2-Hydroxypropyl-β-cyclodextrin strongly improves water solubility and anti-proliferative activity of pyrazolo[3,4-d]pyrimidines Src-Abl dual inhibitors

European Journal of Medicinal Chemistry

Volumn 45, Issue 12, 2010, Pages 5958-5964

  Dreassi, Elena ^a   Zizzari, Alessandra Tania ^a   Mori, Mattia ^a   Filippi, Irene ^a   Belfiore, Amalia ^a   Naldini, Antonella ^a   Carraro, Fabio ^a   Santucci, Annalisa ^a   Schenone, Silvia ^b   Botta, Maurizio ^a,c  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITY OF GENOA   (Italy)

^c TEMPLE UNIVERSITY   (United States)

Author keywords

Anti Proliferative; Cyclodextrins; Inclusion complexes; Leukemia; Pyrazolo pyrimidines; Src Abl dual inhibitors

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ANTINEOPLASTIC AGENT; PROTEIN TYROSINE KINASE INHIBITOR; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL PROLIFERATION; DRUG SOLUBILITY; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; OSTEOSARCOMA CELL; SOLUBILIZATION;

ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PYRAZOLES; PYRIMIDINES; SOLUBILITY; SRC-FAMILY KINASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; WATER;

EID: 78649316138     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.09.062     Document Type: Article

References (28)

