A water-soluble BODIPY derivative as a highly selective "Turn-On" fluorescent sensor for H2O2 sensing in vivo

Biosensors and Bioelectronics

Volumn 56, Issue , 2014, Pages 58-63

  Xu, Jian ^a,b   Li, Qian ^a   Yue, Ying ^a   Guo, Yong ^a   Shao, Shijun ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Fluorescent sensor; H2O2; In vitro and in vivo imaging; N alkylpyridinium substituted BODIPY derivatives; Water soluble fluorescent probe

Indexed keywords

FLUORESCENT PROBES; FLUORESCENT SENSORS; H2O2; IN-VITRO; OPTICAL SPECTROSCOPY; PHOTO-INDUCED ELECTRON TRANSFER; PHYSIOLOGICAL CONDITION; QUATERNARY AMMONIUM SALT;

BIOCOMPATIBILITY; MASS SPECTROMETRY; PHYSIOLOGICAL MODELS; PROBES; SENSORS;

FLUORESCENCE;

4 (BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER; AMMONIA; BODIPY DERIVATIVE; BORON DERIVATIVE; HYDROGEN PEROXIDE; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BIOCOMPATIBILITY; BIOLOGICAL MONITORING; BIOSENSOR; CONTROLLED STUDY; ELECTRON TRANSPORT; EMBRYO; FISH; FLUORESCENCE IMAGING; FLUORESCENT SENSOR; IN VITRO STUDY; IN VIVO STUDY; MASS SPECTROMETRY; MOLECULAR IMAGING; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; PTEROPHYLLUM SCALARE;

FLUORESCENT SENSOR; H(2)O(2); IN VITRO AND IN VIVO IMAGING; N-ALKYLPYRIDINIUM SUBSTITUTED BODIPY DERIVATIVES; WATER-SOLUBLE FLUORESCENT PROBE;

ALKYLATION; ANIMALS; BIOSENSING TECHNIQUES; BORON COMPOUNDS; CICHLIDS; FLUORESCENT DYES; HEP G2 CELLS; HUMANS; HYDROGEN PEROXIDE; OPTICAL IMAGING; PYRIDINES; SOLUBILITY; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 84892854808     PISSN: 09565663     EISSN: 18734235     Source Type: Journal    
DOI: 10.1016/j.bios.2013.12.065     Document Type: Article

References (45)

