Preparation and characterization of CK2 inhibitor-loaded cyclodextrin nanoparticles for drug delivery

International Journal of Pharmaceutics

Volumn 441, Issue 1-2, 2013, Pages 491-498

  Perret, Florent ^a   Marminon, Christelle ^b   Zeinyeh, Wael ^b   Nebois, Pascal ^b   Bollacke, Andre ^c   Jose, Joachim ^c   Parrot Lopez, Hélène ^a   Le Borgne, Marc ^b  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Amphiphilic cyclodextrins; CK2 inhibitor; Drug delivery; Encapsulation; Indeno 1,2 b indole derivative; Nanoparticles

Indexed keywords

1 AMINO 5 ISOPROPYL 5,6,7,8 TETRAHYDROINDENO[1,2 B]INDOLE 9,10 DIONE; ALPHA CYCLODEXTRIN DERIVATIVE; ENZYME INHIBITOR; HEXAKIS[6 DEOXY 6 (3 PERFLUOROHEXYLPROPANETHIO) 2,3 DI O METHYL]ALPHA CYCLODEXTRIN; NANOPARTICLE; NANOSPHERE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CONTROLLED DRUG RELEASE; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; NANOENCAPSULATION; PARTICLE SIZE; PRIORITY JOURNAL; STOICHIOMETRY;

ALPHA-CYCLODEXTRINS; CASEIN KINASE II; DELAYED-ACTION PREPARATIONS; DRUG DELIVERY SYSTEMS; DRUG STABILITY; INDENES; INDOLES; NANOPARTICLES; TIME FACTORS;

EID: 84872826925     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.11.004     Document Type: Article

References (44)

