State of the art of nanocrystals - Special features, production, nanotoxicology aspects and intracellular delivery

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 78, Issue 1, 2011, Pages 1-9

  Müller, Rainer H ^a   Gohla, Sven ^b   Keck, Cornelia M ^a,c,d  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b La Prairie Group   (Sweden)

^c UNIVERSITY OF APPLIED SCIENCES KAISERSLAUTERN   (Germany)

^d UNIVERSITY PUTRA MALAYSIA   (Malaysia)

Author keywords

High pressure homogenization; Nanocrystals; Nanosuspensions; Precipitation; Review; Smartcrystals

Indexed keywords

ATOVAQUONE; ITRACONAZOLE; NANOCRYSTAL; NANOPARTICLE; NEVIRAPINE; PACLITAXEL;

ADHESION; BLOOD BRAIN BARRIER; CONCENTRATION (PARAMETERS); DEGRADATION; DISSOLUTION; DRUG DELIVERY SYSTEM; DRUG UPTAKE; ENDOTHELIUM CELL; HUMAN; LIVER; MACROPHAGE; NANOTOXICOLOGY; NONHUMAN; PRECIPITATION; REVIEW; SPLEEN;

CRYSTALLIZATION; DRUG ADMINISTRATION ROUTES; NANOPARTICLES;

EID: 79953162538     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2011.01.007     Document Type: Review

References (82)

