Design, synthesis, and biological properties of highly potent tubulysin D analogues

Chemistry - A European Journal

Volumn 13, Issue 34, 2007, Pages 9534-9541

  Patterson, Andrew W ^a   Peltier, Hillary M ^a   Sasse, Florenz ^b   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Dept Microbial Drugs   (Germany)

Author keywords

Cytotoxicity; Natural products; Total synthesis; Tubulin; Tubulysin

Indexed keywords

NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIPS; TUBULIN; TUBULYSIN;

AMINES; ANIMAL CELL CULTURE; CYTOTOXICITY; GROWTH KINETICS; SYNTHESIS (CHEMICAL);

ENZYMES;

OLIGOPEPTIDE; TUBULYSIN D; UNCLASSIFIED DRUG;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; HUMAN; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL SURVIVAL; DRUG DESIGN; HUMANS; MOLECULAR STRUCTURE; OLIGOPEPTIDES;

EID: 36649010399     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701057     Document Type: Article

References (16)

1. F. Sasse, H. Steinmetz, G. Höfle, H. Reichenbach, J. Antibiot. 2000, 53, 879-885.
2. a) M. W. Khalil, F. Sasse, H. Lünsdorf, Y. A. Elnakady, H. Reichenbach, ChemBioChem 2006, 7, 678-683;
3. b) G. Kaur, M. Hollingshead, S. Holbeck, V. Schauer- Vukašinović, R. F. Camalier, A. Dömling, S. Agarwal, Biochem. J. 2006, 396, 235-242.
4. a) H. Steinmetz, N. Glaser, E. Herdtweck, F. Sasse, H. Reichenbach, G. Höfle, Angew. Chem. 2004, 116, 4996-5000;
5. Angew. Chem. Int. Ed. 2004, 43, 4888-4892;
6. b) G. Höfle, N. Glaser, T. Leibold, U. Karama, F. Sasse, H. Steinmetz, Pure Appl. Chem. 2003, 75, 167-178.
7. A list of all approved cancer drugs can be found at http://www.fda.gov/ cder/cancer/druglistframe.htm.
8. J. Iley, R. Moreira, T. Calheiros, E. Mendes, Pharm. Res. 1997, 14, 1634-1639.
9. H. M. Peltier. J. P. McMahon, A. W. Patterson, J. A. Ellman, J. Am. Chem. Soc. 2006, 128, 16018-16019.
10. The total synthesis but not the bioactivities of simple tubulysins or tubulysin derivatives lacking the N,O-acetal have been reported: a) A. Dömling, B. Beck, U. Eichelberger, S. Sakamuri, S. Menon, Q.-Z. Chen, Y. Lu, L. A. Wessjohann, Angew. Chem. 2006, 118, 7393-7397;
11. Angew. Chem. Int. Ed. 2006, 45, 7235-7239;
12. b) P. Wipf, Z. Wang, Org. Lett. 2007, 9, 1605-1607;
13. c) M. Sani, G. Fossati, F. Huguenot. M. Zanda, Angew. Chem. 2007, 119, 3596-3599;
14. Angew. Chem. Int. Ed. 2007, 46, 3526-3529.
15. This analogue has recently been reported by Wipf and Wang and was prepared in 20 steps and 2.1% overall yield. See ref. [7c].
16. T. Mosmann, J. Immunol. Methods 1983, 65, 55-63.