1. B. Bertino-Ghera, F. Perret, A. Baudouin, A.W. Coleman, and H. Parrot-Lopez Synthesis and characterisation of O-6-alkylthio- and perfluoroalkylpropanethio-α-cyclodextrins and their O-2- O-3-methylated analogues New J. Chem. 31 2007 1899 1906
2. B. Bertino-Ghera, F. Perret, B. Fenet, and H. Parrot-Lopez Control of the regioselectivity for novel fluorinated amphiphilic cyclodextrins: synthesis of di- and tetra-(6-deoxy-6-alkylthio) and 6-(perfluoroalkypropanelthio)-α- cyclodextrins derivatives J. Org. Chem. 73 2008 7317 7326
3. B. Bertino-Ghera, F. Perret, Y. Chevalier, and H. Parrot-Lopez Novel nanoparticles made from amphiphilic perfluoroalkyl α-cyclodextrin derivatives: preparation, characterisation and application to the transport of acyclovir Int. J. Pharm. 375 2009 155 162
4. M.S. Brown, O.T. Diallo, M. Hu, R. Ehsanian, X. Yang, P. Arun, H. Lu, V. Korman, G. Unger, K. Ahmed, C. Van Waes, and Z. Chen CK2 modulation of NF-kappaB TP53, and the malignant phenotype in head and neck cancer by anti-CK2 oligonucleotides in vitro or in vivo via sub-50-nm nanocapsules Clin. Cancer Res. 16 2010 2295 2307
5. A. Clementi, M. Aversa, C. Corsaro, J. Spooren, R. Stancanelli, C. O'Connor, M. McNamara, and A. Mazzaglia Synthesis and characterization of a colloidal novel folic acid-β-cyclodextrin conjugate for targeted drug delivery J. Incl. Phenom. Macrocycl. Chem. 69 2011 321 325
6. I. Chemin, and F. Zoulim Hepatitis B virus induced hepatocellular carcinoma Cancer Lett. 286 2009 52 59
7. G. Cozza, A. Bortolato, E. Menta, E. Cavalletti, S. Spinelli, and S. Moro ATP non-competitive Ser/Thr kinase inhibitors as potential anticancer agents Anticancer Agents Med. Chem. 9 2009 778 786
8. G. Cozza, F. Meggio, and S. Moro The dark side of protein kinase CK2 inhibition Curr. Med. Chem. 18 2011 2867 2884
9. G. Dobrowolska, F.J. Lozeman, D. Li, and E.G. Krebs CK2, a protein kinase of the next millennium Mol. Cell. Biochem. 191 1999 3 12
10. A. Dubes, H. Parrot-Lopez, W. Abdelwahed, G. Degobert, and H. Fessi Scanning electron microscopy and atomic force microscopy imaging of solid lipid nanoparticles derived from amphiphilic cyclodextrins Eur. J. Pharm. Biopharm. 55 2003 279 282
11. P. Falvey, W.C. Lim, R. Darcy, T. Revermann, U. Karst, M. Giesbers, A.T. Marcelis, A. Lazar, A.W. Coleman, D. Reinhoudt, and B.J. Ravoo Bilayer vesicles of amphiphilic cyclodextrins: host membranes that recognize guest molecules Chem. Eur. J. 11 2005 1171 1180
12. C. Gadras, C. Santaella, and P. Vierling Improved stability of highly fluorinated phospholipid-based vesicles in the presence of bile salts J. Control. Release 57 1999 29 32
13. V. Giroux, J.-C. Dagorn, and J.L. Iovanna A review of kinases implicated in pancreatic cancer Pancreatology 9 2009 738 754
14. S. Giusiano, C. Cochet, O. Filhol, E. Duchemin-Pelletier, V. Secq, P. Bonnier, X. Carcopino, L. Boubli, D. Birnbaum, S. Garcia, J. Iovanna, and C. Charpin Protein kinase CK2α subunit over-expression correlates with metastatic risk in breast carcinomas: quantitative immunohistochemistry in tissue microarrays Eur. J. Cancer 47 2011 792 801
15. C. Götz, A. Gratz, U. Kucklaender, and J. Jose TF-a novel cell-permeable and selective inhibitor of human protein kinase CK2 induces apoptosis in the prostate cancer cell line LNCaP Biochim. Biophys. Acta 1820 2012 970 977
16. K.C. Graham, and D.W. Litchfield The regulatory beta subunit of protein kinase CK2 mediates formation of tetrameric CK2 complexes J. Biol. Chem. 275 2000 5003 5010
17. B. Guerra, and O.-G. Issinger Protein kinase CK2 in human diseases Curr. Med. Chem. 15 2008 1870 1886
18. F. Guittard, and S. Geribaldi Highly fluorinated molecular organised systems: strategy and concept J. Fluor. Chem. 107 2001 363 374
19. R. Hamacher, D. Saur, R. Fritsch, M. Reichert, R.M. Schmid, and G. Schneider Casein kinase II inhibition induces apoptosis in pancreatic cancer cells Oncol. Rep. 18 2007 695 701
20. K. Hamayasu, K. Fujita, K. Hara, H. Hashimoto, T. Tanimoto, K. Koizumi, H. Nakano, and S. Kitahata Enzymatic synthesis of N-acetylglucosaminyl- cyclodextrin by the reverse reaction of N-acetylhexosaminidase from jack bean Biosci. Biotechnol. Biochem. 63 1999 1677 1683
21. Hemmerling, H.-J., Götz, C., Jose, J., Patent US 2010/0056599 A1, March 4, 2010.
22. C. Hundsdörfer, H.-J. Hemmerling, C. Götz, F. Totzke, P. Bednarski, M. Le Borgne, and J. Jose Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors Bioorg. Med. Chem. 20 2012 2282 2289
23. C. Hundsdörfer, H.-J. Hemmerling, J. Hamberger, M. Le Borgne, P. Bednarski, C. Götz, F. Totzke, and J. Jose Novel indeno[1,2-b] indoloquinones as inhibitors of the human protein kinase CK2 with antiproliferative activity towards a broad panel of cancer cell lines Biochim. Biophys. Res. Commun. 424 2012 71 75
