Binding is not enough: Flexibility is needed for photocrosslinking of Lck kinase by benzophenone photoligands

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 19, 2008, Pages 8824-8829

  Kawamura, Akira ^a   Hindi, Sagit ^a   Mihai, Doina M ^a   James, Laurence ^a   Aminova, Olga ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Adenine; Biotin; Bpa; Chemical proteomics; Photoaffinity; SAR

Indexed keywords

4 AMINO 5 (4 PHENOXYPHENYL) 7H PYRROLO[3,2 D]PYRIMIDIN 7 YL CYCLOPENTANE; BENZOPHENONE; LIGAND; PHOTOLIGAND; PROTEIN KINASE INHIBITOR; PROTEIN KINASE LCK; PROTEIN KINASE LCK INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG DESIGN; DRUG SYNTHESIS; LIGAND BINDING; NONHUMAN; PHOTOACTIVATION; PHOTOAFFINITY LABELING; PHYSICAL CHEMISTRY; PROTEIN CONFORMATION; PROTEIN CROSS LINKING; REACTION OPTIMIZATION; STRUCTURE ACTIVITY RELATION; TARGET CELL;

AMINO ACID SEQUENCE; BENZOPHENONES; BINDING SITES; BLOTTING, WESTERN; ENZYME INHIBITORS; LIGANDS; LYMPHOCYTE SPECIFIC PROTEIN TYROSINE KINASE P56(LCK); MOLECULAR SEQUENCE DATA; PHOTOAFFINITY LABELS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 52949094243     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.077     Document Type: Article

References (36)

1. Dorman G., and Prestwich G.D. Biochemistry 33 (1994) 5661
2. Prestwich G.D., Dorman G., Elliott J.T., Marecak D.M., and Chaudhary A. Photochem. Photobiol. 65 (1997) 222
3. Dorman G., and Prestwich G.D. Trends Biotechnol. 18 (2000) 64
4. Kale T.A., Hsieh S.A., Rose M.W., and Distefano M.D. Curr. Top. Med. Chem. 3 (2003) 1043
5. Chorev M. Receptors Channels 8 (2002) 219
6. Kawamura A., and Hindi S. Chirality 17 (2005) 332
7. Mourot A., Grutter T., Goeldner M., and Kotzyba-Hibert F. Chembiochem 7 (2006) 570
8. Uttamchandani M., Li J., Sun H., and Yao S.Q. Chembiochem 9 (2008) 667
9. Salisbury C.M., and Cravatt B.F. J. Am. Chem. Soc. 130 (2008) 2184
10. Salisbury C.M., and Cravatt B.F. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 1171
11. Sieber S.A., Niessen S., Hoover H.S., and Cravatt B.F. Nat. Chem. Biol. 2 (2006) 274
12. Saghatelian A., Jessani N., Joseph A., Humphrey M., and Cravatt B.F. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 10000
13. Chan E.W., Chattopadhaya S., Panicker R.C., Huang X., and Yao S.Q. J. Am. Chem. Soc. 126 (2004) 14435
14. Henry L.K., Khare S., Son C., Babu V.V.S., Naider F., and Becker J.M. Biochemistry 41 (2002) 6128
15. Dong M., Li Z., Pinon D.I., Lybrand T.P., and Miller L.J. J. Biol. Chem. 279 (2004) 2894
16. Wittelsberger A., Mierke D.F., and Rosenblatt M. Chem. Biol. Drug Des. 71 (2008) 380
17. Winnik M.A. Chem. Rev. 81 (1981) 491
18. Wagner P.J. Acc. Chem. Res. 16 (1983) 461
19. Molina T.J., Kishihara K., Siderovski D.P., van Ewijk W., Narendran A., Timms E., Wakeham A., Paige C.J., Hartmann K.U., Veillette A., et al. Nature 357 (1992) 161
20. Anderson S.J., Levin S.D., and Perlmutter R.M. Nature 365 (1993) 552
21. Palacios E.H., and Weiss A. Oncogene 23 (2004) 7990
22. Goldman F.D., Ballas Z.K., Schutte B.C., Kemp J., Hollenback C., Noraz N., and Taylor N. J. Clin. Invest. 102 (1998) 421
23. Marth J.D., Overell R.W., Meier K.E., Krebs E.G., and Perlmutter R.M. Nature 332 (1988) 171
24. Hindi S., Deng H., James L., and Kawamura A. Bioorg. Med. Chem. Lett. 16 (2006) 5625
25. Koresawa M., and Okabe T. Assay Drug Dev. Technol. 2 (2004) 153
26. Feng B.Y., Simeonov A., Jadhav A., Babaoglu K., Inglese J., Shoichet B.K., and Austin C.P. J. Med. Chem. 50 (2007) 2385
27. Arnold L.D., Calderwood D.J., Dixon R.W., Johnston D.N., Kamens J.S., Munschauer R., Rafferty P., and Ratnofsky S.E. Bioorg. Med. Chem. Lett. 10 (2000) 2167
28. Burchat A.F., Calderwood D.J., Hirst G.C., Holman N.J., Johnston D.N., Munschauer R., Rafferty P., and Tometzki G.B. Bioorg. Med. Chem. Lett. 10 (2000) 2171
29. Winnik M.A. Acc. Chem. Res. 10 (1977) 173
30. Qvit N., Monderer-Rothkof G., Ido A., Shalev D.E., Amster-Choder O., and Gilon C. Peptide Sci. 90 (2008) 526
31. DeGraw A.J., Zhao Z., Strickland C.L., Taban A.H., Hsieh J., Jefferies M., Xie W., Shintani D.K., McMahan C.M., Cornish K., and Distefano M.D. J. Org. Chem. 72 (2007) 4587
32. Kato E., Howitt R., Dzyuba S.V., and Nakanishi K. Org. Biomol. Chem. 5 (2007) 3758
33. Fuwa H., Hiromoto K., Takahashi Y., Yokoshima S., Kan T., Fukuyama T., Iwatsubo T., Tomita T., and Natsugari H. Bioorg. Med. Chem. Lett. 16 (2006) 4184
34. Shen R., Inoue T., Forgac M., and Porco Jr. J.A. J. Org. Chem. 70 (2005) 3686
35. Severance D., Pandey B., and Morrison H. J. Am. Chem. Soc. 109 (1987) 3231
36. Wagner P.J., Pabon R., Park B.-S., Zand A.R., and Ward D.L. J. Am. Chem. Soc. 116 (1994) 589