Recent advances in the synthesis of tubulysins

Mini-Reviews in Medicinal Chemistry

Volumn 13, Issue 11, 2013, Pages 1572-1578

  Xiangming, Xu ^a   Friestad, Gregory K ^c   Lei, Yao ^b  

^a LINYI PEOPLE'S HOSPITAL   (China)

^b YANTAI UNIVERSITY   (China)

^c University of Iowa   (United States)

Author keywords

Anticancer agents; Total synthesis; Tubulysins

Indexed keywords

GRIGNARD REAGENT; PACLITAXEL; TETRAPEPTIDE; TUBULIN; TUBULYSIN; UNCLASSIFIED DRUG; VINCA ALKALOID;

ANTINEOPLASTIC ACTIVITY; CANCER CELL CULTURE; CHROMATOGRAPHY; DRUG SYNTHESIS; EPIMERIZATION; MICHAEL ADDITION; MICROTUBULE ASSEMBLY; MOLECULAR WEIGHT; REVIEW; SILYLATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; WOLFF REARRANGEMENT;

ANTINEOPLASTIC AGENTS; HUMANS; NEOPLASMS; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 84888058685     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/13895575113139990063     Document Type: Review

References (19)

1. Sasse, F.; Steinmetz, H.; Heil, J.; Hofle, G.; Reichenbach, H. Tubulysins, new cytostatic peptides from mytobacteria acting on microtubuli. Production, isolation, physio-chemical and biological properties. J. Antibiot, 2000, 53, 879-885.
2. Steinmetz, H.; Glaser, N.; Herdtweck, E.; Sasse, F.; Reichenbach, H.; Höfle, G. Isolation, Crystal and Solution Structure Determination, and Biosynthesis of Tubulysins-Powerful Inhibitors of Tubulin Polymerization from Myxobacteria. Angew. Chem. Int. Ed, 2004, 43, 4888-4892.
3. Kaur, G.; Hollingshead, M.; Holbeck, S.; Schauer-Vukasinovic, V; Camalier, R. F.; Domling, A.; Agarwal, S. Biological evaluation of tubulysin A: a potential anticancer and antiangiogenic natural product. Biochem. J, 2006, 396, 235-242.
4. Peltier, M. H.; McMahon., P. J.; Patterson, W. A.; Ellman, A. J. The Total Synthesis of Tubulysin D. J. Am. Chem. Soc, 2006, 128, 16018-16019.
5. Raghavan, B.; Balasubramanian, R.; Steele, C. J.; Sackett, D. L.; Fecik, A. R. Cytotoxic Simplified Tubulysin Analogues. J. Med. Chem, 2008, 51, 1530-1533.
6. Balasubramanian, R.; Raghavan, B.; Begaye, A.; Sackett, D. L.; Fecik, R. A. Total Synthesis and Biological Evaluation of Tubulysin U, Tubulysin V, and Their Analogues. J. Med. Chem, 2009, 52, 238-240.
7. Wipf, P.; Wang, Z. Total Synthesis of N14-Desacetoxytubulysin H. Org. Lett, 2007, 9, 1605-1607.
8. Sani, M.; Fossati, G.; Huguenot, F.; Zanda, M. Total Synthesis of Tubulysins U and V. Angew. Chem. Int. Ed, 2007, 46, 3526-3529.
9. Pando, O.; Stark, S.; Denkert, A.; Porzel, A.; Preusentanz, R.; Wessjohann, L. A. The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity. J. Am. Chem. Soc, 2011, 133, 7692-7695.
10. Wipf, P.; Takada, T.; Rishel, M. J. Synthesis of the Tubuvaline-Tubuphenylalanine (Tuv-Tup) Fragment of Tubulysin. Org. Lett, 2004, 6, 4057-4060.
11. Friestad, G. K.; Marie, J-C.; Deveau, A. M. Stereoselective Mn-Mediated Coupling of Functionalized Iodides and Hydrazones: A Synthetic Entry to the Tubulysin-Amino Acids. Org. Lett, 2004, 6, 3249-3252.
12. Shibue, T.; Hirai, T.; Okamoto, I.; Morita, N.; Masu, H.; Azumaya, I.; Tamura, O. Total Syntheses of Tubulysins. Chem. Eur. J. 2010, 16, 11678-11688.
13. Pando, O.; Dorner, S.; Preusentanz, R.; Denkert, A.; Porzel, A.; Richter, W.; Wessjohann, L. A. First Total Synthesis of Tubulysin B. Org. Lett, 2009, 11, 5567-5569.
14. Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, A. L. Total Synthesis of Tubulysin U and V. Angew. Chem. Int. Ed, 2006, 45, 7235-7239.
15. Chandrasekhar, S.; Mahipal, B.; Kavitha, M. Toward Tubulysin: Gram-Scale Synthesis of Tubuvaline-Tubuphenylalanine Fragment. J. Org. Chem, 2009, 74, 9531-9534.
16. Shankar, P. S.; Jagodzinska, M.; Malpezzi, L.; Lazzari, P.; Manca, R. I., Greig, I. M.; Sani. M.; Zanda, M. Synthesis and structure-activity Zanda relationship studies of novel tubulysin U analogues-effect on cytotoxicity of structural variations in the tubuvaline fragment. Org. Bio. Chem. 2013, 11, 2273-2287.
17. Shankar, P. S.; Sani, M.; Saunders, R. F.; Wallace, M. H; Zanda, M. Total Synthesis and Cytotoxicity Evaluation of an Oxazole Analogue of Tubulysin U. Synlett, 2011, 12, 1673-1676.
18. Patterson, W. A.; Peltier, M. H.; Sasse, Fl.; Ellman, A. J. Design Synthesis, and Biological Properties of Highly Potent Tubulysin D Analogues. Chem. Eur. J, 2007, 13, 9534-9341.
19. Wang, Z.; McPherson, P. A.; Raccor, B. S.; Balachandran, R.; Zhu, G.; Day, B. W.; Vogt, A.; Wipf, P. Structure-activity and Highcontent Imaging Analyses of Novel Tubulysins. Chem. Biol. Drug Des. 2007, 70, 75-86.