From taxuspine X to structurally simplified taxanes with remarkable P-glycoprotein inhibitory activity

ACS Medicinal Chemistry Letters

Volumn 1, Issue 8, 2010, Pages 416-421

  Castagnolo, Daniele ^a   Contemori, Lorenzo ^a   MacCari, Giorgio ^a   Avramova, Stanislava I ^a   Neri, Annalisa ^a,b   Sgaragli, Gianpietro ^a,b   Botta, Maurizio ^a,c  

^a UNIVERSITY OF SIENA   (Italy)

^b ISTITUTO TOSCANO TUMORI   (Italy)

^c Temple University   (United States)

Author keywords

macrolactone; MDR reversing agents; nonnatural natural product; P glycoprotein; Taxanes

Indexed keywords

GLYCOPROTEIN P; TAXANE DERIVATIVE; TAXUSPINE X; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG INHIBITION; DRUG SCREENING; DRUG SYNTHESIS; IC 50; MOUSE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 78649301900     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100118k     Document Type: Article

References (36)

1. Crown, J.; O'Leary, M. The taxanes: An update Lancet 2000, 335, 1176-1178
2. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J. Am. Chem. Soc. 1971, 93, 2325-2327
3. Rowinsky, E. K.; Cazenave, L. A.; Donehower, R. C. Taxol: A novel investigational antimicrotubule agent J. Natl. Cancer Inst. 1990, 82, 1247-1259
4. Slichenmyer, W. J.; Von Hoff, D. D. Taxol: A new and effective anti-cancer drug Anticancer Drugs 1991, 2, 519-530
5. Horwitz, S. B. Mechanism of action of taxol Trends Pharmacol. Sci. 1992, 13, 134-136
6. Galletti, E.; Magnani, M.; Renzulli, M. L.; Botta, M. Paclitaxel and docetaxel resistance: Molecular mechanisms and development of new generation taxanes ChemMedChem 2007, 2, 920-942
7. Perez-Tomas, R. Multidrug resistance: Retrospect and prospects in anti-cancer drug treatment Curr. Med. Chem. 2006, 13, 1859
8. Teodori, E.; Dei, S.; Martelli, S.; Scapecchi, F.; Gualtieri, F. The functions and structure of ABC transporters: implications for the design of new inhibitors of Pgp and MRP1 to control multidrug resistance (MDR) Curr. Drug Targets 2006, 7, 893
9. Leslie, E. M.; Deeley, R. G.; Cole, S. P. C. Multidrug Resistance Proteins: Role of P-glycoprotein, MRP1, MRP2 and BCRP (ABCG2) in Tissue Defense Toxicol. Appl. Pharmacol. 2005, 204, 216
10. Szakacs, G.; Paterson, J. K.; Ludwig, J. A.; Booth-Genthe, C.; Gottesman, M. M. Targeting multidrug resistance in cancer Nat. Rev. Drug Discovery 2006, 5, 219-234
11. Nobili, S.; Landini, I.; Giglioni, B.; Mini, E. Pharmacological strategies for overcoming multidrug resistance Curr. Drug Targets 2006, 7, 861-879
12. Kobayashi, J.; Hosoyama, H.; Wang, X. X.; Shigemori, H.; Koiso, Y.; Iwasaki, S.; Sasaki, T.; Naito, M.; Tsuruo, T. Effects of taxoids from Taxus cuspidata on microtubule depolymerization and vincristine accumu- lation in MDR cells Bioorg. Med. Chem. Lett. 1997, 7, 393
13. Ojima, I.; Bounaud, P. Y.; Takeuchi, C.; Pera, P.; Bernacki, R. J. New taxanes as highly efficient reversal agents for multi-drug resistance in cancer cells Bioorg. Med. Chem. Lett. 1998, 8, 189
14. Zhao, X.; Gu, J.; Yin, D.; Chen, X. Synthesis and biological evaluation of taxinine analogues as orally active multidrug resistance reversal agents in cancer Bioorg. Med. Chem. Lett. 2004, 14, 4767
15. Botta, M.; Armaroli, S.; Castagnolo, D.; Fontana, G.; Pera, P.; Bombardelli, E. Synthesis and biological evaluation of new taxoids derived from 2-deacetoxytaxinine J. Bioorg. Med. Chem. Lett. 2007, 17, 1579-1583
16. Ojima, I.; Borella, C. P.; Wu, X.; Bounaud, P.-Y.; Fumero Oderda, C.; Sturm, M.; Miller, M. L.; Chakravarty, S.; Chen, J.; Huang, Q.; Pera, P.; Brooks, T. A.; Baer, M. R.; Bernacki, R. J. Design, Synthesis and Structure-Activity Relationships of Novel Taxane-Based Multidrug Resistance Reversal Agents J. Med. Chem. 2005, 48, 2218-2228
17. Brooks, T. A.; Kennedy, D. R.; Gruol, D. J.; Ojima, I.; Baer, M. R.; Bernacki, R. J. Structure-Activity Analysis of Taxane-Based Broad-Spectrum Multidrug Resistance Modulators Anticancer Res. 2004, 24, 409-415
18. Brooks, T. A.; Minderman, H.; O'Loughlin, K. L.; Ojima, I.; Baer, M. R.; Bernacki, R. J. Taxane-Based Reversal Agent Modulation of P-glycoprotein-, Multidrug Resistance Protein- and Breast Cancer Resistance Protein-Mediated Drug Transport Mol. Cancer Ther. 2003, 2, 1195-1205
