3308-3319 (2012).
30. Zhang, J. F., Zhou, Y., Yoon, J. & Kim, J. S. Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). Chem. Soc. Rev. 40, 3416-3429 (2011).
31. 3+, and cysteine: information processing at molecular level. Org. Lett. 13, 366-369 (2011).
32. + based on arhodanineacetic acid-pyrene derivative. New J. Chem. 35, 849-853 (2011).
33. + with an N′-acetylthioureido group as a fluorescence switch. Chem. Commun. 47, 5073-5075 (2011).
34. 2+ ions. Mater. Chem. Phys. 141, 591-595 (2013).
35. Xue, J.-L. et al. Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction. Carbohydr. Res. 363, 38-42 (2012).
36. 2+ selective fluorescent chemosensors. Analyst 137, 5770-5776 (2012).
37. Yang, S.-T., Liao, D.-J., Chen, S.-J., Hu, C.-H. & Wu, A.-T. A fluorescence enhancement-based sensor for hydrogen sulfate ion. Analyst 137, 1553-1555 (2012).
38. 2+ ion. Carbohydr. Res. 345, 2557-2561 (2010).
39. Ast, S. et al. Integration of the 1,2,3-triazole "click" motif as a potent signaling element in metal ion responsive fluorescent probes. Chem. Eur. J. 19, 2990-3005 (2013).
40. Garcia, L. et al. An intrinsically fluorescent glycoligand for direct imaging of ligand trafficking in artificial and living cell systems. New J. Chem. 37, 3030-3034 (2013).
41. Li, K.-B. et al. A per-acetyl glycosyl rhodamine as a novel fluorescent ratiometric probe for mercury (II). Dyes Pigm. 102, 273-277 (2014).