Emission tuning of fluorescent kinase inhibitors: Conjugation length and substituent effects

Journal of Organic Chemistry

Volumn 79, Issue 11, 2014, Pages 4940-4947

  Dhuguru, Jyothi ^a   Liu, Wenjun ^b   Gonzalez, Walter G ^c   Babinchak, W Michael ^a   Miksovska, Jaroslava ^c   Landgraf, Ralf ^b   Wilson, James N ^a  

^a University of Miami   (United States)

^b UNIVERSITY OF MIAMI MILLER SCHOOL OF MEDICINE   (United States)

^c FLORIDA INTERNATIONAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL MODIFICATION; ENZYME INHIBITION; FLUORESCENCE; FLUOROPHORES; OPTICAL EMISSION SPECTROSCOPY;

CONJUGATION LENGTH; EMISSION ENHANCEMENT; KINASE INHIBITORS; OPTICAL SPECTROSCOPY; PHOTOEXCITATION ENERGY; RECEPTOR TYROSINE KINASE; SUBSTITUENT EFFECT; TD-DFT CALCULATIONS;

PROBES;

ADENOSINE TRIPHOSPHATE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; FLUORESCENT KINASE INHIBITOR; OCTANOL; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; WATER; FLUORESCENT DYE; LIGAND; N-PHENYL-4-AMINOQUINAZOLINE;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENZYME INHIBITION; FLUORESCENCE; HUMAN; HUMAN CELL; MCF 7 CELL LINE; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SOLUBILITY; SYNTHESIS; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; METABOLISM; PHOSPHORYLATION; QUANTUM THEORY; SPECTROFLUOROMETRY;

ADENOSINE TRIPHOSPHATE; BINDING SITES; FLUORESCENT DYES; LIGANDS; PHOSPHORYLATION; PROTEIN KINASE INHIBITORS; QUANTUM THEORY; QUINAZOLINES; RECEPTOR, ERBB-2; SPECTROMETRY, FLUORESCENCE;

EID: 84902096277     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500520x     Document Type: Article

References (26)

1. Anastassiadis, T.; Deacon, S. W.; Devarajan, K.; Ma, H.; Peterson, J. R. Nat. Biotechnol. 2011, 29, 1039-1045
2. Davis, M. I.; Hunt, J. P.; Herrgard, S.; Ciceri, P.; Wodicka, L. M.; Pallares, G.; Hocker, M.; Treiber, D. K.; Zarrinkar, P. P. Nat. Biotechnol. 2011, 29, 1046-1051
3. Cortot, A. B.; Repellin, C. E.; Shimamura, T.; Capelletti, M.; Zejnullahu, K.; Ercan, D.; Christensen, J. G.; Wong, K. K.; Gray, N. S.; Janne, P. A. Cancer Res. 2013, 73, 834-843
4. Ware, K. E.; Marshall, M. E.; Heasley, L. R.; Marek, L.; Hinz, T. K.; Hercule, P.; Helfrich, B. A.; Doebele, R. C.; Heasley, L. E. PLoS One 2010, 5, e14117
5. Sicard, R.; Dhuguru, J.; Liu, W.; Patel, N.; Landgraf, R.; Wilson, J. N. Bioorg. Med. Chem. Lett. 2012, 22, 5532-5535
6. Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Zhou, H.; Cody, D. R.; McMichael, A.; Fry, D. W. J. Med. Chem. 1995, 38, 3482-3487
7. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1996, 39, 267-276
8. Yun, C. H.; Boggon, T. J.; Li, Y.; Woo, M. S.; Greulich, H.; Meyerson, M.; Eck, M. J. Cancer Cell 2007, 11, 217-227
9. Wood, E. R.; Truesdale, A. T.; McDonald, O. B.; Yuan, D.; Hassell, A.; Dickerson, S. H.; Ellis, B.; Pennisi, C.; Horne, E.; Lackey, K.; Alligood, K. J.; Rusnak, D. W.; Gilmer, T. M.; Shewchuk, L. Cancer Res. 2004, 64, 6652-6659
10. Liu, Y.; Gray, N. S. Nat. Chem. Biol. 2006, 2, 358-364
11. Krueger, A. T.; Lu, H.; Lee, A. H. F.; Kool, E. T. Acc. Chem. Res. 2006, 40, 141-150
12. Hawkins, M. E.; Pfleiderer, W.; Jungmann, O.; Balis, F. M. Anal. Biochem. 2001, 298, 231-240
13. Sinkeldam, R. W.; Greco, N. J.; Tor, Y. Chem. Rev. 2010, 110, 2579-2619
14. Secrist, J. A., III; Barrio, J. R.; Leonard, N. J.; Villar-Palasi, C.; Gilman, A. G. Science 1972, 177, 279-280
15. Stamos, J.; Sliwkowski, M. X.; Eigenbrot, C. J. Biol. Chem. 2002, 277, 46265-46275
16. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
17. Zucchero, A. J.; McGrier, P. L.; Bunz, U. H. F. Acc. Chem. Res. 2010, 43, 397-408
18. Reichardt, C. Angew. Chem., Int. Ed. Engl. 1979, 18, 98-110
19. Pitter, D. R.; Wigenius, J.; Brown, A. S.; Baker, J. D.; Westerlund, F.; Wilson, J. N. Org. Lett. 2013, 15, 1330-1333
20. Danielsson, L.-G.; Zhang, Y.-H. Trends Anal. Chem. 1996, 15, 188-196
21. Ban, H. S.; Tanaka, Y.; Nabeyama, W.; Hatori, M.; Nakamura, H. Bioorg. Med. Chem. 2010, 18, 870-879
22. Karaman, M. W.; Herrgard, S.; Treiber, D. K.; Gallant, P.; Atteridge, C. E.; Campbell, B. T.; Chan, K. W.; Ciceri, P.; Davis, M. I.; Edeen, P. T.; Faraoni, R.; Floyd, M.; Hunt, J. P.; Lockhart, D. J.; Milanov, Z. V.; Morrison, M. J.; Pallares, G.; Patel, H. K.; Pritchard, S.; Wodicka, L. M.; Zarrinkar, P. P. Nat. Biotechnol. 2008, 26, 127-132
23. Kleiman, L. B.; Maiwald, T.; Conzelmann, H.; Lauffenburger, D. A.; Sorger, P. K. Mol. Cell 2011, 43, 723-737
24. Owen, S. C.; Doak, A. K.; Wassam, P.; Shoichet, M. S.; Shoichet, B. K. ACS Chem. Biol. 2012, 7, 1429-1435
25. Berlman, I. Handbook of Fluorescence Spectra of Aromatic Molecules, 2 nd ed.; Academic Press: New York, 1971.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian '09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.