1. Abo M., Urano Y., Hanaoka K., Terai T., Komatsu T., Nagano T. J. Am. Chem. Soc. 2011, 133(27):10629-10637.
2. Alamiry M.A.H., Harriman A., Mallon L.J., Ulrich G., Ziessel R. Eur. J. Org. Chem. 2008, 2008(16):2774-2782.
3. Albers A.E., Okreglak V.S., Chang C.J. J. Am. Chem. Soc. 2006, 128(30):9640-9641.
4. Brellier M., Duportail G., Baati R. Tetrahedron Lett. 2010, 51(9):1269-1272.
5. Bura T., Ziessel R. Org. Lett. 2011, 13(12):3072-3075.
6. Chang M.C., Pralle A., Isacoff E.Y., Chang C.J. J. Am. Chem. Soc. 2004, 126(47):15392-15393.
7. Chen W., Cai S., Ren Q.Q., Wen W., Zhao Y.D. Analyst 2012, 137(1):49-58.
8. Cheng T., Xu Y., Zhang S., Zhu W., Qian X., Duan L. J. Am. Chem. Soc. 2008, 130(48):16160-16161.
9. D'Autréaux B., Toledano M.B. Nat. Rev. Mol. Cell Biol. 2007, 8(10):813-824.
10. Dickinson B.C., Chang C.J. J. Am. Chem. Soc. 2008, 130(30):9638-9639.
11. Dickinson B.C., Huynh C., Chang C.J. J. Am. Chem. Soc. 2010, 132(16):5906-5915.
12. Dodani S.C., He Q., Chang C.J. J. Am. Chem. Soc. 2009, 131(50):18020-18021.
13. Fähnrich K.A., Pravda M., Guilbault G.G. Talanta 2001, 54(4):531-559.
14. Greene L.A., Tischler A.S. Proc. Natl. Acad. Sci. USA 1976, 73(7):2424-2428.
15. Harriman A., Mallon L.J., Ulrich G., Ziessel R. ChemPhysChem 2007, 8(8):1207-1214.
16. Hong R., Han G., Fernández J.M., Kim B.-j., Forbes N.S., Rotello V.M. J. Am. Chem. Soc. 2006, 128(4):1078-1079.
17. Jiang N., Fan J., Liu T., Cao J., Qiao B., Wang J., Gao P., Peng X. Chem. Commun. 2013, 49(90):10620-10622.
18. Jiao L., Yu C., Liu M., Wu Y., Cong K., Meng T., Wang Y., Hao E. J. Org. Chem. 2010, 75(17):6035-6038.
19. Karolin J., Johansson L.B.-A., Strandberg L., Ny T. J. Am. Chem. Soc. 1994, 116(17):7801-7806.
20. Karton-Lifshin N., Segal E., Omer L., Portnoy M., Satchi-Fainaro R., Shabat D. J. Am. Chem. Soc. 2011, 133(28):10960-10965.
21. Li L., Han J., Nguyen B., Burgess K. J. Org. Chem. 2008, 73(5):1963-1970.
22. Lippert A.R., De Bittner G.C.V., Chang C.J. Acc. Chem. Res. 2011, 44(9):793-804.
23. Lippert A.R., Gschneidtner T., Chang C.J. Chem. commun. 2010, 46(40):7510-7512.
24. Lo L.-C., Chu C.-Y. Chem. Commun. 2003, 21:2728.
25. Loudet A., Burgess K. Chem. Rev. 2007, 107(11):4891-4932.
26. Maeda H., Fukuyasu Y., Yoshida S., Fukuda M., Saeki K., Matsuno H., Yamauchi Y., Yoshida K., Hirata K., Miyamoto K. Angew. Chem. 2004, 43(18):2389-2391.
27. Miller E.W., Albers A.E., Pralle A., Isacoff E.Y., Chang C.J. J. Am. Chem. Soc. 2005, 127(47):16652-16659.
28. Miller E.W., Dickinson B.C., Chang C.J. Proc. Natl. Acad. Sci. USA 2010, 107(36):15681-15686.
29. Niu S.L., Ulrich G., Ziessel R., Kiss A., Renard P.-Y., Romieu A. Org. Lett. 2009, 11(10):2049-2052.
30. Nogueira R.F., Oliveira M.C., Paterlini W.C. Talanta 2005, 66(1):86-91.
31. Onoda M., Uchiyama S., Endo A., Tokuyama H., Santa T., Imai K. Org. Lett. 2003, 5(9):1459-1461.
32. Paulsen C.E., Carroll K.S. ACS Chem. Biol. 2009, 5(1):47-62.
33. Rhee S.G. Exp. Mol. Med. 1999, 31(2):53-59.
34. Rhee S.G. Science 2006, 312:1882-1883.
35. Srikun D., Miller E.W., Domaille D.W., Chang C.J. J. Am. Chem. Soc. 2008, 130(14):4596-4597.
36. Ulrich G., Ziessel R. J. Org. Chem. 2004, 69(6):2070-2083.
37. Ulrich G., Ziessel R., Harriman A. Angew. Chem. 2008, 47(7):1184-1201.
38. Vo-Hoang Y., Micouin L., Ronet C., Gachelin G., Bonin M. ChemBioChem 2003, 4(1):27-33.
39. Wang D., Miyamoto R., Shiraishi Y., Hirai T. Langmuir 2009, 25(22):13176-13182.
40. Winterbourn C.C. Nat. Chem. Biol. 2008, 4(5):278-286.
41. Wolfbeis O.S., Dürkop A., Wu M., Lin Z. Angew. Chem. Int. Ed. 2002, 41(23):4495-4498.
42. Xu K., Tang B., Huang H., Yang G., Chen Z., Li P., An L. Chem. Commun. 2005, 48:5974-5976.
43. Yuan L., Lin W., Xie Y., Chen B., Zhu S. J. Am. Chem. Soc. 2012, 134(2):1305-1315.
44. Zhang S., Wu T., Fan J., Li Z., Jiang N., Wang J., Dou B., Sun S., Song F., Peng X. Org. Biomol. Chem. 2013, 11(4):555-558.
45. Zhu S., Zhang J., Vegesna G., Luo F.-T., Green S.A., Liu H. Organ. Lett. 2010, 13(3):438-441.