1. B.E. Rabinow Nanosuspensions in drug delivery Nat. Rev. Drug. Discov. 3 2004 785 796 (Pubitemid 39242830)
2. C. Jacobs, O. Kayser, and R.H. Müller Nanosuspensions as a new approach for the formulation for the poorly soluble drug tarazepide Int. J. Pharm. 196 2000 161 164 (Pubitemid 30105734)
3. P. Couvreur, P. Tulkens, M. Roland, A. Trouet, and P. Speiser Nanocapsules: a new type of lysosomotropic carrier FEBS Lett. 84 1977 323 326 (Pubitemid 8246984)
4. R.H. Müller, and S. Heinemann Emulsions for intravenous administration. I. Emulsions for nutrition and drug delivery Pharm. Ind. 1993 853 856 (Pubitemid 23311114)
5. L.C. Collins-Golda, R.T. Lyonsa, and L.C. Bartholow Parenteral emulsions for drug delivery Adv. Drug Deliv. Rev. 5 1990 189 208 (Pubitemid 20333024)
6. G. Storm, H.P. Wilms, and D.J. Crommelin Liposomes and biotherapeutics Biotherapy 3 1991 25 42
7. D.J. Crommelin, and G. Storm Liposomes: from the bench to the bed J. Liposome Res. 13 2003 33 36 (Pubitemid 36373342)
8. R.H. Müller, S. Shegokar, and C.M. Keck 20 years of lipid nanoparticles (SLN & NLC): present state of development and industrial applications Eur. J. Pharm. Biopharm. 2010 submitted
9. G.G. Liversidge, K.C. Cundy, J.F. Bishop, D.A. Czekai, Surface modified drug nanoparticles, US Patent5145684, 1992.
10. R.H. Müller, R. Becker, B. Kruss, K. Peters, Pharmaceutical nanosuspensions for medicament administration as systems with increased saturation solubility and rate of solution, US Patent5858410, 1999.
11. S. Khan, G.W. Pace, Composition and method of preparing microparticles of water-insoluble substances, US Patent6337092, 2002.
12. A.T. Florence, A.M. Hillery, N. Hussain, and P.U. Jani Factors affecting the oral uptake and translocation of polystyrene nanoparticles: histological and analytical evidence J. Drug Target. 3 1995 65 70
13. S. Kobierski, K. Ofori-Kwakye, R.H. Müller, and C.M. Keck Resveratrol nanosuspensions for dermal application - production, characterisation and physical stability Die Pharmazie 64 2008 741 747
14. C.M. Keck, and R.H. Müller Nanodiamanten - Erhöhte Bioaktivitat Labor and More 01/08 2008 64 65
15. G. Buckton, and A.E. Beezer The relationship between particle size and solubility Int. J. Pharm. 82 1992 R7 R10
16. J. Möschwitzer, and R.H. Müller New method for the effective production of ultrafine drug nanocrystals J. Nanosci. Nanotech. 6 2006 3145 3153 (Pubitemid 44579994)
17. C.M. Keck, R.H. Müller, smartCrystals - Review of the Second Generation of Drug Nanocrystal, in: V.P. Torchilin, M.M. Amiji, (Eds.), Handbook of Materials for Nanomedicine (Pan Stanford Series on Biomedical Nanotechnology), Pan Stanford Publishing, 2010, pp. 555-580.
18. G.L. Amidon, H. Lennernas, V.P. Shah, and J.R. Crison A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 12 1995 413 420
19. K.P. Krause, and R.H. Müller Production and characterisation of highly concentrated nanosuspensions by high pressure homogenisation Int. J. Pharm. 214 2001 21 24 (Pubitemid 32244072)
20. L.D. Irizarry, T.H. Luu, J.M. McKoy, A.T. Samaras, M.J. Fisher, E.E. Carias, D.W. Raisch, E.A. Calhoun, and C.L. Bennett Cremophor EL-containing paclitaxel-induced anaphylaxis: a call to action Commun. Oncol. 6 2009 132 134
21. L. Szente, and J. Szejtli Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development Adv. Drug Deliv. Rev. 36 1999 17 28 (Pubitemid 29074474)
22. R. Challa, A. Ahuja, J. Ali, and R.K. Khar Cyclodextrins in drug delivery: an updated review AAPS PharmSciTech 6 2005 E329 357
23. H. Auweter, H. Bohn, R. Heger, D. Horn, B. Siegel, K. Siemensmeyer, Precipitated water-insoluble colorants in colloid disperse form, US Patent6494924, 2002.
24. F. Runge, H. Auweter, N. Musaeus-Jensen, H. Haberkorn, J. Rieger, Stable, pulverulent lycopene formulations, comprising lycopene having a degree of crystallinity of greater than 20%, US Patent6235315, 2001.
25. H. Auweter, H. Bohn, E. Luddecke, Stable, aqueous dispersions and stable, water-dispersible dry xanthophyll powder, their production and use, US Patent6296877, 2001.
