Tubulin structure-based drug design for the development of novel 4β-sulfur-substituted podophyllum tubulin inhibitors with anti-tumor activity

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Zhao, Wei ^a   Bai, Jia Ke ^a   Li, Hong Mei ^a   Chen, Tao ^b   Tang, Ya Jie ^a  

^a HUBEI UNIVERSITY OF TECHNOLOGY   (China)

^b TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; COLCHICINE; MERCAPTOPURINE; PODOPHYLLOTOXIN; SULFUR; TIOGUANINE; TUBULIN; TUBULIN MODULATOR;

APOPTOSIS; CELL CYCLE CHECKPOINT; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; HUMAN; IC50; KINETICS; MOLECULAR MODEL; PODOPHYLLUM; POLYMERIZATION; SURFACE PLASMON RESONANCE; SYNTHESIS; TEMPERATURE; TUMOR CELL LINE;

6-MERCAPTOPURINE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; COLCHICINE; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MODELS, MOLECULAR; PODOPHYLLOTOXIN; PODOPHYLLUM; POLYMERIZATION; SULFUR; SURFACE PLASMON RESONANCE; TEMPERATURE; THIOGUANINE; TUBULIN; TUBULIN MODULATORS;

EID: 84929166379     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep10172     Document Type: Article

References (21)

1. Pennisi, E. Structure of key cytoskeletal protein tubulin revealed. Science. 279, 176-177 (1998).
2. Dumontet, C. & Jordan, M. A. Microtubule-binding agents: a dynamic field of cancer therapeutics. Nat. Rev. Drug Discov. 9, 790-803 (2010).
3. Voigt, T. C. et al. A natural product inspired tetrahydropyran collection yields mitosis modulators that synergistically target CSE1L and tubulin. Angew. Chem. Int. Ed., 52, 410-414 (2013).
4. Schönbrunn, E. et al. Crystallization of a macromolecular ring assembly of tubulin liganded with the anti-mitotic drug podophyllotoxin. J. Struct. Biol. 128, 211-215 (1999).
5. Alam, M. A. & Naik, P. K. Applying linear interaction energy method for binding affinity calculations of podophyllotoxin analogues with tubulin using continuum solvent model and prediction of cytotoxic activity. J. Mol. Graph. Model, 27, 930-943 (2009).
6. Hall, L. H. Bioisosterism: quantitation of structure and property effects. Chem. Biodivers, 1, 138-151 (2004).
7. Bai, J. K. Zhao, W. Li, H. M. Tang, Y. J. Novel biotransformation process of podophyllotoxin to 4'-sulfur-substituted podophyllum derivates with anti-tumor activity by penicillium purpurogenum Y.J. Tang. Curr. Med. Chem. 19, 927-936 (2012).
8. Satchi, M. et al. Is treatment with 6-mercaptopurine for colitis associated with the development of colorectal cancer? Inflamm. Bowel. Dis. 19, 785-788 (2013).
9. Martínez-Fernández, L. González L. & Corral, I. An ab initio mechanism for efficient population of triplet states in cytotoxic sulfur substituted DNA bases: the case of 6-thioguaninew. Chem. Commun. 48, 2134-2136 (2012).
10. Ravelli, R. B. G. et al. Tubulin-podophyllotoxin: stathmin-like domain complex. Nature, 428, 198-202 (2004).
11. Abad, A. et al. Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins. J. Med. Chem. 55, 6724-6737 (2012).
12. Joshi, H. C. Palacios, M. J. Mcnamara, L. Cleveland, D. W. Tubulin is a centrosomal protein required for cell cycle-dependent microtubule nucleation. Nature, 356, 80-83 (1992).
13. Sacket, D. L. Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Pharmac. Ther. 59, 163-228 (1993).
14. Hanahan, D. Weinberg, R. A. Hallmarks of Cancer: The Next Generation. Cell 144, 646-674 (2011).
15. Wallace, B. D. et al. Alleviating cancer drug toxicity by inhibiting a bacterial enzyme. Science 330, 831- (2010).
16. Huang, H. S. et al. Topoisomerase inhibitors unsilence the dormant allele of Ube3a in neurons. Nature 481, 185-191 (2012).
17. Marsilje, T. H. et al. Synthesis, Structure-Activity Relationships, and in Vivo Efficacy of the Novel Potent and Selective Anaplastic Lymphoma Kinase (ALK) Inhibitor 5-Chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl) phenyl)pyrimidine-2,4-diamine (LDK378) Currently in Phase 1 and Phase 2 Clinical Trials. J. Med. Chem. 56, 5675-5690 (2013).
18. Riva, E. et al. Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20. Bioorg. Med. Chem. 18, 8660-8668 (2010).
19. Warrener, R. et al. Tumor cell-selective cytotoxicity by targeting cell cycle checkpoints. FASEB. J. 17, 1550-1552 (2003).
20. Diaz, J. F. Andreu, J. M. Assembly of purified GDP-tubulin into microtubules induced by Taxol and Taxotere: reversibility, ligand stoichiometry, and competition. Biochemistry, 32, 2747-2755 (1993).
21. Andreu, J. M. Gorbunoff, M. J. Lee, J. C. Timasheff, S. N. Interaction of tubulin with bifunctional colchicine analogues: an equilibrium study. Biochemistry, 23, 1742-1752 (1984).