1. S. Schenone, F. Manetti, and M. Botta Synthetic SRC-kinase domain inhibitors and their structural requirements Anticancer Agents Med. Chem. 7 2007 660 680
2. S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, L. Mosti, G. Maga, E. Crespan, F. Carraro, F. Manetti, C. Tintori, and M. Botta Synthesis, biological evaluation and docking studies of 4-amino substituted 1H-pyrazolo[3,4-d] pyrimidines Eur. J. Med. Chem. 43 2008 2665 2676
3. S. Schenone, O. Bruno, M. Radi, M. Botta, New insights into small-molecule inhibitors of Bcr-Abl, Med. Res. Rev. 2009, in press.
4. F. Manetti, C. Brullo, M. Magnani, F. Mosci, B. Chelli, E. Crespan, S. Schenone, A. Naldini, O. Bruno, M.L. Trincavelli, G. Maga, F. Carraro, C. Martini, F. Bondavalli, and M. Botta Structure-based optimization of pyrazolo[3,4-d]pyrimidines as Abl inhibitors and antiproliferative agents toward human leukemia cell lines J. Med. Chem. 51 2008 1252 1259
5. F. Manetti, A. Pucci, M. Magnani, G.A. Locatelli, C. Brullo, A. Naldini, S. Schenone, G. Maga, F. Carraro, and M. Botta Inhibition of Bcr-Abl phosphorylation and induction of apoptosis by pyrazolo[3,4-d]pyrimidines in human leukemia cells Chem. Med. Chem. 2 2007 343 353
6. E. Dreassi, A.T. Zizzari, F. Falchi, S. Schenone, A. Santucci, G. Maga, and M. Botta Determination of permeability and lipophilicity of pyrazolo-pyrimidine tyrosine kinase inhibitors and correlation with biological data Eur. J. Med. Chem. 44 2009 3712 3717
7. M.A. Santucci, V. Corradi, M. Mancini, F. Manetti, M. Radi, S. Schenone, and M. Botta C6-unsubstituted pyrazolo[3,4-d]pyrimidines are dual Src/Abl inhibitors effective against imatinib mesylate resistant chronic myeloid leukemia cell lines Chem. Med. Chem. 4 2009 118 126
8. J. Alsenz, and M. Kansy High throughput solubility measurement in drug discovery and development Adv. Drug Deliv. Rev. 59 2007 546 567
9. F. Manetti, A. Santucci, G.A. Locatelli, G. Maga, A. Spreafico, T. Serchi, M. Orlandini, G. Bernardini, N.P. Caradonna, A. Spallarossa, C. Brullo, S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, O. Hoffmann, M. Bologna, A. Angelucci, and M. Botta Identification of a novel pyrazolo[3,4-d]pyrimidine able to inhibit cell proliferation of a human osteogenic sarcoma in vitro and in a xenograft model in mice J. Med. Chem. 50 2007 5579 5588
10. E.H. Kerns, and L. Di Pharmaceutical profiling in drug discovery Drug Discov. Today 8 2003 316 323
11. H. Van de Waterbeemd, and B. Testa Estimation of solubility, permeability, absorption and bioavailability Drug Bioavailability 2009 Wiley-VCH Zurich 9 31
12. E.H. Kerns, and L. Di Drug-like Properties: Concepts, Structure Design and Methods: From ADME to Toxicity Optimization 2008 Elsevier Inc Amsterdam pp. 56-85
13. I.G. Popa-Burke, O. Issakova, J.D. Arroway, P. Bernasconi, M. Chen, L. Coudurier, S. Galasinski, A.P. Jadhav, W.P. Janzen, D. Lagasca, D. Liu, R.S. Lewis, R.P. Mohney, N. Sepetov, D.A. Sparkman, and C.N. Hodge Streamlined system for purifying and quantifying a diverse library of compounds and the effect of compound concentration measurements on the accurate interpretation of biological assay results Anal. Chem. 76 2004 7278 7287
14. T. Loftsson, and M.E. Brewster Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization J. Pharm. Sci. 85 1996 1017 1025
15. K.J. Waleczek, H.M. Marques, B. Hempel, and P.C. Schmidt Phase solubility studies of pure (-)-alpha-bisabolol and camomile essential oil with beta-cyclodextrin Eur. J. Pharm. Biopharm. 55 2003 247 251
16. M.E. Brewster, and T. Loftsson Cyclodextrins as pharmaceutical solubilizers Adv. Drug Deliv. Rev. 59 2007 645 666
17. R.A. Rajewski, G. Traiger, J. Bresnahan, P. Jaberaboansari, V.J. Stella, and D.O. Thompson Preliminary safety evaluation of parenterally administered sulfoalkyl ether beta-cyclodextrin derivatives J. Pharm. Sci. 84 1995 927 932
18. S.J. Collins The HL-60 promyelocytic leukemia cell line: proliferation, differentiation, and cellular oncogene expression Blood 70 1987 1233 1244
19. T. Higuchi, and K.A. Connors Advances in Analytical Chemistry and Instrumentation 1965 Interscience New York pp. 117-212
20. A. Avdeef High-throughput Measurements of Solubility Profiles. Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies 2001 Switzerland Lausanne pp. 305-325
21. B. Bard, S. Martel, and P.A. Carrupt High throughput UV method for the estimation of thermodynamic solubility and the determination of the solubility in biorelevant media Eur. J. Pharm. Sci. 33 2008 230 240
22. K.A. Connors, and J.A. Mollica Jr. Theoretical analysis of comparative studies of complex formation J. Pharm. Sci. 55 1966 772 780
23. G. De Murcia, and D.M. Menissier Poly(ADP-ribose) polymerase: a molecular nick-sensor Trends Biochem. Sci. 19 1994 172 176
24. M. Tewari, L.T. Quan, K. O'Rourke, S. Desnoyers, Z. Zeng, D.R. Beidler, G.G. Poirier, G.S. Salvesen, and V.M. Dixit Yama/CPP32 beta, a mammalian homolog of CED-3, is a CrmA-inhibitable protease that cleaves the death substrate poly(ADP-ribose) polymerase Cell 81 1995 801 809
25. K. Kishi A new leukemia cell line with Philadelphia chromosome characterized as basophil precursors Leuk. Res. 9 1985 381 390
26. A. Spreafico, S. Schenone, T. Serchi, M. Orlandini, A. Angelucci, D. Magrini, G. Bernardini, G. Collodel, S.A. Di, C. Tintori, M. Bologna, F. Manetti, M. Botta, and A. Santucci Antiproliferative and proapoptotic activities of new pyrazolo[3,4-d]pyrimidine derivative Src kinase inhibitors in human osteosarcoma cells FASEB J. 22 2008 1560 1571
27. D. Hudig, M. Djobadze, D. Redelman, and J. Mendelsohn Active tumor cell resistance to human natural killer lymphocyte attack Cancer Res. 41 1981 2803 2808
28. M. Radi, E. Crespan, G. Botta, F. Falchi, G. Maga, F. Manetti, V. Corradi, M. Mancini, M.A. Santucci, S. Schenone, and M. Botta Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents Bioorg. Med. Chem. Lett. 18 2008 1207 1211