26. M. List, H. Sucker, Pharmaceutical colloidal hydrosols for injection, GBPatent2200048, 1988.
27. K. Chan, R.H. Müller, C.M. Keck, Production methods for drug nanocrystals: processes, physical background & regulatory aspects for product realization, Adv. Drug Deliv. Rev., submitted for publication.
28. G.G. Liversidge, and K.C. Cundy Particle size reduction for improvement of oral bioavailability of hydrophobic drugs: I. Absolute oral bioavailability of nanocrystalline danazol in beagle dogs Int. J. Pharm. 125 1995 91 97
29. E. Merisko-Liversidge, G.G. Liversidge, and E.R. Cooper Nanosizing: a formulation approach for poorly-water-soluble compounds Eur. J. Pharm. Sci. 18 2003 113 120 (Pubitemid 36184748)
30. S. Majuru, M.O. Oyewumi, Nanotechnology in drug development & life cycle management, in: M.M. de Villiers, P. Aramvit, G.S. Kwon (Eds.), Nanotechnology in Drug Delivery: 10 (Biotechnology: Pharmaceutical Aspects) Springer, American Association of Pharmaceutical Scientists, 2009, pp. 597-620.
31. R.H. Müller, K. Mäder, K. Krause, Verfahren zur schonenden Herstellung von hochfeinen Micro-/Nanopartikeln, in: PCT Application PCT/EP00/06535, Germany, 2000.
32. J.E. Kipp, J.C.T. Wong, M.J. Doty, C.L. Rebbeck, Microprecipitation method for preparing submicron suspensions, US Patent6607784, 2003.
33. J.E. Kipp, J.C.T. Wong, M.J. Doty, J. Werling, C.L. Rebbeck, S. Brynjelsen, Method for preparing submicron particle suspensions, US Patent 6884436, 2005.
34. J. Möschwitzer, R.H. Müller, Verfahren und Vorrichtung zur Herstellung hochfeiner Partikel sowie zur Beschichtug solcher Partikel/Method and device for producing very fine particles and coating such particles, DE102005053862A1, PCT/EP2006/009930, 2005.
35. J.P. Möschwitzer, Verfahren zur Herstellung ultrafeiner Submicron-Suspensionen/Method for the production of ultra-fine submicronsuspensions, DE102005011786A1, EP 1868573A2, W02006/094808, 2005.
36. J.P. Möschwitzer, A. Lemke, Verfahren zur schonenden Herstellung von hochfeinen Partikelsuspensionen/Method for carefully producing ultrafineparticle suspensions and ultrafine particles and use thereof, DE102005017777A1, 2005.
37. British Standards (BSI), PAS 71:2005/Vocabulary - nanoparticles, publicy available specification (PAS), 2005, p. 2.
38. Amtsblatt der Europäischen Union, Verordnung (EG) Nr. 1223/2009 des Europäischen Parlaments und des Rates vom 30. November 2009 über kosmetische Mittel - Neufassung zur Richtlinie 76/768/EWG des Rates vom 27. Juli 1976, in, 2009, pp. Artikel 2k.
39. L. Illum, L.O. Jacobsen, R.H. Müller, E. Mak, and S.S. Davis Surface characteristics and the interaction of colloidal particles with mouse peritoneal macrophages Biomaterials 8 1987 113 117 (Pubitemid 17032519)
40. F. Koosha, R.H. Müller, and S.S. Davis Polyhydroxybutyrate as a drug carrier Crit. Rev. Ther. Drug Carrier Syst. 6 1989 117 130 (Pubitemid 19270116)
41. R.C. Franson, R.M. Ottenbrite, Cytoprotective compounds, US Patent 6020510, 2000.
42. J. Pardeike, Nanosuspensions and nanostructured lipid carriers for dermal application, in: PhD thesis, FreieUniversität Berlin, 2008.
43. J. Pardeike, R.H. Müller, Tolerability evaluation of PX-13 and PX-18 in primary human fibroblasts and keratinocytes monolayer cell cultures, in: International Symposium on Controlled Release of Bioactive Materials, New York, 2008, pp. #3121.
44. J. Pardeike, R.H. Müller, The use of reconstructed human epidermis for the evaluation of the skin irritation potential of PX-13 and PX-18 nanosuspension, in: International Symposium on Controlled Release of Bioactive Materials, New York, 2008, pp. #3117.
45. J. Pardeike, R.H. Müller, Phospholipase A2-inhibitors - evaluation of the eye tolerability of PX-13 & PX-18 nanosuspensions by het-cam test, in: 6th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, Barcelona, 2008.
46. J. Pardeike, and R.H. Müller Dermal and ocular safety of the new phospholipase A2 inhibitors PX-18 and PX-13 formulated as drug nanosuspension J. Biomed. Nanotechnol. 5 2009 437 444
