Thiocolchicine-podophyllotoxin conjugates: Dynamic libraries based on disulfide exchange reaction

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2848-2853

  Danieli, Bruno ^a   Giardini, Alessandra ^a   Lesma, Giordano ^a   Passarella, Daniele ^a   Peretto, Bruno ^a   Sacchetti, Alessandro ^a   Silvani, Alessandra ^a   Pratesi, Graziella ^b   Zunino, Franco ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b NATIONAL CANCER INSTITUTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL TARGET; BOND EXCHANGE REACTION; DISULFIDE EXCHANGE REACTION; DIVALENT COMPOUND; ESI MASS SPECTROMETRY;

CHEMICAL BONDS; MASS SPECTROMETERS; MIXTURES; TARGETS;

ORGANIC COMPOUNDS;

COLCHICINE DERIVATIVE; DIMER; DISULFIDE; LIGAND; PODOPHYLLOTOXIN; THIOCOLCHICINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHEMICAL REACTION; COMBINATORIAL LIBRARY; CONJUGATION; DISULFIDE BOND; DISULFIDE EXCHANGE REACTION; DRUG STRUCTURE; DYNAMIC COMBINATORIAL LIBRARY; ELECTROSPRAY MASS SPECTROMETRY; EVALUATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLCHICINE; COMBINATORIAL CHEMISTRY TECHNIQUES; DISULFIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR CONFORMATION; PODOPHYLLOTOXIN; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 33645509492     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052677g     Document Type: Article

References (32)

1. (a) Langer, M.; Kratz, F.; Rothen-Rutishauser, B.; Wunderli-Alemnspach, H.; Beck-Sickinger, A. G. J. Med. Chem. 2001, 44, 1341.
2. (b) Safavy, A.; Bonner, J. A.; Waksal, H. W.; Buchsbaum, D. J.; Gillespie, G. Y.; Khazaeli, M. B.; Arani, R.; Chen, D. T.; Carpenter, M.; Raisch, K. P. Bioconjugate Chem. 2003, 14, 302.
3. See as examples: (a) Camps, P.; Formosa, X.; Munoz-Torrero, D.; Petrignet, J.; Badia, A.; Clos, M. V. J. Med. Chem. 2005, 48, 1701.
4. (b) Feng, S.; Wang, Z.; He, X.; Zheng, S.; Xia, Y.; Jiang, H.; Tang, X.; Bai, D. J. Med. Chem. 2004, 48, 655.
5. Choi, S.-K. Synthetic Multivalent Molecules; Wiley-Interscience: New York, 2004.
6. Giardini, A. Ph.D. Thesis, Università degli Studi di Milano, 2005.
7. Danieli, B.; Giardini, A.; Lesma, G.; Passarella, D.; Silvani, A.; Appendino, G.; Noncovich, A.; Fontana, G.; Bombardalli, E.; Sterner, O. Chem. Biodivers. 2004, 1, 327.
8. (a) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455.
9. (b) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898.
10. (c) Cousins, G. R. L.; Poulsen, S.-A.; Sanders, J. K. M. Curr. Opin. Chem. Biol. 2000, 4, 270.
11. (d) Lehn, J.-M.; Eliseen, A. V. Science 2001, 291, 2331;
12. Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Curr. Opin. Chem. Biol. 2002, 6, 321.
13. (e) Karan, C.; Miller, B. L. Drug Discov. Today 2000, 5, 67.
14. Ramstrom, O.; Lehn, J.-M. ChemBioChem 2000, 1, 41.
15. (a) Kerekes, P.; Sharma, P.; Brossi, A.; Chignell, C. F.; Quinn, F. R. J. Med. Chem. 1985, 28, 1204.
16. (b) Rosner, M.; Capraro, H. G.; Jacobson, A. E.; Atwell, L.; Brossi, A.; Iorio, M. A.; Williams, T. H.; Sik, R. H.; Chignell, C. F. J. Med. Chem. 1981, 24, 257 and references therein.
17. Lee, K. H. In Human Medicinal Agents from Plants; Kinghorn, A. D., Balandrin, M., Eds.; American Chemical Society Symposium Series; American Chemical Society: Washington, DC, 1993; p 170.
18. (a) Wallace, T. J.; Schriesheim, A.; Bartok, W. J. Org. Chem. 1963, 28, 1311.
19. (b) Lees, W. J.; Whitesides, G. M. J. Org. Chem. 1993, 58, 642.
20. For recent reports on DCC using disulfide exchange reaction, see: (a) Reference 7.
21. (b) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122, 12063.
22. (c) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Science 2002, 297, 590.
23. (d) Otto, S.; Kubik, S. J. J. Am. Chem. Soc. 2003, 125, 7804.
24. (e) Brising, B.; Sanders, J. K. M.; Otto, S. Angew. Chem., Int. Ed. 2003, 42, 1270.
25. (f) Sando, S.; Narita, A.; Aoyama, Y. Bioorg. Med. Chem. Lett. 2004, 14, 2835.
26. 2 + n)/2.
27. Snyder, H. R.; Alexander, W. J. Am. Chem. Soc. 1948, 70, 217.
28. Shi, Q.; Verdier-Pinard, P.; Brossi, A.; Harmel, E.; Lee, K.-H. Bioorg. Med. Chem. 1997, 5, 2277.
29. 2/MeOH (9:1, 5 mL) was warmed in a microwave oven at 45 °C for 2 h. Evaporation and purification by chromatography gave 12 (or 13) in 65% (60%) yield.
30. For other examples of electrospray ionisation Fourier-transform ion cyclotron resonance mass spectrometry (ESI-FT-ICR) of dynamic combinatorial libraries, see: (a) Poulsen, S.-A.; Gates, P. J.; Cousins, G. R. L.; Sanders, J. M. Rapid Commun. Mass Spectrom. 2000, 14, 44.
31. (b) Cooper, H. J.; Case, M. A.; McLendon, G. L.; Marshall, A. G. J. Am. Chem. Soc. 2003, 125, 5331.
32. (c) Reference 11b.