24. P. Jansook, M.E. Brewster, and T. Loftsson Cyclodextrin-enhanced drug delivery through mucous membranes E. Bilensoy, Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicines: Current and Future Industrial Applications 2011 John Wiley & Sons New Jersey 145 158
25. B. Kaminska, A. Ellert-Miklaszewska, A. Oberbek, P. Wisniewski, B. Kaza, M. Makowska, M. Bretner, and Z. Kazimierczuk Efficacy and mechanism of anti-tumor action of new potential CK2 inhibitors toward glioblastoma cells Int. J. Oncol. 35 2009 1091 1100
26. X. Lin, R. Gao, Y. Zhang, N. Qi, Y. Zhang, K. Zhang, H. He, and X. Tang Lipid nanoparticles for chemotherapeutic applications: strategies to improve anticancer efficacy Expert Opin. Drug Deliv. 9 2012 767 781
27. C.C. Ling, R. Darcy, and W. Risse Cyclodextrin liquid crystals: synthesis and self-organisation of amphiphilic thio-β-cyclodextrins J. Chem. Soc., Chem. Commun. 5 1993 438 440
28. J. Lucifora, I.E. Vincent, P. Berthillon, T. Dupinay, M. Michelet, U. Protzer, F. Zoulim, D. Durantel, C. Trepo, and I. Chemin Hepatitis B virus replication in primary macaque hepatocytes: crossing the species barrier toward a new small primate model Hepatology 51 2010 1954 1960
29. E. Memisoǧlu, A. Bochot, M. Özalp, M. Şen, D. Duchêne, and A. Hincal Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes Pharm. Res. 20 2003 117 125
30. R. Onodera, K. Motoyama, and H. Arima Design and evaluation of folate-appended methyl-β-cyclodextrin as a new antitumor agent J. Incl. Phenom. Macrocycl. Chem. 70 2011 321 326
31. S. Peroche, G. Degobert, J.-L. Putaux, M.G. Blanchin, H. Fessi, and H. Parrot-Lopez Synthesis and characterisation of novel nanospheres made from amphiphilic perfluoroalkylthio-β-cyclodextrins Eur. J. Pharm. Biopharm. 60 2005 123 131
32. F. Perret, M. Duffour, Y. Chevalier, and F. Parrot-Lopez Design, synthesis and in vitro evaluation of new amphiphilic cyclodextrin-based nanoparticles for the incorporation and controlled release of acyclovir Eur. J. Pharm. Biopharm. 2012 http://dx.doi.org/10.1016/j.ejpb.2012.09.013
33. F. Piazza, S. Manni, M. Ruzzene, L.A. Pinna, C. Gurrieri, and G. Semenzato Protein kinase CK2 in hematologic malignancies: reliance on a pivotal cell survival regulator by oncogenic signaling pathways Leukemia 26 2012 1174 1179
34. F. Salas, and R. Darcy Amphiphilic cyclodextrins-advances in synthesis and supramolecular chemistry Eur. J. Org. Chem. 2008 957 969
35. M. Salvi, S. Sarno, L. Cesaro, H. Nakamura, and L.A. Pinna Extraordinary pleiotropy of protein kinase CK2 revealed by weblogo phosphoproteome analysis Biochim. Biophys. Acta-Mol. Cell Res. 1793 2009 847 859
36. S. Sarno, P. Ghisellini, and L.A. Pinna Unique activation mechanism of protein kinase CK2. The N-terminal segment is essential for constitutive activity of the catalytic subunit but not of the holoenzyme J. Biol. Chem. 277 2002 22509 22514
37. G. Sass, N. Klinger, H. Sirma, S. Hashemolhosseini, C. Hellerbrand, D. Neureiter, H. Wege, M. Ocker, and G. Tiegs Inhibition of experimental HCC growth in mice by use of the kinase inhibitor DMAT Int. J. Oncol. 39 2011 433 442
38. M. Skiba, M. Skiba-Lahiani, and P. Arnaud Design of nanocapsules based on novel fluorophilic cyclodextrin derivatives and their potential role in oxygen delivery J. Incl. Phenom. Macrocycl. Chem. 44 2002 151 154
39. C.C. Schneider, S. Kartarius, M. Montenarh, A. Orzeszko, and Z. Kazimierczuk Modified tetrahalogenated benzimidazoles with CK2 inhibitory activity are active against human prostate cancer cells LNCaP in vitro Bioorg. Med. Chem. 20 2012 4390 4396
40. K.M. Taylor, S. Hiscox, R.I. Nicholson, C. Hogstrand, and P. Kille Protein kinase CK2 triggers cytosolic zinc signaling pathways by phosphorylation of zinc channel ZIP7 Sci. Signal. 5 2012 1 9
41. J.H. Trembley, G.M. Unger, V.L. Korman, D.K. Tobolt, Z. Kazimierczuk, L.A. Pinna, B.T. Kre, and K. Ahmed Nanoencapsulated anti-CK2 small molecule drug or siRNA specifically targets malignant cancer but not begin cells Cancer Lett. 315 2012 48 58
42. S. Wang, T. Chen, R. Chen, Y. Hu, M. Chen, and Y. Wang Emodin loaded solid lipid nanoparticles: preparation, characterization and antitumor activity studies Int. J. Pharm. 430 2012 238 246
43. W. Yu, X. Ding, F. Chen, M. Liu, S. Shen, X. Gu, and L. Yu The phosphorylation of SEPT2 on Ser218 by casein kinase 2 is important to hepatoma carcinoma cell proliferation Mol. Cell. Biochem. 325 2009 61 67
44. M.-X. Zhao, L.-N. Ji, and Z.-W. Mao β-cyclodextrin/glycyrrhizic acid functionalised quantum dots selectively enter hepatic cells and induce apoptosis Chem. Eur. J. 18 2012 1650 1658