19. Minderman, H.; Brooks, T. A.; O'Loughlin, K. L.; Ojima, I.; Bernacki, R. J.; Baer, M. R. Modulation of ATP-Binding-Cassette Transport Proteins by the Taxane Derivatives BAY 59-8862 and tRA96023 Cancer Chemother. Pharmacol. 2004, 53, 363-369
20. Zamir, L. O.; Zhou, Z. H.; Caron, G.; Nedea, M. E.; Sauriol, F.; Mamer, O. Isolation of a putative biogenetic taxane precursor from Taxus canadensis needles J. Chem. Soc., Chem. Commun. 1995, 529-530
21. Begley, M. J.; Jackson, C. B.; Pattenden, G. Total synthesis of verticillene, the putative biogenetic precursor of the taxane alkaloids Tetrahedron Lett. 1985, 26, 3393-3396
22. Begley, M. J.; Jackson, C. B.; Pattenden, G. Investigation of transannular cyclisations of verticillanes to the taxane ring system Tetrahedron Lett. 1985, 26, 3397-3400
23. Hosoyama, H.; Inubushi, A.; Katsui, T.; Shigemori, H.; Kobayashi, J. Taxuspines U, V, and W, new taxane and related diterpenoids from the Japanese yew Taxus cuspidate Tetrahedron 1996, 52, 13145-13150 (Pubitemid 26325045)
24. Gupta, M. L.; Bode, C. J.; Georgt, G.; Himes, R. H. Understanding Tubulin-Taxol Interactions: Mutations That Impart Taxol Binding to Yeast Tubulin Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6394-6397
25. Manetti, F.; Maccari, L.; Corelli, F.; Botta, M. 3-D QSAR models of interactions between beta-tubulin and microtubule stabilizing antimitotic agents (MSAA): A survey on taxanes and epothilones Curr. Top. Med. Chem. 2004, 4, 203-217
26. Renzulli, M. L.; Rocheblave, L.; Avramova, S. I.; Galletti, E.; Castagnolo, D.; Tafi, A.; Corelli, F.; Botta, M. Studies towards the synthesis of the bicyclic 3,8-secotaxane diterpenoid system using a ring closing metathesis strategy Tetrahedron 2007, 63, 497-509
27. Galletti, E.; Avramova, S. I.; Renzulli, M. L.; Corelli, F.; Botta, M. Stereoselective synthesis of advanced intermediates en route to Taxuspine U and X: a study of macrocyclization via ring closing metathesis to highly constrained twelve-membered rings Tetrahedron Lett. 2007, 48, 751-754
28. Avramova, S. I.; Galletti, E.; Renzulli, M. L.; Giorgi, G.; Sgaragli, G.; Alderighi, D.; Ghiron, C.; Corelli, F.; Radi, M.; Botta, M. Synthesis of an original oxygenated taxuspine X analogue: A versatile "non-natural" natural product with remarkable P-gp modulating activity ChemMedChem 2008, 3, 745-748
29. Tietze, L. F.; Bell, H. P.; Chandrasekar, S. Natural product hybrids as new leads for drug discovery Angew. Chem., Int. Ed. 2003, 42, 3996-4028
30. Inanaga, J.; Hirata, K.; Sacki, H.; Katsuki, T.; Yamaguchi, M. Rapid esterification by means of mixed anhydride and its application to large-ring lactonization Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993
31. Hitchcock, S. A.; Houldsworth, S. J.; Pattenden, G.; Pryde, D. C.; Thomson, N. M.; Blake, A. J. A tandem radical macrocyclisation-transannular cyclization approach towards the taxanes J. Chem. Soc. Perkin Trans. 1 1998, 3181-3206
32. Kitagawa, I.; Tsujii, S.; Fujioka, K.; Kajiwara, A.; Yamamoto, Y.; Shibuya, H. Chemical transformation of terpenoids. VI: Syntheses of chiral segments, key building-blocks for the left half of taxane-type diterpenoids Chem. Pharm. Bull. 1984, 32 (4) 1294-1302
33. Swindell, C. S.; Fan, W. Taxane Synthesis through Intramolecular Pinacol Coupling at C-1-C-2. Highly Oxygenated C-Aromatic Taxanes J. Org. Chem. 1996, 61, 1109-1118
34. Martelli, C.; Alderighi, D.; Coronnello, M.; Dei, S.; Frosini, M.; Le Bozec, B.; Manetti, D.; Neri, A.; Romanelli, M. N.; Salerno, M.; Scapecchi, S.; Mini, E.; Sgaragli, G.; Teodori, E. N,N-bis(cyclohexanol)amine aryl esters: A new class of highly potent transporter-dependent multidrug resistance inhibitors J. Med. Chem. 2009, 52, 807-817
35. Kessel, D. Exploring multidrug resistance using rhodamine 123 Cancer Commun. 1989, 1, 145-149
36. Aller, S. G.; Yu, J.; Ward, A.; Weng, Y.; Chittaboina, S.; Zhuo, R.; Harrell, P. M.; Trinh, Y. T.; Zhang, Q.; Urbatsch, I. L.; Chang, G. Structure of P-glycoprotein Reveals a Molecular Basis for Poly-Specific Drug Binding Science 2009, 323, 1718-1722