47. Q. Wang, A.Y. Sun, J. Pardeike, A. Simonyi, R.H. Müller, R. Berney, G.Y. Sun, Neuroprotective effects of a nanoparticulate formulation of sPLA2 inhibitor PX-18 in cerebral ischemia/reperfusion, in: International Society for Neurochemistry, Cancún, 2007.
48. Q. Wang, A.Y. Sun, J. Pardeike, R.H. Müller, A. Simonyi, and G.Y. Sun Neuroprotective effects of a nanocrystal formulation of sPLA(2) inhibitor PX-18 in cerebral ischemia/reperfusion in gerbils Brain Res. 1285 2009 188 195
49. F. Domoki, A. Zimmermann, L. Lenti, V. Toth-Szuki, J. Pardeike, R.H. Müller, and F. Bari Secretory phospholipase A2 inhibitor PX-18 preserves microvascular reactivity after cerebral ischemia in piglets Microvasc. Res. 78 2009 212 217
50. R.D. Petersen, Nanocrystals for use in topical formulations and method of production thereof, PCT/EP2007/009943, 2006.
51. C.M. Keck, Nanocrystals as Novel Approach for Dermal Delivery, Annual Meeting of the German Pharmaceutical Society (DPhG), Jena/Germany, 2009.
52. J. Lademann, H. Richter, A. Teichmann, N. Otberg, U. Blume-Peytavi, J. Luengo, B. Weiss, U.F. Schaefer, C.M. Lehr, R. Wepf, and W. Sterry Nanoparticles - an efficient carrier for drug delivery into the hair follicles Eur. J. Pharm. Biopharm. 66 2007 159 164 (Pubitemid 46654773)
53. A.T. Florence The oral absorption of micro- and nanoparticulates: neither exceptional nor unusual Pharm. Res. 14 1997 259 266 (Pubitemid 27160935)
54. P. Jani, G.W. Halbert, J. Langridge, and A.T. Florence Nanoparticle uptake by the rat gastrointestinal mucosa: quantitation and particle size dependency J. Pharm. Pharmacol. 42 1990 821 826
55. P. Jani, G.W. Halbert, J. Langridge, and A.T. Florence The uptake and translocation of latex nanospheres and microspheres after oral administration to rats J. Pharm. Pharmacol. 41 1989 809 812 (Pubitemid 20112141)
56. M. Muchow, P. Maincent, R.H. Müller, and C.M. Keck Production and characterisation of testosterone undecanoate-loaded NLC for oral bioavailability enhancement Drug Dev. Ind. Pharm. 37 2010 8 14
57. H.J. Horst, W.J. Holtje, M. Dennis, A. Coert, J. Geelen, and K.D. Voigt Lymphatic absorption and metabolism of orally administered testosterone undecanoate in man Klin. Wochenschr. 54 1976 875 879
58. R. Cavalli, A. Bargoni, V. Podio, E. Muntoni, G.P. Zara, and M.R. Gasco Duodenal administration of solid lipid nanoparticles loaded with different percentages of tobramycin J. Pharm. Sci. 92 2003 1085 1094 (Pubitemid 36523455)
59. A. Bargoni, R. Cavalli, O. Caputo, A. Fundaro, M.R. Gasco, and G.P. Zara Solid lipid nanoparticles in lymph and plasma after duodenal administration to rats Pharm. Res. 15 1998 745 750 (Pubitemid 28275652)
60. G.G. Liversidge, and P. Conzentino Drug particle size reduction for decreasing gastric irritancy and enhancing absorption of naproxen in rats Int. J. Pharm. 125 1995 309 313
61. R.H. Müller Colloidal Carriers for Controlled Drug Delivery and Targeting, WissenschaftlicheVerlagsgesellschaftmbH 1991 CRC Press Stuttgart, Boston
62. R. Shegokar, K.K. Singh, Antiretroviral nanosuspensions for latent HIV reservoir targeting, in: 36th Annual Meeting and Exposition of the Controlled Release Society, Copenhagen/Denmark, 2009, pp. #588.
63. R. Shegokar, Development and evaluation of novel drug delivery systems for an anti-HIV Drugs, in: PhD thesis, S.N.D.T. Women's University, Mumbai, 2010.
64. B.H.L. Böhm, Herstellung und Charakterisierung von NanosuspensionenalsneueArzneiformfürArzneistoffemitgeringerBioverfü gbarkeit /Production and characterization of nanosuspensions with low bioavailability as novel dosage form for drugs possessing low bioavailability, in: PhD thesis, FreieUniversität Berlin, 1999.
65. B. Rabinow, J. Kipp, P. Papadopoulos, J. Wong, J. Glosson, J. Gass, C.S. Sun, T. Wielgos, R. White, C. Cook, K. Barker, and K. Wood Itraconazole IV nanosuspension enhances efficacy through altered pharmacokinetics in the rat Int. J. Pharm. 339 2007 251 260 (Pubitemid 46977603)
