Generation of novel DNA-binding compounds by selection and amplification from self-assembled combinatorial libraries

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8639-8642

  Klekota, Bryan ^a   Hammond, Mark H ^a   Miller, Benjamin L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; LIGAND; SALICYLIC ACID DERIVATIVE;

ARTICLE; BINDING AFFINITY; DNA BINDING; DNA LIBRARY; DRUG ISOLATION; METHODOLOGY;

EID: 0030819668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10374-4     Document Type: Article

References (22)

1. (a) Szostak, J. W. Trends Biochem. Sci. 1992, 17, 89-93;
2. (b) Tuerk, C.; Gold, L. Science 1990, 249, 505-510.
3. Amabilino, D. B.; Ashton, P. R.; Perez-Garcia, L; Stoddart, J. F. Angew. Chem. 1995, 107, 2569-2572; Angew. Chem. Int. Ed. Engl. 1995, 34, 2378-2380.
4. Amabilino, D. B.; Ashton, P. R.; Perez-Garcia, L; Stoddart, J. F. Angew. Chem. 1995, 107, 2569-2572; Angew. Chem. Int. Ed. Engl. 1995, 34, 2378-2380.
5. Hasenknopf, B.; Lehn, J.-M.; Kneisel, B. O.; Baum, G.; Fenske, D. Agew. Chem. 1996, 108, 1987-1990; Angew. Chem. Int. Ed. Engl. 1996, 35, 1838-1840.
6. Hasenknopf, B.; Lehn, J.-M.; Kneisel, B. O.; Baum, G.; Fenske, D. Agew. Chem. 1996, 108, 1987-1990; Angew. Chem. Int. Ed. Engl. 1996, 35, 1838-1840.
7. Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
8. A recent report has described a method for the selection of compounds capable of binding to guanidinium via a photoinduced isomerization (Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997,119, 1147-1148); however, selection is driven by an external energy source (light) in addition to differences in binding affinity.
9. Huc and Lehn have provided an elegant demonstration of changes in product ratios obtained in imination reactions carried out on mixtures of amines and aldehydes in the presence of carbonic anhydrase: Huc, I.; Lehn, J.-M. Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110.
10. For example, see Trauger, J. W.; Baird, E. E.; Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1996, 118, 6160-6166 and references therein.
11. Mei, H.-Y.; Barton, J. K. J. Am. Chem. Soc. 1986, 108, 7414-7416.
12. Garnovskii, A. D.; Nivorozhkin, A. L.; Minkin, V. I. Coord. Chem. Rev. 1993, 126, 1-69.
13. Dreher, M.; Elias, H.; Paulus, H. Z. Naturforsch. B. 1987, 42, 707-712.
14. The synthesis and characterization of 3 and 7 have been previously described. Compound 3: Inouye, S. Chem. Pharm. Bull. 1967, 15, 1540-1546;
15. compound 7: (a) Duran, M. L.; Romero, J.; Sousa, A. Synth. React. Inorg. Met.-Org. Chem. 1987, 17, 681-683.
16. (b) Ramesh, K.; Mukherjee, R. J. Chem. Soc. Dalton 1992, 83-86. All new compounds displayed satisfactory spectral data.
17. Blackborow, J. R.; Karunaratne, S.; Lockhart, J. C.; Hill, M. N. S. J. Chem. Res. 1978, 119.
18. Schepartz, A.; McDevitt, J. P. J. Am. Chem. Soc. 1989, 111, 5976-5977.
19. 2 to a solution of an amine and salicylaldehyde in water can induce imine formation followed by complexation (B.K. and B.L.M., unpublished data). This suggests that a three-stage equilibrium process could be constructed.
20. 2) rather than a chelate: see Bottino, F. A.; Finocchiaro, P.; Libertini, E.; Mattern, G. Zeitschrift für Kristallographie 1989, 187, 71-77.
21. 12-18 as obtained from Pharmacia Biotech is a mixture of homopolymeric, single-stranded DNA of length 12 to 18.
22. Krugh, T. R. Proc. Natl. Acad. Sci. USA 1972, 69, 1911-1914.