Tetrabiphenylporphyrin-based receptors for protein surfaces show sub-nanomolar affinity and enhance unfolding

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 16, 2003, Pages 2651-2654

  Aya, Toshihiro ^a   Hamilton, Andrew D ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME C; PORPHYRIN DERIVATIVE; RECEPTOR; TETRABIPHENYLPORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; PROTEIN ANALYSIS; PROTEIN FAMILY; PROTEIN FOLDING; PROTEIN SYNTHESIS; RECEPTOR BINDING; STOICHIOMETRY; SURFACE PROPERTY; TEMPERATURE;

EID: 0038149100     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00551-1     Document Type: Article

References (18)

1. Babine R.E., Bender S.L. Chem. Rev. 97:1997;1359.
2. (a) Clark-Ferris K.K., Fisher J. J. Am. Chem. Soc. 107:1985;5007 (b) Regan J., McGarry D., Bruno J., Green D., Newman J., Hsu C.Y., Kline J., Barton J., Travis J., Choi Y.M., Volz F., Pauls H., Harrison R., Zilberstein A., Ben-Sasson S.A., Chang M. J. Med. Chem. 40:1997;3408 (c) Cushman M., Kanamathareddy S., Clercq E.D., Schols D., Goldman M.E., Bowen J.A. J. Med. Chem. 34:1991;337 (d) Fazal M.A., Roy B.C., Sun S.G., Mallik S., Rodgers K.R. J. Am. Chem. Soc. 123:2001;6283.
3. (a) Clark-Ferris K.K., Fisher J. J. Am. Chem. Soc. 107:1985;5007 (b) Regan J., McGarry D., Bruno J., Green D., Newman J., Hsu C.Y., Kline J., Barton J., Travis J., Choi Y.M., Volz F., Pauls H., Harrison R., Zilberstein A., Ben-Sasson S.A., Chang M. J. Med. Chem. 40:1997;3408 (c) Cushman M., Kanamathareddy S., Clercq E.D., Schols D., Goldman M.E., Bowen J.A. J. Med. Chem. 34:1991;337 (d) Fazal M.A., Roy B.C., Sun S.G., Mallik S., Rodgers K.R. J. Am. Chem. Soc. 123:2001;6283.
4. (a) Clark-Ferris K.K., Fisher J. J. Am. Chem. Soc. 107:1985;5007 (b) Regan J., McGarry D., Bruno J., Green D., Newman J., Hsu C.Y., Kline J., Barton J., Travis J., Choi Y.M., Volz F., Pauls H., Harrison R., Zilberstein A., Ben-Sasson S.A., Chang M. J. Med. Chem. 40:1997;3408 (c) Cushman M., Kanamathareddy S., Clercq E.D., Schols D., Goldman M.E., Bowen J.A. J. Med. Chem. 34:1991;337 (d) Fazal M.A., Roy B.C., Sun S.G., Mallik S., Rodgers K.R. J. Am. Chem. Soc. 123:2001;6283.
5. (a) Clark-Ferris K.K., Fisher J. J. Am. Chem. Soc. 107:1985;5007 (b) Regan J., McGarry D., Bruno J., Green D., Newman J., Hsu C.Y., Kline J., Barton J., Travis J., Choi Y.M., Volz F., Pauls H., Harrison R., Zilberstein A., Ben-Sasson S.A., Chang M. J. Med. Chem. 40:1997;3408 (c) Cushman M., Kanamathareddy S., Clercq E.D., Schols D., Goldman M.E., Bowen J.A. J. Med. Chem. 34:1991;337 (d) Fazal M.A., Roy B.C., Sun S.G., Mallik S., Rodgers K.R. J. Am. Chem. Soc. 123:2001;6283.
6. (a) Hamuro Y., Calama M.C., Park H.S., Hamilton A.D. Angew. Chem., Int. Ed. Engl. 36:1997;2680 (b) Lin Q., Park H.S., Hamuro Y., Lee C.S., Hamilton A.D. Biopolymers. 47:1998;285 (c) Park H.S., Lin Q., Hamilton A.D. J. Am. Chem. Soc. 121:1999;8 (d) Sebti S.M., Hamilton A.D. Oncogene. 19:2000;6566.
7. (a) Hamuro Y., Calama M.C., Park H.S., Hamilton A.D. Angew. Chem., Int. Ed. Engl. 36:1997;2680 (b) Lin Q., Park H.S., Hamuro Y., Lee C.S., Hamilton A.D. Biopolymers. 47:1998;285 (c) Park H.S., Lin Q., Hamilton A.D. J. Am. Chem. Soc. 121:1999;8 (d) Sebti S.M., Hamilton A.D. Oncogene. 19:2000;6566.
8. (a) Hamuro Y., Calama M.C., Park H.S., Hamilton A.D. Angew. Chem., Int. Ed. Engl. 36:1997;2680 (b) Lin Q., Park H.S., Hamuro Y., Lee C.S., Hamilton A.D. Biopolymers. 47:1998;285 (c) Park H.S., Lin Q., Hamilton A.D. J. Am. Chem. Soc. 121:1999;8 (d) Sebti S.M., Hamilton A.D. Oncogene. 19:2000;6566.
9. (a) Hamuro Y., Calama M.C., Park H.S., Hamilton A.D. Angew. Chem., Int. Ed. Engl. 36:1997;2680 (b) Lin Q., Park H.S., Hamuro Y., Lee C.S., Hamilton A.D. Biopolymers. 47:1998;285 (c) Park H.S., Lin Q., Hamilton A.D. J. Am. Chem. Soc. 121:1999;8 (d) Sebti S.M., Hamilton A.D. Oncogene. 19:2000;6566.
10. Jain R.K., Hamilton A.D. Org. Lett. 2:2000;1721.
11. Stites W.E. Chem. Rev. 97:1997;1233.
12. Chao Y.H., Bersohn R., Aisen P. Biochemistry. 18:1979;774.
13. Scott R.A., Mauk A.G. Cytochrome c: A Multidiciplinary Approach. 1996;University Science Books, Sausalito.
14. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., Korsakoff L.J. J. Org. Chem. 32:1967;476.
15. A plot of [7] from 5 to 90 nM against fluorescence emission intensity (at 650 nm, excited at 420 nm) was linear, suggesting no aggregation effects at these concentrations.
16. Dutton J.E., Rogers L.J. Biochim. Biophys. Acta. 537:1978;501.
17. Jain R.K., Hamilton A.D. Angew. Chem. Int. Ed. 41:2002;641.
18. Wilson A.J., Groves K., Jain R.K., Park H.S., Hamilton A.D. J. Am. Chem. Soc. 125:2003;4420.