Anilinomethylrhodamines: PH sensitive probes with tunable photophysical properties by substituent effect

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10134-10143

  Best, Quinn A ^a   Liu, Chuangjun ^a   Van Hoveln, Paul D ^a   McCarroll, Matthew E ^a   Scott, Colleen N ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; HAMMETT EQUATIONS; LINEAR RESPONSE; PH SENSITIVE; PH-DEPENDENT; PHOTOPHYSICAL; PHOTOPHYSICAL PROPERTIES; SUBSTITUENT EFFECT;

EQUILIBRIUM CONSTANTS;

FLUORESCENCE;

AMINOMETHYLRHODAMINE DERIVATIVE; ANILINOMETHYLRHODAMINE DERIVATIVE; FLUORESCENT DYE; RHODAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLORIMETRY; EQUILIBRIUM CONSTANT; FLUORESCENCE; PH; QUANTUM YIELD;

ANILINE COMPOUNDS; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; RHODAMINES;

EID: 84886377716     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401323g     Document Type: Article

References (30)

1. Ohkuma, S.; Poole, B. Proc. Natl. Acad. Sci. U. S. A. 1978, 75, 3327
2. Paroutis, P.; Touret, N.; Grinstein, S. Physiology 2004, 19, 207
3. Holopainen, J. M.; Saarikoski, J.; Kinnunen, P. K. J.; Jarvela, I. Eur. J. Biochem. 2001, 268, 5851
4. Smith, J. L. J. Food Proteins 2003, 66, 1292-1303
5. Giannella, R. A.; Broitman, S. A.; Zamcheck, N. Gut 1972, 13, 251-256
6. Martinsen, T. C.; Bergh, K.; Waldum, H. L. Basic Clin. Pharmacol. Toxicol. 2005, 96, 94-102
7. Papavramidis, T. S.; Papavramidis, S. T.; Sapalidis, K. G.; Kessisoglou, I. I.; Gamvros, O. I. Obes. Surg. 2004, 14, 271-274
8. Huang, J. Q.; Hunta, R. H. Yale J. Biol. Med. 1996, 69, 159-174
9. Vavere, A. L.; Biddlecombe, G. B.; Spees, W. M. Cancer Res. 2009, 69, 4510
10. Gallagher, F. A.; Kettunen, M. I.; Day, S. E. Nature 2008, 453, 940
11. Han, J.; Burgess, K. Chem. Rev. 2010, 110, 2709
12. Lin, H.-J.; Szmacinski, H.; Lakowicz, J. R. Anal. Biochem. 1999, 269, 162
13. Nedergaard, M.; Desai, S.; Pulsinelli, W. Anal. Biochem. 1990, 187, 109
14. Myochin, T.; Kiyose, K.; Hanaoka, K.; Kojima, H.; Terai, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 3401
15. Kiyose, K.; Aizawa, S.; Sasaki, E.; Kojima, H.; Hanaoka, K.; Terai, T.; Urano, Y.; Nagano, T. Chem.-Eur. J. 2009, 15, 9191
16. Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910
17. Li, Z.; Song, Y.; Yang, Y.; Yang, L.; Huang, X.; Han, J.; Han, S. Chem. Sci. 2012, 3, 2941
18. Montenegro, H.; Di Paolo, M.; Capdevila, D.; Aramendía, P. F.; Bossi, M. L. Photochem. Photobiol. Sci. 2012, 11, 1081
19. Tian, M.; Peng, X.; Fan, J.; Wang, J.; Sun, S. Dyes Pigm. 2012, 95, 112
20. Hu, Z.; Li, M.; Liu, M.; Zhuang, W.; Li, G. Dyes Pigm. 2013, 96, 71
21. Lv, H.; Liu, J.; Zhao, J.; Zhao, B.; Miao, J. Sens. Actuators, B 2013, 177, 956
22. Best, Q. A.; Xu, R.; McCarroll, M. E.; Wang, L.; Dyer, D. J. Org. Lett. 2010, 12, 3219
23. Wu, Z.; Wu, X.; Yang, Y.; Wen, T.; Han, S. Bioorg. Med. Chem. Lett. 2012, 22, 6358
24. Wu, X.; Wu, Z.; Yang, Y.; Han, S. Chem. Commun. 2012, 48, 1895
25. Li, Z.; Xue, Z.; Wu, Z.; Han, J.; Han, S. Org. Biomol. Chem. 2011, 9, 7652
26. Bender, A.; Woydziak, Z. R.; Fu, L.; Branden, M.; Zhou, Z.; Ackley, B. D.; Peterson, B. R. ACS Chem. Bio. 2013, 8, 636-642
27. Kubin, R. F.; Fletcher, A. N. J. Lumin. 1982, 27, 455-462
28. Casey, K. G.; Quitevis, E. L. J. Phys. Chem. 1988, 92, 6590-6594
29. Gross, K. C.; Seybold, P. G. Int. J. Quantum Chem. 2000, 80, 1107
30. Li, H.; Fan, J.; Wang, J.; Tian, M.; Du, J.; Sun, S.; Sun, P.; Peng, X. Chem. Commun. 2009, 45, 5904