66. W.J. Oyen, O.C. Boerman, G. Storm, L. van Bloois, E.B. Koenders, D.J. Crommelin, J.W. van der Meer, and F.H. Corstens Labelled stealth liposomes in experimental infection: an alternative to leukocyte scintigraphy? Nucl. Med. Commun. 17 1996 742 748 (Pubitemid 26333283)
67. B. Romberg, W.E. Hennink, and G. Storm Sheddable coatings for long-circulating nanoparticles Pharm. Res. 25 2008 55 71
68. A. Genner, B.R. Paulke, R.H. Müller, and T.M. Göppert Protein rejecting properties of PEG-grafted nanoparticles: influence of PEG-chain length and surface density evaluated by two-dimensional electrophoresis and bicinchoninic acid (BCA)-protein assay Die Pharmazie 61 2006 293 297
69. T. Blunk, D.F. Hochstrasser, J.C. Sanchez, B.W. Müller, and R.H. Müller Colloidal carriers for intravenous drug targeting: plasma protein adsorption patterns on surface-modified latex particles evaluated by two-dimensional polyacrylamide gel electrophoresis Electrophoresis 14 1993 1382 1387 (Pubitemid 24042925)
70. M. Lück, W. Schröder, B.R. Paulke, T. Blunk, and R.H. Müller Complement activation by model drug carriers for intravenous application: determination by two-dimensional electrophoresis Biomaterials 20 1999 2063 2068 (Pubitemid 29447628)
71. R.H. Müller, Heinemann, S., Surface modelling of microparticles as parenteral systems with high tissue affinity, in: R.a.J. Gurny, H. E. (Ed.), Bioadhesion - Possibilities and Future Trends, WissenschaftlicheVerlagsgesellschaft Stuttgart, 1989, pp. 202-214.
72. R. Alyautdin, D. Gothier, V. Petrov, D. Kharkevich, and J. Kreuter Analgesic activity of the hexapeptidedalargin adsorbed on the surface of polysorbate 80-coated poly(butyl cyanoacrylate) nanoparticles Eur. J. Pharm. Biopharm. 41 1995 44 48
73. R.H. Müller, M. Lück, J. Kreuter, Arzneistoffträ gerpartikel für die gewebespezifische Arzneistoffapplikation, EP 1 023 052 B1, 2003.
74. M. Lück, Plasma protein adsorption als möglicher Schlüsselfaktor für eine kontrollierte Arzneistoffapplikation mit partikulären Trägern/Plasma protein adsorption as potential key factor for controlled drug delivery with particulate carriers, in: PhD thesis, Freie Universität Berlin, 1997.
75. J. Kreuter, P. Ramge, V. Petrov, S. Hamm, S.E. Gelperina, B. Engelhardt, R. Alyautdin, H. von Briesen, and D.J. Begley Direct evidence that polysorbate-80-coated poly(butylcyanoacrylate) nanoparticles deliver drugs to the CNS via specific mechanisms requiring prior binding of drug to the nanoparticles Pharm. Res. 20 2003 409 416 (Pubitemid 36288370)
76. T. Hekmatara, S. Gelperina, V. Vogel, S.R. Yang, and J. Kreuter Encapsulation of water-insoluble drugs in poly(butyl cyanoacrylate) nanoparticles J. Nanosci. Nanotechnol. 9 2009 5091 5098
77. A.E. Gulyaev, S.E. Gelperina, I.N. Skidan, A.S. Antropov, G.Y. Kivman, and J. Kreuter Significant transport of doxorubicin into the brain with polysorbate 80-coated nanoparticles Pharm. Res. 16 1999 1564 1569 (Pubitemid 29510553)
78. J. Kreuter Influence of the surface properties on nanoparticle-mediated transport of drugs to the brain J. Nanosci. Nanotechnol. 4 2004 484 488 (Pubitemid 39387399)
79. J. Kreuter, D. Shamenkov, V. Petrov, P. Ramge, K. Cychutek, C. Koch-Brandt, and R. Alyautdin Apolipoprotein-mediated transport of nanoparticle-bound drugs across the blood-brain barrier J. Drug Target. 10 2002 317 325 (Pubitemid 34746313)
80. N. Schöler, K. Krause, O. Kayser, R.H. Müller, K. Borner, H. Hahn, and O. Liesenfeld Atovaquone nanosuspensions show excellent therapeutic effect in a new murine model of reactivated toxoplasmosis Antimicrob. Agents Chemother. 45 2001 1771 1779 (Pubitemid 32466347)
81. H.M. Shubar, I.R. Dunay, S. Lachenmaier, M. Dathe, F.N. Bushrab, R. Mauludin, R.H. Müller, R. Fitzner, K. Borner, and O. Liesenfeld The role of apolipoprotein E in uptake of atovaquone into the brain in murine acute and reactivated toxoplasmosis J. Drug Target. 17 2009 257 267
82. N. Schöler, C. Olbrich, K. Tabatt, R.H. Müller, H. Hahn, and O. Liesenfeld Surfactant, but not the size of solid lipid nanoparticles (SLN) influences viability and cytokine production of macrophages Int. J. Pharm. 221 2001 57 67 (Pubitemid 32524035)